Why do we only do it when we’re desperate?

Hello again my friend,

This is the Behind the Work section of the newsletter, where I write about the personal forces behind commercial success. Ego, discipline, politics, ambition, and the quieter things that shape how people actually work.

I now find myself being slightly more social (shocker, I know). But I’m not talking about beers with the boys or going out. I’m talking about the dreaded networking. About 5 events or so in the last couple months. Some coffee chats. A few “meetings,” but nothing major. Mostly about building products, social media, and tech. Between the rooms and the DMs that followed, I talked to about a hundred people.

Everyone was impressive. People had AI agents running real work for them. They were paying for the good models. Some had working prototypes on their phones. These weren’t dreamers. They could actually build things, and some already had.

But near the end of almost every conversation, I’d ask some version of “so how do we stay in touch? Anything we could work on together?” And most of the time, there was nothing. No newsletter to subscribe to. No product to try. No offer I could pass along to someone who needed it. Just something soon. One day. Not in all cases, to be fair, but most.

“I just need a better idea” and “I don’t know what to go in on” came up too. People know they want to do something, but just have not yet. It came up often because anytime beehiiv (my day job) would come up, everyone “wanted to start a newsletter.” Again, brilliant people, but with just one missing piece of the puzzle.

As you know (if you know me) I’m not writing this from above the problem. I might be one of the worst offenders, as I’ll share. That’s why people like this newsletter. Everything is very real.

So is knowing we have it in us to be aggressive in pursuit of our dreams when we’re desperate, then suddenly comfortable, cautious, and timid when we have even slightly more to lose.

Let’s lock in.

You’ve heard part of this story before. The most successful cold email of my life went to Tyler, beehiiv’s CEO. I was unemployed at the time. I had people I provide for and no paycheck coming in, so I didn’t have the luxury of wondering whether the email made me look desperate.

I researched the company, found real work I could do, made a concrete offer, and sent it. There was no job posting for what I proposed. I’d never worked in software. A week later I had a part-time gig, and two weeks later it was my full-time job.

The interesting thing is that despite being able to do that in a matter of a few days, I haven’t sent a cold email since. Not a single one. Not for a different job, side-work, fun projects…nothing. I was desperate, I did the thing, and suddenly that version of me turned off as soon as I wasn’t in desperation mode anymore.

Isn’t that funny? Shouldn’t people with big, ambitious goals always be in desperation mode, until they hit them? Isn’t that kind of the point?

My goals didn’t shrink after joining beehiiv. If anything they got way bigger. I watched a small group of people build a $45M business (recently named #19 on the INC 5000 btw), and realized how much is actually possible. I picked up more skills, more experience, more credibility, and better tools than have ever existed. By every measure, I’m more capable of making bold moves today than the unemployed version of me who sent that email.

I became more capable, and somehow less aggressive.

That’s the sentence this whole post is about. Because I don’t think it’s just me. I think many of those people I spoke with are in the same position. I think it’s going to become the theme for closing out 2026.

Now, to be clear, I’m not doing this to announce I’m looking for another job. I love beehiiv. Behind the Work is about just these questions, and how they pan out in a career.

A few months ago I wrote that when everything becomes possible, nothing feels finished. AI took the list of ten things you could realistically build and turned it into a hundred. The question stopped being “can I build it?” and became “which of these deserves my next six months?”

And look, what you choose still matters. I’ve written about picking the right place for your effort before, and I stand by it. You can even take a one-day side quest now and ship a real product by dinner. Can you do that every day? No. It’ll eat your main thing alive. But if the side quest feeds the main thing, maybe it’s worth the day.

The trouble is that most people I talked to hadn’t settled on the main thing. And staying unsettled feels reasonable, because the moment you pick one direction, it starts competing with the other ninety-nine in your head. The direction you chose has real problems and slow weeks. The ones you didn’t choose are still perfect, because they only exist in your imagination.

No real project survives that comparison. So people keep shopping.

Our social media manager showed us how a single reply on someone else’s post pulled 100,000 impressions. Not a thread. Not a launch. A reply.

