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March 1, 2026
The Start of Sophomore Year

Leaving college is scary but exciting. It's full of changes. But, you've been told for the previous four years (and understood implicitly prior) that the whole process thing is supposed to end at year four, and as part of that the time will come to take the next step, no matter how scary.

If you are like most people I know you will probably start your first job not knowing a whole lot about the working world. It will be challenging and stressful but, you'll also be surprised at how much time you get back when there's no such thing as homework. Maybe you join a rec soccer league or start a supper club or volunteer. It's also an opportunity to try something random. Playing in a sports league or starting a newsletter or running for your local council seat won't help you get into college or get your first job. There's almost no strategic importance to them other than fumbling your way towards what you like to do.

This process of discernment matters and throughout your twenties you are doing this on almost all dimensions. Most people start their first job and realize that's not what they want to do for their career. It's not that there's a perfect job out there but the opportunity to explore can be so appetizing, and the fact that the grass is always greener leads most people to make a pivot at somepoint. While this is happening, in year 3 or 4 or your first job, you're also starting to seriously date. There will be people who are completely uninterested in relationships and people who were married at 23. But for the vast majority of my peers I have found that the dating years from 23-29 can be messy and tough. I was lucky enough to find someone who wanted to date me at 23 and haven't looked back, but I've seen so many of my peers try to navigate the post-college dating world and ask themselves "Is this the person I want to try this with?"

Underneath all of it, the big question: what do I actually want?

I have fluctuated on this one enormously. I've wanted to pursue classic corporate success and also envied the people that seem to just be completely relaxed as they work a job and live for the hours outside of 5pm. I don't have this figured out and this process of discernment has been incredibly challenging. Throughout this I have been trying to ask myself a few questions to help narrow things down, they are below.

  1. Who are you trying to impress?
  2. What does winning look like to you?
  3. What will make you satisfied (what metric, truly will make you happy?)
  4. Is there a person who makes you better than yourself?
  5. What tradeoffs are you willing to make to win, whatever that looks like for you?

There was a class in college offered senior year that explored these questions. That class would be more useful 6 years out of school than it was my senior year.

This phase of life is amazing and challenging and brutal and so incredibly worth it.