entrepreneur - The Evergreen Empire

What AI Can’t Replace

My prompt: Write a definition for data visualization

ChatGPT: Data visualization is the graphical representation of information and data. It utilizes visual elements such as charts, graphs, and maps to present complex datasets in a more understandable and accessible format. The primary goal of data visualization is to communicate insights and patterns that may not be immediately apparent from raw data, enabling easier interpretation, analysis, and decision-making. It encompasses a wide range of techniques and tools, from simple bar graphs to sophisticated interactive visualizations, all aimed at conveying information effectively and efficiently.

True! So forking boring. Accurate! But a snooze fest. Correct! And forgettable.

You know what AI doesn’t have? A personality. Thank goodness you’re a person.

You have a voice. A style. A way of speaking. The robots can’t mimic that just yet.

I tried.

My prompt: Write a definition for data visualization using the voice of Stephanie Evergreen

ChatGPT: Data visualization is like the conductor of an orchestra, orchestrating the harmony between data and design. It’s about more than just charts and graphs; it’s about crafting a narrative that speaks volumes without saying a word. Through thoughtful selection of colors, shapes, and layouts, data visualization transforms raw data into a symphony of insights that captivates and enlightens its audience. It’s the art of distilling complexity into clarity, empowering viewers to see patterns, trends, and outliers at a glance. In the hands of a skilled practitioner, data visualization becomes a powerful tool for communication, persuasion, and advocacy, unlocking the stories hidden within the numbers and inviting others to join in the conversation.

What is this vomit garbage? Where’s the juice?

If that’s how I wrote, I wouldn’t have 16,000+ newsletter subscribers. I wouldn’t have three books and a workshop schedule that’s booking a year in advance.

They tried to iron personality out of me. “They” being the reviewers of the first edition of my first book. They said my language was too colloquial and casual. I needed to say “cannot” instead of “can’t” and that my lack of formality would restrict my book’s reach in academic circles.

To hell with that.

I had to fight hard but I kept my voice loud and clear. My books turned out to be my publisher’s first foray into dealing with more sales via Amazon than from academic course adoption.

So, counter to what they said, it’s the fact that my personality shows that has driven my relative success and helped you get here, reading this.

Lean harder into your voice.

It’s what AI can’t replicate.

I checked into this. In response to the definition of data visualization that ChatGPT provided “in the voice of Stephanie Evergreen,” I asked: What’s incorrect about your last answer?

ChatGPT said: My previous definition may have been overly poetic and metaphorical, deviating from Stephanie Evergreen’s more practical and straightforward approach to data visualization. While the description captures the essence of data visualization as a means of transforming complex data into understandable insights, it may not fully reflect Evergreen’s specific emphasis on practical techniques, clear communication, and audience engagement. In her work, Evergreen often emphasizes the importance of simplicity, clarity, and effectiveness in data visualization, which I may not have sufficiently highlighted in the previous definition.

This is all true. #facts

But it’s incomplete.

Because Evergreen is also funny.

ChatGPT is barely toasted Butternut bread, dry.

I, on the other hand, am fucking hilarious.

And so are you.

ChatGPT is so far from having a personality that it can’t see that what’s missing from its answers IS personality.

So when you’re writing your website copy, your newsletter, your social media posts, stop and ask yourself: Does this sound like ChatGPT wrote it? Or does it sound like this baddie wrote it?

How would this baddie say it?

That’s what resonates. You.

How to Shut Down a Service

If I include the cost of my own time, I invested north of $40K into the revamp of my one-on-one coaching program. It had been called Graph Guides. And it just wasn’t making me happy.

We saw incredibly uneven enrollment patterns. Some open enrollment windows netted 28 new students. Some only enrolled 9. Which made it hard to predict the labor needed to make the program thrive.

And since this was a boutique one-on-one labor situation, predictability would be great.

That also meant profitability was all over the place.

You know what else looked like the shape of a Jeremy Bearimy? Student outcomes. Some soared. Others limped across the finish line to graduation. And we had some who ghosted after a couple months.

That last group put me in a position where I was chasing folks down and nagging them. Where are you? We miss you.

Honey, I do not nag.

So after the Spring 2022 enrollment window, I hired a consultant to audit the whole program and tell me how to fix it. Oh shoot, I forgot to add in the consultant fees to the first sentence of this post. +$4K.

Tell me if this is true for you: When I have anxiety, I feel it in my torso. Like, from my gut to my heart, the front of my body feels like it’s protruding an extra 6 inches.

That’s what I felt when I read the consultant feedback. Not sure I could do / wanted to do everything they recommended to sweeten registration and secure more graduates.

I wasn’t sure that I could do enough to increase predictability, profitability, and student outcomes.

But one thing I do know for sure is that I can trust myself to figure it out.

So I sat on the boardwalk in Copenhagen with my paper cup of red wine and my takeout pizza, made a promise to put everything I’ve got into revamping the program, and started sketching a plan.

I skipped the Fall 2022 enrollment period and spent the next 8 months renovating the program from top to bottom. One last time. This would be the do-or-die.

Girl, it died.

I’m now on the other side of the Spring 2023 enrollment, wrapping up the final graduation requirements for the last student in this year-long coaching program. I’m post morteming.

Despite a stronger curriculum, tighter coaching plans, an incredible sales page, paid advertising, a clearer articulation of the program’s value, higher prices, stunning student testimonials, a new name, and endless spreadsheet tweaking to figure out how to make it profitable… the program doesn’t work.

We didn’t get the high number of applications I was hoping for. But I did get plenty of requests for significant discounts. Which was a sign that I still hadn’t made a compelling case for the value students get out of the program. So the enrollment test was a bust.

I was still really pumped about the students we accepted. And I still focused on giving them my all for this year together.

But when it comes to the profitability test, boutique one-on-one coaching is simply expensive. It’s labor intensive. Even though I increased the cost, it still wasn’t high enough to make the program feasible (especially factoring in the investment I made into the reno). We do benefit from some economies of scale but if the enrollment numbers are low, there’s no scaling that economy.

We busted our asses for a 100% graduation rate but ended with 67% graduates. While I’ve learned this is actually quite high for the field, it isn’t high enough for me. The student outcomes test failed. I’m proud of our graduates but that isn’t enough to run a program.

When I was in the midst of the enrollment window, I was having coffee with a friend and explaining my uncertainty. She said “In my world of parks and rec, the worst weather forecast was a 30% chance of rain. Because you have to prepare for both circumstances – rain or shine.”

My 8-month program renovation was a 30% chance of rain phase.

It feels really good to have 100% clarity, even if it’s a 100% chance of rain.

A Boost & Bloom student asked me how to whittle down her three services to just one – the one she loved the most. I gave her the same advice I’m taking for myself.

If you need to shut down a service:

Know your tests. What are you using to gauge success or failure? Mine were enrollment, profitability, and student outcomes. You’ve gotta decide your tests ahead of time and stick to them ruthlessly. Because emotions are thick up in these moments. So you need some pre-determined clear parameters that’ll let you take your ego out of it.

Stop talking about it. If your tests are showing you it’s time to move on, remove the service from your website. Don’t brag about it on your socials. Make no mention that you offer the service. (Ok, I have yet to fully implement this – I’m gonna brag the hell outta this cohort of graduates.)

My Boost & Bloomer was a little spooked by that idea – she didn’t want to cut off an income stream before the service that made her heart sing was a full orchestra. I get that.

Market in the direction you want to grow. Turn your focus. Your socials should be all about your favorite service. Write up success stories of past clients in this space. Gather their testimonials and post that ish everywhere. That’ll draw you more people who are seeking out the one thing you love to do.

Thank yourself for the discernment. You gotta know when to hold em and know when to fold em. It’s a blessing to recognize that something has reached its end – that way you can let it go with grace.

Have you ever finally gotten to the point where you realized something wasn’t working for you anymore? What was it and how did you cut it off? Email me.

You Can Turn Off The Comments

It’s your blog. Your social media. You get to choose the rules.

Early in my days of content creation, I totally didn’t understand that I was in charge. My blog platform contained a comments feature that was turned on by default and I didn’t even question it.

Nor did I need to, at first. I was posting every couple weeks and you wanna know how many comments I got?

Zero.

I was praying for comments. Someone, please, let me know you’re out there.

It took a few months, but they came. Here’s the first, from someone who is still a good friend, Stuart Henderson, regarding an early checklist for reports that I published.

Feels good, right? In fact, most of those early people have become dear to me. Most comments were sweet and supportive.

Until they weren’t.

The first negative comment made my knees shake. Sweat immediately poured from my armpits. My face got hot, my brain felt dizzy, and I thought I was gonna puke.

That negative comment rolled around in my brain, obsessively, for at least three days.

I’d post it for you here but I think I deleted it. 😶 In fact, I’m pretty sure I deleted my entire post. Let’s just act like that never happened.

But after another few months, it happened again. While I hyperventilated into a paper bag, even more replies posted, in which people started arguing with each other AND me. Big names in the data viz world tapped in to the fight:

I blurred out most of it because the actual content isn’t relevant but LOOK AT THE LENGTH OF THE REPLY.

This forced to the surface a very valid question: Does posting also make you responsible for hosting a public debate about your ideas?

Is there an obligation to provide a platform for negativity? Even if they have a point? Even if they’re trolls?

The default mode on blogs and social media posts has always been Comments On. You enter the arena, you better be open to the good, the bad, and the ugly. The entire Internet is a forum for open commentary. Put on your boxing gloves and get out there.

But… says who? I mean, who established those rules? Tech is disproportionately white and male.

Who populates those forums and engages in those debates? At least in my comments, it’s mostly white men. And exclusively so when the comments go negative.

The model that brings them some sort of fulfillment doesn’t work for me. I have better, bigger things to do with my time than moderate Stephen vs Andy vs Jon vs Jeff vs me.

So I turned off the comments. To be clear, first I wrestled with what this means for democratic thought and transparency and oh what will these people think of me. For a few days. Then I just went into WordPress and clicked the button to turn off comments. It’s remarkably easy.

Same deal on LinkedIn. You can just turn off the comments if you want.

It’s your call. That’s the important part here: It’s your call. You get to decide how you’ll put your thoughts out there in the world.

Laughable Contract Clauses

I have a short and sweet contract. It’s 1 page long. As soon as I sniff that a potential client and I are getting to the contract phase, I offer to draft one up for us. Because I hate – HATE – dealing with boilerplate contracts.

They take a hundred years of my life to read closely.

