This is the story of how I misled myself for 40 years based on what a guru said & what I’m doing about it now.
My grandfather had the knack of having money pass through his fingers. Every time it did the crumbs would fall into his lap. He was a successful local car dealer, a business he started when he & his brother realized they could get a discount on their Packards if they signed up as dealers & ordered 3 cars. That car sold so quickly they ordered more. Thirty years later when I came on the scene he had a thriving business.
It wasn’t just cars, it was everything. Want to use a piece of art as trade-in for car? Sure. Grampy would figure out how to sell it for a profit. Trouble making house payments? Grampy would help & somehow end up with the house. Have a truck coming back from Los Angeles? Grampy would find some oranges to pack in it & sell when they got north. Everything was a potential deal.
Everything. I idolized my grandfather. I spent endless hours in the corner of his office, playing with toy cars & listening to him make deals. To this day I have a negotiation mode that kicks in at certain times & I know I’m channeling what I learned there. But I also saw the price.
Everything & everyone was fair game, including family. He would happily lie & cheat if it improved the deal for him. A part of me recoiled from what I saw. (If you think this was confusing for a kid, you’re right.)
R. Buckminster Fuller
Once I got to college I was looking for direction. I found the writing of R. Buckminster Fuller. I had been aware of him as the inventor of the geodesic dome, but in 1981 he published Critical Path, an only-relatively-readable summary of his work. In it he describes his approach to business:
I assumed that nature would “evaluate” my work as I went along. If I was doing what nature wanted done, and if I was doing it in promising ways, permitted by nature’s principles, I would find my work being economically sustained
More succinctly:
…nature did not require hydrogen to “earn a living” before allowing hydrogen to behave in the unique manner it does.
Eureka! Here was the way out of my dilemma. I wanted to do big things but I didn’t want to become like my grandfather. All I had to do was to maximize the benefit I created for the most possible people & the universe would provide.
It Kinda Worked…
I didn’t do badly. I was able to build a reasonably lucrative consulting business through the spread of object-oriented programming. I built my dream house on 20 acres of southern Oregon. TDD, then JUnit, then Extreme Programming were hits.
I never made comfort money, never became “post economic”. I had several chances but in each case I stood on my fullerene principles—nature would provide. If nature wasn’t providing I would just create more value.
…Until It Didn’t
Two events coincided to break the connection between value creation & value reception. The week after 9/11/2001 the year-long backlog of lucrative work I had scheduled simply evaporated. At the same time I began to grapple with the darker side of my grandfather’s legacy. I had a breakdown.
The years after that were hard. Residual publishing income & the last of my inherited money got us through. Then I put myself back together enough to get into fairly-early Facebook (not before-the-Microsoft-deal Facebook, though). That got all the kids through college.
My divorce took the rest of my assets & left me owing a substantial monthly alimony payment for life. Once I left Facebook, though, I resolved to double down on Fuller’s principles as I understood them. I would do the most good I could for the most people. Nature would provide.
No, nature would not. By the time I got to Gusto I was broke. I’ve described this as being in a kayak just upstream of a waterfall paddling as fast as I possibly could just so I didn’t go over.
And Now…
I’m comfortable again. I have enough & enough more that I can decide how to enjoy life. My work at Mechanical Orchard has been fantastic so far. I raised my speaking rates. I don’t have enough that I can stop paddling. I’m not sure I ever will. But I’m doing okay for now. I’m okay.
And along came SubStack. Honestly all I expected was a few hundred bucks a month to guilt myself into finishing writing Tidy First?. Well, that worked (real books appear at the end of October!) But also the revenue grew enough that I could tell there is a real business opportunity here.
Before I can capitalize, though, I have to wrestle some false beliefs. The first is my naive interpretation of Fuller that “nature will provide”. No, I’m going to have to create a channel for value to flow back to me.
The second is my childhood-formed belief that business is like my grandfather’s business, taking absolutely everything I can for myself & to hell with everyone else. I’m afraid of a business because I don’t want to be that person. I don’t have to be. I can run a business that’s good for customers & good for me.
Whew! That was hard to say. Only took me 50 years to say it.
Next?
I can see 3 trajectories for my SubStack-based revenue:
Status quo. I can buy a car a year. It’s a nice bump to my income but I have to keep doing everything else I’m doing. Nice thing about this scenario is that I know I can do it, I know I like doing it, & I know I can live with myself.
Growth. A 4X growth in revenue seems achievable. I need to run it as a business. I need to execute on all that paid-newsletter stuff, but in a way that’s good for readers. I’d still need other income. This scares me because I’m afraid of sliding into my grandfather’s slimy, “Oh that’s for paying customers only.”
Hit. The most profitable SubStacks are bringing in 20X what I am. At that point I wouldn’t need other sources of income for both daily use & saving for retirement. That would be amazing but I can’t see how to get there from here.
So that’s where I am. I’m still afraid of business because of what it represents for me. I’m finally over my version of Fuller’s “nature will provide”. That was just me running from myself.
I’m ready to care for my whole community to the best of my ability (free subscribers). I feel grateful to my paying subscribers for their support & that gratitude naturally expresses itself (paying subscribers are getting an early look at a project of mine called Thinkies). My founding members have a special place in my heart. And all of it adds up to more freedom for me to express myself on behalf of my fellow geeks.
Not gonna lie, this feels weird. I’m confronting 40, sometimes 50-year-old fears. I have help—business coach, marketing coach, help from SubStack. I can envision a better future—more value for you all, more freedom for me. One paying subscriber at a time.
Sounds like we’ve been walking the same road, brother. Your books have gotten me over more than a few seemingly insurmountable hills. Thank you. Keep walking. You’ve never met me, but I’m walking right beside you trying to balance business with making the world a better place than I found it.
I’m a bit younger (30, not to rub it in) and currently questioning employment, and in general, how I earn a living as a software developer. I love developing software, but I’m terrible at a lot of social dances employment require. I’m neurodiverse, so the hydrogen analogy was both beautiful and sad. I don’t currently have answers, although even finding out I’m neurodiverse has been helpful in understanding that everyone else’s’ “nature” might not be my own, and there’s power in that.
I don’t really have anything to say, just ramblings, but I always appreciate a voice of vulnerability from someone who (at least externally!) looks to have their shit together, as it feels like it validates my own vulnerability. It sounds kinda selfish put like that, ha, but really, thanks so much for sharing.