Raking it in without
breaking your soul

How I Almost Killed My Summer

I’m gonna be honest, I crushed the start of 2022. I launched a new program. People swarmed my Data Viz Academy course. I was holding private webinars weekly. So by the end of the Spring, I was toast.

That’s when my therapist said these words, the ones that unlocked joy in my heart: Why don’t you take the summer off of writing newsletters? Rest, sister.

Look, I love writing newsletters and sharing my hard-won lessons and hearing all about yours. But too much of any good thing is gonna hurt.

Y’all wished me a wonderful summer and I spent it in the sunshine, going to concerts (New Kids on the Block / Salt n Pepa / En Vogue, Billy Joel, Lake Street Dive), singing Take Me Out to the Ballgame at minor league baseball, prepping the barn for my upcoming wedding reception, and traveling Europe while dodging COVID and monkeypox. Sure, I rested too, just like my therapist prescribed.

But here’s how I paid people to ruin my summer:

I’ve been struggling with one of my online courses. Enrollment numbers weren’t where I wanted them to be. The program is really labor-intensive, so even though successful students stunned me with their talent, I’d have to raise the price significantly to keep it in operation. I wasn’t totally sure how to fix it – or whether to just ditch it.

So I hired consultants.

Who took a day to audit my program and sent me ELEVEN FREAKIN PAGES of feedback.

Whew. Ok. I wanted this, I reminded myself. I asked for this. I paid for this.

Cause I know some of you are also interested in building online courses, here’s a quick, paraphrased, rundown of some of the feedback:

Change the name of the program

Rewrite the webpage

Develop freebies

Create an ad campaign to trade the freebie for emails

Create landing pages for the ad campaign

Create emails for people who got the freebie

Develop a free class to deliver when enrollment opens

Create ads for the free class

Develop incentives for waitlisters to enroll early

Write more emails to the waitlist

Create an application process for interested students

Change the onboarding process for new students

Open up enrollment for the waitlist weeks early

Start emailing the waitlist July 11

Those are the highlights, my friend. I’m not even getting into the details. Or the accompanying Loom video breakdown. They were, shall we say, thorough.

I have unwavering faith that I can do all of these things.

It woulda just killed my summer.

Email the waitlist July 11? That means I’m spending June on my computer instead of cold plunging into the Copenhagen canal.

Just because you can do something, doesn’t mean you have to. Right now. Or ever.

Matter of fact, I decided to skip the revamped launch of the course this Fall. I’m postponing the next enrollment period for that course until next Spring. I’m gonna need all the time between now and then to implement the consultant recommendations without burning myself out.

And that Spring enrollment period will be do or die. If the changes don’t result in a profitable program with higher enrollment and happy students, I’m shutting it down. I promise to report back.

The Achiever in me was thisclose to figuring out a way to make it happen.

Writing emails from the beach or something. There are people to help. But there’s one more lesson in here I wanted to pass on to you.

I was discussing whether to rally around this Consultant To Do List with my family. We’re stuffing our faces with miso soup and boogie veggie rolls.

My partner shoves an entire piece of sushi into his mouth (as you’re supposed to do) and says:

“You busted your tail at the start of the year so that you’d have free time right now. You kept saying, to yourself and the rest of us, ‘I know I’m working all weekend, but this means I’ll have a lighter load this summer.’ And now you’re talking about filling up that space you created with more work.”

I woulda kissed him right on the lips, except his mouth was full of sushi.

He’s right. I had totally forgotten about the promises I made to myself when I was up to my elbows in January. It’s very much like me to fill my free time with more work – a habit I’m trying to unlearn, cause I’m tired of burning out.

Every one of us needs somebody in our corner, reminding us of what’s in our best self’s best interest.

So who’s in your corner, rooting for your success and your rest? Me, for one.

And how’d you spend your summer? Hit me up with your favorite non-work-related summer activity.

Signs You Can Quit Your Day Job

THE LEAP! The leap feels so big. Quitting your day job to launch your own empire is full of so much anxiety, fear, curiosity, hope, and thrill.

Most of us aren’t equipped to sort through that many emotions, all happening at the same time. It’s like the Jungle Juice from your college years. And most of us weren’t equipped to handle that either.

So, while there’s no one path to entrepreneurship, let me help you sort out when you’ll know you’re ready to take that leap.

Money & Insurance

The biggest burning questions I get in my DMs are fears about money and insurance.

If you’re in the position to stay in position, do it. By that I mean, if you’re able to stay in your day job while you grow your empire on the side, that’s the most stable situation. Yes, it’ll mean you’re sacrificing some nights and weekends but if you’re just rewatching Breaking Bad again, you won’t lose much.

When you’re earning 75% of your day job salary through your side empire, you’re in a position to walk.

I mean, I walked without having much lined up. People do it all the time. But ideally you’ve built enough of a bridge to make the leap more like a hop.

You only need to get 75% of your salary covered because once you take the leap you’ll have a lot more time on your hands for business development to get you to 100% +.

The + also includes covering your insurance, which is probably the #1 block for people in the US who have to suffer through employer-based insurance programs. It’ll become a cost of doing business. You can handle it. But now’s the time to research how much you’ll be paying and add this cost to the list of expenses you’ll incur regularly (you’ll use that list to help you figure out your pricing).

Thing is – people get jungle juice feelings about money and insurance but it isn’t the first thing to sort out.


What the hell do you sell, Honey? You have to start here.

What do you offer in exchange for money? Usually it’s some kind of product or service. To make a successful leap, you’ve gotta articulate exactly what you sell and package it up in a way that potential buyers can clearly understand.

It’s one thing to say “I’m a stylist and I’ll tell you what to wear.” Dime a dozen.

It’s waaaaay more attractive to say “I’ve got a curated box of clothes in your size and style that I’ll mail to you once a season.” THAT I would buy. It’s packaged. Ok, literally – a box of clothes – but conceptually too and that’s the more important part.

And even more important than that is the underlying mechanism you develop to actually deliver the offer. You can’t just *say* you sell a box of clothes, you have to actually set up the processes by which you’ll find out what customers want, establish relationships with stores, think through the packaging (physical this time – the cardboard box you’ll mail).

You need the idea, plus the processes to make the idea happen. Figure that stuff out first.

Client Demand

The second thing you need in order to quit your day job, right after the idea and process, is the clientele. Almost everyone has their first clients long before they get their first logo.

Client demand can start out small – like, you told your idea and process to a friend, who told a friend, who wants to work with you now. Even if you aren’t ready yet, that counts as client demand.

If you find yourself saying no to some potential work because you’re out of hours in the day, that definitely counts as client demand and that’s how you know you can walk… or leap.

(By the way, I used these same signs to help me navigate my process of cutting out some income streams that I don’t like and leaping over to others that bring me more joy – uh, like Boost & Bloom. This ain’t just for the newbie entrepreneur.)

A strong, sustainable empire will also require branding and marketing and systems and strategies and you’ll build all of that as you go. Don’t worry about it now. Just get product, demand, and money sorted out and you’ll be ready to quit your day job.

Being Strung Along

The thing about being strung along by a “potential client” is that you often don’t know it til it’s too late. Let’s look at what happened to a couple of my students and let their hindsight become your foresight.

No work without a contract.

Sometimes we make it easy to string us along. Like when we agree to work we wouldn’t normally do, for the promise of a future contract.

One of my previous mentees (let’s call her Trudy) accidentally set herself up for being strung along. She realllllllllly wanted to partner with this organization. It woulda been a big fish to add to her portfolio.

In her early conversations with her point of contact at this org, they seemed super eager to work together. So much so, that the client asked Trudy if she’d be willing to jump in on some small tasks (warning sign #1) at a low (warning sign #2) hourly rate (warning sign #3).

Trudy didn’t know me then, so she said yes. The client said it would just be temporary while they write up the bigger contract and get it in place.

Did Trudy ever advance beyond low wage task labor?

No my friend she did not.

And she was too embarrassed about the scope of her work there to ever include this client in her portfolio.

The client doesn’t know what they want.

Another student of mine (code name: Blanche) got stuck in a months-long string-along with a potential client because of “decision by committee.”