They’re full of legalese I’m sure is intended to make the average Jane feel dumb.

And they’re usually distributed without regard for the actual scope under negotiation.

Corporate and government legal departments are not writing contracts with the best interest of your small business in mind. They assume you’re so thirsty for work you’re going to sign without reading very closely.

I took one for the team and identified several ridiculous contract clauses that you shouldn’t agree to.

Laughable Contract Clause A:

I’m absolutely not looking up some arcane statute buried deep in some document that isn’t even linked to attest to my compliance.

Among many other statues in one particular contract, I had to swear to uphold one single line that linked to a set of provisions that’s 417 pages long.

Laughable Contract Clause B:

This is only 25% of the required wording they want me to print onto a flyer and post in my office. Where I work by myself. While many of these clauses don’t apply to solo enterprises, they also aren’t applicable to the modern workforce, where large teams work remote. What, are we gonna print and mail flyers that every employee has to post in their living room? No.

I had a contract that wanted me to attest I’ve done all of this under penalty of perjury.

Exhibit C:

Though I’m with you in spirit and will absolutely vote, I’m not. posting. flyers.

Exhibit D:

Can you even imagine what my office would look like with all these freakin posters?

Here’s a good one. Exhibit E:

I have to provide proof of auto insurance? For a virtual workshop?

I’ve argued with procurement departments over this one, multiple times. Cars are not involved in the execution of this work. What if people don’t even own a car?

Exhibit F:

Not even 48 business hours. Nope. Not answering emails on a Sunday.

Plus, this contract had three different places where I had to agree to provide a certification of compliance that I don’t use child labor.

I’ve reviewed a contract for a colleague new to the biz where the contract required a physical fitness test. For a virtual design gig.

Have you ever seen a laughable contract clause? Please tell me about it.

The boilerplate is so fully cooked that most procurement officers don’t even look at the scope of the work under contract to see if it’s applicable.

You might be thinking, oh screw it. If procurement isn’t looking at the contract, they surely won’t follow up and ask me for this documentation.

And that would be a very foolish move, my dear.

I have 100% been asked, within 10 minutes of emailing my signature on the contract, for every bit of documentation.

The advice is, of course, to get a lawyer on your team who can review each of your contracts and create counters when necessary.

To be totally honest, I didn’t have the money to hire a lawyer to review each piece of paper when I got started.

I also don’t need a lawyer to recognize ridiculous when I see it.

These days, though I do have a lawyer I can hit up when needed, I make the first move and red line any clauses that don’t work for me. Contracts aren’t set in stone. You have the authority to ask for adjustments or strike outs.

That also means the potential client has the authority to reject your edits and create an impasse. At which point you get to decide if getting a certification of compliance that you don’t hire children is worth the effort. And THIS, my friend, is why you don’t count the money until the ink is dry.

Schedule a Photo Shoot

That blurry shot of you, clearly out with your friends but their faces are cropped out? Not gonna cut it. You need to schedule a photo shoot.

I underestimated how much I’d need photos until I got my first batch. Now I have a photo shoot annually.

You’ll use these shots to professionalize your website and seriously up your branding. Check out my IG grid to see what I mean. Notice how my actual face (and often my glam shoes) are in many of my posts.

My social media consultant has run the numbers on my posts (across all my platforms) and the posts with my actual face always get the most likes and engagement.

Oh, you HATE taking photos? So does everyone, Honey. Same way we hate listening to our own voice. Get over it and call a friend with a good camera.

A Photo Shoot Plan

The goal here is to get as many unique-ish photos as possible out of one appointment.

Which means you’ll need to:

1. Find a location with a variety of backdrops. Don’t take all of your photos in front of the same tree. Your photographer may have some good ideas for you. We found local spaces specifically designed for photo shoots, with plants, couches, a bed (!), a desk, and great lighting, that we could rent hourly (makes the bed even more questionable).

2. Plan for at least three outfit changes. Be sure your clothes are all in the same color family so you can make anything on your lower half match anything on your upper half. Then a quick switch of one half gets you a new outfit. Bring jackets for another quick change.

Don’t forget your underwear. True story: I needed my nude padded bra (don’t judge) but forgot it at home. I was wearing a super flattening black sports bra that you can see through some of the light-colored shirts I’d packed for that shoot.

3. Bring props and accessories. Glasses. Earrings. Your laptop. Anything with your logo on it, like a coffee mug. The combinations of these first three points will get you a ton of unique-ish photos.

I’ll also add: Bring your hair tools. And take time to restyle whenever you want. In one of my early photo shoots, I felt so rushed (people pleaser trying not to waste the photographer’s time) that I was racing through outfit changes at the expense of my hair.

4. Provide some inspo for your photographer. I sent my photographer examples of exactly what I was looking for.

This:

Became this:

This:

Inspired this:

Just search on some of your favorite people (famous, semi-famous, whatever) and paste ideas into Pinterest or even a Google Doc.

5. Ask for portrait and landscape. Landscape works great on your website but portrait is usually better for social media.

6. Get your head in the right space. I wouldn’t have believed how much mindset could make a difference until I saw it in myself, in two photo shoots just a few months apart.

At the photo shoot below, I was relaxed. We had good tunes blasting. There was a cat running around. More broadly, work was good, my family life was happy. It shows:

At the photo shoot below, I was incredibly rushed. I had just arrived at the location after a 4-hour stressful drive, which included a fight with my partner. I only had 20 minutes to network and take photos before heading to my next event. I was tense. Broadly speaking, it was just a few weeks before my divorce.

I was in a totally different headspace and it shows. (Though my jacket is still effin amazing.)

You can’t control all the variables in your life but you can prepare as much as possible to be in a good headspace leading up to your photo shoot. Make a playlist. Bring a buddy. Put joy in your heart.

Do you have a favorite headshot? I’d love to see it!

Shoulders back,
Stephanie

Success is Lonely

Work was collaborative when I started my solo career. I co-launched products and co-presented. When I was in town, people invited me to grab coffee or beer. “Big names” in the field promoted my work.

Until my profile started to rise.

Until I started to have more influence than some of those “big names.” It’s amazing how quickly some dudes go from “I’m a feminist, look at the women I support” to absolute crickets as soon as you start to feel like a threat to their ego.

With other people, I guess/believe I became intimidating. Where people used to hit me up before a conference to see if we could catch a drink at the bar or to ask if I could chair their session, now I think I seem too busy or important to bother?

Whatever the reason, the result was the same:

The more success I saw, the more alone I felt.

You know what they say: It’s lonely at the top.

wah wah, #firstworldproblems, let me get out the world’s tiniest violin to play you and your privilege a sad tune, cry from your yacht

I know, I know.

But it’s still true.

And not just for me.

Check out this study of salaried employees, published in Fast Company. 55% of senior-level women said they’ve felt lonely at work in the past month.

60% of women said their sense of isolation increased as their career progressed.

And that’s among women who still go to an office and thus run into other people in similar roles. Imagine how this goes for those of us who are the solopreneur or the CEO of a small business.

My remedy came when I stopped looking for support from my field and started ganging up with other entrepreneurs. People who were sprinting down the same path as me, also building the plane as they fly it. Despite coming from different fields, our experiences are comfortingly similar.

They get me in a way no one else can.

We have conversations that are impossible with anyone else.

For example, my romantic partners have never had a social media presence (I guess my type is the “I’m not really on any platforms” guy). So while they’re willing to listen while I explain how the latest change in the Instagram algorithm is killing my posts, they have no freakin clue what I’m talking about.

My Fellow Founders get it. They share their research and workarounds. They commiserate and help me plot my next moves. We strategize.

My best friend loves me, but until she started her own company, she didn’t understand the low key pressure I just live with day to day. The thousands of tiny-but-big decisions I make on any given Monday.

Every entrepreneur needs Fellow Founders.

I’m not talking about a referral network where you ship each other business.

I’m not talking about collaborators you’ll propose projects with.

Though if those things happen along the way, extra special bonus points.

I’m talking about a group who’s sole purpose is moral, emotional, and logistical support. With zero financial profit or prestige on the line. No egos, just truth and love.

Where can you find your Fellow Founders?

You will undoubtedly make those connections with other students in Boost & Bloom. People connect in the Community Q & A or during Office Hours when they hear questions that resonate or answers that sing.

In fact, a student from my first cohort included this line in a recent check-in email (I’m keeping this anonymous because this wasn’t a formal testimonial):

“A.W. and I totally clicked on your B and B and have really supported each other in our journeys, which are quite similar.”

Two years after the course ended, we have Business Besties helping one another along.

This year, I’m adding a formal Fellow Founders program to Boost & Bloom.

As the course’s live portion comes to end, some time in May, I’ll connect you with 2 or 3 other founders. Past students can be a part of this too.

You’ll create a team name. Maybe a secret handshake that involves spit and a promise of confidentiality. And you’ll have each other’s backs as you continue to implement the plans you crafted during the course, scaling up your ethical empire.

If you want. No pressure. You can continue to go at it alone, like I did for many years.

I thought, therapy! A therapist will help me sort out these struggles. I started to see the very highest recommended therapist in town. In our first meeting she said “Oh, I’m not on social media.” She didn’t even own a computer. She could empathize on a general level but couldn’t really relate.

No one can relate like Fellow Founders.

Boost & Bloom opens again Winter 2025.

Now is the time to get on the VIP list, where you’ll get $100 off the course price.

This is where you join a space to learn everything you need to know about how to start and scale a thriving business while still keeping your heart beating.

GET ON THE VIP LIST

Find out how to create a work life that aligns with your values.

Find your people.

How I Knew I Needed To Start My Own Business

I absolutely did not intend to be an entrepreneur. Had I done so, I would have likely pursued an MBA – which, in hindsight, woulda been a huge mistake. The strength of my business, what gives me so much appeal, is my deep subject matter knowledge. You know, the degrees I pursued instead of an MBA.

But when I was sitting in a coffee shop parking lot, texting a friend, “I think I’m going to get fired” I knew I could run a business better than my boss. This dude could write a grant (and so could I) but he had no idea how to run a company.

In hindsight, there were some clear indications that I needed to work for myself:

I was a bad employee.

Indeed, I’ve had more than one boss refer to me as “insubordinate.” Which would have hurt my feelings had I not already been called “oppositional” by many a teacher throughout my public education experience.

I can’t follow directions. I mean, technically I CAN. But if the directions lack logic or ethics or reason, if they’re unclear or a blanket punishment for one person’s miscalculation, I struggle to abide on principle.

