My Five-Year Plan Has an Unreasonable Number of Dogs

Labor Day seems like an appropriate time to articulate my five-year plan. It’s basically a law firm, a microphone, a lake house, and an unreasonable number of dogs. So far, we’re right on schedule.

A few years ago, I’m not sure I would have predicted that my work life would look like this. I’m building my own law practice. I talk about death into a microphone every week. I spend my summers working from my dad’s house in the Adirondacks. And, with surprising frequency, I have to stop and count the dogs in my house to remember exactly how many currently live here. This was not the career plan I mapped out when I went to law school.

The Career I Thought I Was Supposed to Build

I’ve spent a lot of my career thinking about what I was supposed to do next. There was always another logical step, another credential, another job that made sense on paper, another version of success that was relatively easy to explain when someone asked what I did for a living. And there’s nothing inherently wrong with any of that.

But somewhere along the way, I started asking a different question. Not What am I supposed to do next? But What do I actually want my life to look like? That turns out to be a much more interesting question. I don’t just want work that I find meaningful. I want work that fits into a life I find meaningful.

I want to help families make plans for some of the hardest parts of life without making those conversations feel scary or inaccessible. I want to have enough flexibility to spend the summer at my dad’s house in the Adirondacks and still do work I care about. And I want to sit down behind a microphone every week and explain the things I wish more families understood about estate planning, aging and death. And, apparently, I want to foster puppies despite already having three dogs. That last part may not have been fully thought through.

Maybe the Five-Year Plan Is Really a Life Plan

Estate planning has probably influenced the way I think about all of this. I spend a lot of time asking people to think about the future.

What matters to you? Who matters to you? What do you want to protect? Who do you trust? What would make life easier for the people you love? Those questions matter when we’re talking about what happens if you become incapacitated or die. But they’re also pretty good questions to ask while you’re very much alive. Planning for the future shouldn’t only be about preparing for the things that might go wrong. It can also be about deliberately making room for the things you want to go right.

So Far, We’re Right on Schedule

So on this Labor Day, I’m feeling especially grateful for work I care about and for the freedom to do it in a way that fits the rest of my life.

I’m grateful that my office can sometimes be at the lake, that something I record into a microphone can help someone understand a legal concept that has been intimidating them, and that I get to build a law practice that feels like me. And I’m even grateful that my commute occasionally involves stepping over a foster puppy.

I have no idea exactly what my life will look like five years from now. But I’ve realized that the life I’m building already looks a lot like the life I actually want. So maybe the five-year plan isn’t quite as complicated as I thought.

Keep building the law firm, talking into the microphone, going back to the lake, and making room for the things—and the people and dogs—that matter. There may, however, have been some scope creep on the dog portion. No regrets.