How I torched my biggest career opportunity so far

I probably could have worked for a US Cabinet-level appointee, with an annual budget in the $10 billion order of magnitude, in a capacity where I would have had routine daily access to this person and influence on this person’s decisions, if I had made a better decision at a key time several years prior.

There’s been some discussion of what one’s chances are if one takes more career risks to maximize expected value, using Sam Bankman-Fried as an example. So I want to tackle this from a different angle, looking at my own failure to make good on the most impactful career opportunity I’ve had thus far, in politics rather than earning to give. I also want to discuss other ways I could easily have screwed it up, that would cause me to be unaware of how close I came, because I think if you’ve never had a highly visible near miss like mine, you may not even realize what kinds of opportunities would be available to you if you tried.

I don’t want to dox myself so I have to keep some details vague.

The time from when I started going all out maximizing my efforts, to when the highest-impact opportunity would have occurred, is about 13 years. I did not come from any kind of money, political connections, or other elite background prior to going to college. Where and when I went to college played a role here, but mostly by putting me in the right place at the right time.

I had the opportunity to work for someone who later went on to serve in a Cabinet-level position, where I would have had significant daily one on one time with this person, and I turned it down. This wasn’t a totally crazy decision in light of the information known to me at the time I made it, but I think a person with better judgment would have seen the job offer as having higher expected value than I recognized at the time.

Why did I turn it down? Because it was an entry level job, and I had enough political experience to find something higher up elsewhere. And ultimately, the job I got a few months later was better on many metrics. It was a more senior role, providing better preparation for my goal at the time to hop on a gubernatorial or senate campaign in an even more senior role in the following election cycle, with the goal of then going to work on that person’s staff if they were elected. I succeeded in every step of this plan, except that my candidate the following cycle lost, so the final step was unachievable.

What factors of the situation could I have given more weight to, that might have changed my decision?

1) The job I was offered would have given me a lot of time with the candidate, which lends itself well to upward mobility within the campaign and also provides opportunities to influence the candidate’s views on policy informally.

2) The candidate sought me out, rather than me applying for the job, suggesting they thought I had a lot of potential, either for promotion within the campaign or as someone to bring into government with them if elected. Additionally, I had extremely strong references this candidate was close to, who were not consulted before the decision to offer me the job, so I perhaps could have leveraged them in seeking a promotion later.

3) I ultimately went to work for an incumbent’s campaign, while the job I turned down was on an open seat race. Incumbents have fewer jobs in government to give out if they win, because they’ve already got their team in place. Fine if you are dead set on jumping on another campaign, but obviously something to consider since at some point you have to go into government to make this all worthwhile.

4) The candidate I turned down was one of my own elected officials, meaning I could potentially have run directly for their seat when they won, instead of working for someone else, and I would have made much better connections to set myself up for that by working on my elected official’s campaign.

5) The candidate I turned down was running a bigger campaign, seeking a more powerful office, than the one I ultimately worked for, so despite the lower starting point, there was some potential for internal advancement beyond the level the other candidate could even offer.

6) The candidate I turned down had some national political connections already, and was relatively young to be running for the office they were running for, suggesting they had more potential for upward movement.

So all things considered I think my choice was reasonable, but a more skilled individual would probably not have seen it as the expected value maximizing choice, and certainly in hindsight it was not the best choice.

What could I have done wrong along the way that would have prevented me from even getting the offer?

I could have been lazier. This candidate reached out to me as a result of seeing me working extremely hard volunteering for another candidate on a previous campaign. If I had been a more run of the mill volunteer, or not volunteered on campaigns at all, I would not have impressed this candidate and they would not have reached out. And this was on top of working full time and being in school full time, so it would have been quite easy to come up with excuses to slack off.
I could have been more culturally insular. This candidate was different from me in important ways that were not relevant to policy, but that I think would discourage many people with my particular demographics from developing a relationship with them in the first place.
I could have lived in the wrong place. This one’s pure luck in my case, though I guess you could try to engineer your luck if there’s someone you really want to meet. I lived where I lived because it was cheap, and if I had moved somewhere “nicer” I would have been volunteering in the wrong campaign office and would never have met the candidate.
I could’ve been meaner. I had previously opposed the candidate on a project he was a big proponent of. There are many ways to do this uncivilly and damage your relationships with people. Doing it the right way was important.
I could have handled rejection worse. The campaign I was volunteering for when I met the future bigshot had turned me down for a paid job, for not very good reasons. So it was tempting to take my ball and go home, but I didn’t.
I could have gotten a later start to my career. I made a TON of really stupid mistakes starting out, which in the short term significantly impaired my ability to advance rapidly. I was no longer making them by the time the pivotal events here occurred, but I probably would have been if I’d gotten a later start. This combines well with the work ethic noted above. An earlier start, and harder work once I got started, gave me more opportunities to learn and put me significantly ahead of others the same age, with the same natural levels of talent. Also, people were probably more forgiving about my early mistakes, because I was so young.

So there are at least five ways I could have failed in the 2-3 years prior, and one a few years before that, that would have caused me to blow the opportunity and not even know I had done so. It seems to me that the experience in any of these six cases would have felt like “I have never had any opportunities to have really high impact”, but that wouldn’t quite be true. The reality is, and the reality in any of these other cases would still be, that I had the opportunity and I failed to make the best of it due to my own misjudgment of key decisions. I got it wrong, but perhaps if there were 10 of me trying slightly different things, making slightly different assumptions about the best path, one would have gotten it right.