Successful, Burnt Out, and Quietly Wondering What Comes Next?

In one of my recent leadership workshops, an engineer stayed back to chat with me. She was curious about how I made my career pivot. I went from a high-functioning tech role to the leadership work I do today. It’s a question I get asked often and people are genuinely curious about alternative paths than the one they are programmed to all of their life. Often people think its a leap, a decision made out of the blue where I quit one fine day. The truth is far less dramatic. For me, it wasn’t a leap. It was an intentional and planned path, one that kept me up worrying many nights. I didn’t have all the answers, and sometimes I could only see five steps ahead. Yet, I knew I had to take this path, else I would regret not having done it. I didn’t want this ‘what if’ feeling later in life.

David Brooks calls this the second mountain. It is that moment in midlife when the first mountain, the one you climbed for success, status, and stability, no longer feels enough. The second mountain is where you want more fulfillment, more meaning, purpose and for me it was also in service of something bigger than just me, or a product for a company. I meet a lot of people standing at that base of the first mountain. From the outside these are the people that cause Linkedin envy for others. High-functioning, burnt out, successful, and on the inside quietly wondering if there’s something more. And yes there is, but you have to do the work. You have to ask yourself the hard questions, face reality, be a beginner again, make adjustments, and then take the risk of possibly failing.

This alternative path looks different for everyone. What follows is what I considered, offered in the hope that some of it lands for you.

What do you want? Not what makes sense. Not what pays well. What would you be doing if money weren’t a factor?

This question often stumps people longer than you’d expect. We are so trained to think about money, status and stability that we never pause to get clear on what we really want.

Clarity can be the antidote to anxiety. Start there.

Once you have some version of an answer, don’t wait for the perfect moment to try it. Start doing that work alongside your full-time role. Start small, and let it breathe before you bet everything on it.

And if you’ve never stopped to consider what else you might be good at, start by following your energy. Notice what work lights you up and what quietly drains you. Sometimes living in your zone of excellence can actually hide your zone of genius — you’re good at something, so you keep doing it, and never discover what you’re great at.

It took me years to get here. I didn’t always like the answers staring back at me, because the next question was always: how do I make money doing that? But as you keep moving forward and experimenting, that thing starts to take on a life of its own. I’ve seen people build a side hustle that eventually becomes their main thing. I’ve seen others gain just enough energy from it to return to their day job with renewed purpose. Both are valid outcomes. But you do have to know the direction you’re heading.

During the pandemic, quiet quitting became a thing. People walked away from jobs without a plan. Comparatively, we’re in a very different moment now in 2026, and the stakes feel even higher with AI.

I am a risk-averse person. I won’t tell you to walk away from what makes you unhappy, unless it’s for health reasons, because I couldn’t do it myself. What I did instead was spend months in my excel spreadsheets, running the numbers, until I could see clearly what my runway looked like for 6 months, 1 year and 2 years. I applied different what if scenarios to them.

A friend of mine recently had a rough day at work - one where he wanted to quit the next day. He called me to ask for advice and talk through it. “What’s the plan?” I asked. You have three kids, and your eldest starts college soon. Can you afford not to think this through?

Some people have just left. Walked away and moved to a different country. They became a nomad and are happy. If that is what you want and you have that courage to do it, more power to you. Some people left because they knew their significant other could support them financially through their experimental path.

Your financial runway tells you how much risk you can actually take. A long runway gives you more options. A short one clarifies your constraints. Both are useful. Neither is wrong. It depends on what it is that you are prioritizing for yourself at this stage in life.

This goes deeper than savings. Think about the lifestyle you’ve built - the mortgage, kids, healthcare, the things you’ve stopped noticing you pay for because they’re just part of the rhythm of your life.

A career pivot often asks you to renegotiate some of these, at least temporarily. It helps to look at them clearly, without judgment, before you’re in the middle of making decisions. And sometimes the answer that is glaring back at you is ‘not yet’.

A stable job gives you more than a paycheck. It gives you identity, rhythm, and belonging. Some people thrive when they break free of that structure. Others find the uncertainty harder than they expected, because the real question surfaces: who are you without your title?

I felt this strongly when I registered for a conference that required a current product management title just to be considered for entry. I got in, but the experience stirred up something in me. I realized that when I was no longer using my old title, the external world might not recognize what I was becoming. “Exploring life” doesn’t fit neatly on a form. That quiet discomfort was the identity shift announcing itself, and accepting it was the only way forward.

Ask yourself honestly: how will I do without that anchor? It doesn’t mean you don’t make the move. It means you make it with your eyes open, and ideally with some support around you. If your sense of self has been tied to your title, your company, or the type of work you do - sit with what it means to let that go. Your ego may resist. That’s normal. Talk to people who’ve made a similar shift and ask them not just what they did, but how they handled that in-between feeling of no longer being one thing and not yet being the other.

For me, trading in the big title and the executive track for a path with more adventure, creativity and service to others was a real transition. But looking back, I’m glad I did it when I did.

Here’s the good news: you don’t arrive at the second mountain empty-handed. You bring your experience, your judgment, your hard-won self-knowledge. You’ve become successful before. You know what that takes. And somewhere in you is the quiet confidence, I’ve done hard things - I can do this too.

What we forget is that you still have to become a beginner again. And that’s probably the one thing you’ve been out of practice with.

Try to see it as permission to be curious again, to not know, to ask questions, to be in the learning seat rather than the expert one. It can be uncomfortable. It can also be unexpectedly energizing.

You can’t think your way into this part. You have to feel it in motion. So start moving, and pay attention to what opens up.

When I stepped away from my previous role, an opportunity to do group coaching appeared almost immediately, something I wouldn’t have seen, or had time for, if I’d stayed where I was. And then another opportunity for teaching came up right after that. These experiences gave me confidence to pursue another path within an organization as a Leadership & Development professional.

Once you start moving, the next question becomes - how do you know if it's working? I like applying product management principles to life. Can you treat this as an experiment and do an A/B test? Give yourself a set amount of time, and then actually assess the results. Did it work? How does this make you feel? Do you want to go back, or do you keep following the trail?

This experiment made me feel alive, and I kept going on the alternative path, and new opportunities kept coming up. At times when it got hard, I would remind myself, that I always had the option of going back, and there was no embarrassment in going back to the known path.

I do know of others, who took the alternative path, experimented, and went back to the known path with more vigor and energy because of the adventure. You learn something about yourself regardless of the path you take. And once you’ve done this, it gives you the confidence to take other chances in life. You trust yourself to consider all options, and make the right decision for yourself at that time in life. It could change in the future, but the decision made right now, is the right one.

Making a career pivot in midlife is one of the more courageous things a person can do. But courage and recklessness aren’t the same thing. The people I’ve seen navigate this well didn’t jump. They walked carefully, intentionally toward something they’d already started building.

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