Missing someone who doesn’t exist.

By the summer of 2021, I was two years into my solopreneur journey. And I flew from Nashville to Santa Monica to meet my old bosses, Luke and Travis, the guys who started PatientPop. I'd stayed on as an advisor, and over the previous few weeks, we'd been texting a lot about a real problem the business was facing.

The pandemic had shaken up business quite a bit. Doctors had pivoted to telehealth almost overnight, and PatientPop's physician customers needed something different from what the product was originally built to do.

I ate up the challenge, and jamming with Luke and Travis was stimulating my sales and marketing brain in a way I hadn't felt in years. I love these guys, and the problem was interesting.

At some point, somebody made a joke about me coming back to run the new thing, and we all laughed. But then, the texts got more serious. And they eventually asked if I'd meet up in person. So there I was at the Fairmont Hotel in Santa Monica, waiting for Luke, just like old times. I even snagged a seat at our favorite table outside.

And the moment I saw him, I felt it. The energy of working on a big, challenging problem with people I trusted. The feeling of being a people leader, and a part of something bigger than just me.

I'd spent the past couple of years alone in my home office, grinding away on my business, and I'd forgotten how addicting the feeling of teamwork and camaraderie can be. The energy that comes from being a part of something big and special.

I left the meeting totally lit up and proceeded to tell my wife everything I missed about my old career. She listened patiently, and I could see she was choosing her words carefully.

She was worried

Jennifer remembers things about me that I delete from my own memory bank. How things made me feel (and behave). She knows what happens when I get lost in work where other people depend on me, and I have to depend on other people. Where goals are big, targets come with excruciating pressure, and board members don't mess around being nice.

In that kind of environment, I grind myself down to the nub. Because I'm terrified of failure, or worse, disappointing people I respect. The idea of something not going great on my watch is a situation I'll work to avoid at any cost.

So I push until I'm physically and mentally worn out, and Jennifer has seen it enough to know the whole story before it starts. So she worried I was seeing this opportunity through rose-colored glasses. Couldn't I remember how burned out I was when I left?

But I wasn't ready to hear that. So I went back to the company for eight months, continuing my own online business in tandem.

While we launched telehealth and made a big splash in the market and got the P&L looking good, something was off. And it felt that way almost from the start.

The company was amazing, and the people were fantastic. But the version of Justin I'd been missing wasn't in me anymore. I wasn't excited about doing the actual work. I was excited about the identity. The CRO title. The steady income. The ability to coach and lead a team of all-stars. The C-suite bio. The invitations to speak at SaaS events and popular podcasts. All the stuff that sounds impressive, and feels especially important when you don't have it anymore.

But when I got back into the beast, I realized that none of those things actually make me happy. I'd moved on to building my own thing, to the freedom of controlling my days, to not having to ask anyone for permission for anything.

I'd undervalued those freedoms when I was sitting alone in my home office, feeling isolated. I realized I'd focused on what I was missing instead of what I had.

And when I returned to just running my own business, it was the most relieved I'd ever felt.

What I got wrong

It took me a long time to understand what had actually happened here. Because those feelings at The Fairmont Hotel were genuine. The pull was real, and my excitement was undeniable.

But I never stopped to ask myself a simple question: Why do I actually want this? Not "Do I want this?" That second question is too easy to answer when you're caught up in a moment. The better question is why? And if I'd explored that, the answer would have been uncomfortable, but obvious.

I didn't really want that job. I wanted that title. I didn't miss the work. I missed the identity of being an important C-suite exec in tech. I was trying to go back to a version of myself that was long gone.

Looking back, I should have seen that coming. I've learned that I basically have a five-year shelf life for work. I spent five years in pharma and med devices, five years at ZocDoc, and five years at PatientPop. And every time a five-year anniversary starts creeping up, I get itchy. Itchy for something new, and I start feeling like a different person than the one I was at the beginning of that particular journey.

Going back to PatientPop wasn't a return to something I truly longed for. It was me trying to be someone I'd outgrown.

Why this matters

A buddy of mine runs a small SaaS company in London. A few years ago, he spent 12 months and a lot of money buying out an unsavory business partner. It was a miserable experience, but when it was over, he owned 100% of his company, and that satisfied him.

Then, just a year into full ownership, he started to consider bringing someone else into the business. A new partner with a new equity split. He was ready to give away a huge piece of this thing he'd spent all that time and energy and money fighting to gain ownership of. And when he finally stopped to ask himself why, the answer had nothing to do with needing a partner.

He realized he was just lonely.

He felt isolated sitting alone in his house, running his business. He missed having someone to talk through problems with, someone to share the weight of bad decisions, and the success of good ones. But he didn't need to give up equity and ownership to fix that problem.

He ended up hiring a developer and a sales guy. He kept his ownership and suddenly had smart people to work with every day. Celebrations were better, tough times had more support, and the pull to bring on a partner disappeared over time.

My buddy almost made a costly mistake because he confused being lonely with needing a co-founder. The feeling was real, but he was misinterpreting the signals.

That's something we should all pay attention to. The pull always feels urgent and real, and sometimes it is. But the only way to know what it really means is to stop and ask yourself why you're actually considering the thing. Not whether you want it. But why.

Because "I'm lonely" is very different than "I need a partner." And "I miss feeling important" is very different from "I miss the actual work."

The bottom line

I hit this same crossroads again recently when I discontinued my two most popular courses, The LinkedIn OS and Content OS. In doing that, I parted ways with about 75% of my typical monthly revenue. And wouldn't you know it, a few weeks after I shut it all down, I felt that familiar pull to bring them back. They made great money. It was a proven model. There were millions of dollars a year just sitting there waiting for me.

But this time, I knew the right question.

Why do I want this?

And the answer was that I missed the money and the safety net. But I didn't want to be the guy who teaches people how to use LinkedIn or write content. That's why I discontinued these products in the first place. My five-year itch has me going in a new direction. I was just yearning for the comfort of a stage I've outgrown. And, as David Brooks would say, I'm looking for my "second mountain."

I want mine to be built around creative impact, getting better at things I'm bad at, and doing work that challenges me instead of feeling monotonous. I want to continue writing counterintuitive ideas on earning money, reclaiming your time, and building a life you choose. I'm leaning into a new identity as a writer who asks challenging and interesting questions about life and business, and somebody who definitely doesn't have all of the answers but stays curious.

So here's my question for you today:

Is there something from your past that's pulling at you right now? And if you stop to ask yourself why you actually want it, what does your honest answer tell you?

If you're up for sharing, reply and tell us. While we can't reply to everyone, Jennifer and I love reading every response that comes our way.

That's all for this week.

See you next Saturday.