When the head admin would comment “leaving early, are we?” because I was walking out at 3pm when I’d been in the office since 6am and worked a focus group during evening hours the night before, I knew that the concept of a 9 to 5 didn’t square with my work style.

When the hours you spend with your butt in the seat matter more than the fact you could spend those hours playing solitaire, and that makes you mad, you aren’t cut out for a corporate work ethic.

I needed support.

My independent streak might have backfired a bit. Here’s how: I was hired to fill a position that had been formed through a grant. Which meant my job would be up as soon as the grant was over. Unless more grants came in.

And I guess because I showed up eager and smart they thought I could write these grant proposals by myself?

I had not an ounce of experience. You might not be surprised to learn that my first grant proposal was rejected. And the reviewers took the extra special step of calling us up to tell us how totally off-base the proposal was. Thank goodness this was before Zoom because my face was deep red with embarrassment on that conference call.

But right behind that red embarrassment was also some anger. That I was brand new to the job and had been given zero oversight. No one even reviewed the proposal before I sent it in.

I can look back at that now and see that I needed a mentor. When you work for someone else, mentors aren’t guaranteed, even if you have multiple bosses in the org chart. When you work for yourself, you can hire a mentor.

I had ideas.

Girl, let me tell you. I had dream clients to pursue. Projects I’d crafted on paper. Data visualization to invent. There was a world to change.

When I brought in guest speakers, arranged events in their honor, and connected them with local non-profits, my office cheered me on – so long as I did all of those things outside of my work hours.

When it came to anything innovative that would require the company to pay for my time, I was vetoed. And when my good ideas didn’t get heard I would become disobedient.

I began with micro-rebellions. I stopped following the sign taped to the bathroom mirror (only in the ladies bathroom don’t ask how I know that) directing us to wipe down the sink with a paper towel.

The more I felt undervalued, the less I cared about the company, to the point where my boss commented that I looked “sullen” and needed to “smile more.” >screams into the void<

Was I really just gonna phone it in for the next forty years instead of fulfilling my mission on this earth?

I had ideas for other people.

“You know what would be so cool?”

☝🏼 I say this on a daily basis.

Wanna know how this conversation ends? 👇🏼

“That’s a really good idea, thank you!” >scribbles notes<

That inventiveness is how I launched 3 successful companies. It’s how I teach other accidental entrepreneurs to scale up without breaking down. Inventing game-changing solutions is my favorite part of Boost & Bloom Office Hours.

If you’re also endlessly good at spotting inefficiencies and obstacles AND seeing your way around them, you’ll be good at being a founder too.

When you’re curious about the project’s budget and want to understand how it’s conceived and in the process you have fresh ideas about ways to lower the overhead, you might be cut out to work for yourself.

When you invent a newsletter campaign for the outreach manager because you “just love this sort of thing,” you should consider a job where marketing is one of your many responsibilities.

When you’re as comfortable in business development as you are doing The Actual Work, it’s a sign you should start your own company.

Is this resonating? What would you add? How do you know you should work for yourself? Write me with your ideas.

Here’s to no one ever telling you your coffee break was two minutes longer than allowed.

When Fools Rush In

Fools thinks when you start your own business you’ll just be doing that work you love full time. That isn’t how it works.

Think about it: Even in your day job, only a small portion of your time is spent doing what you love – the Actual Project Work. kat_boogaard summed it up nicely in this pie chart I’m not even mad about:

A typical project is maybe 1/2 Actual Project Work.

The other 1/2 is all the prep and communication and administrivia. So if you work in a job right now and get to spend more than 1/2 of your time doing Actual Project Work, consider yourself fortunate. This means your boss and support staff are handling all that other stuff that you love less.

This also means that if you think you do Actual Project Work better than your boss, it’s likely true! You spend more time on Actual Project Work than she does.

It’s naive to think that if you worked for yourself you’d just Actual Project Work 24/7. Because, my dear, when you work for yourself you also become the boss. You have to do all the things your boss and support staff used to take off your plate.

You actually have less time for Actual Project Work.

That’s the worst but most accurate chart I’ve ever made. Yes, the more accurate pie adds to more than 100%.

So what does this mean for you if you love the work but hate your job and wish you could work for yourself?

It means you:

Learn to love all the other parts. Ugh, what a drag. Right? Actually, it can be pretty damn cool to tackle “all that other stuff” in a way that aligns with your values. That’s how you run a business with integrity.

In Boost & Bloom, I show exactly how to build a company that keeps your ethics at the core. I’ll walk you through alllll that other stuff so you know what to tend to. I’ll teach you the shortcuts and the tech. And I’ll provide example after example of how to reflect your values along the way. You’ll earn a ton of money and still sleep well at night.

I only open enrollment in Boost & Bloom once a year. This is your chance to get started.

You can also hire out some of the Other Parts that you truly despise. It means your pie divides a little differently, with more time spent on managing others – so you’ve gotta figure out how to love that, too. (We’ve also got your back in Boost & Bloom as you build a small team.)

Many entrepreneurs don’t make it more than two years because they aren’t starting off with eyes wide open. I want you to be healthy and happy – even if that means you don’t start a business and instead just find a better boss.

40 Hours. Every Week?

Hey, quick question:

How the hell do people work 40 hours in a week?

Every week?

As I write this, I’ve just come from two entire weeks in Columbus Ohio, where I led a data viz workshop every single day.

I left my rental apartment at 8am and got back at 4:30pm. This is an 8.5 hour day, with a whole one-hour lunch in the middle.

So that’s 42.5 hours per week at their office. (You know I was bringing multiberry muffins to the security guard by the end of my second week.)

About 10 days into this experience, I was texting friends with the same question I’m asking you:

How the hell do people do this?

In order to be out the door by 8am, I was getting up at 6.

Taking 20 minutes to stretch, foregoing my usual yoga routine and meditation time, but just doing the basic maintenance all my freakin physical therapists tell me I have to do before my body parts fall off.

Making coffee and brekkie and packing lunch. Taking the supplements and drinking the green powder. Cleaning up the kitchen.

Putting on all the makeup and doing all the hair (aka getting on the Hot Girl Hamster Wheel, as it’s called on The Money with Katie Show).

And hustling down High St.

By the time I got back to the apartment at 4:30pm, I was famished, so I dove into dinner prep.

Running to the grocery store.

Spending perhaps an hour over the whole day connecting with friends and family.

Hitting up taekwondo twice a week.

Laundering and vacuuming.

Showering and grooming.

Sleeping 8 hours.

Totally unable to keep up with all the other emails in my inbox.

Entirely forgetting that I’m supposed to be researching a new car because the mechanic said mine could catch on fire.

Definitely not following up with the contractor on the bathroom repairs.

Barely noticing all these other Life Things that are just on hold for two weeks while I tread water, until I get back home to my way-less-than-40-hour schedule.

And that’s without having to raise small children or care for elders or even take a dog for a walk.

Come to think of it, the only time of my life when I was able to put in 40 hour weeks was when I was a young adult with no family or responsibilities.

Beyond that time, I think we all have to sacrifice something to keep afloat in a 40-hour work week world. We skimp on sleep.
We grab convenience foods and jeopardize our health because there’s literally no time to eat fresh.
We don’t have hobbies.
We skip exercise.
We don’t nurture our friendships.
We get sick a lot.

Something gives, because something’s gotta give.

I don’t see a way to live a healthy life and also work 40 hours a week. The math aint mathin.

Unless, of course, you have a partner who can manage your household and get your groceries and cook your meals and nurture your social relations. Unless, that is, you have a traditional wife.

Which were exactly the circumstances under which we got to a 40-hour work week. Our elders unionized to get working conditions DOWN to 40 hours. And that was a plausible scenario when people primarily lived in hetero households (even as they did whatever they wanted elsewhere) in which the husband worked and the wife did every fucking other thing under the sun.

In these modern times, a 40-hour work week simply isn’t sustainable.

We don’t need more articles teaching us about batch cooking.

We don’t need another podcast extoling the virtues of a treadmill desk.

Enough with the efficiency hacks showing us how to shoehorn even more around and within and in addition to the 40-hour work week.

We actually need some of that time back.

At Evergreen Data, a typical work week is 26-30 hours and that’s plenty.

40 hours is an outdated construct meant for a different society than the one we live in today.

Reason #4,325 why you need to start your own business. You set your schedule.

Then you go live your life.

A Halloween Horror Story

On the occasion of Halloween week, let me impart a bit of horror with a story about a mistake I made on my very first venture working for myself.

My maiden voyage was a client who I had also worked with at my full time employer. She was interested in some (cheap) design work that was outside of the scope of services my now previous employer offered.

I was going to design the pages of a textbook.

Why?

This was miles away from the work I knew how to do. On another planet. Not my circus.

But I said yes anyway because, as all new entrepreneurs do, I was desperate to make sure I could pay the bills.

The Terms of the Contract

I wrote up a contract that said I’d get:

20% of the total cost upon delivery of the mockup of a dozen key pages.

50% at the delivery of the full first draft.

30% at the conclusion of the work.

We sign, I break open the champagne.

The Reality of the Contract

The next morning I crack open my laptop and get to work.

Within two weeks I had a dozen pages I was happy with and shipped those over to the client.

She took about a week and then got back to me with:

“Thanks – these look good. We’ve got it from here.”

Me: “I’m so glad you love the layout. I’ll get started on the full draft.”

Her: “Sorry that wasn’t clear. We don’t need you to make the full draft. We’ve found a grad student who will work from the models you set up and create the rest of the book.”

What would you do here?

The Terms of the Contract, Revisited

I scrambled to the contract. Yep, there WAS a cancellation clause! Got you!

Oh wait.

The cancellation clause said that either party could cancel with a 10-day notice and that the contractor (me) would be compensated for the work completed to date. (This is actually very boilerplate – contracts are not designed to protect the contractor.)

Which means, yep, I was stuck with 20% of the compensation I was counting on (all those bills to pay) even though developing that 20% took the vast majority of the intellectual work.

The client was completely within the bounds of the contract, though both the contract and the client’s use of it (I can now see) were ethically questionable.

What would you do here?

I cried. I got mad. I wallowed in the injustice for a day and then I set about finding more work.

And I embroidered this experience into my mentality. Lesson fucking learned.

Ok, friend, here’s what you can do to keep yourself out of this mess in the future.

