255: The Dizziness of Freedom

In my work with founders and ambitious outliers, I often meet them in a period of anxious uncertainty—where should they take their company or their life next? Having thrown off the standard life path that their parents and many of their peers have followed, they are confronted with an overwhelming need to optimize their choices. They want to find conviction in their next moves, to try and secure the best possible outcome.

Nearly two centuries ago, German philosopher Søren Kierkegaard described this kind "angst" as a human reaction to the immense possibility of choice within our lives. He called this overwhelming feeling—this sense that we have just one life but endless options—"the dizziness of freedom." In his view, this anxiety kicks in whenever we face the sheer vastness of our existential freedom - our constant ability to take action or hold back, to become something new or stay the same, at every single moment of our lives.

The more freedom we gain for ourselves, the less security we get to fall back on.

There's a fascinating theory that newborns experience what's called the "fourth trimester" after birth. Even though they've left the womb, they still crave its familiar comforts. My 15-day-old daughter, for example, falls asleep much easier when she's wrapped up tight in blankets or snug in a sleep sack – just like she was in the womb. It's funny to watch her occasionally fight against the swaddle though, her tiny arms struggling to break free of their cozy prison.

But then once her arms are out, they tend to flail wildly, and she's often more distressed than when she was bound up. Many infant experts will tell parents not to be fooled by her desire to free herself. That she's actually still seeking the familiarly of restraint—the constraint of the womb—and needs several months to slowly acclimate to having her arms and legs totally free.

Look I love freedom. Quitting your job to start a company removes constraints on your ability to act and gives you greater freedom to operate. I got to experience that freedom several times as a startup founder and now enjoy it as a solopreneur. It's fantastic.

And yet at the same time, I've seen that many of my clients avoid commitment. Committing to a product direction or to a remote or in-office policy. Committing to a romantic partner or to having kids. Partly because they don't have enough data to feel totally sure. There are too many unknowns—it's impossible to calculate the perfect answer. But I think there's something deeper going on too: commitment means giving up options. It means trading some of that precious freedom for something else.

I got married more than five years ago. And I'm now a father. I have significant constraints on my time and ability to act in my personal life. Yet, these constraints have also removed a lot of angst from my life.

When I go to a party or social event, I don't have to look around the room and ask myself if there's someone I might want to ask out. I can just talk to whoever feels easy to chat with, and not worry about getting their number and following up.

When my daughter is crying, I don't feel overwhelmed by the possibilities in life. I have an immediate priority: to make sure she is safe, changed, fed, and comforted.

There's remarkable clarity in knowing exactly what I need to be doing at any given moment because of my responsibilities and duties. I took vows to care for my wife when we got married, and I take them seriously. But she's also a smart, capable woman who can plan ahead, respond to new situations, communicate her needs clearly, and acquire assistance from many sources.

But a 15 day old infant can do none of those things. My daughter needs my attention and support—specifically mine—in a way that no one and nothing else does. Even my clients could, if they really needed to, find another coach or some other ways to getting the partnership they need to write their next chapter.

Kierkegaard knew something important here: chasing perfect certainty is usually a dead end. He believed that truth isn't just cold hard facts—it's deeply personal, built from our passions and the gutsy choices we make. Even as modern life has made it possible to track and analyze everything from our heart rate variability to the number of questions we ask in meetings, there's no app that can tell you how to life your life, and how to make big decisions. Maybe we need to let go of the idea that there's an objective best option and instead lean into making bold commitments that actually mean something to us.

It's easy to embrace the idea that if we could just measure and analyze enough data, we'd have all the answers. But here's what Kierkegaard would have said: it's not just about having the freedom to chose—it's about making choices that move your story forward.

I'm not saying to leap blindly into things. My wife and I debated having kids for years before we finally pulled the trigger. But I am challenging us to trust our gut and follow what feels deeply true to us. For all those founders and ambitious folks out there, maybe true freedom isn't about keeping all your options open forever. It's about having the courage to say "this matters to me" and going all in, even when you're not 100% sure. Because when you commit to something that's uniquely meaningful to you, you're more likely to find yourself on a path that's real and ideally suited to your nature.