“Either you’re really smart or a really great coach, because I’m surprised you even got this far, treating your business like a hobby.”
Well… I was going to delay or just skip this casual annual review, as my book manuscript is due soon (really soon). 2021 went quite well for me, personally and professionally. What was there to say?
I Got Called Out
But then, earlier this month, I booked an intro call with a business coach whose blog I’d enjoyed for several years. I thought maybe for 2022 I’d seek some one-on-one help in growing my business – although buying many random online courses has gotten me this far, it seems like maybe it’d take something different to get me from here to the next level.
That business coach, who I’ll leave unnamed, dropped the bombshell above (kindly!). I was kinda floored. After just 15 minutes of hearing me ramble and half-apologize about my actually-pretty-good business, he’ seen through everything and was totally right.
Entrepreneurship: Play vs. Work
Treating entrepreneurship playfully, like a game, is the dominant mood in my online neighborhoods (Michael Ashcroft of Fundamentals of Alexander Technique and Rob Hardy of Ungated, I’m looking at you!) This is a wonderful, necessary corrective to the excesses of hustle culture, independent types accidentally becoming their own (worst) boss, etc.
And yet, as always the Aristotelian in me notices the golden mean: an appropriate, beneficial, “happy medium” between the play and work modes. This golden mean/happy medium does not exist objectively. Rather, it is a function of the individual and circumstances at hand.
And so, a move more towards play is not right for me in particular. I have no trouble at all approaching my business in this way – I’ve been doing it for over 2 years, to great effect. But the reason I treat business playfully is because I am afraid of failing, and I’m afraid of anything being at stake.
I never had a good chance to take my career seriously, I’ve always just played. And so, just playing some more is harmful for me, whereas it’s beneficial for others. Playing leaves my virtues undeveloped, whereas it allows others to develop theirs further.
Former Wantrepreneur
Many of you don’t know this but, before I got into philosophical life coaching/client work, I had taken several previous stabs at entrepreneurship in the past: tutoring, virtual assistant work, a paid newsletter for moms (think: Emily Oster, but me). None of these got much traction, though, and I was stuck in “wantrepreneur” land. Buying courses, taking halfhearted and sporadic action, spending more money than I made, feeling embarrassed to talk about my work, while an “ugh field” developed around the whole thing. Gross!
Flash forward to May 2019. I’m mega pregnant with child 3, my dog and my father had both just died. In a “fuck it” moment, I put up a shingle as a (lol) “coach” via a basic Squarespace site from a laptop teetering on my belly in bed in a tiny apartment in Williamsburg, Brooklyn. I