Similar to having too many cooks in the kitchen, decision by committee is an excellent way of slowing progress to a casual stroll through I Don’t Know What Do You Think Land. Have you and your partner ever entered into starvation because neither of you could decide what you wanted to eat for dinner? Like that. But with ten partners.

Blanche had a typical initial meeting with this client to lay out the possible solutions she could offer to the problems they were experiencing. They seemed to have come to agreement about the way forward. Blanche went home and waited for a contract.

And waited.

Blanche checked in but by this point, the finer details of the conversation had been lost, so the potential client asked Blanche to write up the plan in a proposal (note to Future Blanche: Write and send the proposal immediately after the initial meeting.)

Blanche sent the proposal and waited.

And waited.

When she checked in again, the potential client said the team needed to really think about whether the proposed solution would solve the right problem. Could Blanche meet with the whole team and help them talk through their problems?

I’m gonna skip to the end of Blanche’s tale: Blanche dealt with so much waffling you’d think she could open an IHOP franchise. This client liked the idea of working with Blanche (or, at least, of having a consultant) but couldn’t ever make a decision about where to start.

I actually suspect they didn’t have the funds to invest in the right solutions but didn’t want to say that to Blanche’s face, so they just let it playyyyyyy out.

Look, some clients really do take months of nurture before the project comes to fruition and you get that sweet contract in your hands. You’ve gotta relationship build. They’ve gotta convince some team members to swipe right on you. Procurement processes and vendor onboarding – the creepy evil twins staring at you blankly at the end of the hallway of consulting life – can take a long, long time.

You’ve gotta learn how to tell the difference between when they really do need time and when they’re stringing you along. Here’s how I tell:

Check-ins should advance the plot.

If you’re not hearing a reply after you send a check-in email, wait a week and send another. We all have those weeks from hell where we can barely breathe. But if you don’t hear anything after the second check-in, move on with your life.

When you do get a reply, it should include some decision or action or next step with a date attached to it.

Like “My team and I have a meeting to discuss this project next Tuesday and I’ll get back to you then.”

or “I have a few more questions. Can we schedule a Zoom to discuss?”

These are check-ins that advance the plot.

If your check-in gets a reply like “Thank you for checking in!” or “We’re still thinking about it.” you’re being strung along and it’s time to walk on by.

Client Red Flags

“What would the price be if we took out the graph makeovers?”

When I hear this question, I run for the hills. I’ve learned to recognize this request as a giant red flag.

This question reflects a potential client who is gonna be a complete PITA (while most business acronyms are ridiculous, this one is important: Pain In The Ass). And I do not want to work with PITAs.

Just like I didn’t want to date jerks. It can be hard to know who’s a jerk at first, right? Everyone’s got maximum charm and best behavior at the beginning.

But once you get burned, you (and your friends) look back at those seemed-benign-at-the-time comments like “I’m such a feminist – I love women!” with fresh eyes. Hindsight teaches you to recognize red flags.

Same with clients when we get burned.

Collect the lessons and form a red flag checklist.

We each have to DIY our own red flag list. But let me seed yours, ok? The question a potential client posed at the top of this post about what the price would be…. that’s nickel-and-dime behavior.

Here’s what isn’t: “Do you have any government or non-profit discounts?” That question is harmless.

First of all, it’s common. Many places DO offer government and non-profit rates.

Second, I respect the fiduciary obligation to inquire about a deal. I get it – we’ve all got budgets. Doesn’t hurt to ask. Reminds me of the way my grandma looked her budtender right in the eye and asked if he had a senior discount. The chutzpah.

But this question: “What would the price be if we took out the graph makeovers?” is different. It’s saying “Even though you’ve developed a well-thought-out workshop package designed to increase our data visualization capacity as much as possible, can I take it apart bit-by-bit?” Nope.

You don’t have to listen to my experience, if you’re interested in playing with fire.

Let me tell you what happened after I said YES one time. YES, we can take out the graph makeovers and lower the price. You know what came a week later?

“Well, what would the price be if we took out access to the Data Visualization Academy, too?”

Run, my dear.

Because the next step will be a request for an hour-by-hour account of your work.

And not only is that a nickel-and-dime situation that breaks the high-quality package I’ve pulled together, it’s micromanagement. This client is gonna be a PITA.

Yes usually comes from a place of fear. No comes from a place of strength.

It isn’t worth the pain.

My friend Toby made me write down my dating red flag list. He’d pull it out over IPAs in the pub, when the occasion was right. When I was about to make a bad decision and repeat a mistake.

You may need to do the same for your client red flag list. Share it with someone else who can keep you accountable to the higher standards you’re setting for yourself. Write to me with your list and compare yours with that of another entrepreneurial friend.

Your red flag list is how you create boundaries. It’s how you generate an empire where the atmosphere is respect. It saves you from stress headaches and new gray hairs. It’s peace.

Find Your Edge

When you have the trazillion dollar marketing legacy of McDonalds behind you, your franchise does NOT need to find your edge. In fact, you want to be cookie-cutter-right-off-the-factory-line samesies as every other McDonalds franchise because customers expect a consistent experience no matter which McDs they roll into.

But when your town has more Mickey Ds than elementary schools, you’ve got competition. The franchise holder down the road is hoping the post prom crowd is going to use his spot for their Tik Toks and french fries and the corporate McDonalds doesn’t care which franchise they visit because it’s still cash in their pocket.

So, my friend, if you want to build your empire, you’ve gotta find your edge. Make yours a Rock-N-Roll Cafe.

You ARE Different

It’s just that you haven’t thought through exactly how you’re different.

It doesn’t matter what industry you’re in – you could be making bespoke broaches for cats – you have competition. Even if you think you’re soooooooo unique. Don’t forget: Sometimes your competition is your potential customer’s choice to do nothing. To not buy. Who actually needs a cat broach?

In other words, your market is crowded, whether you like it or not.

The way to stand out is to find your edge – the thing that makes you unique and different. The cinnamon caramel in a world of vanilla ice cream.

You won’t be everyone’s favorite flavor but you’ll be some people’s go-to, no-questions-asked, extra sprinkles top choice.

Edgy Can Mean Contrarian

Stirring the pot is one of my all time favorite activities. As early as third grade, I was organizing my classmates and mounting campaigns that questioned the status quo. That is, I was every teacher’s most troublesome student (sorry, not sorry Mrs. Jones ❤️) and student hero of the week for getting that English test cancelled in 11th grade.

Questioning the status quo is a part of my constitution. While it still takes some pluck and therapy, it’s what led me to publish blog posts like this one, this one, and this one, which get me emails of admiration and DMs of venom to this day.

To find your edge, list what’s accepted as “common sense” in your field and examine it through your own unique lens. Look for the holes. Talk about them.

It takes a good deal of privilege and a strong support system to buck a trend on Twitter. Some people don’t have the social safety to speak up like that.

But here’s the thing: Contrarian doesn’t mean you have to be cranky, snobby, and up late at night smashing out snarky responses in the depths of the comment thread on your blog. In fact, when your industry is full of cantankerous men cracking at each other online, doing the same makes you vanilla. The contrarian move would be kindness.

So, my Cinnamon Sweet, what’s your edge? Bust out your business journal and write down 5 things that make you different from the others in your field. Then write to me and tell me what they are. We’ll put bells on them and celebrate.

Books Are Not Lucrative

My editor is in my inbox. Again. She gently prods me a couple times a year about writing another book. Or updating an old book. Or writing anything besides newsletters, really.

I’m so resistant.

Writing a book was such a “Should be on my bucket list” notion back when I was in grad school. Before I published a book. Before I knew how much work it would be.

When I was contemplating whether to write it, I was in Indianapolis at a dinner for the keynote speakers of a conference. I was deliberating about this with another keynoter, who told me “Books are your best business card.”

He handed me a copy of his book (yes, he carried copies).

He explained that the book itself won’t make you much money.

Royalties are crap.

Way more recently, I saw this tweet, which validated that things haven’t changed much since then.


By contract, my royalty payments amounted to 14% of sales. Just 14%. For writing the whole damn book (and doing most of the promotion, I might add).

So Mr. Keynoter was saying that the book won’t make you money. But it will open the door for bigger opportunities. You’ll be invited to give keynotes and workshops. You’ll be asked to consult. You can immediately double or triple your prices.

