The Agony of the In-Between: Why Career Transitions Take So Damn Long

Read time: 4 minutes

Welcome to My Musings

Where I share insights that have impacted me, thoughts on personal growth, and actionable strategies to help you navigate career and life transitions.

Today: Think it’s taking a long time? Wait longer.

The Persistence of Memory, Salvador Dali, 1931

Once I left law, I expected the next thing to reveal itself—quickly.

I would vent, complain, whine, rage, and generally spiral in my therapist’s office about how unbearable it was to be in the liminal space between “lawyer” and “whatever comes next.”

One day, after a particularly passionate rant, she looked at me and said: “You should probably expect this whole process to take four years.”

I was livid.

Nothing in my life had ever taken that long—except maybe undergrad, and even that felt optional at times. As a lawyer, I was trained to produce results fast. Certainty was currency. Ambiguity was weakness. And now someone was telling me it would be years before I knew what I was doing with my life?

My immediate reaction was: absolutely not. I needed clarity. I needed income. I needed to know I hadn’t made a mistake. And I needed all of that right now.

It was a Lulu moment. (There’s a book my daughter loves where a tiny character named Lulu screams, “I want a super cute chick. RIGHT NOW.” Her parent gently responds: “No, Lulu. You can’t have a super cute chick right now.”)

Patience, it turns out, is not only a virtue—it’s also a complete pain in the ass.

Especially in the middle.

That murky middle space of a career transition—between who you were and who you’re becoming—is brutal. You’ve left the certainty of the shore but haven’t yet spotted land. You’re floating. Adrift. Waiting.

What helped me survive that phase wasn’t more doing. It was, bizarrely, less.

Less trying. Less striving. Less building and branding and forcing clarity. Instead, I started experimenting with a slower way of navigating change. I learned (painfully) to trust that the new thing wouldn’t come from effort alone.

A client recently said to me, “Jordan, your real expertise is getting people to do less.”

I laughed. But she was right—with one small caveat.

It’s not about doing less for its own sake. It’s about engaging with life in a way that feels less effortful. Especially for professionals who are trained to grind, to problem-solve, to outperform.

Sometimes, the smartest thing to do is stop paddling for a moment and let the current show you where it’s going.

This isn’t some passive “just be” message. We still do things. We still move. But we stop trying to hack our way through the fog. We shift from performance to presence.

In Transitions, William Bridges writes about transitions as three-part journeys: an ending, a messy middle, and then a new beginning. But the beginning doesn’t arrive just because you want it to. It only comes after you’ve let go of the identity and baggage from the thing you left behind.

You can’t rush a sprout. You can’t will a seed into a blade of grass.

Sometimes, the most productive thing you can do in a career transition is wait. Not idly. But patiently. Purposefully. Compassionately.

And in the waiting, something quiet starts to grow.

So—where are you now?

Still paddling hard? Drifting? Standing on the shore?

If you’re navigating your own in-between—whether post-law, post-role, post-anything—I work with people in exactly that space.

If this resonated and you want a space to figure out what’s next (without pretending you already have the answers), I’d be happy to talk.

You can learn more about coaching here, or feel free to reach out directly.