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…
Why keeping your options open is making decisions harder, not easier, and the two-constraint approach that changed how I think about every big choice.
Let's get to it!
Aaron
When I started recruiting out of banking, I told every headhunter the same two things.
I want to get out of New York. And I want to work at a small firm.
That was it. No ranked list. No optimization matrix. Two constraints. And those two constraints made the world very small, very quickly. Most opportunities got filtered out immediately. What was left was a short list of places that actually fit what I was looking for.
That's how I ended up at Artemis. At the time, they had roughly $2 billion in AUM and fewer than 30 employees. They were in DC, not New York. Both boxes checked.
I didn't agonize over the decision. The constraints did the work.
THE QUESTION I KEEP GETTING
"How do I know which opportunity to take?"
Most people ask this question while they're already looking at options. That's too late. The clarity has to come before you see the opportunities, not after.
HERE'S WHAT I'VE LEARNED
Open options feel like freedom. They're not.
Most people keep their options open because they're afraid of missing something. That instinct is understandable, but it's also what keeps people stuck.
Open options don't give you freedom. They give you decision fatigue. When everything is on the table, you end up chasing everything and committing to nothing. And when you finally do pick something, you're not sure you chose well, because you never defined what "well" meant in the first place.
The fear of closing doors keeps people from walking through any of them.
Constraints are the real decision tool
The two-constraint approach works because it forces the definition of "what matters" before you're in the middle of evaluating specific options.
When I set those two filters, I wasn't optimizing for salary, brand name, or deal type. I knew two things I didn't want. What was left almost chose itself.
This applies beyond recruiting. Any major decision, a career pivot, a new venture, a relocation, benefits from the same exercise. What are the two things I'm not willing to compromise on? Start there, then see what's left.
What to do when you don't know your constraints
If you can't name your two things, that's the actual work. Not the search. Not the evaluation. The self-knowledge step.
Most people skip it and go straight into the process, then wonder why they feel unclear at every decision point. The clarity doesn't come from looking at more options. It comes from understanding yourself well enough to filter them.
A few places to start:
What have you already said no to, and why?
What do you find yourself complaining about most in your current situation? Recurring complaints are constraints you haven't named yet.
Think about a decision you made without hesitation, a job, a relationship, a city. What was present that made it obvious? That's likely a non-negotiable, not just a preference.
You're not looking for a long list. You're looking for the two answers that keep showing up.
What you know you don't want is often more honest than what you think you want.
WHAT I'D TELL YOU IF WE HAD 5 MORE MINUTES
Pick two things that are non-negotiable. Not five. Not a ranked list. Two. Then filter on those before you start evaluating anything else.
The goal is to walk into a decision already knowing which doors aren't yours, so you can give full attention to the ones that are.
SHARE YOUR WINS
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