Freedom. Sort of.

My buddy David texted me the other day to ask if I could do a long hike on a Friday afternoon sometime soon. I've been itching to get out to Minnewaska State Park, so I said yes immediately. I opened up my calendar, dragged some time blocks around, and our hike was officially on my schedule.

I felt excited to catch up, get out to the park, and get some exercise. And I took a moment to appreciate that. Because back in 2016, when I was running revenue for a SaaS company, the suggestion of a Friday afternoon hike would have been obscene. An automatic no. No one who knew me would have even asked, because asking an executive to leave work on a Friday to go hiking would've been just ridiculous. I was way too busy. The funny thing is, I'm just as busy now. Maybe even busier. I just have a different boss now.

And that makes me wonder if what I’ve built is really all that different from my old startup life.

Freedom can be a wrecking ball

When I quit my job in 2019, I tried to embrace "freedom" the way most new entrepreneurs probably do. I woke up when I wanted, worked the hours that felt good that day, and I took random days off when Jennifer enticed me.

And I only lasted about eight weeks before I realized that free time, as good as it sounded, wasn’t working out very well. Drinking coffee and relaxing until 11 a.m., news pulled up on one computer screen, and group texting friends on another. I made very little progress building a sustainable consulting business. And two months in, I was already wondering if I'd made a huge mistake.

So I decided I’d better build a schedule. And, even though it's changed over the years, it's almost always ended up tighter than the one I'd quit (which is saying something).

I’m (almost) always up by 5:30. At the gym by 8:30. And sitting at my desk by noon. Three hours of writing, ninety minutes of email, admin, and content creation, and offline by 4:30. Give or take a few edits, it's the same hours and same order, almost every day.

I know that looks rigid. It IS rigid. But it's the engine that makes everything else in my life work smoothly. The Friday afternoon hike becomes doable. We can take sabbaticals in the winter. And I get free mornings with Jennifer. I've built a work schedule that gives me the ability to say yes to almost anything that matters.

Pure freedom looks like drift

What I learned back in those first eight weeks is that the version of freedom most people imagine when they leave a job isn't actually freedom. It's drift. And drift, if you do it long enough, ends in the same place every time.

My friend and former colleague, Craig, learned that the hard way.

Craig was a world-class sales development leader for years. Then in 2020, he left his job to start coaching other people who were new to the role he’d perfected. He's a sharp guy with a great network, and in just a few months, he built a small pipeline of coaching clients, mostly through word of mouth.

But when Craig actually started coaching, he was surprised by how much of his time and energy it required. He really wanted to spend his newfound freedom with his fiancé. So they traveled. They went all over the world to ski. They lived the glamorous digital nomad life that everyone on Instagram envies.

The problem was that between the ski trips and the time zone changes, travel logistics, and actual coaching, Craig didn't leave any time to market his practice. He wasn't producing any content, and cold outreach dried up. His pipeline went from healthy to almost nothing.

Then his first few clients churned, which happens because coaching engagements eventually end. And when they did, Craig didn't have new ones lined up, because he hadn't been doing the work to find them.

Within two years, his coaching practice was effectively dead.

To be clear, Craig wasn't lazy. And he certainly wasn't stupid. He was just trying to live the life he'd quit his job for. He chased the version of freedom that you might picture when you imagine leaving a job. The no-alarm, ski-on-a-weekday, do what I want, follow-the-energy version of life.

What freedom actually is

A hike with David on a weekday is freedom. Traveling for the winter is freedom. Intentionally designed mornings with Jennifer are freedom. Saying yes to almost anything that matters, inside of thirty seconds, is freedom.

But every single one of those things only exists because the schedule does. Because I’ve sorted out all my business requirements and mapped them out on my calendar. Without the rigid schedule, the business doesn't run. And without the business running, none of the yeses are possible.

That's the difference between the life I have now and the one Craig had for a couple of years before the math caught up with him.

The bottom line

The idea of freedom that most of us chase when we leave a job doesn't really exist. The version where you screw around all day, doing anything you want, anytime you want, with no structure holding you up? That’s a myth. That version of freedom ends up the same as Craig's story. Or like my first eight weeks. Or like a thousand other people I've watched quit a job, declare themselves “freedom warriors”, and then quietly drift back to the traditional job world.

The version of freedom that actually works is smaller and more boring.

It's the freedom to put the gym block where you want it. The freedom to decide that 4:30 p.m. is when work ends, and to mean it. The freedom to drag a few calendar blocks around on a Wednesday morning or clear a Friday afternoon, because you built the rest of the week tightly enough that the Friday afternoon can be flexible.

The freedom is the freedom to choose your constraints. Not the freedom from constraints.

That's a lot different than what most people picture when they imagine it.

So these days? Yes, I'm just as busy. But the busy is all mine now.

So here's the question I've been thinking about this week: Have you ever chased a no-rails version of freedom and found out it didn't work?

Reply and tell me about it. While I can't reply to everyone, Jennifer and I read every response, and we love hearing from you.

That's all for this week.

See you next Saturday.