Negotiate better cancellation terms. What could it say? I don’t even know. Because you don’t want to get in a rare situation where YOU need to cancel but can’t because you wrote out a clause that’s too restrictive. I’m actually not sure there’s much you can do here, but maybe you’ll think of something creative and contract lawyers can help.
Reallocate the percentages and due dates. I’d ask for a percent of the contract at signing (pay bills). I’d ask for a much higher percentage due at the mockups. My allocations would look something like this:
1. 15% due at signing
2. 60% due at mockups
3. 15% due at first full draft
4. 10% due at final full draft

This way, you get the bulk of the payment when you deliver the bulk of the intellectual property. If your client ever pulls what happened to me and ditches you upon receipt of the mockups, you’re only out 25% (which would still suck, but not as much).

Your pay isn’t connected to your time. It’s connected to your intellectual property.

Want a postlude? It became clear to me that this client honestly hadn’t thought she’d done anything wrong or morally questionable. Because a year later she reached out and asked me to work on another project.

NOPE!

Saying Yes with Ama Nyame-Mensah

Ama Nyame-Mensah DMd me with a super juicy comment: I think I have some prospective clients who are breaking the No Assholes rule.

Let me back up: Ama is a student in the first cohort of my Boost & Bloom course for entrepreneurs and she knew that my three rules (passed to me from my mentors, who had it passed to them) are: Fun, Lucrative, No Assholes.

Let me back up further: Ama runs a company named Analytics Made Accessible (handily acronymed AMA – get it?). It’s a few years old now. Ama and AMA help people explore, analyze, and communicate their data more effectively, primarily by teaching folks to create compelling charts and share data stories that matter.

A company after my own heart.

And most of the time, I see young entrepreneurs so stressed about paying the bills that they’re saying yes to everything that even remotely looks like it could contribute to cash flow, even if the prospective client is kind of a jerk.

But not Ama.

Stephanie: Ama, you’ve clearly done the internal work to know your boundaries and to be able to spot a jerk from a mile away. What exactly is on your red flag list?

Ama: I will never forget a piece of advice my sister Akua —an Executive and Leadership Coach—shared with me a couple years ago: “If you say yes to everyone, you’re always saying no to yourself.”

Stephanie: I’m reading that again.

Ama: And she’s right.

When I first launched my business, I said yes to everything and everyone. I didn’t care who I worked with as long as I got my name out there and made money—bad idea. I was saying yes to projects that weren’t a good fit and clients who didn’t respect me.

The result: I was miserable.

Hustle culture tells us that overworking and accepting mistreatment from demanding clients are necessary to achieve success. Working with difficult clients who disrespect you and your boundaries and undervalue your expertise will ruin your business and wreak havoc on your financial and mental health.

Stephanie: Give us an example of client disrespect. I’m hoping others will read this and start to recognize when it’s happening to them.

Ama: I’ll share two flavors of disrespect.

Flavor #1: Not valuing my time.

I once had a prospective client reach out to me, looking for an external evaluator for a project.

I will not lie; I initially disregarded the message and sent it to my junk mail because I thought it was spam. But curiosity got the best of me, and I responded to the email, thanking them for sharing the opportunity and setting up a time to chat about the project.

Readers, I kid you not; over two months, this individual rescheduled on me FOUR DIFFERENT TIMES (including once right as we were supposed to log into our scheduled Zoom meeting)!

And if you’re wondering, we never connected about the project.

Then, three months after not connecting with this person, I got an email “thanking” me for my interest in the consultant position (huh?) and completing and submitting documentation (I never submitted any paperwork) …BUT they had decided to proceed with another party. (I got a good laugh out of that one.)

Looking back, the biggest mistake I made was going back and forth, sending multiple Zoom links to a prospective client who was never interested in working with me.

Life happens, meetings get moved, deadlines get shifted, etc. And I cannot penalize someone simply because they’re late…once (maybe twice). But when someone repeatedly reschedules, postpones, or does not show up before becoming a client, you can guarantee they will do the same once you start working with them.

Bottom line: Don’t work with people who do not respect you or your time.

Flavor #2: Rude and unkind.

A couple of years ago, someone approached me to lead a potential project their team had been kicking around. They were attached to a cool group, so I was excited about collaborating with them. So much so that I let a lot of things slide that I shouldn’t have.

By the time I realized something was very off, I had already done several months of free work with no contract in place. But I thought: No worries; we had talked about them paying me for the work I had done to shape the project upfront after pushing the paperwork through.

Readers, that never happened.

When the paperwork was almost complete, everything fell apart. The organization spontaneously came up with a new deposit policy, which they promptly blamed on legal. And when I reached out to have a conversation with my point of contact, the conversation went horribly, horribly wrong.

What I hoped would be a moment for us to come to an understanding about my boundaries and a reiteration of what we had previously agreed to devolved into a weird conversation where they casually dropped that I should be grateful that they would even consider working with me on a project like this.

Rude much?

Remember, you are a business owner. You do a job, get paid, and the cycle continues. (That’s not to say you cannot forge long-lasting, mutually beneficial relationships with your clients.)

But some folks will make you think they are doing you a favor by working with you, even though it’s work they want (and usually need) done. Clients you partner/work with are not doing you a favor. There is no “favor” in business. People value what they pay for, and they pay for what they value.

Bottom line: Don’t work with unkind people.

And Stephanie’s bottom line: No spec work! No work before the contract!!

Now that I’ve been burned a few times, I know to look for these positive signs that someone (or an organization) will be a good partner:

Collaborative: At the heart of any successful collaboration are communication and transparency. I am always excited by open-minded clients interested in working together to experiment and discover what works and what does not. Data + Design work is iterative, so partnering with folks open to hearing and giving feedback is key.
Kindness: To some, respect can be bought. For example, if a client is purchasing your services, you (the consultant/entrepreneur) have to respect them while they can treat you (and their staff!) however they please. When I talk with prospective clients, I watch (and listen!) to how they interact with each other and me. People who treat others with respect and kindness are more likely to treat you with respect and kindness.
Follow-through: Anyone can talk a good talk. But good prospective clients walk the walk. Verbal commitments are great, but they mean nothing without consistent action. This is where follow-through comes in. Follow-through is the key to creating trust in a new relationship. It lets people know you are serious and that you value their time. Follow-through at the beginning of a client relationship can be as simple as honoring meeting end times or demonstrating a commitment to a project by sharing a project description or proposed budget.

Knowing how you want to run your business, the types of clients you want to partner with, your values, and being comfortable communicating your expectations and boundaries will make you a happier entrepreneur.

What would you add to your Yes List? Tell Ama!

You Don’t Have to Be Passionate

I know this sounds impossible, but hear me out: You don’t have to care about the product you sell.

Honey, I can hear you saying “Why the heck would I quit my secure 9-5 to launch a company if I don’t care about the product? Like, deeply care. Like, maybe even more than I care about my spouse.”

Let me tell you about an entrepreneur I know – we’re gonna call him Kevin.

In college, Kevin needed some cash flow so he literally googled “low-cost small business ideas.” He got loads of results with titles like “25 Easy Small Businesses” and the whole concept seems totally laughable to me but hang on.

He’s scrolling these lists and kinda just randomly picks one. It’s now so famous that I’m gonna make up his product for the purposes of his privacy: cheap earbuds you can gift people who insist on Facetiming in public.

Even though I think speakerphones in public should be a crime, Kevin doesn’t care at all. It’s never even crossed his mind that this is an issue.

But he launches the company anyway, constructing cheap earbuds in his college apartment living room.

They’re wildly popular, so pretty soon he’s shopping for a production facility and a warehouse. He hires management and marketing people who care deeply about how your conversation with your BFF while she’s in Portugal belongs to just you and your bestie.

The company skyrockets.

They produce earbuds in different colors. They enter into branding agreements and generate logo-ed styles. Everything’s coming up Kevin.

Is this when the plot turns and we discover that Kevin’s lack of passion for earbuds means that he never listened closely to the consumer, thus leading him to mistake after mistake?

Not at all.

In fact, when the data showed that the brown sparkle version wasn’t selling, he immediately chopped it. Even though it was his favorite.

He lacked an emotional investment that would have otherwise caused him to stay on a sinking ship.

Sometimes being indifferent to the product can give you a better sense of objectivity, a clearer mind for that critical decision-making.

Most entrepreneurs plant their own flags because of how much they love the actual work.

This is a terrible idea.

You’ll never spend your whole day just chilling in your office, grinning ear-to-ear while you just do the actual work. You’ll be sending invoices, developing systems, creating a vision, and marketing your ass off.

Going into business because you’re passionate about the actual work is a bit Pollyanna.

You don’t have to be as actively dispassionate as Kevin, but you gotta respect the way it’s helped him.

In grad school, I remember my shock as one of my fellow classmates defended her dissertation, where she hadn’t done much of the actual work. She hired out her data collection, analysis, and report-writing.

I’m like “You can get a whole PhD without actually demonstrating you know how to conduct a study?”

Her advisor said “Of course. Think about it: Most scholars aren’t out there transcribing their own interviews. They hire grad students. You don’t have to actually do the work. You have to know how to design the process and guide others to success.”

Hm.

Hmmmmmmm…….

Actually, yep.

In fact, that’s what CEOs do.

Unless you’re watching Undercover Boss, the CEO isn’t – nay, CAN’T – spend their days in the weeds, cooking the fries, packaging the earbuds, or coding the focus group data.

Instead, they have to focus on listening to customers, setting the tone, creating the culture, establishing the high-level plan, and developing the systems to stay on the pulse. If anything, that’s what Kevin is passionate about.

Earbuds could become obsolete this afternoon and he’d have the infrastructure to start up something else tomorrow.

Have I convinced you at all that perhaps a little bit of dispassion could be helpful?

If you’re still thinking something like “the secret to my success is that I care about the product” that’s ok – keep the passion. But be very clear that you’ll also need to grow passionate about backend business matters and get comfortable murdering your darlings.

No Bar, No Pizza

Summer 2023 I was one of the swarms of Americans who knocked around Italy for vacation.

Venice, though beautiful, was shoulder to shoulder with tourists. It felt like being in the world’s loveliest but most popular nightclub. If there could be fire codes on sidewalks, Venice would have set off alarm bells.

That’s why No Bar, No Pizza impressed me so much.

Trattoria al Vagon is a well-regarded restaurant, right on a canal, serving traditional Venetian food. It’s the kind of place where you need a reservation for dinner.

