The grind has an expiration date.

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 learning to deliver under pressure or protect your energy during busy seasons, this newsletter is here to help you play the long game.

This week…

How hard you should actually be working early in your career, and what nobody tells you about the tradeoffs.

Three things I wish someone had told me about the math, the reps, and what you're actually optimizing for.

Let's get to it!

Aaron

To know me is to know I’m a bit of a workaholic. And I’ve been that way for a long time.

In college, I played football. 6am practices, film sessions, games on weekends. Academics didn't take a backseat. But the schedule didn't wait for you to catch up either. You figured out fast how to carry all of it, or you didn't.

When I got into investment banking, I went in eyes wide open. The hours were going to be brutal. I knew that. But the point wasn't to do it forever. I wanted to build a hard skillset (fancy talk for Excel, PowerPoint, and project management), create a floor beneath my career, and signal something to the market: that I could take the hours, deliver, and handle the pressure. 

So when I posted something on LinkedIn about working 80 hours a week, the reaction split almost evenly. Some people had lived it and knew exactly what I meant. Others thought I was out of my mind.

Both groups were right about different things.

The frustrating answer is: it depends. But not in the cop-out way people usually mean when they say that. It depends on things most people haven't thought through yet.

The debate online is broken. One side says hustle or get left behind. The other says protect your peace. Neither side is being fully honest about what they're leaving out.

When it comes to work, if you're putting in 80 hours and someone else is putting in 60, that gap adds up fast. After a few years, you've accumulated thousands more reps. Pattern recognition, speed, judgment. It adds up. That's not hustle culture. That's arithmetic.

But I also always had an eye toward the decade mark. From the beginning, the intensity was never meant to be a lifestyle. It was a season with a purpose. The math works in your favor early on. Later, leverage and relationships take over. If you're still grinding the same way at year ten that you were at year two, something went wrong.

Not all hours count the same

This is where most of the "just work harder" advice falls apart.

After banking, I was still putting in serious hours. But what those hours looked like was different. I was fortunate to be in environments where most of what I was working on, I was genuinely learning from. Building models. Writing memos. Sitting in on legal negotiations. Spending time with senior deal people and watching how they thought through complex transactions. Those were the reps that actually made me better.

And on top of the technical work, I was getting reps at managing people. That's a separate skill entirely, and one most people underestimate.

If you're logging hours but not getting sharper, you're just tired.

The question is never how many hours. It's how many of those hours are making you better at something specific. If you can't answer that clearly, the problem isn't how hard you're working. It's what you're working on.

This is the one nobody wants to say out loud.

I saw it as a six-to-ten year season.

I knew going in what I was trading: time with family, time with friends, sleep. I wasn't pretending otherwise. But I also knew what I was building toward, and roughly when the season would end. That made it bearable. The sacrifice wasn't open-ended.

By my late 20s, early 30s, things started to change. I had a partner, a dog. We started traveling more. The job was still demanding, even more demanding. But I had flexibility I hadn't had before. The ability to integrate work into a life rather than have work be the whole thing. And the time I'd given up with family and friends — I’m starting to get it back.

The back end wasn't 30 years out. It was about a decade from where I started.

If you want to be at the top of a competitive field, the intensity is part of the price. Full stop. If that's not your goal, the calculus changes. But be honest with yourself about which game you're playing.

Most people avoid this question because answering it means committing to something. But not answering it is its own choice, and usually not a good one. Pick one. Then own it.

The grind is not the point. The grind is the vehicle. If you don't know where it's taking you, you're just driving in circles and calling it discipline.

Name the season. Name what you're working towards. Name when you expect the season to change. The intensity is survivable when you can see what's on the other side.

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

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