I’ve run iteration or another of the same business since 2009.
The business model shifted, the team changed, and the focus evolved—but one iteration flowed right into the next. But by the end of 2021, I needed to break the cycle. I realized I had built something I could no longer sustain, and I had an opportunity to make a drastic change.
In December 2021, I passed the baton on The What Works Network, transitioned my full-time employee into a new role at a different company, and found myself in a business of one for the first time in over ten years.
I decided to call the first quarter or so of 2022 a sabbatical. I am, after all, a wannabe academic. A sabbatical for an academic isn’t generally time off. It’s time to step outside the relentless cycle of institutional responsibilities and focus on a project.
I’d been subject to my own self-made relentless cycle of responsibilities for over a decade. Almost all of which I enjoyed on one level or another. But at the same time, plenty of those responsibilities messed with my mental health. I’d endured for as long as I could. And I needed to do something drastic to recover.
Fortunately, I was able to complete a book proposal and pen a deal with a publisher in the fall. I had a project to focus on, and I had an advance to cover my salary for the first few months of the year. And, of course, my husband and I had steady, predictable revenue at YellowHouse.Media, for which my current labor is minimal. All the pieces fell into place—and I let out a deep sigh of relief.
Unless you follow me very closely, and I’m going to assume that you don’t, many of these adjustments have probably gone under the radar. I’ve still been producing podcast episodes, sending newsletters, and posting to social media. It might seem like nothing has changed. But the shift for me has been profound, so I want to highlight that. And I know there will be plenty of questions about the book writing process, my time quote-unquote off, and what I’m doing next.
So that’s how I’ll structure this article:
- First is the book.
- Second, what I’ve been doing other than the book.
- And third, what I think I’ll do next.
Chapter 1: Writing What Works
The main project for my sabbatical has been writing my book: What Works: A Comprehensive Framework For Changing The Way We Approach Goal Setting. And yes, it’s available for pre-order anywhere you buy books, as long as you don’t mind buying it without a lengthy description.
I’ve known I wanted to write a book—probably many books—since I was managing my old Borders Books and Music. When I needed to look productive but also needed a break from the stress of retail life, I’d grab a cart full of books bound for the philosophy or sociology section and start to shelve them.
Shelving books is a meditative task. Pick up the book, look beneath the barcode for the section, locate the section on the shelf, and then find the appropriate spot—alphabetical by author’s last name. It was a straightforward mental task with a grounding, tactile component. My fingertips would take in the texture of each book cover as I picked up a title. Often, I’d sit on the ground, legs crossed, and thumb through the books on the shelf to find the right place. I imagined my own book on the shelf as I worked.
That was over fifteen years ago now. The path to publishing was not at all apparent then.
Five years later, though, I’d know exactly what was involved in getting a book deal. By 2012, I’d courted a relatively large audience and a good deal of respect as a writer on the indie maker scene. A book deal felt tantalizingly close. I met an agent who wanted to represent me—before I even had an idea for a book. And drafted my first proposal. It wasn’t great. Or rather, the idea was good, but the book’s premise was underbaked at best. And worse, I didn’t actually have the chops to write what I imagined writing at that time. Unsurprisingly, that book didn’t get picked up. So back to the drawing board.
Over the next 7 years, I danced around writing a book but never focused on the idea for an extended period. I talked to a couple of other agents and thought about what I might write. But nothing felt like it gelled. Part of the problem, I knew, was that everyone expected me to write a marketing book, a how-to profit from your passion book, or a money mindset book. That wasn’t the book I wanted to write, though. Unfortunately, I didn’t have a solid idea for the book I did want to write.
At the beginning of 2019, I received an unsolicited email from Jessica Faust, the founder of Bookends Literary Agency. At that point, I’d put the idea of writing a book out of my head for a while. I thought maybe my opportunity had passed. But I took a call with Jessica anyhow. She told me she’d been looking for women authors who weren’t writing specifically for the women’s market. She wanted to represent female nonfiction authors who wrote nonfiction books for general audiences. Specifically, she had in mind that she was looking for a woman to write something with Simon Sinek’s Start With Why appeal.
Alright, that’s exactly what I wanted to do. I told Jessica I was up for the challenge and excited to get started.
Unfortunately, I still didn’t really have a specific idea for a book. I started to draft some early attempts at a proposal overview. They were not good. I got discouraged and started to ghost on Jessica’s emails—a common coping strategy I use.
In February 2020, Jessica emailed to check in, ever kind and patient. I told her that I knew what I wanted to write. I’d just taught a series of workshops on a different approach to goal-setting. In fact, a planning system that didn’t set goals on purpose. She loved this idea. I loved this idea. This was the idea!
Did I mention it was February 2020? It was actually the last week of February 2020. I started working on the proposal, but then the world changed—and I was in crisis mode like everyone else on the planet. The book simply wasn’t going to be a priority in the short term.
