Either / Or (But Mostly Neither)
The Midlife Professional’s Dilemma
A meaningful life isn’t chosen once - it’s chosen over and over again.
Especially when it scares the shit out of us.
There’s a moment in every professional’s career - usually somewhere between year four and year seven - when the fog lifts just long enough for a single, horrifying question to come up:
“Is this it?”
It’s devastating.
You are too early into it to quit, but it’s too late to honestly say you didn’t know.
And, at this time, you are likely well into your thirties, considering all the things that life usually offers around then - a home, a family, a partner.
It’s the perfect time for an existential crisis.
By this stage, you’re also competent, trusted, and no longer triple-checking every email or document (because you don’t need to). The work is still sort of interesting, but the sheen has worn off.
You’re in what I call the liminal zone, though anyone who’s actually been in it knows that doesn’t really sum it up.
For professionals, especially lawyers, this zone also comes with a bonus fear: If I stay much longer… I might never leave.
And so begins the panic.
Søren Kierkegaard’s Warning
Through some other reading I was doing, I recently came across Kierkegaard’s Either/Or, in which he lays out the “either/or” of how (in his view) most people choose to live:
The aesthetic life - chasing beauty, richness, novelty, possibility.
The ethical life - doing what you’re supposed to do, fulfilling your duty, choosing stability and responsibility.
It’s important to note that he doesn’t say either is better.
But, he is saying that things tend to fall apart when you try to live or work both ways - or, neither.
The Professional’s “Either / Or”
Let’s assume you’re around year 5 of practice. You’ve built just enough identity around your salary, competence, and title that walking away feels not only like it would be painful, but also, perhaps, just dumb.
But you’ve also lived long enough in the profession to know that what’s next - partnership (maybe), bigger files, weightier expectations - are not going to magically fill your cup in terms of meaning, purpose or spiritual clarity.
And this is exactly where Kierkegaard places the main character in Either/Or:
Between the life you’re supposed to want
and the life you secretly hope is still possible.
You are “supposed” to want partnership, prestige, more sophisticated clients and files.
You are “supposed” to be stable and reliable and not have aspirations to anything else besides professional success.
But, you have also been doing this long enough to now remember the other things you hoped you could do. Going back to school. Or, taking that yearlong trip you always dreamed of. Or, moving to another country with your family.
Or, getting back to that career path you sidelined to pursue law instead because it was what you were “supposed” to do.
You’re both the aesthetic self (wanting creativity, freedom, adventure)
and the ethical self (wanting to be responsible, not reckless, admired, safe).
As a lawyer I know and respect said to me when I left the legal profession, “You finally woke up?”
Yep.
That’s when the other questions kick in.
“Is the life I built actually mine?”
“Do I want this story to continue?”
“What else could I be if I wasn’t so damn afraid?”
Kierkegaard would say you’re confronting the “dizziness of freedom” - when the aesthetic and ethical selves finally decide to fight for dominance.
Now, this is not a comment on other people, but - lawyers and other professionals are trained to tolerate absurd amounts of pressure, most people try to just muscle through it.
Have you ever said this to yourself: “It’s fine. I’m fine. Everything is fine.”
It never really is.
But, the ability to tolerate keeps you dizzy and stuck in the liminal zone.
This is how you end up scrolling job postings at your desk throughout the day (and, perhaps, into the night), reading the bios of people who left your profession for UX design, thinking, “Maybe I could do that too?” (You could. But that’s not the point.)
The real issue: identity hardens faster than truth
At year five, your identity starts congealing and you start to believe this story:
“This is who I am.”
“This is what people expect from me.”
“It’s too late to change.”
“If I step off the path, I’ll lose everything.”
This is Kierkegaard’s ethical existence taken too far - duty without self.
Meanwhile, the aesthetic part of you - the part that once wanted more than billable hours or deal closings or prestigious appointments - feels abandoned.
So it starts knocking.
But, what do you do about it? Do you answer?
The way out is not choosing one over the other
I don’t think Kierkegaard intended Either/Or as a binary.
It’s really intended, instead, to be an invitation to integrate the parts of you that want meaning, and stability, and fun, an creativity, and responsibility.
Which is so much harder than choosing one or the other. Because it’s a dialogue - it’s a constant, and often exhausting, negotiation with your own complexity.
And honestly?
Most lawyers and other professionals are uniquely equipped to negotiate… except with themselves.
So if you’re in the “liminal zone”, try asking:
What part of me is starving right now?
What part of me have I over-prioritized to please others?
What have I been postponing in the name of “being reasonable”?
Where am I choosing safety over aliveness?
And, importantly: What small experiment could I run that lets both the aesthetic and the ethical operate?
If you’re sitting in that tension — you’re finally in the real conversation.
And, if you’re there, I’d love to hear from you.
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