A Framework for Selecting My Next Job

About a week ago, a firm in my previous industry contacted me about a possible job opportunity. I ceased looking for jobs within that industry months ago (see my last post about quitting), so I was surprised and admittedly a bit curious about the opportunity. I began discussions with the firm, and have not yet received an offer, so I thought it would be helpful to blog about my framework for evaluating this opportunity (as well as future ones) before I receive any offers. This way I can’t let my future self rewrite history concerning what I actually want.

My ultimate professional goal (a key assumption underpinning my job framework): Run a company where I own a significant stake. I am generally industry agnostic – the company could be in my prior industry or something totally different.

My Framework:

  • Agency and Equity
    • I require decision making authority. I don’t need to be the CEO, but want to be in charge of my unit/section (or in charge of my own risk if investing). Making decisions (a.k.a. bets) and living with the consequences is what appeals to me most about the business world.
    • I need to either own meaningful equity in the venture, or have an explicit profit-sharing agreement in place (particularly if it relates to investment management). If I perform well then I should reap the fruits of my labor. If I fail then I should be fired and/or lose the money I risked initially (if it is a startup venture). There is no free lunch, but I don’t want to be cut out of the pie if things go well.
    • I need to work in an environment totally focused on performance, not on corporate BS such as: facetime, politicking, showing up to meetings, fighting to be heard in meetings, caring about how you look, etc. I prefer to workout mid-afternoon…
      • Side note: medium-length memos >>>>>> needless meetings! See: Amazon.
  • Growth
    • The potential role needs to improve my long-term skills and abilities
      • As in skills that only matter for this role, but will not apply to more senior roles/CEO do not count in this calculation.
    • The potential role must move me closer to my ultimate CEO goal
      • Closer totally depends on the industry. If considering an internet-driven startup with essentially 0 up-front costs, the only thing moving me closer to that goal is just doing it – there are no constraints.
      • Whereas closer concerning more of an investment-fund type business (that requires raising initial capital) may mean I need to first build a track-record of investing success. The constraint is that I might have to obtain this experience working for someone else’s fund first. Or maybe this is a myth that I tell myself…not entirely sure.
  • Geographic flexibility
    • Ideally I would want to work in a remote-optional environment where I can bounce around geographically at will.
      • I’m not sure how important this piece is to me, and I think it will be timing dependent. I have 0 interest in working in an office over the next 3 months, but I’m not sure if I will be willing to sacrifice geographic flexibility in the 3-6+ month time horizon (assuming more people begin to return to office life). If I go full nomad for the next 1+ years then maybe a return to a more permanent situation will actually be attractive at some point.
    • If I end up with an opportunity at a company that requires in-person work, should I require an allowance for some remote work during the year? For example, have the contract stipulate 2 months of remote work allowance every year?
    • I have a lot more questions than answers in this section…more thinking to be done.
  • People/company
    • Do my potential co-workers seem ethical, ambitious, kind?
    • Will I learn a lot from them?
    • Do I want to be associated with them?
    • Do I want to be associated with the company?

My job framework is a massive work in progress, but this is my first cut. I’m looking forward to both seeing how this framework evolves over time, and more importantly if I end up pursuing opportunities that are consistent with what is written here.

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