When I started writing about becoming a pro bono planner, I thought maybe a few people would read the first few posts. I didn't expect thousands of impressions, more than a hundred reactions, dozens of comments, texts, and DMs. No doubt, the largest response I've ever gotten to anything I've ever posted on LinkedIn.
What surprised me most wasn't the volume. It was who responded. Of course, there were close friends and former coworkers and people I haven't talked to in years. But surprisingly, there were strangers. Second and third-level connections who must have seen it through someone else's feed and stopped scrolling long enough to actually read it. That's when I knew it had touched something real.
Why This Path?
Not because this is some late-career vanity project, it was never really about me. The CFP® was a proof statement that I was serious about becoming a pro bono planner in underserved communities. A commitment that if I was going to spend the next chapter focused on providing advice, I needed to earn the right to do it.
What I didn't expect was how many people would quietly write back and say, "I've been thinking about something like this too." That part caught me off guard. And honestly, it moved me a little.
People kept saying versions of the same thing:
- "I want to give back in a more meaningful way."
- "I just don't know where to start."
That last line has stayed with me. Because it's exactly where I am too. The desire is there. The how is not.
Options
In my conversations, many people jump straight to the idea of teaching financial literacy in schools. Great instinct, but those doors don't open just because you had a successful career and a nice resume. The systems are different from what most people realize, and they are very difficult to enter.
What I'm finding instead is that community organizations, nonprofits, churches, and local programs are desperate for people with real experience and real empathy. But finding them, building trust, and understanding how to actually show up and help takes its own kind of work and commitment.
If you are a CFP® (or work with one), the Foundation for Financial Planning has resources, tools, and training, along with a site called Pro Bono Planner Match to help point people in the right direction. If you've thought about becoming a pro bono planner, the Foundation for Financial Planning is a great place to start.
Finding a Way In
So, I'm figuring it out as I go, learning out loud and helping to build it for Diversified too. Which means asking for help from people I don't know. Scheduling calls with strangers. Sitting across from people doing work I've never done and admitting, "I'm trying to figure this out too."
After a long career where I was usually expected to have the answers, that's a strange place to be. Humbling as well. And it certainly doesn't always come naturally. Reaching out to someone cold takes effort. Asking for advice after decades in the business feels more vulnerable than I expected. But if the mission is right, you push yourself into uncomfortable places. And here's what I keep finding on the other side of that discomfort: people are generous. Remarkably so.
Actually, maybe that’s what surprised me most. Not the reactions or impressions, but the realization that so many experienced people are quietly carrying around the same thought: “I want to do something meaningful with what I’ve learned.”
I may not have my pro bono planner roadmap yet, but I’m beginning to think the path gets built by people willing to start the conversation before they have all the answers and open enough to share what they’ve learned so far.