For Directors, VPs & Execs Navigating Mid-Career

Your next decade starts with knowing what you have to say.

Nobody warns us about the wall we hit 15-20 years into our careers. Roles that used to excite us don’t. Options don’t feel quite right. Our lives have changed, and it’s unclear how it all adds up anymore.

And nobody hands us the map.

You’ll get the standard advice: talk to a lot of people, hone your story, list your criteria, make smart choices. But you can follow this for months—sometimes years—and still be in the same spot.

The problem is that our whole navigation system has been built around a ladder instead of a platform. We try to find the next rung instead of asking the real question at this stage: “What am I here to say? What’s the mark I actually want to make?”

Everything changed when I answered that.

I got my MBA from Yale and spent a decade climbing the ladder. I loved it. But as a Senior Director in tech, I spent over a year trying to find my next move—interviewing, talking with recruiters, looking for internal transfers. Eventually, I was so out of ideas I laid myself off and took a sabbatical.

During that time, my finger literally wouldn’t open another job application. That forced me to ask different questions, and to name the mark I want to make on others. What I discovered was a reservoir of creativity I hadn’t explored.

I trained as a coach, started writing again, launched my business, and the right work keeps finding me. And I’ve never felt more useful or more ambitious.

What I went through myself is exactly what I do for clients: put your purpose into words, connect to the voice that moves it forward, create from that, and use it as the lens for what to pursue. It takes courage. But on the other side of that voice isn’t just a new role. It’s a clear direction and a new way of being.

Voice is the shortest path to impact.

There’s a myth I bought into like everyone else: that bigger impact lives in bigger roles—that titles, companies, and industries unlock your future.

But now I believe the unlock lives somewhere else: your voice.

Every senior leader has papered over something inside them to get here. They’ve been rewarded for their filter and polish. But polish isn’t what creates change. Edge does. The thing you stand for. The thing you see that others don’t.

I built this practice because I think connecting to that edge—excavating it, saying it out loud, and leading from it—is the whole game. And it’s how the best next chapters begin. The ones with real clarity, meaning, and adaptability. The ones the world actually needs right now.

Develop a strategy for your next chapter.

I make a bet on behalf of every client: there’s a whole lot stored inside that’s ready to come out. We work 1:1 to use that as your guide and to get you making moves. Most of the core work takes about six months. Most people continue the work well beyond that.

If you’re interested in exploring this together, let’s start with a no-pressure 45-minute conversation. It might be the most useful conversation you have this month.

Elliot Greenberger
Elliot
Elliot Greenberger
Founder, Big Decisions Lab
A bit about me

I live in Los Angeles with my husband, our 9-year-old son, our dog, and a zoo of small animals. When I’m in motion, I like to dance, swim, and hike. When I’m more still, I like to read, cook, and play board games. I try to keep things simple when I can.

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What people say

Real clients who did this work and made real moves.

Christian
Managing Director, Consulting
Left a senior role to pursue his own venture

“I felt like Sisyphus pushing a boulder uphill. Everything was on the table, but I was stuck in an echo chamber of advice. This work shaved years off my journey and helped me stop playing by other people’s rules. I’m finally playing a different game now.”

Dhruv
Senior VP, Healthcare
Stepped into a significantly bigger role

“I used to look back on the last seven years and think, ‘What have I even been doing?’ Once I named my purpose, everything snapped into place. I’m having bigger, bolder, more focused conversations. I’m aiming much higher than I would have before.”

Miranda
Senior Director, Tech
Launched a consulting practice

“I was stuck at a major crossroads. Fear of failure had taken the wheel. This work got me unstuck—and I walked away with a personal framework I can come back to.

Alex
Senior VP, Finance
Landed the right role after a layoff

“I was hitting a wall with networking that kept leading to more of the same. This work gave me a purpose that summarized everything: what I want to do, can do, and will do. It opened a lot of doors and closed a lot of others—in a good way. Without it, I would have settled just to end the search.”

Emma
Head, Marketing
Pivoted into a new industry

“My friends would just say ‘get a new job’ and I was like, ‘I did that but it didn’t work.’ Turns out I didn’t need a new job—I needed a whole new outlook. This work had a regrounding effect. Now I know what I want to wake up and do, and I’m confident in the decisions I’m making and the opportunities I’m turning down.”

Jonathan
Director, Talent
Took on a new role while writing a book

“My career would’ve gotten very still, very quickly. Now I feel back in the driver’s seat. I got real clarity about what I’m building, which makes it so much easier to act with confidence.”

Jeremy
Director, Healthcare
Pitched a new role in his organization

“Elliot helped me connect the dots, anchor in my mission, and see bold asks as a form of service. I made moves I never would’ve attempted before. I can finally say I’m not leaving anything on the table.”

Rachel
Principal, Talent
Earned two job offers while out of work

“I got way more out of this work than I thought I would. It blew the roof off of where I wanted to go. Now I trust myself to make decisions that will get me closer to peace, fulfillment, and purpose.”

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