Your Own Transitions Are the Training Ground for Empathy

So you want to see how much you can improve your empathy as a leader or as a coach?

Good. Buckle up, because we’re not going to talk about emotional intelligence as some abstract concept you toss into a slide deck. We're going to get personal. Not over-sharing-at-the-airport-bar personal, but close.

Because the truth is: empathy isn't built in the classroom. It’s built in the moments where you felt like your life was duct-taped together. The job you didn’t get. The city you moved to and instantly regretted. The baby that wouldn’t sleep. The breakup that cracked something open. The reinvention you didn’t ask for.

Those transitions? That’s where your empathy lives. And if you haven’t looked back at them lately with some curiosity, you’re leaving a lot of potential on the table—in your coaching, in your leadership, and in your relationships.

Life transitions: the ultimate empathy training ground

Every human being goes through transitions. But coaches? We need to study them. Not just academically—but in ourselves.

Empathy doesn’t mean you’ve had the same experience as someone else. It means you know how to meet someone in the emotional neighborhood of their experience. And the only way to do that with depth is to know your own emotional zip codes.

Start here:

• When in your life did you feel like the rug got pulled out from under you?
• When did you feel like a beginner again—awkward, unsure, a little sweaty?
• When did you surprise yourself with resilience?
• When did you not show up well—and why?

Transitions expose the stories we tell ourselves under pressure. And coaching is often a process of helping people rewrite those stories. If you’ve been through your own plot twists, you’re better equipped to hold space while someone else is rewriting theirs.

My favorite trick: the transitional time capsule

Here’s a tool I’ve used for myself and with fellow coaches I mentor. I call it the transitional time capsule. You can do this in a journal, a voice note, or even with a trusted peer.

Pick a past life transition—big or small. Maybe it’s the time you moved cross-country. Changed industries. Became a parent. Came out. Got divorced. Went back to school. Canceled the wedding. Signed the lease. You know the one.

Ask yourself:

• What did I believe was true about myself or the world at the start of that transition?
• What was I afraid of?
• What did I hope for, even if I couldn’t say it out loud?
• Who surprised me with their support—or their silence?
• What did I learn that still shapes me today?

This is gold. Not just because it makes you wiser, but because it softens the way you sit with someone else’s uncertainty.

Your mess makes you trustworthy

There’s this myth—especially among executive coaches and leaders—that we need to be perfectly put-together in order to be credible. Nope. What makes you credible is your humanity. Your ability to connect dots. Your willingness to listen without fixing.

When you’ve gone through something hard and come out a little scarred but still standing, you gain the kind of presence that can say, “I don’t have your answers. But I know how it feels to not have any yet.”

That sentence, by the way? More comforting than a dozen checklists.

Empathy isn’t about coddling. It’s about seeing. And we can't truly see others until we’ve looked at our own lives honestly. That includes the ugly crying. The mixed feelings. The “I don’t know what the hell I’m doing” moments.

When you know your own storylines well enough, you start to catch the subtle ones in others. You hear the self-protection behind someone’s dismissiveness. The hope under the sarcasm. The fear hiding inside the perfectly polished LinkedIn post.

Why this matters in coaching—and in leadership

Let’s be real. Most of the time, people aren’t asking for advice. They’re asking for understanding. They want to feel like they’re not broken for feeling lost, or scared, or stuck.

And you? You can’t fake that kind of understanding. You either have it, or you don’t.

But the good news is: you can grow it. And it doesn’t come from reading more Brene Brown. It comes from sitting with your own discomfort long enough to mine it for meaning. From seeing your past self not as a cringe-fest, but as someone doing the best they could with the tools they had.

If you want to be a better coach, facilitator, or leader—don’t skip over your own transitions. They’re not detours. They’re the training ground.

One final prompt

Ask yourself:
What is a transition I’ve lived through that could help me show up more powerfully for someone else?
Write about it. Talk it out. Reflect on how it shaped your lens. Then look at your clients, your team, your family—with fresh eyes.