The Case for Caring Less
A founder friend of mine — she runs a multi-billion-dollar company — said something recently that I haven't been able to shake.
A few years ago, she was completely gripped by the outcome. She wanted to build something huge, and she felt personally responsible for everything — every decision, every number, every swing in the business. You could feel it when you were around her — how much she cared, but also how much it weighed on her.
Fast forward to now. It’s the same company, though now it’s actually a much harder macro environment. But she’s different. Being around her, you can tell she feels calmer and less reactive, like she has more ground under her feet.
She told me: “I think I’m actually a better CEO now because I care a little less.”
What she meant wasn’t that she lowered her standards or stopped showing up. It was that she stopped needing the company to turn out a certain way. She accepted that there are things she can’t control, that she’s going to do her best in the face of chaos, and that there are a lot of possible good — even great — outcomes. Once she let go of needing it to be one version, her decision-making got clearer and her energy got steadier.
That shift is subtle. It’s also, I’d argue, a sign of someone becoming a better operator.
For most of my career, I would have told you the exact opposite.
One of the things that made me effective early in my career was how much I cared. I cared about everything! Every project, every detail, every deadline as if it were my responsibility and mine alone. That caring showed up in very concrete ways — I was the person making diving catches, pushing on decisions that needed to be made, making sure the right thing happened, regardless of whether it was technically my job.
And it got rewarded. Not because anyone said “you care so much” — but because things got done. Problems got solved. Fires got put out. My bosses loved it. Over time, the message I internalized was: hold on tighter, care more, this is what good looks like.
And for a while, that’s true. Caring is a genuine superpower, especially early in your career or inside a smaller company where individual effort can still meaningfully change outcomes. The surface area is small enough that stepping in everywhere isn’t just possible — it’s often necessary. Caring deeply is often what gets you into the room in the first place.
But there’s a version of it that backfires.
I burned myself out twice in large part because of this. I was carrying way too much of the company in my head, taking mistakes personally, fighting every fight, operating at full intensity all the time. It didn’t feel like a choice — it felt like what being good required. When I finally recognized the burnout, it was too late. The only way I could recover was to leave.
As my brilliant friend Wendy Chow puts it: “Care less, so you can care longer.”
Burnout is the obvious cost, but there’s a subtler one that I think matters more: caring too much about outcomes you can’t control eventually makes you worse at your job. You end up more reactive and emotional. You attach yourself — your self-worth — to every decision going your way or everything going right. It becomes harder to see what actually matters. It’s so hard to realize this when you’ve built your career and your brand on caring, but the person who takes everything personally, who needs things to turn out a specific way — that person isn’t more invested than everyone else. They’ve just lost their objectivity. And objectivity is what you actually need to make good decisions.
There’s one more layer to this that I think is easy to miss, and it’s where many operators specifically get hurt. If you care deeply about a company, it’s very easy to start believing the relationship is mutual — that if you show up with loyalty, the company will show up with loyalty. Sometimes that’s true with individual people. It’s almost never true at the system level. Companies are systems designed to survive and succeed. They will reorganize, change direction, and let people go — even people who care deeply and have given a lot — because that’s what the system requires. If you’ve been operating as if the relationship is personal and mutual, those moments feel like betrayal. Not because anyone intended it that way. Because you gave more than the system was ever designed to give back.
That mismatch is where a lot of the emotional damage comes from. And the earlier you understand it, the more protected you are.
All of which is to say: the caring itself isn’t the problem. The problem is where it goes.
So “care less” is directionally right, but let’s get more specific. The real shift is learning to place your care deliberately — to get good at telling the difference between what’s strategically important and what’s just noisy. A lot of what happens inside companies is frustrating without being important. Reacting to a messy call that you personally wouldn’t have made as if it’s a strategic risk is what drains you. So is holding on to every detail as if it’s existential. Not everything deserves to be treated with equal importance. A gut check that helps: Will this matter in a year? If not, it probably doesn’t deserve much energy now. What’s the worst-case scenario? Often, it’s not that bad.
The harder piece is changing your relationship to outcomes. My friend Don Faul has a great line that you’ll hear in an upcoming episode of WorkLife: “Managing adversity is often about perspective.” Instead of “I’ve failed if this doesn’t work,” the shift is: “I’m going to do my best.” That sounds small, but it changes how you operate. It focuses you on what you can actually control and creates real distance from what you can’t. Most of what we’re doing inside companies is an experiment. You don’t control the outcome nearly as much as it feels like you do in the moment.
More senior operators are often more objective because they’ve learned to stop conflating caring with controlling. They’ve stopped taking the company’s chaos personally. They’ve gotten good at asking what actually matters, instead of treating everything as equally urgent or important.
That’s the real goal — not detachment, but selectivity. Caring deeply about the right things, and having enough distance from everything else to actually think straight.
What else?
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