As it often does, the short-term turned into the long-term. I couldn’t make the mental space to work on the idea as a book. But I was still excited about the concept, so I took the free workshop I’d taught at the end of 2019 and expanded it into a 4-session workshop series called The Commitment Blueprint. I figured that I could learn more about what the book would be while also helping people plan amidst the current uncertainty. It turned out that was an excellent move. I taught the workshop series several times throughout 2020, and the final time I taught it lived, I wrote out the content of each workshop in the series.
By January 2021, I had a 20,000-word ebook. This was going to be the seed of my book. In January, I put reconnecting with Jessica on my to-do list. I was fully prepared for her to let me know she’d moved on… but before I could even get an email off to her, I had one in my inbox from her! Two years after her first email, I sent off the ebook version of The Commitment Blueprint, and she agreed that this is what we would move forward with.
I worked up the first half of the proposal: the overview that describes what the book is and who it’s for, the about the author section where I have to sell myself, the marketing section where I explain how I’m going to sell the book, and the table of contents. It didn’t take long to get that part of the proposal ready to go. But then I was faced with writing my sample chapters. I got a bit stuck again. My depression and anxiety raged despite medical intervention. It was all I could do to perform the most basic functions of running my business, let alone pen the first 10,000 words of a book.
But by June, I’d gotten them done. Or at least I’d gotten a really shitty first draft done. Jessica checked in, and I told her that I wouldn’t have the mental space I needed to revise them until August, when I was planning to take a significant step back from my responsibilities and work half-time while in Montana. I let the first week of August pass without cracking open my draft. I was afraid to look. I was confident that I would be embarrassed by what I’d written.
During the second week, I got over myself and dove in. I read through what I’d written in the spring. And sure, I cleaned some stuff up—but overall, I was very proud of what was on the page. It felt deeply personal while also connected to fears and anxieties I’d heard echoed by so many business owners over the years. I sent the chapters off to Jessica the next day.
I prepared myself for a blistering critique. Within a few weeks, Jessica had read the chapters thoroughly… and loved them. My only task was to proofread and clean up the formatting of the proposal. From there, it was up to her.
I was prepared for a long wait—but the book sold relatively quickly. I set a timeframe for submitting the manuscript that would allow me to finish up the year and focus on writing in 2022. And thanks to Wiley’s speedy process, the book should be available in time for 2023 goal-setting and planning!
I spent the holidays and early January deep in research. The original workshop had drawn on quite a bit of cultural and psychological theory, but I didn’t know exactly where it came from. So I waded into academic journals and key texts. I familiarized myself with ideas via podcasts and books. And then I got to writing. I completed the first 50,000-word draft by the end of January.
I completed a second draft from early February to mid-March, adding another 10,000 words.
By April, my editor and I had gone through the manuscript again, and we felt good about wrapping up this phase. I took one more pass through the book before submitting it yesterday.
If all you look at is those three-and-a-half months of book writing, it probably seems like I was working fast. And part of me always worries that fast equals sloppy—because that’s precisely what it meant for much of my life. But I remind myself—and I remind you—that I’ve been working on this book since the end of 2019. I’ve drafted it in slide decks, blog posts, and podcast episodes over the last 3 years. I’ve been doing research on it since college. While there was a burst of energy and speed at the end, book writing has been anything but fast.
Now, when I say that I’ve been drafting this book in various forms for years, I don’t mean that it’s all old material. The book’s core is The Commitment Blueprint process, which I’ve shared in various forms. But only maybe 4% of it resembles anything I’ve put out previously. In book form, I explored all sorts of ideas and stories that could never have made it into an ebook or workshop series.
Today, I’m really proud of my manuscript—and I’m also nervous as hell that it’s a piece of crap! So, you know, normal author feelings.
Chapter 2: What I’ve been doing when I’m not writing the book
Despite the sabbatical, I’ve still been working about forty hours per week, Monday-Friday, 9-5. I’ve even been working most weekends. Some weeks, book writing took up about half of that time—rarely more, often much less.
I spent some of that time—typically less than five hours per week on YellowHouse.Media.
And the rest of the time has been primarily devoted to some aspect of figuring out how I want to move forward. For the most part, that’s meant a lot of time thinking about and working on my craft.
When I say “craft,” I mean the care and skill that one brings to work, especially creative work. The choices I make, the philosophy behind the approach, the experiments I conduct. Craft has always been important to me—but it wasn’t always something I felt I could prioritize.
Most of what I’ve written or podcasted before 2022 was content marketing. Content marketing, no doubt, has an element of craft. But its top priority is to attract potential buyers and lead them through the buyers’ journey. I’ve broken many of the rules of content marketing over the years. But I never lost sight of the top priority. I’ve had varying levels of success with maintaining a unique voice and valuable product as content marketing—sometimes veering too far into marketing, other times veering too far into a unique voice. Last year, I felt like I hit my stride where I created content that balanced craft and strategy.
This year, as part of my sabbatical, I wanted to see what would happen if I dropped strategy all together. What would I want to make? How would I conceive of my creative work? What formats would it take? How could I stretch myself and my skill? Where would my curiosity lead me, and would you care?
