Survivors in the tech echo-chamber

Maybe it’s just me, but I’ve been hearing the phrase “hell yeah or no” more and more over the last couple of years. In the tech startup space, it seems to have become the new mantra. In Derek Sivers’ “Anything You Want” (which I believe is where the phrase originates), the author proposes this simple phrase as a razor. It’s a way to make choices about what opportunities to pursue or perhaps, to restate in the negative: a way to determine what not to do.

To me, this idea juuuust starts to resonate — but is quickly overtaken by overtones. On one end, I wholeheartedly believe that sometimes we find ourselves with “too much opportunity”, which I think is where Sivers found himself with CDBaby. In a tech startup, too many potential directions can be more devastating than no apparent directions at all. I battle this same feeling on a smaller scale when I find myself with a few hours of uninterrupted time to myself on a weekend.

Quick! Rest, my old friend! Read and exercise and cook and write and program and tinker and build and see nature and work on those side projects and—

Instead, I do dishes while trying not to think at all.

On the other end, Sivers’ creedo reads similar to “do what you love and you’ll never work a day in your life.” Is this… true? I understand that Sivers has been able to get by, but can the world actually operate in this way? Who is this even written to?

Sivers does not help his case by providing contradictory evidence. You can cross out the “You don’t need funding” chapter once you get to one of the last chapters where he talks about legal mistakes he made when taking initial funding. This is not an exercise in trashing Sivers, however. I appreciate reading honest experiences of honest people trying honestly to make sense of the world, and I think Sivers is genuine in his approach. The book contains a number of great ideas. Unfortunately, the book is a bit naive as to the realities of circumstance and — dare I say —to privilege.

This is a common issue with these types of books, in tech/startup circles specifically.

Dalio’s Principles: Life and Work is similarly structured. Lots of probably-great advice that is heavily tied to unspoken circumstance. Of course, Dalio’s book has other issues as well. You could probably sum up Prinicples as “it’s okay to be a douchebag as long as you’re a rule-driven-douchebag”. Okay, maybe I am trashing Dalio’s book.

Thiel’s “Zero to One”, pretty much anything by DHH, the Bill Gates documentary, various Jeff Bezos or Elon Musk interviews — maybe it’s just rich tech guys but at the end of each one I tend to exhale, roll my eyes, and think “cool, so… circumstances.”

I’m not mad that these people write books or give interviews or talks that influence the tech industry. I value their experiences and I cannot deny them their experiences. I have even taken some of the things out of these media and applied them successfully to my processes. However, I also have to fight hard to keep their “wisdom” in check against their survivorship.

The tech industry at large drinks deeply of the tech-successful without drinking deeply of… well really, any other experiences. With no evidence at my disposal, I would guess that most of Dalio’s readers have not read much about the story of C. J. Walker: America’s first female self-made millionaire. Not only is it appalling that self-made women apparently didn’t exist in America as recently as 103 years ago (?!), C. J. Walker would have… let’s say, a “slightly different” set of principles than Dalio. This is great. This is what tech needs. I want both sets of principles gingerly sprinkled into my internal Bayesian network.

I know I make it look easy to dig into people for ignorance of their own circumstances. That’s probably because it’s… well, pretty dang easy. The most chilling part? I type this, sitting comfortably at the stern of the circumstance boat, pointing fingers at the stem. Oof. Sometimes it just takes reading other people being daft to realize how daft I am.



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Benjamin Jordan

Benjamin Jordan


Tech, thought, teaching. CTO @BigRunStudios, Adjunct Professor @SaintLouisUniversity. Former CTO @Enklu, Studio Tech Director @NCSOFT, Sandwich Artist @Quiznos.