All of those things are 100% true. Publishing a book will not make you rich. You aren’t Stephen King. You don’t get advances. You’ll wait years – literally – after signing the book contract before you’ll see your first royalty check and it’ll be nice but you can’t quit your day job on those dollars.

Writing a book makes you more visible. So if it’s something on your bucket list, the moment you send the manuscript to your editor, you need to start preparing the services (workshops, keynotes, etc) you’ll sell to your new audience.

Books aren’t lucrative.

The opportunities you get from publishing are.

Of course, not everything has to be lucrative. You can write for the pure joy. You can write because you have something to share with the world.

But you don’t need a book to do those things.

See, Mr. Keynoter was advising me at that dinner back before social media became A Thing. Before anyone could start a podcast or a newsletter and grow a following of thousands. Pre-Tik Tok.

15 years ago, books may have been your best business card but now your social media could be even better.

If you want to write, start writing.

Don’t wait for the book deal. Your social media or blog or podcast will likely be the thing that attracts a publisher anyway. So just get to the writing.

Your writing, no matter where you do it, will open up opportunities that make you a lot more money. Writing a book takes months to years of intense focus, patience, and organized thought. Most people underestimate the amount of time and energy required. If you put the same time and energy into your podcast/newsletter/Tik Tok, you’ll get the same opportunities.

If, after reading all of this, you still want to write a book – awesome. Prepare for the opportunities. Get your promotional house in order. Keep writing – that online course, that pitch deck, that story for Forbes.

Once you see that career growth doesn’t come from the book itself, but from the promotion and offers that stem from the book, you might even consider a popular route among many authors I know – self-publishing. Where you keep 100%, not just 14%.

When You’re a Threat

I’ve gotta tell you about the *funniest* thing that happened to me at work in 2021. I mean, in the whole entire year.

Let me set the stage:

My team was hired to help a group of scientists redesign their go-to graphs and, in fact, their entire PowerPoint template. Their main audience was other scientists so the bar isn’t usually very high in these cases but lemme tell ya, they needed help.

I wish I could show you what their slides looked like before, but I’ve gotta protect the innocent.

As we do in all design projects, we developed a handful of options for design directions and had a Zoom call to walk through and talk through the strengths and shortcomings of each possibility.

These folks were suuuuper drawn to the direction that included icons for each section of their talk.

Totally cool. Icons can be fun.

But then came the real work: Getting them to agree on each icon.

I say this with all the love and humor in my heart: Leave it to a group of scientists to totally overthink the meaning held in each icon choice.

Bless the hearts of all nerds, everywhere.

The Great Icon Debate led to a few more Zoom calls, where we’d decide on a finalist for some sections of the PowerPoint and, for others, they’d send me back to the icon ocean to fish for more options.

Third or fourth call that included icons on the agenda and lemme tell you what went down.

We’d been walking through some of the icon choices they needed to make for the first half of the call.

I wrapped up the deliberation by saying “ok why don’t we move on and you all can decide about these icons on your own and get back to me.”

And someone who had her camera off and thought she was muted yelled out “BECAUSE YOU’RE OBSESSED WITH FUCKING ICONS!”

On a work Zoom meeting. In front of 10 of her colleagues. Including her boss.

I couldn’t control my face.

Her colleague on the line said “What was that?”

And the sailor suddenly found the mute button. I can only imagine their sheer horror.


Aside from being a hilariously human moment, there IS a business lesson in here.

It took me a second to see it because I had to catch WHO, exactly, had gaffed so well. It was the in-house graphic designer.

Now can you decipher what was going on?

I’ve witnessed this situation before (though this was the funniest instance, by far).

In the past, it ended up revealing that the unhappy staff person was not really frustrated with the topic at hand. More so, they were unsettled by the fact that they had the skills to do what I was doing and weren’t pleased that there was an outside consultant brought in.

Underneath that coulda been a turf / ego protection mechanism.

Or it coulda been that this person knows a lot more about managing an icon discussion than I do.

Or it’s possible the project made them feel like their skills aren’t where they should be and this, therefore, was a threat to their security.

It’s not really my place to find out what’s underneath. As the outsider, it’s my place to recognize that something deeper is going on and strategize on what to do about it.

I haven’t run into this situation that many times, but I can tell you that I tried:

  1. Partnering with the internal expert to come up with something even better
  2. Transitioning the project to the internal expert & staying on hand to be a resource
  3. Totally ignoring the problem

And I added a point to my Discovery Call Checklist to specifically ask about existing internal talent. Better to strategize how to handle them with my point of contact at the very beginning of the project instead of waiting until the Best Zoom Outburst of 2021 happens.

Ok, let’s trade. What’s the funniest business moment you had last year? I know you remember it. Write back and share. (It’ll stay between us.)

Robin Hood Pricing

Tell me if you can relate to this newsletter reader who wrote:

“I really want to find ways to use my business skills to help my local community and neighbors instead of working 50+ hours a week so a bunch of rich guys in Connecticut can get even richer.”


I don’t know who the rich guys in Connecticut are, but in my mind’s eye, they look like this:

man holding two bags of money, twisting the end of his moustache

Is that how people in Connecticut dress? I don’t even know.

This dear reader was struggling to reconcile working for clients who can pay the big bucks while her heart belongs to the local nonprofits and small businesses.

The super pious among us might conclude that the only choices are to cast your lot with your community and commit to a low salary or sell out with Mr. Moneybags and beat yourself up with endless guilt.

Let me offer a third option.

Robin Hood Pricing

When you Robin Hood, you say yes to a few Connecticuts and use that income to subsidize your time working with your locals.

I know, I know. My cheeky “Robin Hood” name is a bit inaccurate. You aren’t stealing anything. You’re doing your job to the best of your ability. And getting paid handsomely.

Which gives you to the space to charge much less for those you want to help the most.

This means you charge higher prices for the work you do in the corporate world (where higher prices are expected).

Robin Hood Giving

To make this all sit right in my soul, I take my approach one step further. Robin Hood Giving.

When I work on one of these helping-the-rich-get-richer contracts, I take some of the profits from that project and give them directly to the local nonprofit that does the exact opposite thing as the big corporation.

Like, when I work with Facebook, I donate to local journalism efforts.

When I work with global credit card corporations, I give to an underground group here in town that provides cash seed money to launch baby businesses – no interest, not even a loan, just cash.

Every time I work with Chick-fil-A, I cut a fat check to Outfront Kalamazoo, my local LGBTQA+ resource center.

One way or another, you can Robin Hood your way through these seemingly irreconcilable duels in your heart. This isn’t an either/or proposition. This is, my friend, is using the power of AND.

Have you ever partnered up with someone slightly (or more) questionable? How did you make it sit right with your soul?

My Epic Pandemic Business Mistake

I hate learning painful business lessons when I’ve been around the block this long. But here we are.

It’s almost two years to the date. I was in Ottawa giving a workshop to a room full of very distracted Canadians. Their phones were buzzing with emails about mandates to work from home, starting pretty much immediately. Their childcare was closing, come pick up your kid.

In retrospect, we should have cancelled the workshop but you know how it was back then – everything was changing hour by hour.

I flew home through the quietest I’ve ever seen DTW, chatting up my verycloseneighbor about how weird life had gotten, as we bathed our seats in Purell, maskless.

There was just so much we didn’t know.

Like, what’s this going to do to my business?

Uncertainty is every entrepreneur’s enemy.

I used to spend at least a week a month jet setting from city to city, racking up Delta miles and teaching my heart out. If you wanted to get into my speaking schedule you had to book about six months in advance.

So in March 2020 I was looking at half a year of work that needed a Plan B, ASAP. Nearly every client was happy to shift to virtual work and I’m grateful. My online workshops are totally rock-n-roll, I knew we’d be ok.

But everyone else was at a standstill. I spent afternoons completing puzzles with my teenager instead of negotiating new contracts.

Though I didn’t know it at the time, as I was finding the corner pieces, anxiety about my future was on the rise.

So when the Are You Available emails started rolling back in, I made a rookie mistake.

I said yes to everyone.

Uncertainty breeds desperation.

When I launched my first business, I was definitely desperate to make it work so I said HELL YES to anyone, no questions asked.

