Raking it in without
breaking your soul

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.

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.

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.