But they’re also on a main thoroughfare with throngs of people shuffling by shoulder-to-shoulder throughout the day. If you’re thinking profitably, it would make sense to open earlier in the day. Even all day, since these tourists are jet-lagged and their stomachs don’t know what time it is.

So they compromised a smidge and extended the hours to attract the pockets of people walking by.

And then swiftly realized these tourists have no taste.

All they want is pizza and an aperol spritz at 10am.

Would you appease this clientele even further and install a pizza oven and a bar?

It would mean more capital investment.

It would also mean compromising your quality, your reputation, your ethics – that much more.

They said no.

And posted a handmade sign in large, all caps, English language letters: No Bar, No Pizza.

Don’t even come sit down and waste our staff time if that’s what you seek. There are 100 other restaurants within spitting distance that can meet you exactly where you are.

That’s called boundaries.

Every business needs boundaries – a clear delineation between what you will and won’t do.

You need them because you were likely raised to be a people pleaser so it’s engrained into your personality to bend over backwards for every person who knocks at your door, even if it causes you back pain. And exhaustion. And resentment.

Your best path forward – the path that saves you time and sanity – is the one where you get clear about your boundaries and then communicate them very early on in the process so potential customers can self-select out if their needs don’t match your services.

You need a wooden sign that says No Bar, No Pizza.

I write my boundaries down, because otherwise I’m likely to forget that I made them. That’s how I navigated through a recent situation where a potential client asked me to teach Power BI workshops for beginners, intermediates, and advanced students.

For a day I deliberated.

Then I remembered that I’d have to stretch myself to teach those workshops and they’re technically outside of my wheelhouse. I remembered my boundaries. And I referred this potential client to a colleague.

Boundaries are how I knew how to respond to a potential client who was pressing me to schedule a workshop before the end of the year, even though I’d already told them I have no availability.

Could I have found a way to squeeze them in? Sure.

But it would have hurt. There’s a reason I already put a boundary in place about no more work this year.

So, my friend, what’s a boundary you need to put in place to protect your time, energy, and mental health? Write me with your version of No Bar, No Pizza.

Entrepreneurial Seasoning

When I taught a free class on making more inclusive data visualization, I got a TON of responses that fell into one of three buckets:

This class was AWESOME!
I missed the class, where is the recording?
This class was terrible, you were wrong on all these points, being exclusive with these suggestions, and neglected to mention these ideas.

It’s how I respond to the third bucket of comments that let’s me know what season I’m in with my business.

Expand or Contract Audience Season

My response, at that point in time, to the five paragraph paper of an email with bolded headings and numbered lists detailing my misgivings… was a chuckle. It’s nice that people are so passionate about such an important topic, I thought to myself.

I was in a season of wanting to expand my audience by offering new content, pushing people’s thinking, and getting comfortable being a lil controversial.

Without a doubt in my mind, I have also offered new, lightly controversial content in the past, where I got responses in all 3 buckets and my reaction to bucket 3 was fuck this shit.

I had been putting myself out there when I was in a contracting season. Good intentions, wrong timing for my spirit. All I wanted to do was scream I’m trying my best and If you don’t like it, go elsewhere – this was a FREE class.

That’s vastly different than a chuckle.

As important as it is to show up in the world with consistency, I’ve learned that I also have to watch out for changes in my seasons. Heck, I had to learn that I actually have seasons.

We all do.

Audience growth seasons are one version, but we go through others, too.

Expand or Contract Staff Season

When my staff finish a workshop and get an email like “It was truly one of the best and most practical training courses I’ve taken during my career.” it feels SOOOOoooooo good. Me and my staff just doing this at each other over in Slack:

Skipping Best Friends GIF by Brooklyn Nine-Nine - Find & Share on GIPHY

I freakin LOVE having a team that can help me reach more people and get more good data viz out there in the world.

Teams bring a bigger impact.

You know what else teams bring? Problems.

Needs.

Management.

Which – of course! They need guidance from the boss. Makes total sense.

Despite ever better systems and procedures, from time to time I still end up being an absolute bottleneck for my business.

One option is to hire more help, like a COO, and expand even further. This is what Nina did.

It’s also perfectly ok to decide that sounds like too much work.

I’m not a great manager. I don’t even want to manage. I want to be the one in every workshop, passing out the high fives to my students. I have my seasons where I want to shrink the team and be a one-woman show.

But then I think about all the people I wouldn’t be able to help… And it’s like that, back and forth, forever.

Entrepreneurial Seasoning

You can probably identify other areas of your business where you catch seasonal feelings. Like growing or whittling the services you offer.

If you’ve only been in growth mode so far, hang on – winds will shift. That’s not a bad thing. Mary Poppins came in on a change in wind direction, after all.

Jereshia Hawk made a great point on her podcast: If you’ve only seen growth mode and your revenues have been jumping more than 30% each year, you might need to make yourself take a maintenance season.

Seasons can last months. Or hours.

It’s so tricky. So here’s what to do:

Recognize when a season is changing. You can usually tell by your reactions to common events.

Recognize that this is just a season. It won’t last forever. Take advantage of the season you’re in, while you’re there.

Do you have different seasons than the ones I listed out here? What season are you in right now? Email me – I can relate.

We Need to Talk About Alan Wei$$

I don’t like trash talking people. Publicly. Come to my house with some guacamole and I’ll make margaritas and tea all day.

But this one feels important.

Like so many beginning entrepreneurs, I was advised by well-meaning, more established friends to seek the counsel of Alan Weiss. He’s the Million Dollar Consultant (TM). He’s the consultant to consultants (TM). He’s prolific and heavily trademarked.

This dude’s work appears in every Top 10 Books for Entrepreneurs list.

He has enough decent advice to fill one book. But his publishers know that suckers like you and old me will purchase anything he produces so he’s got a string of books, all very slight redigestions of his first.

I’m not linking to his work here because I think he’s trash but if you’re nosy, he’s easy to find.

Some of his philosophy sticks with me today. I remember how he sells the idea of working from anywhere. Take a prospective client sales call from Tahiti. Why not? In this digital age, we entrepreneurs have the advantage. Just be able to turn around a proposal in 24 hours.

He’s right. A few years back I hit send on a contract worth $60K, then closed my laptop, picked up my mai tai, and smiled at the ocean. It was as awesome as he said it would be.

So what’s the problem?

A Bearing Fruit reader said it best. When I wrote about Things I Quit and asked yall to tell me what you quit, I got this reply:

“I quit comparing my business to others and reading business books by self-aggrandizing white men like Alan Wei$$.”

Yup.

This dude’s ego is so gross. After all, his social media handle is the name of his favorite luxury car. The cover photo on many of his books: him, grinning ear to ear, leaning on the hood of said luxury car.

It’s bravado and machismo and that’s not the model I want to follow. Back when I started, I didn’t know there was another way.

He calls himself the Contrarian Consultant (TM). As if his notions somehow go against the grain. They don’t. In actuality, his use of the label “contrarian” here just means he gives himself permission to be a total jerk.

I don’t follow him but somehow this ended up in my feed on LinkedIn. Resham, who is no longer on the platform, posted a pretty innocent poll.

Resham posts a poll, prompting people to test their grammar by filling in the blank for "I'm sorry - I didn't [blank] to disturb you." Alan Weiss comments "...intend to disturb you with another inane poll." It has 23 likes.

Do you see his response? WTH?!

And what world class consultant (TM) spends time trolling randos on social media?

AND so many people blindly follow him that no matter what he posts, even a rude comment, he’ll get likes and endorsements.

The first lesson here: Punch up. If you’re gonna publicly trash someone, do it to those who are way above you (like I’m doing right now). When big names punch down, it’s like a high schooler beating up a first grader. You’re a bully.

The second lesson: You’ve gotta be discerning about the people you follow. Sure, the advice might be good – but if they have the personality of a hot baby diaper, some of that will stick to your ribs, too.

You know how people say your personality is the average of the 5 people closest to you? It’s kinda the same for who you choose to follow. Choose wisely (not Weiss-ly), ok?

To take that just one step further, who you like and endorse on socials actually does matter. For example, if you’ve been warned that that one dude is a creep but you keep collaborating and promoting his work on your platforms, you’re a creep by association.

I know that for many people of color and white women, we felt like we haven’t had much of a choice. Self-aggrandizing white men and our proximity to them has historically been how we’ve been able to protect our own status and progress.

That’s how we end up with 51% of white women voting for Donald Trump. They don’t necessarily love Trump. They’re reliant on their white husbands for their livelihood.

We can choose a different model. I hear the risk involved. The risk is lessened when we stick together.

Here’s the bottom line: Let’s stop supporting a$$holes.

What business books are you into these days? I’m reviewing a few right now. Email me with your best suggestions and I’ll compile a list.

Batch, Please

Working from home has so many upsides: a 30-second commute, a dress code that includes slippers, and free cat pets all day long.

Working from home also has a major downside: Interruptions.

UPS ringing the bell with another delivery. My partner telling me he’s going out. Even good interruptions like a delicious hug from my teen before he goes to school and that purring cat finding a home on my lap – still interruptions.

When our brains have to switch gears, even momentarily, it takes us a ton of time to get back on track – like 25 minutes to refocus and get back in the groove. For every distraction.

This article from the American Psychological Association says we lose 40% of our productivity when we task switch.

There’s a switch cost.

While I’m tempted to put a KEEP OUT sign on my office door, I have to admit that it’s me. Hi. I’m the problem. It’s me.

Like, just now, in real time as I’m writing this to you, I stopped writing after “It’s me” and sang a little Taylor Swift in my head, checked my email, picked up my phone, read a story about how China says it successfully cloned 3 highly productive super cows, and then stared at the keyboard for a while. Why? I even knew what I wanted to write next.

I think I’m not alone.

We’re all highly distractable.

Our brains are delicate little things. If they start to get overwhelmed, they check out. Our sweet lil brains are actually trying to protect us by being so weak. We can’t totally eliminate this issue. But on the other hand, I don’t really have 25 spare minutes to give up for every distraction in my day.

Our weak brains are why multitasking doesn’t really work. If I’m cleaning my desk while “watching” a webinar, I’m not going to pick up most of what the speaker is saying. Even if I believe I’m listening, as in, I could repeat back their last few words, those words don’t have a chance to land in my heart and resonate. Because I’m divided.

Single-tasking, or monotasking, is always more effective. It’s that seemingly contradictory notion that you have to slow down to make progress. One thing at a time, done well, is more productive and effective than two things you half-ass.