You don’t realize it til later but the trouble with the Yes to All Approach is that you lose your focus. You don’t have a clear audience. Your marketing gets murky. And you backbend your offer to make it fit what each client wants, even if you aren’t actually flexible.

In other words, it hurts.

It took me years to finally trust that the work would come and that I could be choosy about my projects (just like I’d always wanted when I was dreaming about working for myself).

I thought I knew better. After all, this is the counsel I had given to the students in my business mentoring course for years.

Find your niche! Have self respect! Set boundaries!

But there I was, in late 2020, giving four talks in one day.

I was quickly back to booking six months in advance. Which meant that even in early 2021, when I realized I’d made a rookie mistake, it was too late. I already had dozens of workshops on the books.

Literally, dozens. In December 2021 I posted this on LinkedIn and then laid on the green shag rug in my office for 20 minutes.

Beyond the risk of losing your niche, saying yes to everyone is taxing to your soul.

Your girl was tired.

If I could rewind to the plane ride home from Canada, I would have (1) put on a mask and (2) assured myself that even if things appear uncertain, the best play is to honor the natural limit of my working capacity.

I 100% respect that this is easier said than done.

Too much business is definitely better than too little.

I’m profoundly grateful that things weren’t worse.

I need, like, just two days where no one emails me or wants anything from me.

^ All of these thoughts ^ co-exist, side by side, in my head.

Here’s to calendar caps and regular naps.

What about you? What was your pandemic mistake? Write back and confess.

Singing into the Ocean

I just made one of my dreams come true. I launched an online course while I was at the beach.

I’ve always wanted to be in such a well-prepared place that I could put some work on auto-pilot while I snorkel with sea turtles and lobsters.

I arrived.

I answered a few emails each day from prospective students who wanted to join the Data Visualization Academy. But mostly I drank mojitos.

You’d think it’d be all sunshine and starfish but I have had a teenager in tow, who was being very teenager-y. Why is it so hoooooooot? Why is there sand evvvvvverywhere?

My teen was (rightfully) irritated after an unexpectedly long and sweaty hike back from an unexpectedly amazing tide pool. How looooooong until dinner?

When I told him it would be another 90 minutes, his mood turned so sour, it would have aged me 10 years had we been making direct eye contact.

We diverted to a beachside bar and ordered pineapple juice (with added rum and mint in mine) to see if that would turn that tide.

It didn’t.

But while we sat on the top of a picnic table, watching the sun set into the waves, I spotted this week’s hero.

Just as the sky was starting to turn colors, this guy at the bar faced the water, turned up the tunes playing in his headphones, and danced in the sand.

He sang along, too – loud enough for us to hear him, even over the ocean waves. I couldn’t tell what song he was singing but let me tell you right now this man was doing something holy.

Even though signs from Kohl’s like “Dance like nobody’s watching” makes my guts cringe, that’s exactly what was happening here.

He didn’t seem to care about the cranky teenager brooding nearby.

He didn’t pay attention to the two young girls ripping around the courtyard threatening to put everyone in their Tik Tok video.

He didn’t get distracted by the cook and the bartender, who were married and in a screaming match.

Dude put on his red LED headphones and jammed.

Just him and the music and the sky and the water.

At the risk of romanticizing what was going on in this guy’s head, let me stop here and pull out the lesson for the rest of us.

Prepare for In the Zone time.

You know The Zone. It’s when you’re in that coveted state of flow, where it’s just you and your task/project/focus. Where time passes without you knowing it. That’s The Zone I’m talking about.

It doesn’t just happen by chance. Being In the Zone is a result of how you set up your circumstances.

Like, this guy needed to be at the beach. At sunset. With his headphones. And his playlist. He wouldn’t be singing into the ocean without those ingredients. He came ready.

What circumstances do you need to prepare for your In the Zone time?

For me, I need my mornings. After a cup of coffee and a meditation. With my phone on silent and my social media tabs closed. That’s when I’m at my best.

Because I know that about myself, I don’t schedule meetings in the mornings. I protect the time when circumstances are most favorable for being In the Zone. What takes me a half hour when I’m In the Zone would take me 90 minutes in the afternoon.

What works for you? Write to me and tell me.

I also gotta point out:

he didn’t over-engineer the circumstances. He didn’t demand to be surrounded by silence and good vibes. He didn’t sweat a lot of what could have been distractions.

It’s really easy to find reasons (excuses) for why you can’t just get to work. This is why people have the most beautifully decorated home offices but generate zero income. Time to stop shopping for succulents and publish that website.

We tend to prop up a goal of perfection so that we look productive without actually producing. Actually producing means that people will see our work. And they might point out our flaws.

Next time I find myself lacking the courage to do something I know I want to do because I’m too scared of what my peers on social media will think, I’m going to recall Jam Man on the beach in St Croix, doing his thing.

Just Close Shop

Jeremy Chard handles my highlights. While he’s waiting for the foils to hide my grays, he checks his phone and reads off: “I have to move our haircut scheduled for tomorrow.”

“Ugh!” he says, “Another one.”

Another cancellation?

Yep. His fourth one so far that week.

It was only Monday.

Not just any Monday – the Monday of Thanksgiving week.

Jeremy’s week is going to be potholed.

Like when you only have 15 minutes between Zoom meetings. There’s not much you can productively do in that time.

The solution is to just close shop the week of Thanksgiving.

Once you see the pattern of cancellations, that’s your clue of what’s to come next year too. Wonderful! Use it as feedback and plan around it.

When I started my first business I got high from every email asking to be my client. So much so that when Thanksgiving hit and my supply of new clients went dry, I would go through withdrawals and cry to my father that nobody loved me. It took me a few years to recognize that, in my industry, it’s a pattern.

It’s as quiet as the moon from Thanksgiving until New Years Day.

Budgets have run out for the year and everyone is distracted by fellowship and family (and consumerism).

Now I know to plan around it. I don’t rely on December to contribute to my annual income goals. Heck, now *I* start closing up shop around Thanksgiving.

Plan around it.

Don’t expect responses from potential clients. Don’t try to launch a survey. This is not the time to launch a new course or a book.

In Europe, somehow everyone vacations for all of August (I’m jealous). When I was preparing for a September workshop and needed input from clients in August, I got nothing but out of office replies. Now I know better.

If you can’t NOT work (which we can address in another letter), plan to use this quiet time to generate future work.

Hatch your next marketing campaign.

Reflect on your year’s successes and what you want to accomplish next.

Draft up 2 months of your email newsletter content.

You can still be productive – if you need that – while closing shop to clients, who are already closed themselves.

Plus you get to avoid the awkwardness next time you see a client who was part of Cancellation Week. No need to try to hide the hint of resentment in your voice or enact revenge by letting a gray stick out.

What periods are quiet as a moon in your industry? Write back and tell me when it’s quiet and what you’ll do in that time.

Listen to this.

The largest obstacles you face in growing a business live in your head. You accept thought patterns and limiting beliefs as Absolute Truths and Very Good Questions.

And chances are, you aren’t even doing this on purpose. More than likely, you’ve inherited these beliefs from people around you who think success is “for those other people” and a society that says “not you.”

Let’s rewire some of those circuits and get your head in the game.

Think of this as a curated playlist from me to you. A mixtape for your mindset.

Your responses to my questions in previous newsletters have been the muse for this mindset mix.

Jay Acunzo – Maker Monsters

I got this email from one of yall: “I’d like to ditch [my current job], but I’m daunted by the notion of having to run my own business.” Sound familiar? While there’s a LOT packed into that statement, I detect a good dose of “I’m not sure I’m good enough to pull this off.”

My friend, Maker Monsters are the mean, nagging questions in your head that really don’t have an answer so they never show themselves out. Their ongoing presence actually clouds up your ability to just think and work and be creative, unburdened.

Jay has three different episodes on Maker Monsters (eps 161, 167, & 170) where he interviews a wide range of relatable creatives about the gremlins in their heads and how we make friends with them in order to get back to the good work.

Listen here.

066 When You Think You've Tried Everything - HelloSeven

Rachel Rodgers – Boo, You Need Boundaries

I hear this statement a lot, especially from women: “I’ve been running my business for 4 years and I’m ready to scale but I don’t know how because I’m already overworked and stressed out.”

