Leadership Coach Leo Widrich on Emotional Wellness for Distributed Workers

Imagine starting a company with your buddy, turning into a multi-million dollar business, and offering a service used by brands all over the world. And then walking away from it all to go live in a monastery. That's exactly what this week's guest did, and you're going to hear all about why he did it. With his startup Buffer, Leo Widrick has achieved success by any measure, but something was missing. His dissatisfaction with the lifestyle led him to pursue deeper truths that he came to realize could not be found in the blind pursuit of material success. Leo studied Buddhism, spent some time living with monks, and learned to appreciate an intentionally slow lifestyle. Now, he coaches entrepreneurs and even other coaches with the goal of helping them manage the stresses of their careers with a combination of ancient wisdom and a sprinkling of modern neuroscience. He wants people to learn how to build emotional resilience and the ability to self-regulate their emotions so that they can deal with their issues and avoid the full-scale burnout that he suffered. Buffer is a remote company, so it's clear that Leo has a passion for unconventional work arrangements. However, he's extremely sensitive to potential emotional and psychological pitfalls associated with working from home. In this episode, I learn about the loneliness spiral, what can happen if you don't exercise your social engagement circuits through regular social contact. And Leo shares a few tools that we can use to care better for ourselves and the people we work with.

I started a company called Buffer close to a decade ago with a friend, and we worked completely remotely. Where, where were you both when it started? We both first lived in Birmingham, UK, so in England. So we both kind of studied there and then we flew out to San Francisco and said like, "Hey, Silicon Valley is the spot." That's kind of how we got started. And we kind of, you know, went through all the startup struggles and ups and downs. And a couple of the things that were really wonderful as we built social media management software and we did it eventually fully remote also. To a level of transparency where I really wanted to put everything on the table about what was going well and what wasn't going so well in the business.

An unheard of level of transparency. So Buffer publishes its revenues, its salaries, its options, kind of everything, right?

Right. That was a real kind of desire for us to bring that kind of level of transparency to the business world to kind of reduce some of the sense of secrecy and some of the sense of that this is a fight and make it a little more collaborative.

Tell me about the why there. So why were you distributed if you were starting at the same place? And then why the transparency? And are they related at all?

I think that the distributed part, we were in San Francisco and the team was growing, and I'm sure you notice as the team grows in San Francisco, your office space needs to grow, and we were in the middle of, should we expand and get a new office? And I remember even meeting with some brokers and the prices, they seemed— incredible. And we were like, huh? And some of us were barely even coming to the office. And I think that was a moment where we all kind of thought, well, why don't we try not being in the same office? And we had tried that before because of visa problems. So at first that was totally not a choice. We just had to be all over the world because we couldn't stay in the US. My partner Joel, he was from England and we had a third co-founder. He was also from England. I was from Austria. So it was really hard for us us to actually be in the country, so we like had to be distributed. But eventually it was a question of cost and a question of joy and ease too, right? Like, oh, why don't we get to work from wherever we want to?

Great. And when was this?

It must have been 2013, over 6 years ago that we decided, okay, well, before it was kind of like unclear, like more like an unwritten rule because we were so small. But then we decided, no, I think we will allow people to be wherever they want to be and then made that the kind of a a more official commitment, so to speak. And that was also the time when we did start to be more transparent because we wrote down our values. We were very inspired by a company called Zappos at the time.

Yeah, of course.

Right? Tony Hsieh is kind of like a real mentor in that space of really defining your values and having your purpose. And that was also one of the things that came out of that, committing to, working remotely and committing to being transparent as a way to share with the world what we are learning and to kind of foster a sense of collaboration and openness.

What was your kind of biggest lesson from being distributed like that?

At first it was so wonderful. We were traveling around the world. We got to really live a life as well as we were working so that we weren't kind of deferring enjoying life, so to speak. But over time, for me personally, what started to creep in a little more was this sense of loneliness, this sense that I feel not as connected. I don't need to have a base, so I'm not committing to a base. That kind of untetheredness, the longer it went on, the less enjoyable it became, the more almost painful it became, I would say.

When you left Buffer, what was next for you?

I started to feel like I was kind of hitting a wall. You know, this thing that I always dreamt of to have a, profitable company, be financially secure, to have a team, like a lot of things that I started to aspire to when I got in touch with this idea of startups early on. I felt that having that success, having some of that financial security, it left me kind of unfulfilled in a lot of other areas in the sense of deep lasting connection and also just a lack of emotional resilience to deal with the ups and downs that startup life comes with. So I felt kind of exhausted and we weren't quite fully in agreement anymore with my co-founder. I kind of took that as a sign and said, maybe this is just no longer the right thing for me. And I took my hat and I left and it started this really, really interesting journey from outwardly doing stuff and accomplishing stuff, which I kind of was the only thing I knew at the time to go inward. And I started to go and live in Buddhist monasteries and do some therapy training and really start to understand, okay, there's so much I was externally striving for, but what's actually here? What's this kind of foundation, this house that is my body and my psyche?