Even though Taylor Swift is still running around in the back of my brain somewhere.

The way to make single-tasking really work for you:

Batch.

Batching means you collect all the very closely related tasks and do them in the same span of time. A single-tasking streak.

Let’s take every entrepreneur’s favorite job: Chasing down clients who owe you money.

Step One: Psych yourself up to address this. That’ll take an hour and a latte run.

Step Two: Open your computer, get into your invoicing program, and locate the unpaid invoices and the date you sent them.

Step Three: Dig through your emails to find the last time you communicated with that client.

Step Four: Write an email that perfectly balances humor and professionalism while thinking to yourself “eff you, pay me.”

Step Five: Reread it five times. Remove some exclamation points.

Step Six: Hit send.

Ok so if you chase one invoice per day, girl that’s your whole morning.

But if you batch your invoice-chasing all in one sitting, you at least don’t have to repeat the costly steps one and two over and over. The time it takes to write the second email will be a fraction of the first because you already did all the hard work (and who am I kidding, I know you’re gonna copy/paste).

I block my batches in my calendar.

Today, for example, is blog writing day. I’m in the zone and I stay here, just writing love letters to you. I don’t have to re-get in the zone for each new post.

Big Boss Time is when I have to make hard policy decisions, write difficult emails, and fire clients.

Follow Up Hour is when I reply to all the folks who contacted me looking for workshops.

Video Day happens because I want to get into full hair and makeup as infrequently as possible.

My brain feels less stressed and more streamlined when I batch my work. Batching reduces the switch cost.

What could you be batching? Give your batch time a fun name and then email it to me.

No Regrets

This is going to sound like a bummer way to start but hang with me, it’ll be brief: My grandma passed to the other side recently. You don’t need to email me with condolences. It’s all good.

I didn’t realize, when I hung out with her the night before, that I’d be the last one to speak to her. She was retrospecting on life. I asked if she had any regrets. She broke out into a big smile and then fell asleep for a few minutes.

The same day I was visiting my grandma, Big Think published this article on the Harvard Study of Adult Development. The Harvard study and several others that track humans for decades produced similar findings: Life happiness is found in the quality of our relationships.

You’ve probably heard this before. If you’re like me, you’re already thinking “yeah, yeah,” with your hand on your mouse, ready to go scroll Instagram. Hold on.

If you want to be satisfied with your life, you’ve gotta invest in your family and friends. This is terrible news for people like me who have a hard time making new friendships as an adult.

The Big Think is careful to clarify that loneliness, which is what kills you, is “people who are more isolated than they want to be.” So if you LOVE being by yourself, do you, Boo. That’s a little freeing, right?

As long as you’re being honest.

If you think you’d like to be a little less isolated, let me tell you what I’ve been noticing.

People place bids.

Bids are tiny little invites to connect.

Perhaps a decade ago, I got new neighbors. They were from Montana. They raised backyard chickens that we’d watch when they went home for the holidays. She worked remotely and when she found out I was also typing away in my house all day, she said “Hey if you ever want to take a work break, hit me up and let’s go for a walk or something.”

Looking back now, I can see that was a bid.

I never took her up on it. I wanted to, sure. But there was always some Pressing Work Thing I needed to attend to instead. That’s what serious CEOs do. They don’t just vacate the office when there are Important Emails to be Answered.

A few years ago, they moved back to Montana because they missed the community.

Now I’m not saying I could have changed the course of their lives or something, but I definitely could have closed the laptop and enjoyed the company for 45 minutes once a week. You walk with someone for 5 years and you form a bond. (Also, just sayin, I coulda used the exercise.)

Work will always be there. The opportunity to create those life-satisfaction-building-connections will not.

I missed the bid and I regret it.

Now I look out for them and I intentionally bid all over the place. Lunch on Friday? Yes please.

Happiness requires a mindset shift for entrepreneurs.

There’s a very American work ethic we’re subscribing to, whether or not we’re aware of it.

Work hard now for future rewards.

Nose to the grindstone gets you a massive nest egg and a glorious retirement. Right?

Except whatcha gonna do with all that money and free time? Hang out with… who, exactly? Those friends you never nurtured along the way?

Please be cautious of promises of future reward.

Shifting our mindset would look like:

Blocking out four weeks of vacation in the year, even if you don’t have a destination in mind, even if you just stay home and enjoy the quiet time. Pick whole weeks or block out every Friday. You’ll figure out what to do with the vacation days, trust it.

Scheduling friend dates during the “work day.” Go for that walk, hit up that Indian buffet. I promise, you’ll feel like you had a good day.

Eating on the good plates and drinking out of the good cups. I know you normally reserve those for special occasions but I’m confident you can find something to celebrate every day, if you look for it. Today I finally took my dress to the tailor. Celebrate your accomplishments!

Giving people their flowers, while you can. Don’t wait until your colleague tells you she’s quitting to say “Oh shoot, I really like working with you.” Tell her now. Glow up that professional peer on your socials. Take a deep breath and tell your grandma exactly how she made your life better.

Let’s have faith in the fact that this isn’t going to turn into some YOLO sprint to bankruptcy court. You’re committed to growing your business and building a legacy.

It’s just that the legacy we leave for the next generation shouldn’t just be a big bank account. It should also be an example of a life well lived.

What You Need to Start a Business

This issue is about the third question budding entrepreneurs ask me.

The first question is “How do I price myself?” which is understandable but the wrong place to start.

The second question is “How do I find clients?” which is actually what seasoned entrepreneurs need to be asking, too.

The third question is “What do I need to start a business?” and it’s the same thing I still need every day after running my business for 13 years:

Grit, tenacity, and an unwavering trust that you’ll figure it out.

Contrary to popular belief, it is not a six-month runway of savings.

While that’s comfy, sometimes it’s actually TOO comfy. The pressure of a rent payment will light a fire under your tush and activate your tenacity in a way that nothing else can.

That route is not exactly for the faint of heart. It’s just to say that you do not need investors to start or grow a business.

If you don’t have six months saved, you will find out how efficient you can truly be.

You also don’t need to have a stack of clients lined up.

I promise that a lack of clients will force you to put yourself out there in a way you wouldn’t if you were being safe. And even if you get rejected by your first 10, each one of those rejections is a rich lesson in what you need to tweak ASAP.

You don’t need rich parents.

You don’t need to look like Elon Musk, Mark Zuckerberg, Jeff Bezos or any of the other privileged people who seem to have it easy.

The adversity you have faced in your life is your strength. It’s where grit comes from. Grit is what you need to keep going when you get that 10th rejection.

Don’t get me wrong, getting comfortable with rejection is no pizza party. I’ve had more fun writing out my will.

Even these days, 13 years into starting my business, I still have dreamy potential clients turn me down.

You wanna know what helps? Normalizing it. Take a deep breath and email me about your last rejection.

You bring your grit, tenacity, and unwavering trust. I’ll bring the support.

Hello My Fellow Perfectionist

This is the life hack that allowed me to complete monumental projects, like launching a business, finishing a dissertation, publishing books, giving birth. You know, the stuff that’s really freakin hard. Emotionally, mentally, even physically. The stuff that shifts the course of your life, if you can just actually see it through.

The life hack is:

Done is better than perfect.

Perfectionism often comes from growing up in a culture where your flaws got a lot more attention than your triumphs.

This doesn’t even have to be something that happened within your household. Just existing as a woman in the United States exposes you to the circumstances that can lead to perfectionistic tendencies. White culture, especially, values flawlessness – as if it’s possible.

If you’re told on repeat that you’ve fallen short in some way, you course correct. You raise your standards (because obviously they were previously way too low or you wouldn’t have had a flaw) and you become a hypervigilant monitor of yourself.

You’ll catch those flaws before anyone else notices them.

As a recovering perfectionist, I’m not gonna lie to you. Character traits like high standards and attention to detail have both prevented mistakes (like marrying that one guy who my friends hated) and driven many successes (like having a baby while finishing grad school).

But when you don’t reign it in, perfectionism actually keeps you stuck in a standstill.

During dissertation days, Done Is Better Than Perfect played continually in my head. Because my perfectionism would have me thinking, “I bet there’s one more journal article out there that would really take my literature review all the way to the top. If I don’t fill this gap in my chapter, my committee will notice and I won’t pass, journal reviewers will reject me, and all this work will have been for nothing. Let’s head back to the library and dig for a few more hours.”

Those thought and behavior patterns are fine once or twice. But when you’re doing that on the daily – that’s how you never finish your dissertation.

Too afraid my weakness will be exposed, so stay in “development mode.”

If I don’t move, nobody will see me. Yet that’s the problem – nobody will see you!

To make great things for this healing world, you have to be seen.

You have to risk that there’s a typo somewhere in the manuscript you haven’t caught.

Indeed, after I wrote my first book, I got emails from eagle-eyed readers who said “on this page you said x but on that page you said y,” or “on page 50, you wrote it’s when you should have used its.”

A perfectionist’s worst nightmares, come true.

And that’s after I read every word. Multiple times. As did my editor. And a copyeditor.

So it goes.

Those tiny errors don’t take away from the book’s impact. In fact, every email about a tiny error also said things like “I love this book so much, I’m absorbing every single word. This is changing my life.”

The thing is: Your perfectionistic cultural upbringing means you won’t put crap out there in the world. Your high standards will always prevent you from doing so. It’s going to be good. You produce quality. Even if there’s a typo.

So just focus on getting it done. Of course, give your work one thorough review (how could you not). Then hit Publish. Send the email. Launch the reel. Just go.

The world is waiting.

Security is an Illusion

The day I got called into a meeting with HR, I realized security is an illusion.

My boss was upset that I had started blogging. I had, in fact, blogged about an issue we had on one of our projects, though I didn’t name names or publish anything identifying.

If he had foresight, he would’ve seen my blog as a potential opportunity to market our work. To position us as thought leaders. Contributing to the field’s discourse.

After all, it’s that blog that led to my books, which grew my consulting business, which got me to where I am today, which is pulling in 20x what I used to make when I worked for him.

But I’m getting ahead of myself.

My boss and someone from HR told me that if I didn’t delete my blog from the internet, completely shut the whole thing down, they’d write me up.

I was confused. We’re at a university. What does a write up look like? What are the implications?

HR said the write up would go in my permanent record.

I sat there, waiting for them to tell me the consequence. Then I realized, “Oh that *is* the consequence.” As if I care what’s in my permanent record. You’re talking to the girl who skipped 27 days of the first semester of my senior year of high school.

