In early 2024, I was on a group trip, sitting around a large table on the first night.

That's where I met John.

We hit it off straight away. It turned out he and his wife lived in San Francisco too. A few weeks later we were doing double dates back in SF. Me, Caroline, John, and his wife.

At the time, I was in a rough spot. I had decided to shut down my first company and I genuinely had no idea what to build next.

I was cold calling chemical distributors, exploring defense tech and generally rotating through different ideas and buyer profiles, trying to find anything worth building. It was messy and demoralizing and I had no clear direction.

John's situation looked a lot better on paper.

He had a good job, earning a decent salary. But he'd been doing it for 6 years and hated it.

On the first night I met him, he’d told me he wanted out. He was ready to find something new. I was really excited for him.

We made a habit of catching up every 6 months or so. Dinner, usually somewhere in San Francisco.

The next time we met, I told him I'd been posting on LinkedIn. I felt like there was something there, but it was still too early to tell.

Then I asked about him. Had he started applying to new jobs yet?

Not yet. He'd been really busy with work travel and hadn't gotten round to it. But soon.

Six months after that, we went on another double date. By this point, I was optimistic about the potential of LinkedIn but still felt uncertain.

John was in the same job. He'd been busy with a big project but was going to start looking for a new job soon.

A year later, we were at dinner again. By this point, Saywhat was in full swing and things were working.

John was still at the same job. And he still hadn't applied for new jobs.

I think about him a lot.

He had a lot of very reasonable reasons to say “not this week.”

But over time, every not-this-week became a year. Then two.

The gap between me and John now has nothing to do with talent. We both recognized we wanted change at the same time.

The only real difference is that I started and he didn't.

And starting didn't have to mean quitting. John could have committed to one thing a week. One application. One updated section of his CV. One conversation with someone working where he wanted to be.

None of it would have changed his life on Monday morning.

But it would have changed where he was sitting a year later.

So if you have something pulling at you… an idea you keep coming back to, a direction that won't leave you alone…

The longer you wait, the more it costs.

There is never a right time. It will always suck for a while.

Build a rough plan, start small, and accept that it will feel uncertain for a long time.

That's just what it looks like before it works.

See you next week,

Will

P.S. If this got you thinking about getting started on LinkedIn, Chris Donnelly and I just finished the Q1 2026 State of the Algorithm report. We analyzed 397,605 LinkedIn posts and identified the top 10 trends working on LinkedIn today.

We’ll be sharing them all live on a free webinar on Wednesday May 6th at 9:30am US PT / 5:30pm UK time.

Will McTighe

Forwarded this email? Sign Up Here
Connect with me on LinkedIn | YouTube | Instagram