Chip Conley: Hotelier

Chip Conley: I am 61 years old, and I wake up quite early. I think in a past life I was either a farmer or a monk because I tend to wake up at 4:30 every morning.

I will say it’s been a curse in some ways. I’ve never loved the idea of it until more recently. The last maybe five years I’ve enjoyed it. More and more of my friends are dealing with it, too. Back when I was in my twenties, I was waking up at that age. I laughed in my thirties when I said, ‘No matter where I am on the globe, I will wake up at 4:30 in the morning,’ even if I went to bed at 2:00 in the morning. My body calibrates itself that way. It now serves me, especially living in Mexico, where siestas are commonplace. It was really hard in my fifties when I was traveling all over the world with my Airbnb job and very jet lagged and then also waking up too early – I grew old pretty quickly during my fifties as a result of that. 

A career in hospitality

The first chapter was starting one of the first boutique hotel companies in the United States called Joie de Vivre. I was CEO of that company for twenty-four years. Then I joined Airbnb as the mentor to Brian Chesky, the CEO, and I was the head of global hospitality and strategy and then shifted out of a full-time role into strategic advisor role. And finally, I am the founder and CEO of the Modern Elder Academy, also known as MEA, the world’s first midlife wisdom school. 

Embracing the day

I meditate. That is really what sustains me in so many ways. I tend to write early in the morning. That’s part of my profession and I do my best writing in the morning. My writer wakes up before my editor. I almost take dictation because I really feel like I’m channeling something and it flows through me, and then I’ll start doing some exercise, as soon as the light comes up.

I run, I swim, I do yoga, I do some strength and balance work with a trainer from South Africa. We do it by Zoom. I ride a bike; isometrics with a band. I have a lot of interests. I surf a little bit. I’m not very good.

I think the most important thing when it comes to exercise for me, at least, is to not get bored with it and to sort of say, What do I want to do right now? I’ve been that person who goes to the gym four or five days a week and just does the same old damn thing, and I don’t really want to do that anymore. Fortunately, I live in a place, a very rural part of Mexico, where there’s not an easy gym to get to. And so I just have to figure out my way of entertaining myself while I exercise. 

I try to do three things a day. And that sounds sort of strange, but I try to do a minimum of a 15 minute workout three times a day. And one of those might be an hour or two hours long. If I’m going on a hike somewhere, it might be a two-and-a-half-hour hike or if I’m going to a yoga class an hour and a half long. But three-a-day is my thing. Isometrics might be 15 minutes. My swim will be about 20 to 25 minutes, bike ride no more than 30 minutes. That’s my thing is, you know, shorter bursts, but consistently three things a day. 

I do a little bit of intermittent fasting, my tendency is to, unlike some friends of mine who do this, I tend to eat in the morning and then get rid of dinner as my meal, and so I concentrate my food in the morning and lunchtime. I’ve done it differently but given that I tend to wake up pretty early, it’s harder for me to miss the first meal. And then just by the afternoon, I’m really dragging. One of the nice things about missing dinner is there’s a lot of evidence that it’s good for your sleep to not eat directly before you go to sleep. I don’t know how the people in Spain and Italy in places like that or in South America are able to have dinner at 11 o’clock at night.  

For breakfast I have a green juice. That’s a staple in my diet. It’s all about local fresh food. I don’t eat a lot of meat. I love salads, so that’s my thing. I eat way too much chocolate. I drink alcohol more than I should. Not to the point of feeling like I have a problem with it. But, you know, drinking alcohol five or six nights a week, that’s not so good. But it’s partly because, frankly, I’m in a place where it’s part of the culture. And so I have to just watch that. 

I tend to be extremely concentrated. I live in a beautiful place on the beach and my office doesn’t face the beach. My office is on the second floor in a little, almost like a little closet. It doesn’t get a ton of sunlight. Because when I’m actually concentrating on something, I’m concentrating on that. If I need to be creative or if I need to have a creative meeting or things like that, let’s go use nature as our teacher and as our classroom. But when I’m concentrated, I do bursts of work and I get a lot done.

The Modern Elder Academy

The Modern Elder Academy is a midlife wisdom school. What the heck is that? Well, we don’t have a whole lot of schools that help people understand how to cultivate and harvest their wisdom in midlife, nor help them understand what they’ve built mastery around. And so that’s what we do. We are dedicated to not lifelong learning, but long-life learning. And that is based upon the premise that people in midlife and later may have a different way of learning and different interests and passion for what they want to learn. You know what you want to learn at age 30 is different than age 60. But when it comes to the term lifelong learning, it’s sort of a one size fits all. So long life learning is about creating a life that’s as deep and meaningful as it is long. So focusing on not just the quantity of life, your years, but the quality of your life. 

My biggest challenge is how many meetings I have a day, and so I have a rigid calendar with commitments to other people in the world we’re living in right now. Zoom, you know, it’s all about Zoom. I don’t have enough time in between these calls to have spaciousness to focus on something new, especially if it’s writing. And that’s where meditation comes in. So I meditate in the morning. But if I am in between two calls and there are two pretty important calls or two podcasts or something like what we’re doing right now, I will spend five minutes just breathing and meditating. And that’s my way to renew myself for the next thing I’m doing. 

Winding down

Usually around 9:30 or 10 is when I’m when I will fall asleep. I sleep deeply, but I wake up a lot. I’ve had my sleep studied and I go into REM and deeper sleep pretty readily, but I wake up a lot. I don’t know what to say about that. And as I get older, I wake up more often. I’m someone who sleeps an hour less than the average person. So if the average person sleeps, let’s say, seven and a half or seven hours, I sleep, you know, six and a half to six. That’s just how I am. So that’s one one extra hour a day there. 

My wind down is wrapping up my work about an hour and a half before I want to go to sleep. And then sometimes going for a walk with my dog. It’s usually nighttime looking at the stars because I live in a place where the stars are very readily visible. I do look at the news sometimes. It’s a bad habit, but I’ve gotten used to it. I like to just give myself the luxury of reading two or three articles by or op eds by people I really admire and appreciate their point of view. 

I read something that brings joy to me, and I spend probably half an hour doing that. And then I finish where I listen to meditative kinds of sounds or words that help put me to sleep. And that’s how it works.