The mental hurdle of hitting send

Welcome to Expertise to Insights, a 2x/month newsletter where I share the practices that help experienced leaders turn what they know into insights they can actually use.

He has hundreds of notes in his phone.

Voice memos, journal entries, half-finished thoughts typed out at odd hours. Fifteen years of investing in early-stage companies has given him a pattern-recognition and experiences that most people in his world would pay for. 

But when he sits down to turn those notes into something he can share, the same thing happens every time. He gets two or three paragraphs in, gets stuck or decides it's not good enough, and closes the draft. 

He's watched the founders he invests in build trust, attract deal flow, and open doors, just by sharing what they know online. He's seen it work up close dozens of times.

But just can't get himself to do it.

I had coffee with this guy last week. And I've talked with dozens of people with similar stories. Heck, I even experience it myself.

And the more I talk to people about it, the more I realize it's not a knowledge problem. The people I'm talking to have the ideas and are not short on things to say.

The problem is the publish button.

These days it’s pretty common knowledge that founders and executives should be sharing their ideas online. They understand the logic: sharing what you know attracts the right people, opens up opportunities, and builds trust faster than almost anything else.

They get it. And then they don't do it.

When I ask these leaders what stops them, the most common answer is something like “the ideas don’t feel fully formed yet” or “it needs more thought and refinement”

So they wait.

The standard they're holding it to (i.e., the polished, airtight, fully-developed version) isn't something we can achieve right away. It’s something that gets developed through testing ideas on social media, gathering feedback from people, and refining it over time. 

Not by constantly tweaking it in a Google Doc for 6 months.

The very thing that makes these people worth listening to with their high standards, their precision, and their hard-won expertise is the exact thing that keeps them silent.

I've been writing a personal newsletter for 2+ years.

The pattern is pretty consistent: the posts that don't resonate get opened and forgotten. People read it and go on with their day.

That used to feel like failure. Now I use it as a signal that my piece wasn’t engaging enough or the topic wasn’t relevant.

But every so often, something lands.

A while back I wrote about getting into the business school at Michigan. My grades and ACT scores were lower than a lot of other applicants, but before I applied, I'd met with one of the admissions guys. I always believed that conversation played a role in getting me in and that it wasn't purely about the numbers.

One of my readers replied after that post. He'd had a similar experience getting into his MBA program. But for thirty years, he'd felt ashamed about it. He didn't believe he deserved to get in and carried it for three decades.

My story helped him see it differently. He wrote to tell me he finally felt proud of what he'd accomplished.

That's the post he will remember. Not the others that might have been confusing or had a few spelling errors, but the one that connected with something real in his life.

We are writing for those people. And every piece isn’t going to be for everyone. 

But when a piece does hit home, it will be remembered. 

I cringe when I go back and read my early newsletters.

Big bulky paragraphs with no white space. No clear insight or throughline. Just a long brain dump that read more like a journal entry than something meant for another person.

But as I was recently reading some of those old posts, I realized the actual ideas I was writing about were solid.

Recently I published a piece on my 30th birthday on the 30 things I believe. A few of the items on my list were concepts I was talking about two years earlier in my second-ever newsletter.

But when I wrote about them in my recent piece, I had more clarity and precision than I could manage the first time.

The ideas hadn't changed, but my ability to express them had.

It's about building a new skill: the ability to get those ideas out of your head and onto paper in a way other people can use.

You don't have to be a good writer to start. You just have to be willing to be a beginner at the craft while being an expert at the content.

The reps are what close that gap. There's no shortcut around them.

It will never get easier to hit publish for the first time.

It only gets easier after you've done it over and over that the discomfort fades. All the things I've benefits that come from writing and publishing your ideas publicly around clearer thinking, new opportunities, and deeper connections only start to show up once you start putting reps in. 

There's no way to think your way to those outcomes. You have to publish your way there.

That investor I mentioned couldn't bring himself to actually send. So he came up with a solution: he and a friend agreed to hit publish on each other's stuff. His friend would send his posts. He'd send his friend's.

I thought that was great because it's honest about where the real friction lives. It's not in the writing. It's in the moment right before you hit send.

If that's where you are, find a friend who has the same problem. Give them your login and have them hit send.

And if you don't have someone to do it, hit me up. I'd be happy to be that accountability partner.

Catch you on the next one,

Andrew