A few days ago, I was watching my daughter make her way across a creek by stepping from one rock to the next. And what struck me was how she was doing it. She wasn't looking ten rocks ahead or trying to map out the entire crossing before taking the first step. She was simply looking for secure footing for the next one.

I realized that's exactly where so many people get stuck with estate planning. They imagine they'll have to make every decision at once. They'll need to understand trusts, taxes, beneficiary designations, powers of attorney, guardians for their children, business succession, family dynamics, and every “what if” scenario before they can even begin. No wonder so many people put it off.

If you've ever received a draft Will, Trust, Powers of Attorney, and a summary email from your attorney, you probably know the feeling. You open the attachment, see dozens of pages of legal language, and suddenly cleaning out the junk drawer, folding laundry, or taking a nap seems like a much better use of your time. I don't blame you.

Estate planning documents aren't meant to be read like a novel. Many of the most important decisions are hidden in language that can be difficult to interpret if you don't work with these documents every day.

Every morning before I start my run, I cross the same section of trail. Then, about forty-five minutes later, I cross it again on my way back. It's become so familiar that I usually don't give it much thought. But one morning last week, I stopped, pulled out my phone, and took a picture. I remember thinking, There's got to be an estate planning metaphor here. And it turns out there was.

The solution to your life's biggest anxieties might not be on a trail in the Adirondacks with a sausage dog. But you should probably check. The last time I was here was in December, the trails were covered in snow, and I was snowshoeing with one of our other dogs while trying to sort through a lot of uncertainty.

This summer, my office is in a familiar place: my childhood bedroom in the Adirondacks. If you see photos or videos from me over the next couple of months, you might notice the safari wallpaper in the background. I picked it out when I was eleven years old, and somehow it has survived all these years.

Every time I sit down at this desk, I'm reminded that rooms can hold stories. This one certainly does. My mom helped me choose this wallpaper. Fourteen years ago, this is also the room where she died. On paper, it sounds like this room should be filled with sadness. But that's not what I experience when I'm here.