Three random yeses changed my career

Welcome to Nights & Wknds, a weekly newsletter for ambitious professionals building successful careers and lives.

Honest reflections. Practical frameworks. Lessons learned the hard way, written by someone who's been in the trenches and is still learning.

Whether you're protecting your time carefully or wondering if you have room for one more thing, this newsletter is here to help you play the long game.

This week…

Three times I almost didn't say ‘yes’, and what came to fruition. Why the opportunities that matter rarely look like opportunities when they first show up.

Let's get to it!

Aaron

Seven years ago, I got a LinkedIn DM I almost ignored.

I was leaving my job, headed to business school in the fall, and the plan for the summer was simple: rest. Read some books. Decompress after five years of 10-12 hour work days, 5-6 days each week.

Instead I said yes to something random. Then I did it twice more over the next few years. None of those yeses were on my roadmap. All of them shaped where I ended up.

I hear a version of this a lot, usually from someone who's overwhelmed and wondering whether or not to take on one more thing.

My answer has changed over the years. Be thoughtful about how you invest your time. But if you have any bandwidth at all, say yes to things that seem random, but interesting. They take you out of your comfort zone, and you never know what comes from it.

Easier said than done, I know. So instead of arguing for it, let me walk you through the three seemingly random times I said yes.

A woman I knew from undergraduate finance recruiting had moved to a new role, and her team needed help teaching real estate to junior finance professionals. She sent me a Linkedin DM asking if I was interested in teaching. There was a clear argument for saying no: I wasn’t “qualified” with just 3 years of experience, and I was supposed to be resting. But I had the summer free and figured I could make a little extra cash before business school. That was the entire decision.

I thought it was a one-time thing. It wasn't. After that first week, the CEO reached out about something bigger.

That bigger thing was this: they wanted a full real estate course, built from scratch, and nobody in-house knew real estate.

Here's the part that still surprises me: I don't think I could build that course today. I know too much now. I'm not in the granular details the way I was back then. There's a window where your experience level is exactly right for a thing, and you don't realize it while you're in it.

After business school, I came back to my firm and sourced a multifamily development in Texas. Debt markets were a mess, SVB had just collapsed, nobody was lending. We needed a way to capitalize the building, and the answer was bond financing. Something I had never done.

I had to learn it fast. I asked a lot of questions. Leaned on people who had done it before. Got curious about the risks, how to mitigate them, and how to explain them to our investment committee. We got it done.

That's one of the parts of my work that I love most. You're constantly adding to the toolkit. But it only works if you're willing to ask questions, stay curious, and lean on relationships. Nobody expects you to know everything. They expect you to figure it out.

The thread through all three: somestimes you just have to say ‘yes’ and then go figure it out. Great learning and great opportunity can come from saying yes to things you’re unsure about.

Opportunities that can change your trajectory rarely arrive labeled as such. And they even show show up as inconveniences. A DM you almost ignore. A project you don't have time for. A capability you don't have yet.

You don't need to say yes to everything. You need to notice when the ‘random’ thing is really a door. If you have the bandwidth, walk through that door.

One of my favorite parts of writing this newsletter is hearing how these ideas show up in real life.

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