🎙 Did I set myself up to fail? Part Two
Why did I ever think I could succeed at this goal? Revision: Why did I give myself permission to try? Was that, in itself, a mistake?
“Shout-out to Nate: the fantasy of him being a long-term boyfriend then gave me the audacity to drive my totaled Corolla (‘Do not drive this,’ said the mechanic) two thousand miles in fits and starts (it broke down three times) across the Rocky Mountains.
Forgetting about the presence of the Rocky Mountains between Minnesota and California was a metaphor I would take in later. Yes, your dreams might come true, but there are going to be these massive obstacles that anyone could have told you about, historically documented peaks to climb that were clearly marked on a map. Moving to California might be described by most rational people as ‘a good time to get some feedback before making a more well-thought-out plan.’ Unfortunately, for me, as a twelve-step-higher-power-head with light mania, it was what I called a GOD SHOT!”
—Maria Bamford, Sure, I’ll Join Your Cult
Catch up on earlier posts in the series first: part one, part two, part three, and part four. Where we left off . . .
The question lingering now is not why (or how) I failed at my goal to earn a living via podcasting (🤣🤣🤣).
That only requires easy math: I failed to grow the audience sufficiently before my financial runway ran out. My flywheel sputtered to a stop instead of generating the momentum it needed to spin ever faster on its own. *I* failed to feed the flywheel with proper advertising and marketing (aka money) and possibly with sufficient skill and differentiation in the first place.
Why did I ever think I could succeed at this goal? Revision: Why did I give myself permission to try? Was that, in itself, a mistake?
When I interviewed , whose Substack handle is aptly @thedecisiongeek, for the Pivot podcast earlier this year, she explained that good decision-making is not about omniscience or clairvoyance—it’s about resilience.
Outcomes do not define a good or bad decision; when it comes to post-game analysis, it’s what happens leading up to the results that counts. Michelle explains further:1
“Every decision has three components: objectives (what is it you care about?), options (what are you choosing among), and information (about how those options might play out).
Most of my colleagues from the Society of Decision Professionals agree on some version of the 6 links of decision quality. What’s key to remember is that you must be able to assess your decision quality at the time you make the decision in order to avoid conflating the quality of the decision with the quality of the outcome.
Finish the following sentence: I can move forward at peace with this decision because . . .
Maybe you can move forward feeling at peace because you clarified your objectives; maybe you took the time to generate some creative options beyond the obvious, or you recognize that it’s too costly (in time, opportunity, or other resources) to collect more information beyond what you already have.”
I didn’t know if I could succeed, but I was one-hundred percent at peace with the decision to try. Creative risks are, by definition, baked with the very real possibility of external “failure” while still reaping great internal rewards. Imagining looking back on my life, I knew would regret not trying more than failing.2
I tried my best, and you know what? I HAD A BLAST!!! I was playing an infinite (joy) game at the same time I set finite-game goals.3 I loved every single conversation (okay, almost every single one). For three years, I spent the majority of my time doing what I loved most in the world. This alone was an enormous success. I paid for (invested in) the taste of creative freedom, even if I landed me in debt by the end.
What would have been the alternative? Bury the dream and do soul-crushing work so I could ensure my pristine savings went untouched, knowing deep down that those alternatives offered no guarantee of success either, merely the illusion of it?
No thanks, never been my style.
My neurosis issue now is not so much with having failed at going pro—the odds could have told me that, and I merely met those odds, the same way telling the dealer to “hit” on 20 all but guarantees a bust.4
It’s that, combined with a handful of other experiments yielding middling-to-failed financial results, I am no longer sure which voice to heed for future efforts: the realistic one or the hopeful one? The naysayer or the noob?
My business is actually profitable—it is just that the net profit converted into a salary I pay myself (gouged by taxes on the way to my checking account) doesn’t cover the higher level of complexity in my life from my pre-pandemic, pre-NYC mortgage, pre-married, pre-German shepherd Era.
One small example: two vet visits for Ryder and follow-up prescriptions, plus two ER visits between me and my husband these last six months, have put us out thousands of dollars, and we have pet and health insurance.
