Stay Upwind

My remarks to the Hellgate High School Class of 2024

A couple of months ago I saw an email in my inbox from “Hellgate High School Student Government.” That’s odd, I thought. The students leaders asked if I would speak at their graduation. My immediate sensation was that this has got to be some sort of elaborate prank…

Nope…it was for real. I quite enjoyed the process of preparing - chatting with the Hellgate students about their goals for the ceremony, asking my class of UM freshmen their thoughts on their own commencement experiences, consulting my middle-school daughters as well as several friends and trusted advisors. I experimented with various ideas and landed on something simple - do hard things and work hard at them.

I then used a sailing metaphor* to frame the concept. It was a fun exercise in thinking and writing that tied together many expereinces from various life stages. I was honored and grateful for the invitation and hope the talk offered something useful and memorable for the students.

Here’s the script:

Being a professor means I’ve been to a lot of these things. I’ve heard a lot of talks and never have I complained that one was too short. Mr. Miller asked me to keep it under 5 minutes, so I promise you I’ll deliver.

Stay upwind. I’ll repeat those two words throughout this talk. I hope you remember them. 

Stay upwind.

I grew up sailing. Sailing is about harnessing the wind to get where you want to go. It’s much easier to sail with the wind than against it. So when you start a trip, it’s great to head upwind first. Sailing upwind is difficult, you have to tack back and forth, and it can a take long time. But once you get upwind, you have many options. This is useful even if you don’t know where you are going. If you stay upwind, you’ll have many destinations to choose from. If you don’t, you’ll cut off opportunities before they even present themselves.

Stay upwind.

Doing hard things and working hard at them gets you upwind. Evolution shaped us through a process of stress and adaptation. We don’t learn or improve unless we stress our systems and allow them to adapt. The trouble with this model is that it’s really difficult to choose stress. Getting upwind is hard. Generally, we don’t like to do hard things. Because they are hard. Staying upwind means doing the hard things first.

For me, I used to run 100 mile races. I even won a few. People think that means I’m a fast runner. I am not. But I’m good at running slow for a long time. The hard thing I needed to do to compete with faster runners was convince myself that I could outlast them. Building that belief got me upwind.

For you, staying upwind at this point means doing the hard work of developing useful skills. Learn to write really well. Learn how to express yourself through art. Develop your social skills. Learn how to deal with conflict. Get good at math. Be curious.

Stay upwind.

Surround yourself with smarter, more talented people. They will make you better. Students often ask me what they should major in…majors are meaningless. Major in great teachers and hard classes. Show up on time and raise your hand.

Stay upwind

Staying upwind means getting things done, but also trying things you’re not sure you can do. You’ll never know your limits until you find them, and they are usually far beyond what you expect.

The challenge you face is that there has never been a time quite like now. The confluence of technology, politics and economics has created an addiction industrial complex. Not only does this complex steal our attention, it constantly serves us with attractive alternatives to doing hard things. In other words, it pushes us downwind.

You don’t have to exercise anymore…we have Ozempic

You don’t have to write anymore…we have ChatGPT

You don’t have to talk anymore…we have Snapchat.

These conveniences feel like tailwinds, making life easier, but if you allow them to carry you too far downwind you’ll end up with very few options. 

Stay upwind.

Staying upwind means asking interesting questions. What’s an interesting question? It takes a long time to figure that out. You need to ask bad questions before you can ask good ones. The good news is that there are so many interesting questions and hard problems to work on right now.

Climate change, housing, drug policy, social justice, immigration, restoring some semblance of functionality to our democracy.

Take any issue with a vast divide between opposing slides and figure out the space in between. That’ll get you upwind. Understand the best arguments against your point of view.

Staying upwind means saving money now. Understand compound interest. It works a lot like gravity. Learn how to harness it and good things happen, but disregard it at your own peril. The same holds true with other people’s emotions. Being kind, generous and grateful gets you upwind.

Staying upwind means taking care of your body. It’s the only one you’ll ever have. Follow Michael Pollan’s advice - eat real food, not too much, mostly plants. Move around as much as you can and lift heavy things on occasion. Do burpees.

Staying upwind looks like getting up early, like calling instead of texting, like hand writing thank you notes. It looks like reading books and saying you’re sorry when you mess up. 

Staying upwind is an investment in yourself. Whatever you do next, college, work, military service, demand a strong return on that investment. Staying upwind is hard. And if you get good at something hard, chances are you’ll start to love it.

A couple weeks ago one of your classmates told me, “it’s our turn to experience the cliches”

Indeed it is. Congratulations. You’ve done the work to get yourself upwind.

Stay there.

* as I was working out the sailing upwind metaphor, a former student pointed me to a similar thought exercise, articulated by Paul Graham.