There’s no one better than Rachel Rodgers at shifting your mindset from Broke Boo habits to Rich Boo habits. While her whole podcast is full of hits, this episode is actually her reading chapter 4 of her book.

Listen here.

And, ultimately, be good to yourself and read her whole book. If you think that money makes you evil and empires are for colonizers, this book is one loving therapy session. She addresses money mindset issues that get baked into our gray matter and how to reframe “rich.”

10. How Much Content Do You Need to Create Before You Can ...

Jereshia Said – How To Overcome Your Fear of Success

A student once said to me, “I think I might be fighting growing.” <mind blown> What a huge insight! If you find yourself procrastinating on the things that will actually grow your business, you might have an unacknowledged fear of success.

For those of us who grew up eating SPAM for dinner like I did (not because you liked it, but because it was cheap), success can be awkward.

And we can do some real weird self-sabotage. Like, for years. Without realizing that we’re getting in our own way.

Because (1) we’ve got some deep rooted belief systems to re-wire and (2) we’ve generally lacked role models of how to be successful and sane.

Jereshia Hawk peers right into your soul in this episode and talks you through to the other side.

Listen here.

Hidden Brain – The Psychology of Self Doubt

I’ve heard you say, “I have so many things I want to do but I’m a Jill of all trades – not sure I’m actually good enough at any of these to make a living at it.” Sweetheart, recognizing your value is hard work made even harder with self dout.

Shankar Vedantam’s podcast is a classic but this episode with psychologist Kevin Cokley is an absolute must listen. Dr. Cokley studies the make up of self doubt aka imposter syndrome. And how everyone has it – even Michelle Obama.

But more than just feeling like you aren’t alone, Dr. Cokley shows you how to make self doubt an ally. This is the podcast to replay when you’re having a bad mental health moment.

Listen here.

Jay Shetty – Eliminating Self Doubt

“Stephanie, I’m not sure how to reach new customers. I feel stuck.”

“Ok, let me send you a strategy for getting new referrals.”

<sends strategy>

“Stephanie, I’m not comfortable with any of these ideas.”

Your brain is designed to keep you alive. Which often means taking as few risks as possible and conserving all atoms of energy. And that’s going to prevent you from trying new things and living a life you’ve dreamed about. This episode is about how to get your brain on board.

In this episode, Jay interviews Mel Robbins, a popular motivational speaker. They talk about how to become kinder to yourself. How the only person who can convince you to be happy is the one who stares at you in the mirror every morning. The real work has to happen internally.

Listen here.

It takes a lot of love to uproot those mental blocks. So don’t be hard on yourself for holding onto bad thoughts. Be compassionate. This journey isn’t easy but you aren’t alone. Listen to the words in this mixtape and rewrite your internal script.

Hear one more thing from me: The risk of sending you a playlist is that you’ll stop everything you’re doing and listen. Pause growth – I must learn first.

But that’s not how it actually works. You learn as you do. Which means you should listen to these episodes (likely, more than once) while you continue to grow your business. You can work on your mindset at the same time that you reach out to a new client or update your website.

There’s no such thing as getting ready, then making business dreams happen. Being an entrepreneur is an ongoing process of getting ready.

Figuring Out Your Next Big Move

Back when I was only running a research company, in my pre-dataviz days, I had the can’t-be-ignored sense that my heart just wasn’t fully in it anymore. And I hadn’t even been there very long.

Sure, I was making plenty of money, paying the bills, investing back in my community.

But I had the whisper. THAT whisper. The one that says you can do more.

It’s really annoying, that whisper. Because it doesn’t have good follow through. Like, what’s that more? What should I be doing?

So if you’re trying to figure out your next move and you’ve got the whisper in your ear, here’s my advice.

Spend six months to a year dabbling in some low-stakes spaces.

Pick spaces that seem like possible candidates for your next move, even if you’re only 10% leaning in that direction.

So if you’re looking for a career pivot, any kind of career pivot, you need stints in any place that seems appealing. A younger Stephanie woulda sought out job shadowing or internships in forestry, restaurant management, and journalism.

The goal is to accumulate a crap ton of experience in a wide range of places so you can see what makes your heart sing.

What resonates in your bones.

Plenty of people become millionaires without their heart coming along for the ride. Get this: I know a guy who launched his multi-million dollar empire by choosing it from a list he found on the internet about quick business ideas. He’s pretty dispassionate about the actual product.

But life is exponentially better when you feel like your work aligns with your life’s purpose.

Life is also reallllllly big, which is why it can take some time to play around so broadly that you find where the tuning fork is your pitch.

Read some. Experience more. It’s one thing to read about something in the abstract but you’ve gotta get your feet wet. Travel, if you can.

In her epic graduation speech, Shonda Rhimes says, basically, get off your tushy and do something. You can only dream for so long. You’ve gotta test the waters. Get experience.

At the very least, schedule some informational interviews with people currently in the field. Ask about pain points, victories, growth possibilities, and the ugly stuff no one likes to talk about. And then listen to what, if anything, is resonating in your heart.

You’ve also gotta be good at it.

Listen, I love LOVE the smell of baking bread. I love kneading the dough. I love slicing into the fresh loaf, spreading some butter, and taking that first bite.

However, I suck at baking bread. Trust that I tried several times a week during the darkest times of the pandemic. I just can’t figure it out.

Bread baking is not my next business move.

Better to figure that out before investing my savings into a commercial oven.

So – something you love AND you’re good at. Both. Together.

But there’s more:

The world pays for it.

In your adventures you might find that leading a girl scout troop is makin your heart sing. The kids love you. You’re GOOD at this.

That’s nice. But that job doesn’t pay. It’s a hobby. A cool hobby! But still.

Your next business move has to actually bring in business.

So if you’re zoning in on a potential next step but you aren’t sure people will pay for it yet, here’s what to do:

Talk to potential clients. Get the scoop on whether this is something they’ve ever hired for or see an actual business need for. It’s ok to send someone a $5 coffee shop gift card and ask for 15 minutes on Zoom to get at this.

Don’t try asking if they’d be willing to pay a certain amount. That doesn’t work because people will say yes to seem supportive but when it comes to brass tacks they may not actually buy.

If you want to test the pricing, try putting a pre-launch into the universe. A pre-launch is when you sell your service before it’s fully formed. You’ll say if you buy now (at a lower cost) I’ll share as a build and you’ll have a hand in shaping the offer. If you get traction here, you’ve funded your build. Cool! You can keep testing pricing strategies from there.

Whether you’re looking for a full career pivot or itching to form a new branch of your existing business, you’re taking a big leap into the unknown. What if you hate it? What if no one wants to buy it?

Six to 12 months spent exploring these three areas should tell you which way to go.

And if you love your current job, it’s probably hitting all three of these points.

Well…. is it? Write me back and tell me which it’s hitting and which it isn’t.

Two Phrases Every Entrepreneur Should Know

Would you take a wine recommendation from a teenager? Of course not. People want to partner with someone who has experience.

Which is why the question Tom sent me is so common among those of you considering entrepreneurship: “How much experience would you recommend having before going it on your own doing the consulting route? Do I need to consult beforehand?”

Though it might look like it on the surface, this question is not just for newbies.

Seasoned entrepreneurs who want to expand their empires into new (and perhaps more lucrative) markets run into this same issue.

People pivoting to new fields, despite a decade of experience, face the same fear.

No matter how long you’ve been on the block, you need two key phrases in your entrepreneurial vocabulary:

“In my experience with similar situations, I recommend…”

The purpose of this phrase is to convey confidence to your clientele. You can be trusted. You’ve done this sort of thing before.

All this means is that you need enough experience to say I’ve seen this.

You don’t have to have that experience in the same industry you’re trying to break into right now. In fact, your cross-industry experience is an asset.

You don’t have to have that experience through paid work. Real life grad school projects or free time portfolio development exercises absolutely count here.

But the truth is that even though I’ve been in business for a dozen years and I like to think I’ve seen it all, a client will still surprise me every once in a while. That’s why you need this second key phrase:

“I haven’t run across this yet, but I have some ideas and I’ll do some research and get back to you.”