If 2018 me were talking to 2024 me, my Pivot advice-to-self would be to run smaller, safer pilots. But none of the pilots I have run in the last few years have quite taken off, either. Going big hasn’t worked, and neither has going small. Or at least it hasn’t worked yet. Or if it is working, it’s working at a deeper level than I can see and perceive—particularly my empty bank accounts and exorbitant credit card balances 😭
All I can say now is, I know nothing, Jon Snow. I’m sorry if you find that disappointing.
Perhaps the better questions to ask in assessing the quality of my podcasting decisions are:
Would I do it again?
Did I have fun while pursuing it?
Am I glad that I tried?
Can I live with the consequences of (real or perceived) failure?
✅ Yes,5 yes, yes, and yes.
Since the start of the attempt, I’m older (aren’t we all—lol), and my life is richer. I am wealthy in time and love. I am learning how to juggle increased adulting responsibilities. I am shedding outdated ideas and expectations, and I am slooooowly getting in touch with truer aspects of myself.
Still, my confidence has evaporated while I work through this prolonged liminal state. (Exploring facets of failure through this series has been quite cathartic, though, as have the comments many of you generous readers have left on the earlier posts—thank you!)
If you want to shake me and tell me to just get my act together, join the club. I get it. It must look so much easier to do from the outside, so obvious what to do next.
My intuition has been a guiding light for ten years, the primary way I steer. It’s just strange to steer through and beyond failure, knowing my intuition is what sent me there in the first place.6
❤️
P.S. I’d love to hear your thoughts in the Doh discussion post that wraps up this series . . .
💬 Is there such a thing as failure?
“It’s easy to be an armchair contrarian. It’s hard to take contrarian action: to question the dominant narrative, to be honest with yourself, to tell the truth even when the immediate outcome is pain—like losing the chance to sell my company, and instead getting buried under an avalanche of debt. I try to have skin in the game. This time I had too much.”
You can listen to that episode on “Decision Engineering and Evaluating Quality instead of Outcomes with ” here:
And here’s a related conversation with one of my earliest career coaches and favorite recurring podcast guests, . Check out our full 12-episode playlist here »
If you’re curious about the six links in the decision chain:
In Pivot, I propose that for those of us who are High Net Growth, we don’t have FOMO, we have FONT: Fear of Not Trying.
From James Carse’s fantastic book, Finite and Infinite Games. From the description:
“A finite game is played for the purpose of winning, an infinite game for the purpose of continuing the play.
Finite games are the familiar contests of everyday life; they are played in order to be won, which is when they end. But infinite games are more mysterious. Their object is not winning, but ensuring the continuation of play. The rules may change, the boundaries may change, even the participants may change—as long as the game is never allowed to come to an end.”
🃏 For those who are curious (or will be playing blackjack over the holidays), chances of busting at different card counts, from BETUS:
Hit on 21 = 100% chance of busting
Hit on 20 = 92%
Hit on 19 = 85%
Hit on 18 = 77%
Hit on 17 = 69%
Hit on 16 = 62%
Hit on 15 = 58%
Hit on 14 = 56%
Hit on 13 = 39%
Hit on 12 = 31%
Hit on 11 or less = 0% chance of busting
To be clear: I wouldn’t do it again right now, with my savings all but wiped out. But I would do it again three years ago when I still had abundant financial runway and hope 😆
If you enjoyed this post, you might also appreciate:
Thanks as always for this generous and vulnerable reflection, Jenny. I keep wondering whether your ONLY other alternative is "bury the dream and do soul-crushing work." Is there a sacred third option? While I don't know the answer, in my own life, it's worth asking. Whenever I start thinking in either/or binaries I know I've got a stubborn inner saboteur at play.
I'm in a prolonged liminal space too, and my savings buffer has run quite low as well. I'll need to figure out how to balance my creative impulses with the need for cash flow also. Not ALL jobs I've had have felt soul-crushing, though I know it's a story I've told for a while as well.
We're in an era of profound change, it feels to me. I have no reason to trust that things will be okay. And yet somehow, I do. Wishing you delightful opportunities in the year ahead. 💗
This resonated so deeply, Jenny. Thank you, as always, for your thoughtful and candid reflections - they have been a constant companion over a rollercoaster year.