The response to my first post about pro bono financial planning in this new direction was overwhelming to say the least. I heard from many friends and colleagues and believe me, I appreciate the support. More than one of you asked me to dig in deeper on “the why” before I spend time on the what and the how. So here It goes.
Over the past year, I’ve found myself coming back to an idea from David Brooks’ book The Second Mountain. It’s a simple concept. The first part of our lives is often spent building something. A career, a reputation, a sense of success that, if we’re being honest, is at least partially defined by how others measure it. The second part shifts. It becomes less about building for yourself and more about contributing to something beyond yourself. I’m not sure I would have framed it that way a few years ago, but it resonates now.
Framing it
I left the place where I worked for 28 years in November 2022 , and at first, it felt pretty natural. There was a different pace to life. More time with family, some great travel and concert experiences. There were books that I never had time to read and contemplate and there was space to catch up on things that had taken a back seat for a long time. It was good, and honestly, it was needed. But somewhere in that third year, something started to shift.
I found myself asking a different set of questions. Not about what was next in a traditional sense, but about what was meaningful. I started thinking about how much of my time had been spent building that first phase of my career, and what may have been left on the table along the way.
I always felt I was present with my family. I coached teams, went to school plays and activities, showed up for the moments that mattered and I wouldn’t trade any of that. But when I zoomed out, I realized there were parts of community and contribution that I hadn’t fully leaned into. Not because I didn’t care, but because there was always something else that needed to get done. That realization stuck with me. And it started to shape how I think about what comes next. For me, part of that answer is rooted in something I’ve been close to for a long time but maybe haven’t fully applied in this way before.
Financial advice
In this profession, we spend so much of our time working with clients who are already in the system. People who have access, who have resources, who know where to go and who to call. And there’s nothing wrong with that. It’s important work. But it’s also a very small slice of the population.
There are a lot of people out there who don’t have that access. Who could benefit from thoughtful, real financial advice and have no idea where to start. And if you’ve spent enough time in this business, you know that gap exists. That gap is exactly why pro bono financial planning matters. The more I thought about it, the harder it became to ignore.
What’s been interesting is that these thoughts haven’t just been mine. In conversations with peers, I’ve heard a similar sense of curiosity, and maybe even a little restlessness. People asking, in different ways, what the next chapter is supposed to look like. What can I do? Who can I be? It’s time to give back, but how?
Those conversations have a way of confirming that this isn’t just an individual moment. There’s something broader happening for a lot of people who have spent years building that first mountain and are now starting to look around and ask what comes next.
Foundational
What also became clear is that there are resources out there to help. I recently spent time with the team at the Foundation for Financial Planning, and it reinforced something important. You don’t have to build this from scratch. There are people, tools, and frameworks already in place for those willing to step into pro bono financial planning. That matters, because one of the biggest barriers is simply not knowing where to begin.
So this is where I find myself right now. Trying to connect what I’ve spent a career learning with a need that has always been there but is harder to see if you’re not looking for it. I don’t have all the answers yet, but I do know this feels like the right direction.
And if you’re someone who has spent years in or around this profession, there’s a decent chance you’ve had a similar thought at some point. Maybe you’ve even said, “I should do something like that someday.” I think that time might be closer than we think.
I’m going to keep exploring this and share what I find along the way. Not because I have figured it out, but because there are probably others who are asking the same questions and looking for a place to start. Why not learn together?