Defining Your Work and Your Life (RebootHQ)

Inspired by RebootHQ's 1st self-guided course.


Thoughts After the Assignments

I defined, after shutting Subtense, what I want in my next CTO co-founder.

To guarantee I meet this person, I study what I believe they should know.

This way, if I never meet another who fits, I can turn to myself to fill this role.

I also apply this practice for CEO-centric education and values.


One thought instantly dispels any depression around a business I founded failing.

It's new, and I never had it at the end of any of my other failed businesses/projects.

I explained it to Brad Schildt—invest in anything he creates—one of my co-founders like this.

If I met me from a year ago and started a business with him:

1) I believe that team would succeed in whatever it set out to do, and whatever it set out to do would be fascinating.

2) I would invest in that team.

This judgement centers on character and drive and capacity to grow because using my track record—How many fails, jiveass?!—would shut down the conversation right quick.


I became a person I want to work with and struggle with and succeed with.

I did so through entrepreneurship, and having a ludicrous, powerful team in Subtense.

"I'm in love with the man I've become." - Jerry Colanna


Writing Assignment

Q: When I rush from task to task, I a) experience an adrenaline rush b) feel superior to others who are “not working as hard” c) get affirmation from the rushing d) expect that people will respect me more.

A: When I rush from task to task I believe I build trust in the people I love and with whom I want to work, and I build trust in myself as efficiency replaces rush through experience.

Q: Who would you be more likely to turn to for advice: a hard-charging “successful” person or a person who you feel is “thoughtful”? Are there advantages to one or the other?

A: I look for advice from folks who are core happy, where their happiness comes self awareness. I don't give a shit if they're a gardener, an artist, a monk, or an investment banker.


Podcast Notes

  • The startup nexus: a place for meaning, paying bills, and security.

  • Meaning drives startup folks. (Most outsiders focus on the money.)

  • "I'm in love with the man I've become." - Jerry Colanna

Thought: Is my focus on meaning out of balance?


Reading Notes

Note to RebootHQ: Dead link for "Disappearing into the Fire" post.

Summary: The passage points out the concept of balance of constant reaching without getting consumed.

  • No concrete steps or practices, not that there should be yet.