You don’t need to know e-v-e-r-y-t-h-i-n-g but you do need to have the unwavering faith in yourself that you can figure it out.

Talented entrepreneurs can find the answer even if they don’t have it right now. They’re resourceful. They’re also timely – you’ll get those ideas back to your client within 48 hours.

I’ve seen the experience question hold too many would-be successful entrepreneurs back from starting their empires.

How much industry experience did you have before you launched your business? Click here to tell me in an email. My hunch is that it’ll be a very wide range. The path into entrepreneurship has 1,000 different entry points.

How to Get Sh*t Done

The first rule is getting shit done is to be really choosy about what you do.

You definitely can’t do everything.

At the moment, I’m building two 6 and 7 figure businesses and planning a third. I write two newsletters and stay active on social media. It looks like I’m doing a lot but here’s a list of the things I used to do and let go of to make space for my priorities:

hosting a podcast
participating in any sort of committee work
pro bono work
hosting a webinar series
writing books
my own accounting
worrying about what some big names in my fields think about me

Behind every person who looks like they’re doing it all is a long list of what they aren’t.

And it’s super important to emphasize that while I don’t have a partner at home to make my meals and tend to the children, my kid is a teenager and he pretty much wants nothing to do with me. For the first 13 years of his life I didn’t have the bandwidth to do as much as I can today.

It’s ok to pace yourself.

The second rule is to prioritize your priorities.

Say your priority is to write a book. Cool! You’ll need long, solid, silent blocks of time to write.

This means you might choose the pay-what-you-can silent retreat center for a long week rather than the NOLA Mardi Gras extravaganza your friends are going to.

Even if social connections are one of your priorities. Book writing could fall higher for you, for a short period of time.

I can’t think very far head into the future (sometimes I can’t even think about tomorrow cause I’m so busy dealing with today) so I plan quarterly priorities. That way, I’m not sacrificing something (somewhat) important for too long. There’s always a time to reconsider and readjust.

But for that quarter, your top two or three priorities take precedence over other competing demands or dreams or distractions. When a little devil pops on your shoulder and tells you to ditch the writing and go for margaritas with your bestie, you’ll need to remind yourself that you have a bigger focus right now.

The third rule is to find out what rules you.

You’ll need a system that cues your brain focus on the priorities you’ve elevated. So the trick – and I think this is the biggest key to massive focus and productivity – is to figure out what rules your actions.

For me, it’s my calendar. I do whatever it tells me to do. So I know I can book time on my calendar for book writing and ain’t nuthin gonna pull me away until that window on my calendar is over. And before I get up, I book the next spot on my calendar when I’ll focus on this priority again.

Other people are ruled by their to do list. Those people need to break down their priority into tasks that can be checked off, one by one. When they finish one task, they make a mini to do list of the next things they’ll tackle when they sit back down again.

Some folks are driven by other people’s expectations. That means their motivation to sit down and work, even when they don’t want to, will be stimulated by the fact that others are waiting on them to finish.

Some are ruled by deadlines and can’t really put in the effort until the deadline gets close. Ok. No prob. Set deadlines.

Are any of these resonating with you? Or does something else drive your actions? Write back and let me know.

If none of these seem to rule you, listen to this podcast episode by Jay Shetty on 10 Ways To Get Things Done Even When You Don’t Feel Like It. Maybe you’ll recognize yourself here.

Find out what drives you. Use it to structure your energy around your selected priorities. Set the other stuff aside temporarily. Get sh*t done.

Biting Off More Than You Can Chew

Learning from other people’s mistakes is so much better than making them yourself. But this is one mistake we all make from time to time: We get too ambitious and bite off more than we can chew.

Let me tell you a story that I wish was less icky.

We had a month before the workshop. Usually this is plenty of lead time.

For me, when I conduct my own workshops. Which is 99% of the time.

But every so often, another company who needs a specialist in data visualization will hire me to co-lead a workshop with them.

Collaboration takes six times longer than doing it yourself.

I wish this wasn’t true. I wish the world was ruled less by time and more about the quality of the output.

But the workshop date was already booked by my collaborators with one of their big, household-name clients. I wasn’t in charge.

Even though we had collaborated on the workshop before, during the pandemic my collaborators shifted their platforms from Microsoft to Google. The transition meant our PowerPoint had to be remade in Google Slides.

What’s more, my collaborators updated their brand during that dark time, so the design of every single slide needed to be revised.

Can I add one more wrench into these gears?

The usual suspect I traditionally co-presented with was pulled for another assignment, so they swapped in a well-intentioned substitute who had never seen the content before. No script, no prep, not even a finished slide deck to work from.

Are you feeling uncomfortable yet?

A team of 5-6 of us met for hours each week, trying to get the slides in shape while also customizing the agenda for the client and learning new material. Building the plane as we fly it, as the saying goes.

The closer we got to the workshop date, the more we were saying “we are just going to have to call it good right here” aka we started compromising the level of quality that lived in our hearts because we were up against a deadline.

I hate being in that place.

I’ve seen a version of this go down countless times as ad hoc teams wait until the last minute to pull their conference presentation together.

So, of course, the answer is Start Earlier.

Easier said than done.

One approach I often use: I list out all the tasks that have to be done to complete a project, along with a generous estimate of time needed for each task. (The less experience you have doing similar projects, the more time you should estimate for each task.)

Then I plot the expected end date on my calendar and schedule the tasks backwards from there.

At that point I can usually see, within the context of the rest of the events on my calendar, whether it’s realistic for me to get this project done on time, with the level of quality I want.

I’ve conducted so many workshops at this point in my life that I already know the schedule. It takes me about 2 months, given all of my other life events, to get a workshop together.

This means that way back at the stage where a potential client and I are doing the negotiation dance, I can start managing expectations. If they want a workshop next month, I have a very quick and easy answer.

Because I’ve been there. I’ve bitten off more than I can chew. More than once. The anxiety it gives me isn’t worth the income.

When was the last time you bit off more than you can chew? Did it give you anxiety? Or make you hustle harder? What did you do about it? Write back and let me know.

Nights & Weekends

You know how babies have that really soft spot on their heads for a while? Their skulls aren’t fully formed yet, in order to leave room for their lil baby brains.

Well, let me tell you about a fun piece of Mom Guilt I still carry around.

I was in my master’s program, studying how to be the best teacher in the gd world. I was taking a full course load, as required by the fellowship I’d landed. But I also needed to work for that bill-paying part of life. And I had a fresh tiny babe.

In hindsight, I cannot recommend all three of these things at once.

To this day, I remember trying to get my little dude to stay sleeping in my lap long enough for me to finishing tapping out this essay before I dashed to my evening job.

When I finally took a breather from the writing and looked down at my kiddo, I saw that I’d been jamming the edge of my desk into the soft spot in his skull. Like, there was a dent.

He’s ok. He’s actually great.

The Mom Guilt I carry is a battle scar from working nights and weekends.

As he got older and I was writing a book or starting my first side hustle, my nights and weekends shifted to mornings and nap times.

That’s the thing about starting your own empire – it takes your time and attention.

When I was first hatching the idea of my business, I got advice about how to know when it’s time to quit your day job. There are a dozen ways to answer this question (future newsletter) but my mentor told me “When your full time job is 100% and your side hustle is 80%, you can walk away.”

This advice inherently means you’re working nights and weekends to get your side hustle up to 80%. You’re tucking it in around the edges of the rest of your life. You’re sacrificing something in order to make a dream come true.

It’s exactly what I’ve been doing the past couple months as I prepped Boost & Bloom.

People can successfully function on shortened sleep, a lack of exercise, and no social life. But only for so long. You actually need sleep, exercise, and friends in order to be creative and thoughtful and ambitious. (You know this, but you try to ignore it.)

If you’re still in the mood to receive unsolicited advice, let me gently suggest that you pace your empire-building.

Schedule the time into your calendar and attend like it’s a class you can’t miss.

When you are there, really – mentally and emotionally – be there. Stay focused.

But only go to class a few times a week. Tuesday and Thursday nights, half of Sunday. Something like that.

See your people. Take a walk. You’ll be better CEO for it. You’re in control here, so set it up for sustainability.