Well, that's a big step. Tell us about this Buddhist monastery.

It's a big step, and a lot of people at the time they looked at me and they said like, oh, you're crazy.

I'm so curious, like, is there like an Uber for monasteries? How do you find where you go? Where did you end up? Like, just walk me through the whole thing if you don't mind.

For sure. I started to become very interested in and kind of soothed by the writing of a Buddhist monk called Thích Nhất Hạnh. And that is really the person that I think brought me into this world. And he wrote this book called Peace Is Every Step. That's the first book I read. It really touched me. It set something off in me. He talked about a sense of living in the world and being in the world without that constant striving. And here I was finding myself striving so much and trying so hard to make something successful, to be successful. And he was kind of challenging that idea. And so I saw him speak in 2013. That was kind of when I was more on the sidelines. I was just kind of learning about this stuff. And I was living in New York. And there's a monastery called Blue Cliff Monastery in upstate New York. That I wanted to check out. And I went there and went there for a few retreats. And I went there to see what is this life like that seems the exact opposite from the rapid-fire startup life. All these Buddhist monks and nuns were living, going so slowly, you know, barely any agenda on the day, every day. And so it was this very different life, very slow. There was very little content other than what was bubbling up from within me, right? So it was really making a lot of space.

So we went from startup founder to— I don't know if you call it a monk, but you were at a monastery for several years, and now you're like a coach. So you work with clients? Yep.

I call it emotional resilience training. That's kind of the tagline I have.

So assuming that you can't tell your clients to also go away for 2 years, right? What's kind of a middle ground?

Yeah, you don't need to go off for 2 years, but there needs to be some sense of regularity to coming inward, coming internal. And that is what allows us to build that muscle of emotional resilience where we can not be so cut off from ourselves in the face of difficulty that happens to us, and instead to flow with it, to surf the wave of pain, of anger, of sadness, whatever it is. And I started to kind of incorporate that with executive coaching, with a kind of framework that Yeah. And do you want to also keep contributing to the world? A lot of people don't want to just step away. Oftentimes they can't, right? They have a family to support. They need to keep working or to have a startup to run. And so it became, and it is still becoming this combination of offering this deeper emotional work alongside more dialed-in direction setting for where you want to take your company or your career or your life.

So give me an example. You say you need this daily habit. What would be something I could do to start to connect and avoid that burnout?

If it's possible to you, I would recommend to find something that is not solitary.

So not sort of self-meditation.

I really, I would not, yeah, not self-meditation. I would recommend against that unless that's the only thing available to you. I would recommend that if you can to find a therapist or find a coach or find a mentor in your company that you can have regular conversations. So even a trusted friend, there's a beautiful practice that people can Google. It's called Empathy Buddy Calls.

Hmm.

And if there's a framework for this, how to have kind of these deeper conversations with a friend, because often they, even though we might trust someone or have a great friendship, they don't always go to these deeper levels. And it's a great framework. That would be my suggestion to have some support. And the reason I think this is important is because the very idea to do things alone, especially for the likes of me, are only further perpetuating the way I see the world, that I need to be hyper-independent, that I need to pull myself out of a lake by my own bootstraps, that I need to, you know, it's about strength and doing things alone. And I find that, again, back to like kind of evolutionary science, is not really how we evolved. It's not how our brains are wired. And it's not as effective as doing it with another person. Even when I lived at the monastery, it was so interesting that none of these monks meditate alone. Every meditation is together. And this monk, Thích Nhất Hạnh, he emphasizes sangha so much. He says, like, if you don't have a sangha, which is a Buddhist word for community, it's almost impossible to really go to the depth that you need to go to, to deeply transform within yourself.

That's so interesting because I've definitely read also— I want to say it was Naval Ravikant who sort of made fun of how Westerners turn solitary things like yoga yoga, meditation into group activities.

Interesting.

Team sports.

Interesting.

Yeah. And I forget the exact tweet, but I kind of took it to heart a little bit because I do often like to exercise or meditate with at least one friend, if not more. And I was like, oh, am I doing it wrong? Maybe I need to be more comfortable being alone.

Right. And, and I can see the point of that too, right? I can see the point of that.

But your advice is different for your clients.

