Raking it in without
breaking your soul

The Three Part Pitch

Trish had been trying to land this dream client for over a year. In that time, she’d sat through many meetings, co-creating a scope and work plan. But, especially after a change in leadership, the group was adrift in thought and Trish was working without a contract.

Trish needed a three part pitch.

When you start to get the sense that you are being strung along – even unintentionally – take that as a sign that it’s time to propose a three part pitch.

When your clients can’t quite seem to crystallize their thinking, that’s your cue to write a three part pitch.

I’ve used this successfully in two different styles, so I’ll tell you about both. They have a common and important characteristic: The three part pitch is you taking control of the situation and suggesting a formal plan, in writing.

You bust this out when someone, anyone, but especially you pulls from your wisdom and experience to be a leader and set the ship on its course.

Pitch Choices

Choice A is the one the client thinks they want. You know what to write here because you’ve listened to them so much and those conversations include gentle (and not-so-gentle) suggestions for what they believe you should do to solve their problems. It’s usually incomplete or totally incorrect and you can say that, nicely, in your pitch.

Choice B is what you think they actually need, based on your previous work in similar situations and what you know, if anything, about their budget.

Choice C is what you would ideally do if money was no option. It’s more than they asked for and solves problems they didn’t even know they had. It’s a stretch. But it’s here to make Choice B look more reasonable.

Spend no more than 1 page writing up each choice.

Pitch Phases

Phase A is a first step on the project. Sometimes that involves just writing up the plan for the next phases. Sometimes it includes a formal assessment of the scope of the problem to be solved. Or a mini solution to a baby problem as a pilot to determine what to do next. It’s a small commitment to test the waters.

Phase B is an expansion of Phase A that is often to be determined.

Phase C is an even larger expansion of the above.

These often have time frames associated with them but costs may not be spelled out beyond Phase A because you don’t know what you’ll be getting into yet. But Phases B and C are in the proposal so your potential clients can see a road map without making a price- or scope-based commitment just yet.

I have used the phased approach when I’m not 100% sure the potential gig is actually viable, fun, or good for me. It gives me the option to back out if Phase A is a circus.

But it puts a future on paper so you have something to refer to later on when it’s time to talk next steps. It keeps folks from getting foggy again.

Trish went with the phase approach.

Why It Works

The pitch comes in three parts because people like options, but not too many. Too many options leads to analysis paralysis and that’s the LAST thing a group in this state needs, after they’ve already been in the fog for so long.

The pitch works because people need to see something in order to react to it. They need to see the shape of the idea (and the price tag associated with it) in order to make a decision, one way or another. Even if they reject all three parts, at least you got to an answer and can move on with your life.

The three parts of the pitch intentionally cover a range of commitment levels so that even if the group is only ready for a bite-size step, you can take it with them. Under contract. For pay.

The three part pitch puts you in a guiding, leadership role.

If you use one of these approaches, email me and let me know how it went.

Do you know someone who could use this advice? Send them this link to get on my newsletter list, too.

Friendship Folders

“Hi Stephanie, I’m Yan. Nice to meet you.”

“Hi Yan. Tell me, what’s the scariest choice you made in the last three years?”

Awkward, right? This is why it’s hard for me to make friends. The light, fluffy, small talk is a challenge for me. I don’t give a crap about the weather. I just want to dive straight into the deep end.

I once (accidentally!) made a new friend cry when I asked why she and her partner had chosen to never have kids. I admired their life of adventure. But, yeah, perhaps our second time hanging out was too soon.

My StrengthsFinder results are high on action and meaning. One of my very lowest strengths (ok, I guess that’s called a weakness) is Woo. I just can’t.

But woo is glue. It’s the stuff that cements connections and, in the business world, makes clients into friends. Or at least friendlies. Who want to work with you again and recommend you to others because you’re a freakin joy to be around.

Woo is how you make people feel special.

And I really do want that, even if I have to consciously strive for it.

So let me tell you about the new woo strategy I’m trying. Sorry for the sharp turn we’re about to make to get there.

My best friend’s father just passed away. He was a veteran with a purple heart. He started a police academy in a part of Michigan that needed standards and training. And even though we only saw each other a few times a year, he’d ask me about details in my life that I was surprised he remembered.

After his death, my best friend’s brother was looking through their father’s iPad. They found out how he did it.

He kept Friendship Folders.

There was one for me. It was called Stephanie Evergreen (Karen’s friend). In my folder, he had notes about my life. Things he’d picked up in the course of our conversations. Like

  • Son is Byce. High schooler. Likes video games and science.
  • Runs her own business. Travels a lot. Data stuff.
  • Lives in Kalamazoo. Downtown. Historic home.
  • Married May 2020 to Michael.

Even if six months had gone by, he would roll up at Karen’s birthday party and chat with me about historic home repair or where my travels have taken me while we down cake and ice cream.

He made me feel like he cared about me. He knew how to woo.

It might not be a tuck jump off the high dive into the deep end of life’s mysteries but it was way more meaningful and relevant than the weather.

I’m adopting Friendship Folders.

Especially for my business contacts. I can be so focused on the work that I forget to make human connections. My emails can be like “Contract attached.” LOL.

I know people are dropping little details about their lives because I respond to them in the moment but I forget them the moment we x out of Zoom. I believe I can build better relationships if I create a Friendship Folder as soon as I get off the call.

How do you Woo?

For some people, this comes so naturally they probably haven’t even really thought about how they woo. They just do.

Do you have some strategies that help you make woo glue? Write to me and tell me about them.

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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.

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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.

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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.

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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.

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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.

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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%.

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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.)

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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?

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