I am a corpse collector of failed business ventures. I’ve tried and failed ideas across industries, interests, and even skill sets. It’s what has hardened my tolerance to rejection and made life wildly easier (and more interesting) to work through. I’m also the laziest “business owner” you’ll ever meet.
Modern culture is rife with inspiration-porn. I suppose the idea of a “reel”, after all, is to broadcast all evidence of success.
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I stand proudly with my sizable collection of failures.
And yes, I opt to use the word “failures” instead of its gentler synonyms like “fail-forwards”, “hiccups”, “pivots”, or the like, as recasting failure as something worthy of a makeover helps no one. The more effort we put into watering down the labeling and phrasing of “failure”, the less equipped we will be to leverage it when it inevitably occurs.
I derail my own ideas and plans for reasons I struggle to comprehend. Some refer to this as “self-sabotage”. I see it more accurately as, “I’m unafraid of failing and also love the risk of trying something that may end horribly.” By clinical standards, it’s easy to assume I have ADHD or some other brand of mental impairment. By my own standards, it’s just something I’ve come to accept about myself.
The degree to which I’ve managed to over-commit, under-commit, and completely mismanage my time and efforts will surely be of benefit to those who recoil at motivationalizing everything. It’s refreshing to hear someone recount their tragedies as mere tragedies versus “windows of opportunity for personal self-growth and development” or, worse yet, “healing journeys”.
I’d like to first start off by saying it’s acceptable to want a simple life. A simple life where you’re mildly miserable in a job you feel stuck in for reasons either financial or emotional is, contrary to millennial-belief, not an emotional death sentence. You can also have a thousand interests without “niching down” into any of them. You can kickstart projects in a passion-fueled frenzy only to find yourself a week later entirely uninterested by the thought of seeing any of them come to fruition. This usually is not pathological, even if it becomes a nuisance to other people. My husband would be happy to vouch for the 50 different side-gigs, contracts, business ideas, and sales pitches I’ve entertained over the years…
The “Side Hustle” Graveyard
Side Hustle #1: Portrait Commissions
I’ve taken many art commissions across the past 10 years and have made a decent amount of “side money” doing so. Financially, it ‘paid off’; psychologically, it folded me like a lawn chair. Although I had initially committed to university for fine arts, I panicked at the last moment and decided to go forward with clinical psychology instead. Regret occasionally tugs at me and manifests into these sporadic urges to take on commissions. Without fail, every time, I agonize over the product being too far from “perfect”. This tendency taints the entire artistic process to that of spite.
Side Hustle/Primary Business #2: Parent Coaching Business
I started a parent training business that survived for a few years based entirely on referrals. By modern business doctrine, this sounds like a success. And I’m still mildly impressed/proud of myself for the connections that I made which were powerful enough to foster new business. To again speak to the financial gain, what I earned was undeniably ‘good’ and better than any amount of money I could’ve made working for an employer. But, similar to the art gig--- I couldn’t handle the uncertainty and the natural ebb and flow that comes with generating your own income. When referrals eventually fizzled and leads became sparse, I found myself aching for something recurrent and predictable, like a W2 position.
Side Hustle #3: Writing A Book
Somewhat related to my parent coaching business, I wrote a book somewhat informally about protocols parents can implement to raise resilient children. I didn’t publicly try to market the book because I, admittedly, was terrified of how it would be received. I’d already gained some notoriety at this point (unintentionally) for being a straight-shooter whose words “have teeth”, and the fuss kicked up around my attitudes, I feared, would jeopardize my income. The book went essentially nowhere other than a few close colleagues. I’ve since taken to writing Substack pieces, which I far prefer.
Side Hustle #4: Debate-Based CEUs
I’m a Continuing Education Provider for behavior analysts and have spent hundreds of hours developing webinars and live lectures-turned-debates. Regardless of whether or not I’ve decided to charge for them, they’re a source of joy each and every time. They also have filled up pretty quickly and people seem genuinely intrigued by the format, which I have to say is quite unconventional compared to the more traditional trainings provided. Months and months have gone by without my offering a live CE, and I still get requests for their return.
Side Hustle #5: Private CrossFit Coaching
Long before I became a licensed behavior analyst and common sense connoisseur, I had dreams of opening my own health and fitness studio. I became USA Olympic Weightlifting certified, CrossFit certified, USA Powerlifting certified, Strength and Conditioning Assessment and Program Design certified by the time I was 23 years old. I had taken on several private clients by this age, as well as coaching nearly full-time at two CrossFit gyms. While at the time it felt like more money than I’d ever made before, I can’t fathom spending that much “person-contact” time at my ripe old age of 33. Most forms of coaching, at least those in person and on a 1:1 basis, are unsustainable and highly unscalable.
