Freedom. Sort of.
What if the freedom you quit your job for isn’t really freedom?
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.
The Saturday Essay by Justin Welsh is a weekly email for ambitious people living and working on their own terms.
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This essay was originally published here.
This is something I wrote recently. I realize that it isn't "apples-to-apples" - I wrote the following about retiring early and you're talking about quitting a job to work for yourself - but they're both about the concept of freedom. I am about seven months away from leaving work and admit that I am very curious to see whether I end up keeping some sort of schedule or not. I'm generally pretty structured, perhaps having a routine and waking up without an alarm clock will be freedom for me.
I skimmed the opening paragraphs of a Substack article about a woman's therapist asking her who she was without her job - after she cried through talking about sleepless nights and missing the gym to try and make deadlines at work. She said her mind went blank. She said she thought about the question for a week and was still finding nothing.
I am utterly incapable of relating to this. I say that without judgement. I feel for this person, and it felt like it was the beginning of her story of figuring it out. Which is great. But I am exactly the opposite. Without her job... her mind went blank. Ask me this question and my mind runneth over. I am the books and music I consume, my workouts, the meals my wife and I enjoy together, an excellent cup of morning coffee, a good conversation with an old friend, my next trip...
My job doesn't define me. It limits me. It is a hindrance. The best thing I can say about it is that it’s a means to an end. Now, maybe this woman likes – or liked – aspects of her job. Maybe it's less extreme for her. For her sake, I hope so. I know this is true for many people, but it’s never been true for me.
I hear people talk about the idea – or the reality – of losing meaning after retiring and I'm incredulous. I can spend an entire morning, and then some, perusing the news or poring over my investments. All while enjoying a coffee or two. I also like to get my workouts in before lunch. An afternoon? How about getting lost in a novel, picking tomatoes, throwing together a legume salad with just too much olive oil and garlic, writing, or helping a neighbor in his yard...
As someone planning on retiring early and moving abroad, I often come across content by and/or about people who have done just that. Inevitably, in the comments are questions about what they do with their time. There are replies. And then comes the question: “But what do you do after that…?”
I see these exchanges and I feel for those people. Not haughtily, as someone sneering at the uninitiated, but rather as someone who knows all too well how hard it is to feel like you’re always chasing something, feeling like you need to be productive, like there are never enough hours in the day. And, thankfully, I also know the languorous feeling of being present, the sense of utter contentment that can be experienced simply hanging the laundry to dry on a sunny afternoon.