How to Tell When to Keep Going (and When to Run)

What building Stripe actually felt like — with Claire Hughes Johnson

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My first two years at Facebook were 2008 and 2009. When I started, we were smaller than MySpace. Everyone thought Microsoft was going to buy us. There was nothing obvious or inevitable about Facebook — not from the outside, and honestly, not from the inside either.

But there was this conviction. We knew what we were building was bigger and more important than anyone understood yet. And still — some of my most vivid memories from those years are of feeling like we were about to drive the car off a cliff.

Like we were one bad decision away from destroying everything we’d built and all the opportunity in front of us. When I give my Legos talk inside rapidly scaling companies, I usually put up that picture ^^ and this one:

These are my best explanations of what building something feels like most of the time. Even the wildly successful companies that look so fancy and inevitable from the outside feel like a messy chaos-fest on the inside.

So: how do you know the difference? What’s normal mess — the kind that’s just part of building something real — and what’s the kind of mess that should send you running for the hills?

I invited Claire Hughes Johnson, the former COO of Stripe, on the WorkLife podcast to talk about this. Claire joined when Stripe was around 200 employees and roughly $30–50M in revenue. She still sits on the board today — now it's about 8,500 employees and valued at $159B.

From the outside, Stripe’s story looks inevitable. But a while back, Claire had mentioned something to me offhand that I couldn't stop thinking about. She and Patrick Collison (Stripe’s co-founder and CEO) had been talking about the most surprising thing about their Stripe journey, and they agreed: it was that they just kept going.

I don’t think anyone would guess that answer. That’s the most surprising thing??? But that answer gives you a glimpse of how hard it was from the inside.

So I wanted to ask her about it. What does building something successful actually feel like when you’re in it? And how do you tell the difference between mess that’s normal and mess that means something’s actually wrong?

Here’s a sneak peek of the convo and some takeaways:

Look at the whole board, not just the square in front of you

Early at Stripe, there were so many crises. When things were blowing up, Claire would zoom out and ask herself one question: is this existential, or is it overcomeable?

Those are really different things. And most of what feels existential… isn’t.

Claire tells a great story in the episode about a moment when Stripe went down. Payments not processing, customers freaking out, support teams getting hammered. For a company that is effectively infrastructure for other people’s businesses, downtime is very bad for your reputation.

Claire had left a very stable senior role at Google to bet on this company, and there were definitely moments where it felt like it might all fall apart.

But when she zoomed out, she knew that the business was fundamentally strong: the product was real, the customer base was growing, and the people around her had the conviction to fix it. So yes — there were brutal moments, but it was also overcomeable.

The mess was bad. The fundamentals were good.

I just want to add my own note here to say that I think this is probably the most important thing, and one that I haven’t paid enough attention to at times. Is the business truly strong and growing despite whatever chaos you are currently in? There are going to be really bad moments in most businesses, but if you zoom out and look at the overall trajectory — years, not days — what does it look like? That is the trend to pay attention to when you are thinking about normal mess versus bad mess.

Know your “keep going” criteria before you need them

In addition to the business fundamentals, there’s the personal side. Is it worth it for YOU to keep going through all the hard?

Claire has two questions she goes back to when things get hard:

Am I still learning? Am I still having an impact?

If yes — and she can see a path where she has some agency — she keeps going. Even through really rough stuff.

If the answer to one or both is no, that’s gut check time.

Her other point is that it’s important to think about this — the criteria — before you’re in crisis. Because when you’re in it, you won’t be able to think clearly. You need something to anchor to ahead of time. What does “worth it” mean to you?

I think this starts in the job search and acceptance process. I wrote about it in a different Substack article, but my favorite test for taking a job is: If this company struggles or fails, will I still be glad I took the job? That gives you such solid ground for choosing your role and knowing your why regardless of whatever tornadoes or hurricanes come your way.

When you’re stuck, go outside your own head

Claire mentioned a boss she had early in her career who, whenever she’d come in panicking about something, would say (somewhat snarkily): “Huh. Has no one ever experienced this before???”

Meaning: go find them. Someone else has been exactly where you are right now.

When you’re stuck, you’re probably not going to unstick yourself. I’ve made this mistake so many times. It can feel like a black hole; it can feel embarrassing. It’s really hard to reach out (or to even think straight), but if you can remember to do it, it is one of the most powerful tools for perspective. You’re closer to the problem than anyone, which means you’re also the least qualified to see it clearly.

Sometimes the answer is “run”

I want to be clear: the message here is not “just keep going.”

Claire and Patrick’s answer wasn’t that they powered through on grit and conviction alone. It was that when they zoomed out, the ground was solid. The fundamentals were real. That’s what made keeping going the right call.

Claire actually tells a story in the episode about someone she was advising who was in a hard situation at work. Her advice wasn’t “keep going.” It was: run. Because when she looked at the fundamentals — the leadership, the traction, the trajectory — they were off. Keeping going there wasn’t resilience. It was just wasting that person’s most precious resource: their time.

So the question isn’t: can you muscle through this? It’s: what does the ground actually look like under your feet?

Check the fundamentals. Know your criteria. Find someone who’s been there. And then — if the ground is solid — yeah. Keep going.

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What else?

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