Side Hustle #6: Supervisor & Mentor for Behavior Analysts
In tandem with the webinars, I worked with supervision students in graduate school for behavior analysis, and mentored a small cohort of freshly-minted behavior analysts. This was something I genuinely loved doing and have considered getting back into. I’d meet with students throughout their practicum to troubleshoot clinical problems, role-play scenarios with administrators, management, families, and clients, and plan for what sort of role they’d hope to work in once licensed.
Side Hustle #7: Greeting Cards & E-Commerce
I made snarky greeting cards, stickers, and coloring books in short bursts. My kryptonite was again my unwillingness to get “salesy” and put my work out there more frequently. I still create these for fun.
Side Hustle #8: Health & Fitness Coaching, Again
I frankly can’t remember every form of health and fitness related coaching I’ve done, when exactly I started and stopped, and what the format was, but this was my attempt to move into a more remote type of service. It was far more sustainable than in-person work but was still very difficult to scale.
Side Hustle #9: School SEL, PE, & Health Consulting (Again…)
Lastly, I started a side-company called Mind Your Motion, which is an effort to build physical education and health programs in schools that are geared more towards resilience and critical thinking. While I don’t say this directly to potential clients (which tend to be large educational organizations), I’ll call a spade a spade: it serves to replace any and all SEL frameworks, which only make children (and adults) weak-minded.
As a quick aside--- business-minded people are probably looking at this manifesto of failures and saying to themselves, “it’s because you’re trying to do too many things; you have to pick one and go all in on it.” This may be true. But here’s my overall point. Going “all in” on one thing, and spending all of my time and energy trying to bolster up that one thing… that’s not freedom, at least not to me. And the amount of time, energy, and effort I’d have to put forth to match my current income would drastically cut my weekly free time into pitiful shards. It’s because of my stable, predictable income (which is a damn good income, may I add) that I have the freedom to pick up any side hustle I want--- and ditch it whenever I want.
The Myth of Freedom
I’m realizing I perhaps never wanted freedom from work. Maybe I just wanted freedom from the spinning wheel that is professional ambition, financial “goals” or “benchmarks”, and the stink of bureaucratic bullshit.
What if a cubicle (or an office, or a conference room) is actually freedom? What if you’re making great, sustainable money through the mindless gig our culture demonizes, and you’re able to drop it all come 3:00 PM? So what if it comes with fluorescent lighting and ultra-processed vending machine food and socially awkward colleagues? And, to be blunt, who cares if bored and unfulfilled? It’s a “job”, not a “fun”.
On paper, I’ve profited in every single one of the side-gigs I’ve started. It was never enough to sustain a full-time income, though, as I genuinely despise “the hustle” required to build a successful, thriving business which operates largely outside of the owner’s direct and chronic involvement. I’m not sure I was ever built to develop something like this. While I demand freedom and freewheeling autonomy in any gig I take on, one thing I’ve realized about myself is certain: stability trumps autonomy. And I’m willing to sacrifice some aspects of the reckless abandon I so crave if it means I can expect, every week, to be paid exactly what I worked for.
If you’re like this, jump on in. The water is warm. Do not be swayed by the incessant chatter of ditching your 9-5 so you can “go all in on your business”. It’s courageous to do so. It’s impressive to see people younger and younger starting their own “thing” with minimal education or mentorship as to how to execute. But don’t be fooled into thinking that this is the only path toward liberation, toward a rich life. Conversely, if entrepreneurship sounds inviting, who am I to tell you not to go for it?
People tell me constantly that I should “start my own business”. I’ve been told this nearly every time I show proof of my abilities, whether those be strength-related, art-related, clinical-related, or otherwise. It’s similar to those who tell me I should compete in an event to showcase my athletic skill (which I don’t believe I have much of anymore).
At the end of the day, I gain very little from edging out other people. Competition actually makes me crumble in ways I’m embarrassed to admit. I don’t like sitting around and waiting to see where I rank amongst other people; that’s what I have myself for. I so value my own personal accomplishments, stacked against myself, rather than others, that I will actively avoid most forms of “friendly” contest.
How I Over-Optimize Nothing
I can sleep without checking content statistics at 2AM. I don’t have to show my body to be successful or noticed. My social interactions aren’t plagued by thoughts of profit opportunities. I can adopt 53 hobbies on a Saturday and ditch them all come Thursday, should I so choose. My constellation of interests has zero effect on my income and my ability to provide a rich life for myself and my family.
I am not an entrepreneur. I’m an entrepre-never.
And I’m richer than most in all the ways that matter.
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