So, what’s your schedule? How are you building your site hustle around the rest of your life? Write to me and let me know.

3 Ways to Beat Back Imposter Syndrome

Done is better than perfect. 

^ This was my motto ^ during grad school, when I was trying to wrap a dissertation while working a full time job and parenting a toddler.  

I pass this new motto to you in hopes it’ll help you manage the #1 killer of dreams: Imposter Syndrome.

Someone sent me this sweethearted question: 

“I recently made the decision to go independent, and my question is about how to manage fear of failure and imposter syndrome. I’m excited! But also terrified!”

Welcome to entrepreneurship. These feelings don’t really go away. The trick is to figure out how to manage them. 

Strategy 1: Get comfortable.

I mean, everyone has some imposter syndrome. Well…. almost everyone. Those people who don’t? They’re the ones who should. 

Say “Hello Imposter Syndrome, my old friend.” Have coffee together. Catch up on old times. 

Just don’t let it stop you from actually taking action. 

Imposter Syndrome often hangs out with Perfectionism. The reason we feel less than deserving of success or worth is often because we feel like we aren’t good enough yet. 

But what actually earns the doctorate is the finished dissertation. What actually gets you in front of people is the social media post. Not the draft you are endlessly tweaking.

Done is better than perfect. 

Get ok with “good enough.”

Strategy 2: Record success. 

When was the last time you tried something – and it worked? Probably already today. 

It doesn’t even have to be anything business related.

Took a gamble on takeout from a new restaurant and discovered a place in your heart for fried goat cheese. 

Swiped right and matched.

Tried a new shampoo. Even if it tangled your hair, you tried it and you learned new information about what you’ll never buy again. Awesome! Wisdom! Success!

Keep a record of what you try and what you learn. For a while, even record the supposed small stuff. The documentation is your track record that you are capable of risking failure and surviving. 

This evidence builds your confidence. 

In fact, write to me with one of these successes right now.

Strategy 3: Start paying attention to your competitors. Or stop.

Your competition is far from perfect. If you look carefully enough, for long enough, you’ll notice a typo in a tweet. Or a client they didn’t win. Or the absence of a strong marketing campaign. 

The point is, no one has it all figured out.

People don’t turn a spotlight on their shortcomings but if you study them, you’ll notice that your competitors or role models are just humans also struggling with imposter syndrome.

On the other hand, try muting your competition.

Stop letting them get in your head. That’s intimidating AF. Geez. Be kind to yourself. You don’t have to be like them to grow an amazing business.

In fact, the business model that makes you most comfortable won’t look like anyone else’s.

Cake Bakers

Being an entrepreneur is more trendy than ever. More and more people are looking to make money on their own terms while following their passions and keeping their sanity intact. I’m all about this.

Except, like any trend, entrepreneurship is not for everyone. Come to think of it, neither are Crocs, but that’s a topic for another time.

There’s A LOT that goes into the business side of growing an empire.

And in my experience, the things that should stop people from starting their own businesses usually don’t. The inverse is also true: the things stopping most people are misconceptions that need to be trashed.

So what actually should stop you from becoming an entrepreneur? Well, one of the signs that this game isn’t for you is if you’re really only interested in doing the thing you love all the time. 

I call this personality the Cake Baker.  

The reality is, opening a bakery doesn’t mean you bake cakes all day. And starting your business doesn’t mean you’ll do the one thing you love doing all day long.
You actually wear all the hats in the business. You get to think strategically about growth. You handle the spreadsheets and budgets, decode the legalese in contracts, manage clients (and their expectations), market your tushy off, the list goes on. 

If you’re the right person for the job, you see all of that as an exciting opportunity. Cake Bakers see it as a drag.

Wanna just bake cakes all day? Get a job at someone else’s top tier bakery, Babe.

My First Million

“Quick, take my picture.” I said to my partner. This is what he snapped.

It’s the moment I became a millionaire.

I knew the day would be coming soon and I was expecting the email from my financial planner to drop any second. My partner and I happened to be in San Francisco at the moment, on a little side venture after I led a workshop in Napa Valley, when word came in.

Record scratch – what? I had a workshop in Napa Freakin Valley? I took a “little side jaunt” to San Francisco? I have a financial planner? Who does that??

I had never even dreamed this day would have come.

Back in 2010, when I was so fresh I didn’t even call myself an entrepreneur, I met with an accountant to make sure I wouldn’t go to jail for tax problems.

Dave told me something like “Withhold 23% of your income right now. When you reach six figures, we’ll have to re-adjust because you’ll be in a new tax bracket.”

I literally LOLed. No way would I EVER make six figures.

I made a million the following year.

Before too long, I was paying six figures in taxes. Yes, I pay more in taxes than I used to make as salary in a whole year at my old job.

These days I look back at the photo of this sweet moment, with my complete swagger and San Francisco-styled hair, and I remember thinking “This will be the best year of business I’ll ever have.”

How wrong I was. Million dollar years are the new norm.

See, this is the thing about growing an empire: It’s hard to see exactly where you’re going.

It’s hard to trust that customers will keep coming.

The economy, a pandemic, an injury, and everything could crumple. There are most definitely forces beyond your control.

That lack of control, that uncertainty, can cause so much low-grade (or high-grade) anxiety that it clouds our ability to think clearly and creatively.

Anxiety gets us listening to so many conflicting, external voices that we freeze.

We stop dreaming big. We start making some abrupt, erratic choices. We wonder whether we should look for a salaried job.

Listen, I never know what my income will look like in 8 months. It’s been that way for 13 years now. At some point in there, I just had to trust that things would work out, because history was showing me that they kept working out.

The sooner you can get comfortable with uncertainty, the more you can stay focused on your work.

My advice is not to relax. My advice is to channel that energy into the #1 trait you need to get to your first million: Absolute faith in yourself that you will figure it out.

You will figure out how to market yourself to bigger, better clients.

You will figure out if, how, and when to hire who in order to increase your business capacity and gross income.

That might mean getting some advice and, if that’s the case, check out my online course, Boost & Bloom. Enrollment opens February 1.

We may not be able to see what’s coming down the road. We may not be able to predict the day we’ll get the email from the financial planner with the million dollar news. But we can trust ourselves that we’ll figure out the very next step to get there.

If you look carefully at your life, I’m sure you’ll find places where you trusted yourself to figure it out. Write back and tell me about it.

Easy Social Media

Why is social media so freaking scary? Oh yeah, because people on the internet can be real jerks.

So much so that a lot of folks are pre-intimidated. Like, too afraid to even put anything out there in case a jerk happens to come along.

I just heard Glennon Doyle say that waiting for jerks on social media is like watching a jack-in-the-box.

Surprise jerks suck. For sure. So we let our fear of them keep us from using social media to be in community and help others with what we know.

We do nothing.

The cost of doing nothing is expensive. Social media is one of the key places future customers are going to find out about you and make a decision to listen to your advice. Creating that relationship builds trust and eventually turns some of those people into paying clients.

Even if you can nod your head along to everything I’ve been saying so far, I still don’t see you tweeting, Honey.

Like, even if you know you need to be on social and you are able to confront the fear of offending someone or saying the wrong thing, you still don’t know WHAT to post. Coming up with ideas for content can be hard.

So let’s talk about easy social media.

Start with a post a day, during the week.

That’s just 5 posts to write in a week. You can do this.

Try structuring your weekly posts in a pattern. Here’s an example:

Monday – promote someone else’s cool work

Tuesday – quick tip about my main service (should be educational in and of itself)

Wednesday – pose a question related to my services

Thursday – a light brag about a client win

Friday – cute cat or kid photo (Fridays are good for something casual)

A pattern structure helps you generate ideas for your posts.

And bonus: It creates a balance so you aren’t ONLY promoting other people’s work or ONLY ever talking about your services. You are a real person with a real cute dog.

No one else is paying enough attention to recognize or predict your pattern. Stay chill, ok?

Sit down on Friday afternoon and think up next week’s posts. Make a calendar for yourself of your upcoming posts so that if you come up with an extra (and you will – you’ll get good at this) you can queue it up for the week after.

At first, planning out next week’s posts might take you an hour. As you get into the routine, you’ll get faster and faster.

Social media doesn’t have to be scary. Or a giant time suck.