So starting off with the first content I created in 2022, I dropped any notion of marketing strategy or promotion. The only call to action was to share the show or the newsletter with a friend.
Now, I want to be clear before I go further: I am not recommending this as a marketing strategy. Say it with me now: This is not a marketing strategy. This isn’t some new marketing idea that all the movers and shakers are using. It’s just me, doing my own thing because I can.
Got it? Okay, good.
When I say I’m doing this because I can, what I mean is that I’ve intentionally accepted an utter collapse of revenue. I’ve deliberately chosen to step back to get my health back on track. The choice was a little easier because I had the book advance and some royalties from my old CreativeLive classes.
Alright, now that’s out of the way… Last fall, I started to work on craft when I took a creative nonfiction writing class through NYU’s professional studies program. That was a game-changer. It allowed me to not only step away from writing-as-marketing but also step away from writing about business at all. At the same time, everything I was learning started to flow into my writing about business.
In December, I took a workshop through Catapult on how to pitch publications as a freelance contributor. That 3-hour workshop completely changed my idea of what I might be able to work toward this year. I could not only write books, but I could also write essays and features for magazines, news sites, and other online publishers—and get paid for it. And while making hundreds of thousands of dollars selling online courses is one kind of sexy. Spending my days writing, researching, and getting published in major publications is another kind of sexy—even if it doesn’t pay well and involves doing a lot of work that gets rejected.
And what about podcasting? I’ve been working on my craft as a podcaster, too. That means exploring more challenging topics, attempting different storytelling techniques, and generally making some risky choices when it comes to how I produce each episode. Again, I’m doing it because I can—not necessarily because I believe it’s the most strategic thing you can do for your business. I assure you—it’s not.
I also decided to focus my efforts this year—and combined essay writing with podcasting. In 2021, I created a 45-60 minute podcast episode each week, plus a 2-4000 word newsletter essay. This year I thought I should probably try to do just one and make it as good as possible. This choice has been a game-changer. I still don’t always have the time and space to get an episode or essay where I’d ultimately like it to be—but I’m able to spend twice as much time on it as I was.
What I haven’t been doing during this time is spending much time on Zoom. I pitch in on some of our YellowHouse.Media consultations. But really not much else. In 2021, I averaged 10-12 hours per week in meetings. This year, it’s closer to 2. That’s been a significant quality of life improvement.
So that’s what I’ve been doing while I’m not working on the book. What’s next?
Chapter 3: Venture into the unknown
As I mentioned, I’ve run one iteration or another of the same business for 13 years. But the only part of that business that I carried with me into 2022 was the podcast and newsletter audience. I have lots of options. I could build a profitable, small business coaching practice. I could create digital products or online courses. I could sell sponsorship on the podcast. I could double-down on YellowHouse.Media.
What’s on my mind as I contemplate the next steps feels… almost forbidden. Do you want to know what it is?
I’m questioning whether there’s a business that I really want to continue with. I wonder if “business owner” is really the right way for me to identify—at least for the foreseeable future.
For the first time ever, I’m getting comfortable with being a full-time creator, an independent journalist, a multi-disciplinary public intellectual. Okay, “public intellectual” is probably one of those titles you need to wait for others to confer on you—like thought leader—rather than to take it on for yourself! But still, that’s the dream.
And if that’s the dream, why not do it now?
As I wrote the “about the author” blurb for the book, I instinctively jotted down that I’ve been studying small business owners for over 13 years. Light bulb moment. Yes, I’ve been running a business, hopefully helping you think differently about how you run your business. But another way to look at it is that I’ve self-funded a decade-long immersive research project in the sociology of entrepreneurship through small business. When I consider my next steps, starting from that realization is exciting.
Financially, there are a few ways forward from there. And the solution for me will probably be a bit of each.
The first way forward is freelance writing. There are a lot of upsides to this, including getting to write about topics that wouldn’t fit here on the podcast or in the newsletter and getting distribution through prominent publications. My first success was at Fast Company back in March. Of course, there are a lot of downsides to freelance writing, too: unpredictable pay and lots of rejection among them.
The second way forward is audience-supported journalism. That could look like a tip jar, paid newsletter, or Patreon-like model. Despite the relatively large size of my audience, the truth is that I don’t have a large enough audience to make the math work on this one by itself—at least, I don’t think I do. I started running an experiment with a tip jar in March, and, so far, it’s generated about $235 from 15 contributors. I appreciate each and every one of those tips! Truly! And also, I can’t pay my mortgage that way.
The third way forward is to start work on the next book. You probably won’t be surprised to find out that I’ve started work on another proposal.
Regardless, I’m trying to follow my own advice and focus on satisfying my personal variables before I start worrying about money. I have the privilege of a second company with consistent, sustainable revenue. I can’t rest on my laurels—but I definitely have a bit more wiggle room to take my time to figure out what’s next.