Sitting in my desk chair, a voice called my name and I turned and froze: a former student had showed up for our run. A run I’d completely forgotten about.  He was dressed in tank-top, shorts and running shoes.

Ten minutes later, I was wearing an outfit cobbled together from the lost-and-found: a sweatshirt two sizes too small, running shorts, and a baseball cap with the school’s logo.

On that run, we talked about the same thing we used to talk about when he was my student and I was his teacher: reaching your goals, overcoming fear, being true to yourself. And it was the same running route, too: Scott Street. Presidio. Marina. The hill.

That hill, stretching from the bay to the Pacific Heights, 3 excruciating blocks, used to be a major topic of conversation on our runs. It was the central symbol in our talks about life.

“Keep your eyes on what you’re doing now. Don’t get discouraged by how far away the goal may seem. Promise that you will only climb for the count of 10. When you’re done, recommit to another 10. True victory comes when you’re no longer counting.”

Here we were, two years later, and each of us had grown so much, the same running loop, the same scenery, the same running loop.

Maybe a level higher, maybe a level deeper.

Seersucker Phase 1: 7 Years Ago

Moving topics, from the Fillmore Street hill to Capitol Hill:

In less than 24 hours, Washington DC will honor Seersucker Thursday.

Former Mississippi Senator Trent Lott inaugurated this day in the 1990s to revive this storied fabric. Once, it was the only thing a Senator could wear on a pre-air conditioned, muggy June day.

In my closet, I have three seersucker jackets.

The first is from Urban Outiftters, and I bought it seven years ago, with the remainder of a gift certificate. It’s essentially an unstructured blazer, without the actual pucker that seersucker is known for. (Incidentally, the word Seersucker means milk-and-sugar in Persian, referring to the color of the stripes)

The second two are from Brooks Brothers, and I bought them two years apart.

Seersucker Phase 2 departs from the norm, in that the pattern is the same, but the jacket and trousers are actually a different color.

Seersucker Phase 2 : Three Y ears Ago

I had to get used to Phase 1 to do Phase 2.

Then came along Phase 3. The stripes in the jacket are a different width from the pants, and since Gabi and I were at a festive (and blazing hot) outdoor wedding, I went gangbusters and yanked a parasol from a parasol-pile to keep us in the shade. And to add to the outfit-awesome.

Seersucker Phase 3: One Year Ago

Seersucker never went away, but I moved on.

Old rules, like “Don’t match your tie and jacket” and “you can’t wear seersucker after Labor Day” went out the door. (For a list of Trent Lott’s other Seersucker taboos I also advise ignoring, click here).

I was finding my own voice, and pushing the rules as far as I cared to.

Here, on the cusp of my 41st birthday, many of the challenges in my life (most of them in my head) are no different than the challenges I faced when I was 31. But I’m better able to handle them. I can climb a much bigger hill.

Same hill. Same material. Same style. Different me.

One level deeper. One level higher.