Day in the Life of Headspace CEO Tom Pickett, a Former Navy Pilot

This as-told-to essay is based on a conversation with Tom Pickett, the 57-year-old CEO of Headspace, a mental healthcare platform. He started his career as a pilot and graduated from TOPGUN, the US Navy Strike Fighter Tactics Instructor program. He is based in Menlo Park, California. This story has been edited for length and clarity.

I became the CEO of Headspace in August 2024.

This is my first time in healthcare. I was the chief revenue officer at DoorDash for the last four years before coming to Headspace. Before that, I spent 10 years at Google and also ran a startup.

I spent the first part of my career as an F/A-18 pilot. I deployed on aircraft carriers and ended up going through TOPGUN. It was a great time in my life. I loved the operational nature of it, and it was exhilarating. People talk about jumping out of airplanes and feeling high for the day. I had that on a regular basis.

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Sleep was easy back then. Now, it’s the thing I focus on the most. I have more stress as a CEO. As you get older, it’s harder to get the same sleep. I think about it as a practice, because you never quite nail it.

I’m not super-regimented, but there’s comfort in structure and patterns. I try to stick to regular sleep times, and I like structuring the weeks and grouping things in certain ways. I find it more efficient.

Mental health continues to rise as one of the biggest challenges of our time — and it’s not like much has changed in the last 20 years. In the midst of this AI transformation, there’s an opportunity to rethink how we approach mental health. I thought it was a great opportunity to do something good for society and try to make a dent in a problem that matters.

I wake up around 6:45 a.m.

I try to keep my wake-up time as regular as possible. Part of good sleep is maintaining a consistent schedule.

I have a pretty quick morning routine. I get up, shower, get ready, grab a cup of black coffee for the road, and start heading my way into the office.

Some days, it’s a good opportunity to catch up on the news. Some days, I’m thinking about other things. I use ChatGPT’s voice mode to test out different ideas, and Headspace’s empathetic AI companion Ebb to unpack what I’m feeling emotionally.

I work Monday through Thursday in person

I like to get to the office between 8:15 and 8:30 a.m. Usually, my schedule starts at 9 a.m.

Generally, I try to stack the more thought-intensive meetings in the morning because my best thinking happens then.

I typically have a mix of external meetings and calls with partners, investors, and potential customers. I also meet with my direct reports for one-on-ones once a week. Tuesdays are staff meetings, Wednesdays are business reviews, and Thursdays are more like strategy sessions.

I like the flexibility of working from home sometimes. If my daughter has a track meet in the afternoon, I can spend time on that.

I have lunch around noon

I usually have two to three cups of coffee in the morning, and then I cut myself off. I spend the rest of the day hydrating with a lot of water, and sometimes electrolytes.

I typically fast until lunch. Usually, around noon, I’ll have something like a chicken salad. I try to keep it fairly healthy, with some mix of greens and a protein.

Running helps me process my thoughts

Flying used to be my high for the day. Now running is my outlet.

I try to leave work around 4:30 or 5 p.m. Three times a week, I try to squeeze in a run before dinner. I really struggle to get up early enough to do a workout, but I really enjoy decompressing after work and getting some physical activity before dinner.

Running is like a brainstorming session. Sometimes, halfway through a run, I’ll stop and take notes.

I usually listen to music or podcasts while running. I don’t have one podcast that I regularly listen to. We have an internal stream of industry news that comes in through our Slack channels, including podcasts. I listen to ones that are typically about a company, a leader, or an industry that I’m trying to learn about.

I’ve been cold plunging recently

It’s a mental battle to get in the cold plunge, but afterward, your mind is clear, your blood is flowing, and it’s a really good feeling. Even my kids have started doing it with me.

A lot of my friends have invested in cold plunges — it’s become a little bit of the thing to do in Silicon Valley. My wife wouldn’t let me buy one at first because she thinks men impulsively make purchases that they stop using after two weeks.

She convinced me to use our pool as a cold plunge during winter. We’re at the point where our pool is warming up and no longer serves its purpose as a cold plunge. So we’ve decided to get one.

Dinner with my kids at 6 p.m. is a key priority

Work consumes a lot of my life, but the rest of it is being there for my family. Dinner is the one time that everybody is together each day. So I try to leave work to be home for that. We catch up on the day. It’s usually quite boisterous. There’s a lot of energy.

Three out of my four kids are at home. One of them is in grad school at UC Berkeley. Two of them are twins in their sophomore year of high school, and one is in seventh grade. They’re in the thick of it, between school and all the activities and sports.

We all work after dinner

The kids are pretty busy because they’re pretty stacked with homework after their sports and dinner. I usually put in another couple of hours of work while they’re doing homework, which is great, because it’s shared time together.

I help them with math and science when they let me, but they turn to Grok and ChatGPT now, too. I’ve used those moments to have conversations about responsible AI use.

My wind-down routine begins at 10:30 p.m.

I don’t always get off my computer an hour before bed, so I try to minimize the effects of screen time by wearing blue-light glasses. I try every tool in the toolkit.

Sometimes my heart is still elevated before bed, so I try to do some basic box breathing to get it down. Sometimes I do a wind-down, focusing systematically on my breathing and going through each part of my body to release tension. I try to do anything to get outside my head because that usually cascades through sleep.

I find that reading for 10 minutes, or a chapter of a book, can get me out of my head and help me change my mindset. That usually helps me fall asleep.

The issue is that I wake up many times during the night, sometimes for 30 or 40 minutes. When I wake up in the middle of the night, it’s not that I’m necessarily stressed about something at work. Sometimes I’m thinking about benign things.

When I look at my Oura stats, my sleep efficiency is not great. The time I spend in bed relative to the sleep I get is very frustrating. I’m putting in the time, but not getting the full impact.

I fly a couple of times a month

I try to fly a couple of times a month in a Cessna 172. It’s not the same as an F/A-18, but I enjoy getting back up in the air a lot. I joined a flying club, and they have a bunch of airplanes that you can rent by the hour.

I don’t have my own plane right now — but when I think about retirement, it’s having a plane and flying. I’m not there yet.