Sabbatical Stories: Emily Drake

This is the first in a new series called Sabbatical Stories - a collection of candid Q&As with professionals who have experienced a sabbatical first hand. Each story offers a different window into what happens when we finally make space for ourselves and what we learn when we stop moving long enough to listen.

This week we’re featuring Emily Drake. Emily is the CEO and co-founder of The Collective Academy, where she helps leaders and teams build cultures grounded in connection, curiosity, and care. A licensed therapist, executive coach, and creator of the Who’s Missing?podcast, her work spans from boardrooms to classrooms, including leadership programs for organizations like Kirkland & Ellis, the MacArthur Foundation, and Walgreens. She also serves as a career coach at Northwestern University’s Kellogg School of Management.

Emily is stepping into this new feature as both the subject of today’s interview and the ongoing editor of this series for The Midlife Sabbatical.

This is Emily’s sabbatical story.

ED: My sabbatical was a response to a cultural, political, and economic moment. In other words, it wasn’t planned. But it was right on time.

I had just come off the most successful year revenue-wise for my business, The Collective Academy, supporting a team of four, including myself. That felt like an important brick in the foundation. But still - there was the 2024 presidential election. When the results came in, a few key clients immediately tightened their belts, taking leadership development and coaching in-house or off the table entirely.

I knew 2025 would be a marathon. I had a decision to make: do I sprint on a new sales cycle, something I know to be intense and effective? Or do I... not.

At the same time, I was choosing not to pursue a business partnership I had been nurturing for two years. That no was huge. It was thrilling, actually. Because it meant I was saying yes to something else: space. A resource so rare for midlife professionals, and one I didn’t realize how much I needed.

ED: Deciding not to sell anything or return to the rigor of business development was liberating.

Owning my own business meant I was always thinking about which levers to pull, which products to create or re-engineer, and how to manage staffing decisions. I hadn’t realized how much of my value was tied to earnings. When that pressure lifted, I could finally ask: Do I even like what I do?

I’m good at it—but that doesn’t always mean it’s fulfilling. That was a revelation.

ED: Living with the shame of not bringing in an income was hard, but important. Independence is my number one value.

We were fortunate to have savings, but my willingness to actually use it was the real challenge. I’ve often asked myself, “Do I deserve this?”—a new car, a trip, even something small like home beautification. It’s such a buzzkill. So I decided to reframe it: This is what we were saving for.

Money, to me, has always been about freedom. And choosing to use it to create space was the best possible investment.

It was also hard to rely on my partner, Arnie. But therapy has taught me something beautiful: it’s okay to need someone. For someone who prizes independence as deeply as I do, that was a radical realization. Turns out—I need him. I need people.

ED: An unsolvable tension I live with is this: I want to be part of a team, and I want independence.

If I double-click on that, what I really want is to control the cultural tone. I’m at a point in my career where I know exactly how I want to work—and how I want to feel while doing it—and I’m uncompromising about that.

I’m still ambitious, but not at any cost.

So much of my consulting work kept me on the periphery by design. I couldn’t get close enough to the real action for it to feel juicy and meaningful.

Whatever I do next, it has to put me at the nucleus of something—or someone. I’ve learned I can get creative about how to reach that epicenter. That’s the fun part.

ED: Before this, I thought it was impossible to take a break while things were good.

I had success by every cultural measure—a solid book of business, a strong reputation, and real pride in my work. But when the opening appeared, I took it.

For once, I wasn’t burned out. I had my wits, my energy, and my curiosity intact. I got to slow down and learn about myself, my relationships, and what truly matters. That’s a profoundly different experience from stepping away because you’ve hit a wall—which I’ve done twice.

If the commodity you need is space, and you know it, check your finances, talk to your people, and take your break. You’ve earned it. There’s a whole community of people who will help you into the next season.

ED: Pro tip: deactivate your social media.

I move, love, write, read, and live so differently when I’m not thinking about how I’m being perceived. I spend more time with the people who are part of my nucleus. Who and what I care about becomes crystal clear.

It’s amazing how much more potent your sabbatical becomes when you take away the performance of it.

[Interview has been lightly edited.]

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