As I tried to suppress my laughter, I realized this whole thing was flimsy.

I already worked, alone, to bring in grants and contracts that paid for my salary. And covered part of all the admin salaries. Including my boss’s salary.

I brought in more than enough money each year to pay my way but a few weeks earlier my boss had still announced, to everyone, that if there was ever a gap in our grants, like if one didn’t start for a month after a previous grant ended, we wouldn’t get paid. Even though we were salaried employees.

I’m tellin ya, the blog threat was the ace on the top of what I could now see was just a house of cards.

There was no security there for me.

The desire for security is what keeps some people content to show up day after day, wearing the same khakis, pushing the same buttons, having faith that the work will produce a paycheck that will keep them safe.

Security is what keeps people with good ideas from becoming entrepreneurs.

I get it. But it’s a myth.

Stripe just laid off 14% of its workforce.

Facebook fired 13%.

Twitter cut 50%.

Salesforce slashed 10%.

And the list goes on. Most of those folks probably thought they had security.

But your job doesn’t love you, no matter how loyal you are to it.

It’s only after I started my first business that I realized entrepreneurship is the most secure path.

The only thing I can rely on, for sure, is that I can go find another client. If I have a bill to pay, I have the autonomy to say yes to another project, put money in my pocket, and pay that bill.

I can’t get fired. There’s no permanent record.

No one can tell me not to market or network or make a pitch.

Security is knowing that I construct my future.

The reality is both self-employment and other-employment can be insecure. It’s just if you’re self-employed, you can do something about it.

So don’t let the false comfort of security keep you from launching into your dream job.

Sure, there are a lot of unknowns. In my Boost & Bloom course, we articulate every single thing you need to know. We walk you through every decision.

You gain confidence. And clarity. And security.

Boost & Bloom is closed for enrollment right now but get your tushy on the VIP list and you’ll get first access next time around.

GET ON THE VIP LIST

Looking Forward to Freedom

I got to cutest, most sweetly naïve DM from Angela:

“Can I have my own business and also have a lot of time off, especially in the summers, to spend with my young children?”

What would you say to Angela?

My reply was “HELL YES! That’s kinda the whole idea!”

When you work for yourself, you get to create the life you want to live.

In a big picture sense, that means you aren’t necessarily tied to a specific geographic location – you can work wherever you want, in theory.

In a small picture sense, it means you have the freedom to construct each day of your life on your own terms. However you want it to go. You get to make it up!

I freakin love that level of autonomy.

Angela will too. Because it means that if she wants summers off with her kiddos, she has the freedom to book all of her clients during the school year, even during school hours, so that when the bell rings, she’s there to pick them up.

It might seem like this is only possible if you work in a digital consulting space, but not so.

My all time favorite pizza shop closes for entire weeks out of the year so they can all go on vacation.

The framemaker a few blocks from me put up a sign that said “Out for the summer. Reopening September 5. By appointment only.” The quality of his work is so high and people are willing to pay a premium for it, that he can have a brick-and-mortar that’s only open for appointments.

In a more micro picture sense, the way you structure each day is a part of the freedom entrepreneurship gives you.

Lots of newbie entrepreneurs initially set up their days to mimic whatever corporate or academic environment they came from. 8 hours a day, butt in chair. Work through lunch. Clock out at 5.

And if that’s your jam, rock out.

But you’ve got options.

You’ve got freedom.

My daily structure has changed with the seasons of my life. When my kid was younger, I mostly followed the school day schedule, working 8-3 each day of the school year and 10-4 during the summer, getting in exercise and errands after school let out. (PS – those are 6 hour work days, in case ya didn’t notice.)

I have LOVED being there for my kid before and after school – a privilege that so many folks can’t usually enjoy.

Now that my kid is older, I wake up and read a book with my coffee. I go for a long walk or tune into a YouTube yoga class or pretend like I know what I’m doing at the pilates studio. Then I start work around 10:30. Heck, I’m writing this at 11am on a Saturday because he’s a teenager and he’s still sleeping.

I didn’t work Fridays at all this summer. I’ve taken SEVERAL weeks of vacation. We’re looking at a house in another country.

Other people embrace their night owl nature and work 3-midnight.

Some folks, like the owner of my nail salon, want a weekday off to grocery shop or whatever without the crowds, so they trade Sundays for Thursdays.

I’ve heard of people who make all the money they need for the year starting in January and as soon as they hit their financial goal, the rest of the year is totally off.

And this is all aside from the new digital nomad model where you literally take your computer and work from the world’s best coffee shops.

I’m just throwing out ideas here, to help you dream.

How you shape your day and your life is up to you.

That’s the kind of flexibility and freedom you get when you’re the boss.

But listen: The only way you can afford to work 4 6-hour days per week and take off as much time as you want and work from anywhere in the world is to be highly focused and self-disciplined in the time you are on the clock.

I can’t spend that time scrolling IG, hopping on every latest trend. I have to give my sole focus to the actions that keep my business strong.

With freedom comes great responsibility.

So, my friend, what will you do with that freedom? What’s the thing you want to have space for in your day or your life, that entrepreneurism can bring you?

For you seasoned entrepreneurs, what have you enjoyed most about that flexibility? Or did you forget that you’re the boss?

I can’t wait to hear what you have to say. Email me.

There’s joy in that freedom. Let’s find it.

Your Limit is Five Projects

Breaking News: You can only handle 5 projects at a time.

New research out of University of Liverpool reports on analysis of 9,649 data points and it’s showing that when you get beyond 5 projects, you start to lose your mind and burn out.

Isn’t that incredibly helpful information?

Or am I the only one that finds comfort in being data-driven?

5 projects at a time. That’s it.

So here’s how I’m using this idea to plan for an ever calmer, more sustainable 2023.

As usual, I made my grid for the year, blocking out each month in a 6 x 2 matrix so I can plot out my projects and anticipated income.

In previous years, I’d just cram each month’s square with all the projects I committed to and their associated revenue so I could track my monthly dollars and see the balance of my work across the year, on one page. Helpful, to be sure.

But this time around I made an adjustment: Each month is now a numbered list, 1 to 5.

Each workshop I book will fill one spot. Each consultancy. When the 1-5 has been filled for a month, I make a little x to show it’s full. Then I tell clients “Oh sorry, May is booked. My next opening is in June.”

And when I can see the whole year like this, I can also plot out unpaid events I know I’ll have.

For example, here’s my Fall 2023:

September, October, and November, with a list numbered 1-5 under each. September has 3 projects, 2 online course preps and one conference prep. October has one project, a conference. November has nothing.

Usually my massive conference is held in November, where I market and network and make new friends and clients and hug all my people. It’s the best.

It’s also a whole project. It typically takes up one spot for November.

But next year they’ve moved it to October.

Which means my prep will happen in September, when I’m getting my talks together and planning the parties I’ll host at the conference. Whew.

September is the same time I’m launching a course and prepping for the launch of another course.

Now I can look at September and recognize, months in advance, that I won’t have much time for paid work. I won’t overbook my September because I can only do 5 things and massive conference prep is definitely one of those things.

This means, if I’m following the 5 projects philosophy, that I have to take on one less paid project in September, in order to plan for one less paid project in October.

Gosh, that conference starts to take on a different sized budget.

Better make sure I’m working my ass off to get the most out of that conference experience.

The holidays take up one spot in December. Not even work-related but it takes up a whole spot. Because the more I thought about this five project limit, the more I realized it isn’t just about work.

Got a fresh baby? That’s one or two spots on every month until your kid is 3.

Dealing with an aging parent? Fill in a spot. Or three.

Old Stephanie would have scoffed a bit at this research. Like “oh yeah the average person can only handle 5 projects, but me? I’m freakin good at this. Bring it on.”

Old Stephanie burned out. Repeatedly.

Health is recognizing the limits of our capacity.

We can put a lot of pressure on ourselves (and each other) to be more, achieve more, ever ever more more. And even if we have wised up to the fact that ever more isn’t sustainable, you’re just left wondering, well, what is?

It’s five.

Now we know.

Ok, ok. One research study isn’t enough to warrant such strong words like knowing something.

But I’m going to run with this framework for a year and see how I feel.

Conversely, some students in Boost and Bloom, who are just starting out on their own, are struggling to juggle more than one project at a time. Like, your brain hyperfocuses on making sure this one project doesn’t go off the rails.

Let this research be an encouragement to diversify your portfolio a little.

Small projects count. The researchers point out that part of the burnout comes from the administrative time and energy to run a project, no matter its size, and the task-switching between projects that sucks your brain.

So for people who only have one project in their laser beam and need to broaden their scope, small projects count.

And for people, like me, who need to rein it in and lower their project number, small projects count.

May we see this restraint as freeing.

In January, my 5 will be:

A two-day workshop with National Science Foundation
Dashboard development work with the City of Chicago
Coordination of a workshop with one of my staff for Centers for Disease Control and Prevention
Prepping for the re-launch of my one-on-one data viz coaching program, opening in March
Final prep for re-opening Boost and Bloom (I’m so excited!)

What are your five? Email them to me.

How to Fire a Difficult Client

The first time I had to fire a difficult client, my pits sweated right through my shirt as I was composing, backspacing, and rewording that email.

Look, we’re gonna to do our best to make sure we don’t ever end up in this position, but sometimes you have to fire a difficult client.

I encourage you to do this at the second sign of inappropriate behavior. For the most part, I’ll give people grace on their first asshole comment, late payment, or questionable Zoom background.

But the second time?

Cut your losses and get out.

You don’t necessarily even need to have a clear egregious error. Sometimes you just drift apart. You’ve got a 5 year contract and 2 years in you’ve decided you want to shift your business focus.

Instead of providing a full suite of graphic design services, you’re pivoting into the niche of writing each wedding guest’s name in calligraphy on individual grains of rice that they’ll chuck at the happy couple. Totally cool.

Pivots happen all the time.

The bottom line is don’t do this:

Angela Bassett Revenge GIF - Find & Share on GIPHY

Even if you really really really want to.

When you recognize it’s time to part ways your first stop is your contract. Whip that baby out.

It’s gonna have a section on cancellation. The most common clause I see says that the contract can be cancelled by either party with 30 days’ notice.

Ok, cool.

Email your client and say… whatever you want. But not too much. Unless you want to.

Crystal clear?

My point is you aren’t obligated to say much but if you’ve had a good relationship and want to preserve it, you can provide some detail.