I don’t think people appreciate how far twenty minutes of ripping comments can go. Pick twenty people in your niche, show up in their replies consistently, be useful or funny, and you’re suddenly familiar to everyone watching those conversations. I’m not a natural social media person, so honestly, this took me embarrassingly long to understand.

What nagged at me after was what happens when those hundred thousand people click through to a profile, what do they find?

For most of the room, the answer was nothing. Nothing to buy, nothing to join, etc. Everyone wanted distribution. Very few had decided what the distribution was for. A room full of people learning how to post and grow on X, and only one of them has his own business (as far as I know)…and he was one of the speakers.

So it all goes in a circle: we follow each other, like each other’s stuff, agree we should all be posting more, and go home with a slightly bigger audience pointed at nothing.

But why? How is it that in 2026 so many of us are either stuck, or barely dipping our toes into the pool filled with our dreams? Why don’t we dive in?

Misplaced fear that failure follows us, and the pain of closing doors too soon.

It’s a weird combination of things, but hear me out.

The fear is some version of: if I go all in and it flops, it goes on my record. Everyone will remember the thing I announced that didn’t happen. I will look bad, and hurt my chances at future success because of today’s failure. And it’s so debilitating that people don’t try.

The doors are the idea that if we pick one thing, and cut the others, those cuts will hurt until our actual choice benefits us. Most people can’t handle that pain, so they never really cut some ideas. And for that reason, they’ve never picked one.

Enter the room of people saying “I don’t know what to do,” when millions of businesses have proven to work.

To give you an idea, let me tell you about my record.

I left a stable job to start a newsletter that never got off the ground. I tried a course that didn’t go well. I tried a community that didn’t go well either. I built a writing business that actually worked, then planned the exit so poorly that selling it probably cost me more than keeping it. To top it all off, I launched a paid product that failed badly enough that I refunded $20,000 to the people who bought it.

That all happened within two years. How many of those did you know about before today? Maybe two? And I talk about these things in a newsletter to you. Think about my acquaintances who heard about my business once or twice and that was it, like 4 years ago. That’s the whole point. No one sees or cares about your record.

As for mental uncertainty (pain) from closing doors. When I was unemployed, the missing paycheck closed the doors for me. It didn’t matter how much it freaked me out or hurt mentally. There was no version of that month where I considered “What will people think of this email.” It didn’t matter.

Then I got the job, and the fallback came with it. Every uncomfortable move became optional. And optional, for me, was borderline never.

Now, I’m not romanticizing being broke. Being broke is not a productivity system. But the desperate version of me had one thing right. He moved.

Now, failure isn’t free. I lost time and real money, and that $20,000 wasn’t fun to send back. But the obligation was never “don’t change your mind.” It’s to treat people right when you do. Refund what should be refunded, communicate honestly, and appreciate everyone who gave you their time, money, or attention. Do that, and you can try things, walk away, and try again. The world mostly shrugs.

If people can resolve these two things:

Almost all cases of failure by hesitation go away with them.

I’m not saying this is right. I’m sharing what I’m doing in case it resonates.

While I’m (very thankfully) employed, I find myself holding back over things I’d do in a minute back when I was desperate. I’m cringing at all the moments I saw opportunities and let them go.

And I really believe the word of the year should be gumption:

Extremely underrated word.

Nothing wrong with a little deadline. A price you can afford to lose. An email or two. Not catastrophic pressure. Just enough that something stops being optional. It doesn’t matter if you build apps, bake cookies, or write for a living.

We pick the thing, and suck it up for a few months. If it is not working, we change it, but respectfully if we made promises. Changing your mind is not a crime. Never really going for something could feel like prison, though.

Here’s what I keep coming back to. If you’re waiting until you’re desperate, you’re waiting for the worst possible version of the moment. The one where you have no leverage, no cushion, and no choice. You don’t need to lose anything to act like you have something to prove.

So send the email while things are good. Make the offer while you don’t need the answer. Pick your thing while you can still afford to be wrong about it.

Gumption 2026, my friend.

The version of you that shows up when there’s no other choice is available right now. I hope you don’t wait for the emergency to meet them.

Thanks, as always, for reading.

Darwin