Not Every Friendship Is Built for the Long Haul — Here's How We Figured That Out

There's a version of this post where we sound like cold, calculating people who sit around grading their friends on spreadsheets. That's not what this is. But we'd be lying if we said we didn't get a little systematic about it — and we'd also be lying if we said it didn't change things for the better.

It started, like most of our bigger realizations, during a road trip.

We were somewhere in the middle of Nevada, the kind of stretch of highway where there's nothing to do but talk, and we were debriefing a dinner we'd had the weekend before with a group of people we'd known for years. On paper, it was a perfectly fine evening. Good restaurant, decent wine, no drama. But we both drove home feeling weirdly hollow — like we'd spent three hours performing a version of ourselves that neither of us particularly liked.

"Why do we keep doing that?" Benny asked.

We didn't have a good answer.

The Framework We Already Had (We Just Hadn't Applied It Here)

Anyone who's followed us for a while knows we have a whole thing about intentional decision-making — especially when it comes to travel. Before we commit to a trip, we ask ourselves a set of questions: Does this excite both of us? Does it fit where we are right now, financially and emotionally? Will we come back from it feeling fuller or just exhausted?

We've turned down trips that looked amazing on Instagram because the honest answers to those questions were "not really," "no," and "probably the second one." And we've said yes to scrappy, low-budget weekends that ended up being some of the best experiences of our lives.

Sitting in that car in Nevada, it hit us: we had never once applied this kind of thinking to our friendships.

We were operating on autopilot — maintaining relationships out of history, proximity, or a vague sense of obligation — without ever stopping to ask whether those relationships were actually serving us. Or whether we were genuinely showing up for the other people, either.

What the Audit Actually Looked Like

We want to be clear: we did not make a spreadsheet. (Okay, Benny made a loose spreadsheet, but we're burying that detail.)

What we actually did was sit down one Sunday morning with coffee and ask each other a few honest questions about the people in our lives:

• After we spend time with this person or group, how do we feel? Energized, neutral, or drained?
• Do we look forward to plans with them, or do we feel relieved when something comes up and we have to cancel?
• Is this friendship reciprocal? Do they show up for us the way we try to show up for them?
• Does this person support who we're becoming, or are they more comfortable with who we used to be?

That last one hit differently than we expected.

A lot of our social circle had been assembled in our mid-twenties, before we started the blog, before we quit our jobs, before we decided to build something together. Some of those people had grown alongside us. Others — and this was the hard part to admit — seemed almost unsettled by the changes we'd made. Not maliciously, just... they knew an older version of us, and the new version didn't quite fit the friendship they'd signed up for.

The Uncomfortable Part

Here's what nobody tells you about this kind of reflection: it doesn't always point the finger outward.

Some of the friendships we were draining energy from? We were the problem. We'd gotten so wrapped up in our own world — our projects, our travel plans, our little two-person bubble — that we'd stopped being genuinely present for people who actually cared about us. The audit forced us to look at that honestly.

There were a few friendships we'd been passively neglecting that, once we actually showed back up for them, turned out to be exactly what we needed. One of Katie's oldest friends from college falls into this category. They'd drifted, not because anything went wrong, but because life got busy and neither of them had made the effort. A single intentional phone call cracked things back open in the best way.

So this wasn't just about pruning. It was about pruning and watering.

What Changed After

We didn't have any dramatic falling-outs. We didn't send anyone a breakup text. What we did was get a lot more intentional about where our social energy went — which, when you're running a business together and also trying to maintain a functioning relationship, turns out to matter more than we'd realized.

We started saying no to group hangs that felt performative and yes to smaller, more honest evenings with people who actually knew us. We stopped filling our weekends with obligations that left us feeling like we needed a weekend to recover from the weekend.

And weirdly, our relationship with each other got better too.

When you're spending a lot of time in social situations that feel like work, you start to resent them — and sometimes you start to resent the person you're doing it with. Clearing out some of that noise gave us more space for the people and experiences that actually mattered, and more space for each other.

A Note on Doing This as a Couple

Friendship audits are tricky when you're a unit, because your social lives are partially shared and partially separate. We had to be careful not to let one person's feelings about a friendship override the other's completely. Benny might genuinely enjoy someone that Katie finds exhausting, and vice versa — and that's okay. Not every friend needs to be a couple's friend.

What we were really evaluating was the shared social life we'd built together, and whether it reflected who we actually were. Your individual friendships are your own to navigate.

The question we kept coming back to: Does our life together have room for this, and does it make that life better?

Sometimes the answer was yes. Sometimes it was a quiet, honest no.

Worth Asking

We're not prescribing this for everyone. Some people thrive in big, sprawling social circles and get genuine energy from keeping lots of plates spinning. That's valid. This is just what worked for us, and it came directly from applying a framework we'd already built — just in a direction we hadn't thought to look.

If any part of your social life feels like it's running on fumes rather than genuine connection, it might be worth asking why. Not to blow anything up, but just to look at it clearly.

The best trips we've ever taken started with honest planning. Turns out the same is true for the people you bring along for the ride.