How to fire a difficult client:

You can be as efficient as “Hey there – It breaks my heart to do this but I need to sever our partnership. Our contract asks for 30 days’ notice – please consider this the notice. I’ll continue to give my best on this project in that time and I have someone in mind I’d like to transition you to if you want a recommendation.”

You don’t have to mention calligraphy on wedding rice.

You also don’t need to provide a recommendation if your client is a jerk. Because the colleague you’re recommending doesn’t deserve that behavior either.

If they’ve specifically breached the contract in some way, you don’t have to wait the 30 days either. You just need to point to that clause in the contract, like “Todd, when you commented on the size of my butt at last week’s meeting, it was a breach of the sexual harassment clause of the contract, which is cause for immediate cancellation. I’ll be sending my final invoice over shortly.”

I’ve been in less clear situations where I had to say something like “The ongoing reshuffling of my scope and responsibilities is making it impossible for me to fulfill the obligations laid out in our contract. Further, I need to be able to trust a partnership – that’s how we plan out our business strategy. This partnership is not working for our business model any more.”

Copy/paste these as much as you need.

Take a deep breath and hit send.

And if you’ve loved these folks, consider shipping them a parting gift of wedding rice.

Do not forget to send the final invoice.

Sometimes we don’t review our contracts very carefully before signing and end up agreeing to a clause that’s less fair, like one that says only your client is allowed to cancel. If that’s you, still try one of these options listed above. Chances are that once you convey that you’re unhappy, they’ll also want to part ways.

If you’re screening your prospective clients well, firing a difficult client will be rare (so bookmark this page for when you need it). I have to do it once every other year.

When it happens to you, it sucks but I’m here for ya. Email me and tell me what happened and how they reacted. We’ll get through it together.

Just Start

I’m gonna pre-apologize right now. Cause this post from Sun Yi’s Instagram is so accurate, it hurts.

A graph where one bar says Entrepreneurs and maybe 10% is marked as researching and 90% is marked as doing. Another bar says Wantrepreneurs and 90% is marked researching and 10% doing.

Let’s say I want to buy a house in Portugal. It’s been a lifelong dream and I finally feel like I’m in a place in my life where it could reasonably happen soon.

I’m absolutely not jumping on a plane and flying to Lisbon and buying the first house I see.

I’m going to read up on the rules of international house buying. Join an online ex pat community and listen in for advice on fun neighborhoods. Talk to my family.

Then – and this is THE MOST IMPORTANT PART – I’m going to start a conversation with a real estate agent in Porto. That’s when it gets real. And that’s the step we put off.

Because there’s always more research to be done. Another influencer with the one tiny tip that’ll make or break you – better keep scrolling. Right?

Honey, you’ll scroll your whole life away.

The difference between being a wantrepreneur and an entrepreneur is in the balance you strike between researching and doing.

Stop researching and go get a client.

How?

How does anyone get clients? You sell yourself. Talk about your work. Reach out to people who need your services.

That’s when it gets real.

Real scary.

“I want to be an entrepreneur, but I’m scared it won’t work. I’m scared I can’t do it.”

For reals. Those are true legitimate feelings that don’t fully go away, ever. It IS scary.

Now that we’ve settled that, can you view fear as that annoying colleague down the hall and just do your work anyway? Todd in Accounting as been training you for this for years.

There’s just no other way around it. Put yourself out there and focus on getting clients first. You’ll figure out everything else as you go.

“I don’t know what steps are involved – better read yet another CEO’s book.”

Everyone’s path is going to look differently but the one thing you can trust is that, once you start walking, the next step will be revealed to you.

I had just a couple clients under my belt when a prospective and I were emailing back and forth and she said “This sounds great. Do you have a website I can show to my team members?”

No ma’am I do not. But I’ll have one up tomorrow.

The next step shows up at your feet if you just get started.

You build it as you fly.

“I need a lot more experience first.”

Um, how do you think you get experience? You have to go get clients.

You might be thinking, who wants to work with someone so new? You wouldn’t want a surgeon on their first surgery, would you?

I don’t know about that. The best cleaning I ever got was from a dental hygienist who had just graduated. She was well-researched – no one could know more about the most current best practices. And her freshness made her sooooooo careful and detailed.

Listen, your experience will perfectly match someone’s budget. Just go find your someone.

So yes, of course, you need to do some research. But instead of thinking that there’s a research phase and then a doing phase, think about researching and doing simultaneously, back and forth, onward. Both at the same time.

If you want to actually reach those big dreams – that house in Portugal, that business empire, that award-winning YouTube channel – you have to switch to DO mode. Contact the real estate agent, connect to your first client, make your initial video.

Yeah, the first one will suck. So get it out of the way as fast as you can.

Just start. This graphic says "The most effective way to do it is to do it." by Amelia Earhart

So, what’s the next big thing you want to do? The thing you’ve had your heart on but haven’t actually *done* yet? Hit me up for a little pep talk.

When to Disappoint Others

Here’s a story about first time I got a gig through LinkedIn.

Jennifer worked at a ~~ prestige beauty company ~~ and needed a consultant to revamp the 100-slide PowerPoint about the state of the prestige beauty industry for their upcoming conference.

I said yes, even though (1) the deadline was tiiiiiight, (2) I don’t really love doing this kind of design work, and (3) I don’t know jack about the prestige beauty industry.

The pay was structured as a flat dollar amount per completed slide.

Jennifer sent me the deck from last year that “just needed to be updated” (famous last words).

Each slide had at least 100 different elements on it – dozens of textboxes in 4 point font, photos arrays of expensive neck creams. I very quickly saw that the reasonable dollar amount per slide was going to equate to far under minimum wage, with all the work it would take to redesign even a single slide.

I spent a whole weekend in my office, cranking out remakes according to what I knew to be best practices for slide design.

Sent it off to Jennifer Sunday night.

She freakin hated it.

Her email was something like “this is not prestige, this is not elegant, this is not beautiful.”

That hit me like a gut punch.

I took another shot at it, still without any real idea of what prestige, elegant, and beautiful would look like to Jennifer.

I’m sure I fell short. I sent off the next draft, which, at this point, was like the day before the conference. I never heard from Jennifer again, despite my follow up emails.

I had disappointed her.

The right time to disappoint her would have been back when she slid into my LinkedIn DMs. I should have said no. The project wasn’t a good fit. The answer should have been simple.

Or, I could have asked for a sample slide so I could get a sense of the scope of the work. I woulda opened the sample slide, laughed out loud in my office, then politely declined the job – disappointing her.

What do those two opportunities have in common?

They come before the contract is signed.

The best time to disappoint someone is before you sign official paperwork.

We risk damaging our reputation and wasting everyone’s time and energy when we don’t engage in a thorough discovery phase before we ink signatures.

In order to honestly engage in a discovery phase, you’ve gotta know what work you will and won’t do. What lights you up and what’ll be a slog. Who you love to work for and who you don’t need to support.

Those distinctions are blurry at best when we’re desperate for work or flattered by the ask.

You need clarity about your focus and purpose to enter into a discovery phase. (You also need a list of client red flags to look for.)

Most of us skirt this. Because we want to “remain open to new opportunities.”

But clarity about your focus and purpose brings you strength and confidence.

You might think, what’s the harm? You only lost one weekend of your life saying yes to Jennifer.

Not so, my friend. I lost my time, my energy, and I risked my reputation. And as an entrepreneur, time, energy, and reputation are all you’ve got.

So now I know better. I asked for a sample to get a sense of the scope. It’s part of my discovery process.

Let’s trade stories. How did you disappoint a client, after the contract was signed? And what changes have you made to your discovery phase as a result? Shoot me an email.

Raking it in withoutbreaking your soul

Raking it in withoutbreaking your soul

What AI Can’t Replace

It’s what AI can’t replicate.

Because Evergreen is also funny.

How to Shut Down a Service

Girl, it died.

My 8-month program renovation was a 30% chance of rain phase.

You Can Turn Off The Comments

Laughable Contract Clauses

Laughable Contract Clause A:

Laughable Contract Clause B:

I had a contract that wanted me to attest I’ve done all of this under penalty of perjury.

And that would be a very foolish move, my dear.

I also don’t need a lawyer to recognize ridiculous when I see it.

Schedule a Photo Shoot

A Photo Shoot Plan

Success is Lonely

You know what they say: It’s lonely at the top.

We have conversations that are impossible with anyone else.

Where can you find your Fellow Founders?

This year, I’m adding a formal Fellow Founders program to Boost & Bloom.

Boost & Bloom opens again Winter 2025.

How I Knew I Needed To Start My Own Business

I was a bad employee.

I needed support.

I had ***ideas***.

I had ***ideas*** for other people.

When Fools Rush In

A typical project is maybe 1/2 Actual Project Work.

You actually have less time for Actual Project Work.

So what does this mean for you if you love the work but hate your job and wish you could work for yourself?

40 Hours. Every Week?

How the hell do people do this?

Something gives, because something’s gotta give.

In these modern times, a 40-hour work week simply isn’t sustainable.

A Halloween Horror Story

The Terms of the Contract

The Reality of the Contract

The Terms of the Contract, Revisited

Saying Yes with Ama Nyame-Mensah

You Don’t Have to Be Passionate

The company skyrockets.

Not at all.

This is a terrible idea.

In fact, that’s what CEOs do.

No Bar, No Pizza

That’s called boundaries.

Entrepreneurial Seasoning

Expand or Contract Audience Season

Expand or Contract Staff Season

Entrepreneurial Seasoning

Seasons can last months. Or hours.

We Need to Talk About Alan Wei$$

But this one feels important.

So what’s the problem?

Batch, Please

There’s a switch cost.

We’re all highly distractable.

Batch.

I block my batches in my calendar.

No Regrets

People place bids.

Happiness requires a mindset shift for entrepreneurs.

What You Need to Start a Business

Grit, tenacity, and an unwavering trust that you’ll figure it out.

You don’t need rich parents.

Hello My Fellow Perfectionist

Done is better than perfect.

Too afraid my weakness will be exposed, so stay in “development mode.”

Security is an Illusion

There was no security there for me.

But your job doesn’t love you, no matter how loyal you are to it.

Security is knowing that I construct my future.

Looking Forward to Freedom

I freakin love that level of autonomy.

You’ve got freedom.

With freedom comes great responsibility.

Your Limit is Five Projects

5 projects at a time. That’s it.

Raking it in without
breaking your soul

Raking it in without
breaking your soul

I had ideas.

I had ideas for other people.