A few weeks ago, my daughter Caroline graduated from high school. Between prom, senior events, graduation itself, and all the logistics of getting a kid ready for college. At the same time, my son Jack was in the middle of training for his taekwondo black belt, which if you've never watched someone do, is not a small thing. Months of practice and discipline, all building toward one long, intense testing session. Somewhere in the same few weeks we also celebrated my birthday, Father's Day, and the start of summer. It was wonderful. It was also, if I'm being honest, a lot.

Right in the middle of all of it, a few of my closest friends from high school started talking about meeting up in Washington, D.C. One of our best friends is touring with a Broadway production as the lighting technician, and this was the perfect chance to spend a weekend together and see the show. I hadn't seen some of these women in years. I wanted to go before I'd even finished reading the text.

And if you've been around my work for any length of time, you know boundaries are basically my whole thing. I spend a lot of energy telling capable women to stop waiting for permission to do things that matter to them. So naturally, my first reaction was “absolutely, I'll figure it out.”

Then I looked at the calendar.

Caroline's graduation was Thursday, we'd have a celebratory dinner Friday, I'd catch an early train Saturday morning, see the show Saturday night, then take another early train home Sunday so I'd be back in time for Father's Day, with enough hours left over to grocery shop for our family's traditional lobster boil.

Technically, it fit. I could make it work.

And that's exactly when I caught myself asking the question I ask on autopilot more than any other: how can I make this work? I started negotiating with myself. Maybe I'd sleep on the train. Maybe I'd grocery shop the second I got home. Maybe I'd just be tired for a couple of days, so what. Until finally I stopped mid-negotiation and asked myself a different question. Not “can I make this work,” but “what will this actually cost me?”

That one changed everything, because I realized I wasn't trying to fit one meaningful thing into my life. I was trying to squeeze three meaningful things into a single weekend. I would have gone to Washington, I would have had a wonderful time, and I also would have spent the entire trip half-present, quietly doing math about train schedules and grocery lists in the back of my mind. I'd have come home wiped out and tried to flip a switch into hosting and celebrating with my family. Nobody would have gotten the fullest version of me. Not my friends, not my family, not me.

So I passed. Not forever, just for now. We'll go when I can actually enjoy being there, stay up too late laughing, sleep in the next morning, and linger over breakfast instead of watching the clock.

That decision stuck with me longer than I expected, because it made something click: the hardest decisions in life are rarely between something good and something bad. They're between two or three things that are all genuinely good, which is exactly why they feel so heavy. And once I saw that clearly, I realized the question I'd been asking my whole life, can I make this work, was the wrong question entirely.

If this story sounds familiar, it's because I shared a shorter version of it in an email not long ago. It's stuck with me enough that I wanted to sit with it a little longer here. Here's what I've been asking myself since.

Is this mine to carry?

Capable women have a real talent for adopting responsibilities without even realizing we're doing it. Someone forgets something, so we handle it. A problem shows up, so we solve it. No one else raises a hand, so ours goes up automatically, like it has a mind of its own.

Sometimes that comes from generosity, sometimes from love, and sometimes it's just habit dressed up as helpfulness. The trouble is, the more capable you are, the easier it becomes to assume everything is your responsibility by default. That's the Competence Trap in a nutshell: not that you can't handle it, but that you never stopped to ask whether you should be the one handling it in the first place. The Washington trip wasn't really about this question, but plenty of my everyday decisions are. Before you say yes on autopilot, pause and ask whether this is actually yours to carry. You might still land on yes. But now it's a choice instead of a reflex.

Is this the right season?

This is the one that came up loudest that weekend. Timing matters just as much as desire, maybe more, and we tend to assume that if something is worthwhile, we should make it happen right now. But life isn't lived all at once, it's lived in seasons: some for building, some for resting, some for taking care of other people, some for finally chasing the thing you've been patiently sitting on.

It's a bit like trying to plant a tomato outside in the dead of winter. There's nothing wrong with the tomato plant. It's just the wrong time. Washington wasn't a no. It was a not-this-weekend. I still want to go, and we'll get there, but that particular season already had Caroline, Jack, my birthday, and a lobster boil in it, and there simply wasn't room to add a fourth glass ball without dropping one of the others. Maybe “not now” isn't a rejection…maybe it's wisdom wearing a disappointing outfit.

If I choose this, what am I also choosing?

Every decision comes with a trade-off, and the problem is we usually only look at the part we're excited about. We celebrate the opportunity and conveniently ignore whatever quietly gets pushed to the background because of it. When I actually looked at the Washington trip through that lens, I realized I wasn't just saying yes to seeing old friends. I was also saying yes to exhaustion, to rushing, to spending the whole weekend mentally split between where I was and everything waiting for me at home.

That doesn't mean every trade-off is a bad one; plenty of opportunities are absolutely worth what they cost. The point is making that trade consciously instead of discovering it after you've already signed up.

The goal isn't perfect decisions

These three questions didn't make the Washington decision painless. I was disappointed. I still am, a little. There will still be moments when two genuinely good things compete for the same slice of your time, and the answer won't be obvious. That's fine. The goal was never to eliminate hard choices. It's to stop making them on autopilot.

What surprised me most wasn't that the decision got easier, it's that it got clearer. Nothing about my calendar changed that weekend. What changed was that I stopped measuring success by how much I could carry and started measuring it by how present I could be for what I'd already chosen. Every time you pause to ask these questions, you're building something more valuable than better decision-making, you're building trust in yourself. One responsibility you don't pick up, one opportunity you save for a different season, one commitment you accept with total confidence because you actually thought it through: those small moments of intentionality add up to a life that feels a lot less reactive and a lot more like yours.