We’ll talk so much more about where to put your social media energy in Boost & Bloom, the online course for entrepreneurs reaching for seven figures. Enrollment opens February 1. I’m still tweaking the webpage with details but since we’re friends you can get a sneak peek and sign up for the VIP list here.

Once you know what your pattern will be, write to me and let me know, along with a link to your account so I can watch you work your magic.

Make Yourself Take Vacation

This is what my face looks like on vacation.

It isn’t just the culture, nature, and sunshine giving me that glow. It’s that I’m not at work.

Don’t get me wrong. I often send tweets with #ILoveMyJob because all of my work is deeply fulfilling.

But it’s also exhausting.

Caring deeply about something (anything) often means we put in extra time. We get up early and steal time from the weekend to create its infrastructure. It takes up part of our brain space even when we’re playing with our kids.

There’s a reason clergy and academics take sabbaticals.

Their traditions recognize that we need deep rest from mental work.

Yet Hustle Culture makes it seem like if you rest for just an afternoon, you’ll miss your chance at making a million.

Maybe this is just me (but I don’t think so): Even when I’m on vacation, my business has still set up shop in my head, the shop just shrinks temporarily. My empire is still a part of the low key background noise.

When I take a step away from being IN THE WORK, the background processes are still kicking and I end up hearing my own insights loud and clear.

That’s how, on a hike through the rainforest, I got the best idea for a newsletter article.

On a weekend trip to Chicago, I realized I don’t want to take on any more design projects.

I don’t know about you but by Summer 2021 I was in a streak of burnout so bad that I knew I was going to self destruct if I didn’t get a little break.

So my partner and I found a location within driving distance (so we could stay isolated and also because we had teenagers), and rented an AirBNB (again, no contact with others), right on Lake Erie. We hiked and kayaked.

On Day 4 I woke up at 3am with the idea for Evergreen Empire.

The AirBNB was set up as a vacation home for a family with small children. Perfect. I cracked open the art supply tub and pulled out fluorescent note cards.

Me, my coffee, and my new note cards stared out at the dark lake and sketched out the architecture of this new adventure.

When my partner shuffled into the living room at 5am, I said “Babe, I just started a new business.”

I can guarantee that you wouldn’t be reading this newsletter right now had I ignored my signs of burnout and continued to push through. It’s almost like I have to get away in order to do my best work.

It took me 9 years of running my business before I set up an actual out-of-office reply. In my head, I thought, I’ll lose a client if I don’t write back to them immediately.

The pandemic helped me remember that the world needs a little less pressure and a little more grace. Nothing would fall apart if I didn’t respond within 24 hours.

When you build your own empire, you get to be your own boss. So be the best boss in the world. The best boss in the world would make you take vacation.

Now for your moment of truth. Write to me with the last time you took a proper vacation.

Where did you go? The answer could just be “I went to my couch, not computer, for a whole week.” Vacations, especially in a pandemic, don’t have to involve travel. My dear friend Kate commits to a week off per quarter and most of the time, she spends it just hanging around her house, petting her pup, not thinking about work.

Do you recall getting any clarity or insights when you stepped away from the grind for a moment?

Too Many Cooks in the Kitchen

I am not proud to admit this, but I spent $10,000 on 8 weeks of business coaching. The course was pitched for high-earning (that’s me), executive-level (also me) women who were burning out (ahem, me too).

I’d be happy to share that I forked up 10 grand if I had actually learned something that made my life easier and my business run smoother.

Not so much.

I learned that you just need to stop yelling at your husband. And if that doesn’t work, try the keto diet.

Can I just repeat: TEN. FREAKIN. GRAND.

I coulda taken my whole family to the Virgin Islands, first class, five star resort with that kind of money.

I wish I could tell you that this disaster was an isolated incident but the truth is that I’ve spent years consuming business advice. I’m a lifelong learner, I can’t help it.

Trouble is, when I started implementing what I’d learned, I realized everyone’s advice conflicted.

One podcaster said “Don’t worry about the social media algorithms because the algorithms change too much for the every day Jane to keep up with it.”

A blogger wrote “Placate the algorithm gods, that’s the only way your posts will get seen.”

The $10K course instructor told me, specifically, that my struggles with social media were because I am unwilling to give up control over my brand’s voice and that I should pay (another $10K) to someone else to run my social media for me.

The next time I opened Instagram, I froze. All of that advice was duking it out in my head.

I had too many cooks in the kitchen.

It took me a minute to realize that just because someone has a podcast on business doesn’t make them an expert in running a business. Duh, Stephanie. I get so impressed by the glitter sometimes.

In fact, too many business coaches have business experience limited to… being a business coach.

I don’t know about you, but I’d rather learn from someone who has been in the same hot kitchen.

So let me tell you what I did with that conflicting advice: I tried it all. I sautéed every cook’s recipe.

Some stuck to the wall and some ended up as compost. I’ll tell you the good stuff in future newsletters. For now, I’ll pass on one solid, consistent, enduring lesson.

Listen to your audience.

Sounds vague and vanilla, I know. But it really is the secret trick. 

In my newsletter, I asked readers to write back with their most pressing business questions. I got soooooo many awesome responses that both broke my heart a bit (y’all are stressin!) and built my heart a lot because I know I can help.

The solution for at least 50% of what you sent me is to listen to your audience.

Don’t know which of your many talents should be the focus of your business? Your audience will tell you which they want the most.

Don’t know how to price yourself? Oh honey, your audience will tell you when you’re too expensive. And they’ll tell you when you’re too cheap.

Don’t know how to find customers? Your audience will tell you where to show up. 

I swear, it sounds corny, but this truth is so universal it might become my next tattoo. 

I promise to expand on all of these ideas and more in upcoming newsletters.

Until then, let’s make this a potluck. Write to me with the best piece of business advice you’ve heard.

In some ways, consuming every business book out there is just my slightly masochistic hobby. In other ways, I should have been more discerning early on. I would have saved a lot of confusion, time, and money (I’m still pretty sad about that) if I had just chosen wisely about who to listen to.

You know how Brené Brown said, “If you are not in the arena getting your ass kicked on occasion, I am not interested in or open to your feedback.”? That applies here, too. Let’s use our time and energy judiciously.

Do you know someone else who needs to make this mindset shift? Send them the link to this page so they can sign up for my email list.

Building an empire can be a lonely venture. It’s easier (and more fun) to share your journey with someone who has been there before and can tell you what to do next. I’ve got the company you need in my newsletter. See you in your inbox.

Don’t Freelance

“I’m a freelancer” sounds sexy because media imagery involves rich athletes looking to trade teams or courageous journalists helicoptering to the next international assignment. But in reality, saying you freelance is more like packaging a Le Beccherie tiramisu in a Tootsie Roll wrapper.

Don’t be freelancer.

Freelancers trade their hours for money.

This will, inevitably, stretch you. If not today, SOMEDAY, you’ll find yourself wondering how to scale, how to get more hours in the day, how to get to six or seven figures.

If you worked (and billed) 40 hours per week and never took a vacation or sick day, you’d have to charge $480 per hour to reach seven figures in a year.

Trading hours for dollars isn’t the way.

Freelancers are treated like crap.

When organizations do business with an individual freelancer they act differently than they do when the exchange is business-to-business.

They are less respectful of boundaries and more likely to expect you to be available 24/7. They request the draft on Saturday and the final on Monday. They count your hours.

Somehow freelancers are interpreted as part-time, not really fully employed, and therefore available at the ring of a bell.

Don’t freelance. Own a business.

Your business doesn’t have to be any larger than a company of one. This isn’t about breaking ground on a new HQ. It’s simply a very important shift in position.

The position shift happens in your own head.

When shift your mindset to owning a business, you carry yourself differently. You are doing something bigger than yourself. This might seem small but it solidifies your identity in a way that brings extra confidence and maturity

When you represent a business, other companies treat you as an equal partner. I don’t love this fact, but you get more respect.

To shift from a freelancer to a business owner you don’t need to file any new legal paperwork. You just need to shift the words you use to talk about yourself. And your entire concept of who you and your business are. You know – nothing major.

Do you know someone else who needs to make this mindset shift? Send them THIS LINK to get on my email list.