• Am I trying to have the best of both worlds?

1. What I’m trying to do

Two worlds

World 1: flexibility & experience

1a. Flexible, part-time, remote role

  • So that I can focus on family stuff, and thinking stuff
  • Figure out family stuff
  • “Learn to think”
  • Elucidate values and what I want to do

1b. Some career capital/upskilling

  • I don’t know what career I want, long-term
  • But, I know what I enjoy and am good at, so getting more experience in those realms
  • I also think that I don’t want to become a specialist (e.g., in automations/systems) - I’d rather be a COO/CoS type, than a “systems specialist”
    • I’d like to be e.g. a “Founders Associate”

1c. Money

  • Some money coming in

World 2: “as much money as I can get”

  • Makes sense to optimise for earning as much as I can
  • I’ve been depleting my savings for a while, so to top them up at the fastest rate
  • Also, more money = more training, tutoring, things like therapy, etc

Founders Assistant > Automation Guy

  • Imagine I work at Outcapped for a year (hypothetical, imagining my CV)
  • I would rather be Rob’s “special projects” guy, “founder’s assistant”, than “the automation guy”
    • Like Brent’s reference: “I feel like I’ve found a right-hand guy”, vs “Alex is really good at automations” - boooo, boring! Too specialised! Not meta-level enough!
  • Maybe I need to pitch this to Rob more clearly. What “special projects/founder’s assistant” could look like.
    • 🚨 this feels like the most important thing to communicate
    • Lock in a pay that allows me to be a founder’s assistant, rather than an automation guy?
  • I don’t want “automation guy” to be my career path.
    • I don’t have a clear plan/career path, but I have a strong sense that “COO/CoS-type” is much more likely to be right than “automations/systems guy”
    • I have the meta brain for systems and automations, for sure. I just don’t want it to be all I do. I want to have the meta, broad skill set of a COO/CoS. I don’t want to be a “systems specialist”. I’d much rather be a Rob than a Mikee Mercado of Anti Entropy. I don’t want to set up CRMs to a living!

2. High pay as useful forcing function, or blocker to my ideal kind of work?

Potentially can’t “have cake and eat it too” at a cash-strapped startup

  • Rob has said that higher pay would mean certain things would make less sense for me to do
  • So, would I rather charge less to do a broader range of stuff?
    • I don’t want a higher rate to force me to only do automations stuff, rather than “founder’s associate”-type stuff
    • Pay at upper limit of affordability = from “pitch in wherever is useful” to “no longer can do “schlep-y” things, can only do things that are high leverage immediately”
      • But, at an early stage company, there may be more “schlep” needed, than high leverage things lying around
    • Maybe I’d rather do broad ops generalist stuff too (and things like client acquisition)
      • Upskill → learn how to onboard clients, learn how to do all the schlep-y stuff like incorporating them, setting up payroll etc. Useful broad experience, even if I just do it once. Vs “you cost too much for it to make sense, we’ll just have you doing backend automations”
  • Or, is higher pay a useful forcing function?
    • As Rob said, maybe this is good - maybe this is a forcing function for finding the high leverage stuff.
    • However, as above, as there’s limited cash flow currently, maybe it’s also tricky re: not being able to afford paying me to do “schlep”-y things
    • And there may not be loads of high leverage things lying around
  • It would make sense, if my plan was something like “I’m happy to charge less for 1/2/3 months, in order to get onboarded, do some schlep-y things, help the business grow, and then charge a more competitive rate (or, be an employee) once there’s more cashflow”
  • If I feel that it’s true that I could work there for a year, then I think I’d feel better about this “start with low pay” thing. I guess because I don’t have know it feels to work there yet, it’s harder to know
    • So maybe there’s a “low pay for 2 weeks or a month, to get a feel” thing?

3. How true are these stories?

Story 1: “I’d rather be more useful and paid less”

  • “Pay doesn’t make that much of a difference to me”
    • Not true. More capital, more savings, more ability for trainings, expanding opportunity space due to higher net worth. More future-proof
    • I have a naive part that’s like “whatever man, money is fake, the amount of money in my savings has never correlated to my happiness, it’s not a big deal as long as I’m not ‘in the red’!” - vs another part which is like “it’s better to have more savings, it gives more flexibility, autonomy, possibility-space. Don’t be naive”
  • “I’d rather be able to do whatever is useful, without worries about the economic feasibility of what I’m doing per hour""

Story 2: “I’d rather be paid more”

  • It’ll mean that I have more circumscribed AORs and I won’t get to see as much of the company
  • It may actually make the career capital worse, as I’ll be more specialised/niche
  • But, maybe neither the “COO/CoS” or the “automations guy” path are correct, as I’m stumbled across both with ~poor epistemics and awareness of my own values. So perhaps, better to earn more in the short term, if I’m likely to pivot away from this path entirely anyway