On “Climbing the Wrong Hill”

The turning of the calendar from one year to the next is a time of reflection. As part of my reflection process, I read a short blog post that I heard referenced in a podcast episode I listened to on one of my afternoon walks. The post is titled “Climbing the Wrong Hill,” and reading it a few times has beaten me over the head with a mental model I will be carrying into this year.

The blog’s starting point is a conversation the author had with a young employee of an investment bank. The young banker had decided he had no interest in being in finance long-term and that he wished to join a technology startup. When he told his bosses this, they responded by telling him about all of the additional responsibilities he would soon have (and the accompanying rewards) if he stayed. The young person decided to stick it out instead of leaving Wall Street, leaving the author disgusted.

The blog then goes into a discussion of computer algorithms to describe a more optimal solution to the problem of how to spend one’s professional life. Instead of merely climbing whatever hill/ladder/other metaphor on which you happen to find yourself, you should engage in some exploration to determine if there is another hierarchy where you could reach a much higher level. In the parlance of the post, this is the highest hill. The way to do this is to explore many different options, especially early in one’s career when the feelings of sunk costs are less, before committing fully to climbing in a single domain. And this does not preclude reaching the top of one domain after a period of several years, deciding that you no longer want to participate in that domain, and choosing another pursuit.

I have already experienced this phenomenon myself. After I clerked for Judge Siler, the greatest job anyone could have in the legal profession, I was an associate at a large firm in DC. It paid very well, I worked on cases that made national news, and I wanted no part of the lives I saw my bosses living. So I left. No, it wasn’t easy. The golden handcuffs are notoriously difficult to unshackle. The period since hasn’t been straightforward either, but leaving was the correct decision then and remains so today.

Now I’m a corporate lawyer who handles mergers and acquisitions in the lower middle market and acting general counsel for a few tech startups. Will any of this last forever? Given my own work history, probably not. At least now I’ve decided that that’s okay.

If you wish to read the blog post for yourself, it is available HERE. If you do, I hope that you incorporate the thinking into your strategic goals for this year (and those that follow) and that you aim for those goals that will bring you the greatest achievement and satisfaction.