Muddled brain seeks career advice in Tech (+ Entrepreneurship?)

Cross-posted from a rationality network discussion group

Hey all, thanks for clicking this. I’ve started thinking about jobs (life purpose generally, but most solutions seem to be jobs, and in any case I need money). However I’m somewhat at a loss how to market myself or even what exactly to look for, and could do with the perspectives and feedback from anyone else in tech (which I’ve been in for 6 years now), or entrepreneurship (which is not my current field but I want to get into for both utilitarian and selfish reasons).

I’ve reached what I feel is strong competency in full-stack web developing (mix of pure general programming competence and understanding the tech landscape); as well as solution architecture, and the start of a few complementary skills like management, marketing and (I think) business. I’m very interested idea-generation and problem solving but not quite confident enough in my current business ideas or interpersonal capabilities to see doing a startup of my own as certainly viable, given my current finances particularly. Nonetheless I did work on building a social network idea recently (, projects like which I’d like to continue doing as a way of honing (and evidencing) my skills.

Successfully looking for a role in a prestigious company would seem to solve a lot of my cravings, particularly earning me financial runway, although depending on where in those companies I end up, feels could vary a lot in terms of skill development. Even this route has problems: 1) am I at this level? 2) am I capable of evidencing that I’m at this level? 3) will I just get bored after 6 months as in my previous roles? My going answers to these have been “yes”, “perhaps no” and “probably not?” respectively. Bit of a chicken-and-egg around me not having the confidence to apply to jobs, and thus not applying. Definite interactions between rejection and motivation I need to correct here tho unsure exactly how to proceed with fixing.

Another solution would be finding a good startup to join, as senior dev or CTO (tho the idea of having terminal responsibility like that is a little scary, generally having always had superiors, and my knowledge while mostly solid has not yet grown to encompass scaling, specifically, which seems a big deal).

Worth noting I’m currently in the UK and could tolerate working in London again, but long-term I want to work in new cities generally (naming a few, Tel-Aviv, big European capitals or South America), and specifically in the long-run, one (or all) of SF, LA or NY.

A few things I’d be interested in feedback on (other than generally whatever comes to mind reading this as something you think it’d be useful for me to hear), would be:

  1. advice based on the impression of my CV/website (,, and whether it matches up with my goals and self-description here,
  2. 1:1 skype mentorship, as I’m sure I can’t give the full picture here, and might be missing optimizations novel to my situation,
  3. (long-shot) if you have leads for roles that seem like a fit, I’d much prefer something from this alumni network than any other method of discovery I’ve encountered
  4. knowledge about methods of job discovery that are good for what I’m looking for
  5. any links that come to mind of personal stories that describe career journeys like the one I want to be making.

A few goals I have pending related to my job search, which maybe you might want to criticize, are:

  1. Continue personal projects, try to hit upon something profitable or at least useful in an open-source way
  2. Maybe reformulate my website / resume; although I’ve overhauled the former quite recently the latter has probably gotten stuck in some local maxima
  3. Improve my fitness / social satisfaction so that executing all this is generally more easy, as I currently have some troubles with motivation and concentration which I suspected were an ADHD anxiety tag-team but won’t be able to get checked out for a while

Would be most grateful if anyone whose career has similarities with my own or with relevant experience could help me out with some insights on my situation and what good next steps for me are.

Thanks for reading!

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