What I'm Hiding from the IRS

Photo by Despina Galani on Unsplash

Come closer, I'll tell you a little secret. Do you have any friends like me— solopreneurs and consultants— mad enough to make their monies online? Want to frighten them? 

Wander into their bedroom and whisper "Tax Deadline Day" into their ears while they're sleeping. Watch them shake and shudder as they picture piles of paperwork floating above their heads like treacherous bogeymen. See them quiver as three-lettered acronyms flash through their minds—LLC, EIN, SSN—each triad swelling in size and scaring the daylight of your friend. You'd get a good giggle.

I know because I've been auditing my finances recently, and I realised I omitted some assets when filing my taxes this year. Scary stuff, yes, but the deed's been done. April is long gone. All I can do now is come clean. Honesty is the best policy, right?

Sigh, I hope this works.

You're supposed to report your income and loss in Schedule C of a 1040. Line 1 asks for Gross Income. That's pretty easy. I counted my coins, the monies minted from technical consulting and the dollars dolled out from selling Untethered (thanks to all of you!) 

But I got stuck on these three lines. 

Line six: “Other income”??

I stared at Line Six. What does "other income" entail? I added receipts from random freelance gigs earlier in the year. But that accounting felt incomplete. How could I file my taxes without listing my biggest asset from the year?

In April, Michelle and I taught our first cohort of How to Thrive on Sabbatical. During our first office hours, one of our students, an experienced manager broke down and cried happy tears. "Thank you guys, because no one ever told me, I could….question this stuff, and write a different path for my life." 

That moment— tender-to-the-touch and deeply personal— was colossal. I heard the chains fall down. I felt all the toiling—the endless spinning in circles, the anxiety sweats, the existential worrying, the tireless pursuit of an unwanted path— come to a stop. Listen, if we delude ourselves that Ethereum has value—so much that I own some—how can be say PROFOUND EMOTIONAL UNLOCKS are worth $0? 

What was I supposed to do? Measure the ounces of her tears? Weigh her sobbing against her salary? Accounting doesn’t account for this kinda stuff, but it’s the stuff that really matters.

TurboTax doesn't have tutorials for this stuff. So I left line six blank.

Line 13: Depreciation

Line 13 stumped me. Depreciation? Excuse you, I'd argue the value of our course and community has appreciated over time. Three months after our class, we hosted a catchup call, and Michelle and I sat there mouths agape listening to the incredible things our graduates were doing. 

Traveling around America to film a Bourdain-esque food series. Starting a research think tank. Dreaming up an IRL Wellness Center. Marrying people at City Hall. Getting ridiculously good at pottery. Taking chocolate-making classes. Making sneer-worthy sourdough bread. Trading, consulting, and returning to well-paying jobs.

Our students were high-agency, highly motivated professionals in tech, consulting and media, five to fifteen years into their careers who felt lost. Whether employed, unemployed, or reluctantly job-hunting, they all shared that moment of realization that yelled “Enough!” If you’ve been there, you know this feeling!

Through the cocktail of luck, that afforded us such a wonderful cohort of open-minded students, and vulnerability (we shared our honest highs and lows, our worries and our wins) about our own sabbatical journeys, we turned the ship around. Michelle and I shared lessons from hosting calls with 100s of people about sabbaticals. We taught them how to rest, not the phony fake rest, but how to really rest, how to wander, discover lost hobbies, and play — without guilt or shoulding one's self into an anxious mess. We showed them how to run and evaluate creative experiments, and how to ultimately land the plane.

Five months later, we've seen our grads meet up with each other in SF and NY. Grads have shared fun little updates in our WhatsApp group. So um, Tax Man, I didn't know how to file this one. Do I put a negative number in the depreciation box? Would that break your software?

Line 38: Materials and Supplies

I filled this box with pride: $0. 

Let me take you behind the scenes of an online course. We spent weeks designing the curriculum creating group exercises, breakout sessions, curating reading lists for students. We over prepared just in case we had eager beavers who wanted more.

But you never really know how much reading to assign students outside class. What's a good balance? Some of our students were working, busy interviewing, or taking care of kids. We assigned one or two readings per class thinking that would suffice. But every class, they asked for MORE homework and MORE readings. That stumped us.

So uh, IRS man, our students took all our supplies. Arrest me if you must, but I have nothing else to declare. 

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Jokes aside, the ROI on a sabbatical is life-changing. That’s why Michelle and I are running our course again this September. Over six sessions, we’ll equip you with practical frameworks for rest, money management, and running creative experiments.

We’ll share our personal highs and lows, and reveal how we found our first paying gigs post-tech. We’ll also explore the inevitable money and identity shifts. Our space is designed to be both vulnerable and empowering. We are not gurus, we won’t prescribe paths for you, but we’ll help you explore fulfilling possibilities.

🚀 Want a sneak peek?

Join our FREE, one hour Lightning Lesson next week — Sabbatical Math: Find Your Formula for Time Off. We’ll show you how to
1) Calculate your runway
2) Measure the Life ROI of a sabbatical
3) Handle the skeptics (family/friends who may not understand your decision)

Not sure if a sabbatical is right for you? If you see yourself here, then you might benefit:

1. You're employed but deeply unhappy

2. You're burnt out (again)

3. You want time to work on those passion projects the pandemic stole from you

4. You're unemployed, by choice or season

5. You dislike your job but it pays so damn much

6. You want….sorry, you NEED a break

7. After your latest quarter-or-mid-life crisis, you realised….you're a writer! 

8. You want to explore other models of work (consulting, fractional work, nomadism etc)

9. You're tired of applying for jobs you don't want

10. You realise life is short and unpredictable. You'd rather experiment now you're young and healthy vs "someday in retirement"

Here’s a testimonial from India, one of our graduates from a previous cohort.

Tobi and Michelle’s course really changed my life. After chugging along in the rat race of media for several years without a serious break between jobs, I felt I had lost touch with who I was and what I was meant to do. The course allowed me to think outside the bounds of the corporate world where were told the only way to have a career is to climb the ladder without breaks, pauses and reflection. Through the course I realized what I needed most was a sabbatical and to untether myself from the whims of an industry that doesn’t care about my personal well being.

Because of the course I have allowed myself to experiment, start up hobbies for pleasure (not to monetize), reactivate and recharge my creativity and remember to invest in myself. There is no one way to live life, and through my reflections in the short but mighty course, I found the beauty in thinking outside the default path. Tobi and Michelle did a great job of sharing articles and modalities that help shift my perspective and give me the confidence to take a leap of faith. For me that looks like taking a few weeks to not work and travel before quitting my job and taking a proper 6-12 month sabbatical next year. Highly suggest this course, Michelle and Tobi are really lovely and really care about everyone in their cohort. 

So check out our course and let me know if you have any questions, please!