The Dizzying Freedom of Self-Employment
I’ve always had mixed feelings about my own self-employment.
The conflict isn’t hard to imagine: I love the freedom. But sometimes I just want someone to tell me what to do and deposit money into my account every two weeks.
My divorce ended most of that ambivalence.
When I decided I needed to leave, I hadn’t made a significant amount of money in years. If I’d tried to get a full-time job, I’m not sure I would’ve been hireable after stepping away from my career for so long. And there was no way a traditional job would’ve let me keep my house or maintain even a semblance of my old lifestyle.
I’ve been grateful ever since that I had a business I could rebuild. The path was really fucking hard, but another path back into the workforce would have been impossible.
So over the weekend, when I heard Fareed Zakaria quote Kierkegaard on Ezra Klein’s podcast, it hit hard.
Yes, Kirkegaard. Ready?!
He said, “Anxiety is the dizziness of freedom.”
They were talking about Ezra Klein-y things, but the phrase really resonated in the context of entrepreneurialism.
What’s the “safe path” now?
Lately, I feel surrounded by layoffs.
Talented friends with real seniority. New clients coming to me because they were let go, even though they’re at the top of their game. People realizing that the “safe” corporate path isn’t safe at all. Apparently October was the worst month for layoffs in 22 years.
It used to be that full-time employment was the responsible, secure choice.
That’s just not true anymore. The time of company loyalty is over.
It’s kinda wild to say this, but self-employment is starting to feel like the safer bet.
Being in charge of your own destiny is a double-edged sword, of course. It’s exhilarating in its possibility and terrifying in its risks. But that mix—the thrill, the fear, the vertigo—is exactly what Kierkegaard was describing.
When you’re self-employed, that “dizziness of freedom” is the reminder that you’re free enough—and capable enough—to build the life you actually want.
A little anxiety can also be just what you need to inspire action.
Anxiety that works for you
So how do you make that anxiety work for you and not paralyze you?
I’ve shared before that I spent the first decade of my business flailing and fucking around. I was technically working for myself, but I wasn’t running a business. I was letting the business happen TO me, taking whatever clients floated in and building no real systems.
True entrepreneurship didn’t start until I got intentional.
After my divorce and the end of a couple long-term retainers, I knew I needed to get serious. Hello, financial anxiety!
That meant finally niching down, creating an actual marketing strategy, and building systems that let me scale beyond trading hours for dollars.
Anxiety? Who dat?!
If you build it, they won’t necessarily come
Most people don’t want to hear this, but you can’t grow a business in secret.
I’d love to build you a beautiful website with clear, conversion-focused copy. But if you don’t tell anyone it exists, it’s going to sit there looking pretty and doing nothing.
The other thing that’s sometimes hard to hear: building a business takes time.
Everyone’s timeline is different, but many people say to give it at least a year of trying things, failing, iterating, and showing up consistently before deciding something “isn’t working.”
The good news: marketing a service-based business can be simple.
Here’s what keeps my pipeline full and pipeline-ing:
In-person and virtual networking
Regular connection calls (aka coffee chats)
Posting regularly and intentionally on LinkedIn
This here weekly email newsletter
I focus on showing up, building relationships, and consistent messaging. I’m always clear about what I do, who I serve, and what problem I solve. And that messaging is repeated everywhere I show up: in conversations, on LinkedIn, and in this newsletter.
That kind of consistency builds trust. And trust keeps the calendar full.
No complicated funnels. No paid ads. No TikTok dancing required.
Where anxiety meets strategy
In addition to consistent marketing, here are a few other things that make self-employment feel safer and more sustainable:
A real point of view or a clear niche. Everyone feels safer working with an expert. And being known for something makes you easier to refer.
A clear, simple service suite. The fewer decisions clients have to make, the easier it is to buy. And avoiding too many custom proposals will make your business more profitable and a lot less full of bullshit.
Predictable marketing and lead-generation rhythms. Create one weekly action that connects you with new people or moves the ball up the field. I find it helpful to treat myself as a client I can’t let down.
The dizzy part is the point
The older I get, the more I realize that anxiety isn’t a sign you’re on the wrong path. It’s a sign you’re standing at the edge of possibility.
That fluttery, vertigo feeling we get as entrepreneurs?
That’s freedom. The reminder that nothing is fixed. Evidence that YOU get to decide what is possible for you.
Self-employment isn’t safe because it’s easy. It’s safe because it puts the reins back in your hands.
I’ll take that dizziness over a full-time job’s illusion of stability any day.
Goodies Just For You
WHAT I’M THINKING ABOUT: If you want to listen to what Fareed Zakaria and Ezra Klein were really talking about (hint: it wasn't entrepreneurialism), you can look it up here. It's a great conversation that's mostly about the transition from people voting on economic issues to voting on cultural issues. I was gratified to hear them talk about White “Identity Politics” for once.
WHAT I’M BAKING: I’m planning to make Mark Bittman’s Apple Crisp for Thanksgiving this year. I do use the chopped nuts (walnuts). And I always double the topping. It’s the only correct way.
WHO I’M ADMIRING: Last week I had the pleasure of attending an intimate event hosted by REIGN with Shannon Watts, the founder of Moms Demand Action (the nation’s largest grassroots volunteer network advocating for public safety measures to protect people from gun violence). Shannon’s on tour promoting her new book, Fired Up: How to Turn Your Spark into a Flame and Come Alive at Any Age. A few minutes into the talk, I thought, I wish this was being recorded! Because she was so fucking inspiring. She was encouraging us all to be activists and organizers in our own way. Luckily my friend Laura took notes. A few gems I’m still chewing on:
“If I had waited until I knew everything, I'd still be planning.”
“Men fulfill desires. Women fulfill obligations.”
“Democracy is like a sick child. We have to hold its hand until it’s better.”
“Hope is a discipline and progress is frustratingly slow. But if you give up every time you lose, you’ll never win.” And then, “Women are expected to disappear when they fail.” Oof.