Absolutely. And it has become different. You know, if he had asked me 4 years ago, I would have— I've been meditating on my own for years and years before going to the monastery. And I agree on the point that if it becomes a sport, or if it becomes like a co-exercise, that is not what I'm talking about. What I'm talking about is to enter spaces together that have a certain depth, where you and I say, if we were to do this together, I might still have a solitary experience by you holding space for my experience. But from a nervous system perspective, the charge that is needed to allow some of these deeper things to come up through the vagus nerve and through my amygdala, in order for that to be held— the amygdala is kind of the fear center in our brains— for that to be not going all over the place, having a second nervous system there to create a sense of safety, I believe, is so extremely vital.

So that would be your advice to someone starting out, say, find a buddy and do some of this more mindful activity together.

Absolutely. If that's possible, that I think is— and talk about it.

How do you think about, you know, we've used the word burnout already. What does that mean to you?

In the same way that the word stress, I like to use it less so because it doesn't really give us a sense of what underlying thing is that is happening. I think I even like to use the word PTSD better.

That's a heavy one.

Right. For most people that will sound heavy, but most of—

And it has stress in it.

And it has stress in it, right? But the interesting thing when we talk about PTSD, and I don't talk about the way it's defined for psychologists, I talk about post-traumatic stress. And maybe we can leave off the the D, the disorder, because I don't really think it's a disorder. But I think it's anything that when we feel kind of tense in our bodies, it's because it's post-traumatic stress. There has been a certain event in our lives, and that may have been in our childhood, or that may have been, you know, a meeting or a presentation, and our brains weren't able to integrate fully what was going on. So I'll give you a common example, right? Maybe you're a founder, you have a meeting with your board, and it's a very heated debate. You're not getting the buy-in, you're not getting the agreement for something they really wished you could do. And you leave this meeting feeling quite distraught, feeling quite activated. Your nervous system is kind of charged. You feel angry or you feel sad, or there's something you no longer regulated. Now, most people don't have a way to resolve that. They have a way to autoregulate. It's different from self-regulation, and I'm bringing in a few terms here, but most people then autoregulate. They have a glass of wine or they have a drink, or maybe they watch something on TV to soothe themselves.

What's autoregulate mean?

So the way it's defined in kind of neuroscience terms is our natural unconscious coping mechanisms to deal with deregulated states. And deregulated states means when we're not relaxed, in a relaxed alertness. So That means eating sweets, right? That's a common autoregulation pattern that I have. When things get tough, my mind sometimes goes to the ice cream tub in the freezer. And, and, and, and—

For me, it's a matcha latte. If I'm tired from the day before, I just like, you know, the afternoon comes along, I'm like, mm, matcha latte. I deserve this. And, you know, I get addicted a little bit to that. I don't have very much caffeine, so it does have a big effect on me.

And that's a wonderful example. You know, autoregulation doesn't mean it's bad. We all have that. This is, you know, it can have extremes like heroin is autoregulation, right? In the same way that going for a walk in the forest is autoregulation, right? Things that we don't think about too much that just some come to us that have been sort of ingrained patterns and habits and we do them.

Is burnout avoidable?

I think so. When we have self-regulation. So self-regulation is a way to deal with the actual effects of what happened in the meeting and to fully process it. For example, if you go back to the example of the board meeting, the body always keeps the score of whatever we haven't fully processed. And so the more of these episodes you have, and in a startup very quickly, you might have a lot of meetings where things don't go on. If you don't have the time to self-regulate, to talk through this, with a friend or with a therapist or with a coach or somebody, or with a partner. You know, some people have very healthy self-regulation coping strategies there. You're actually getting to the root. After the meeting, say I had a hard meeting and you're my good friend Matt, and we sit down and you ask me, "Hey Leo, you know, how are you doing? You look a little upset. You look a little tired." And I could just say, "Yeah, I'm so upset. You know, this sucked." in this meeting, and you reflect that back to me, you help me and say, yeah, it sounds like you weren't heard and you didn't feel seen, and that sounds— it was very painful. And you just keep holding space for me. And I might cry because it just makes me so sad, and I might shake my fist because I'm so angry. Letting the bodily states come in— I can't shake my fist at the investor in the meeting. If I have a chance to self-regulate with someone I trust later on then something magical happens. Then this stuff doesn't build up. And 5, 10 years in, you know, you don't feel like all of a sudden your body's tense, you know, from so many different things and you don't even know why. And you just need to lie down and we call it burnout. When really, if we looked closely, we could trace it back that it's all these individual episodes of moments that haven't been processed.

Let's say that I had a friend who had been through something tough. How can I best hold space for them?

The most important thing that you can do to a friend that's going through a hard time is to offer what neuroscience calls warm accompaniment. It used to be called empathy, but empathy has kind of used to be— it's got a little, you know, it's empathy feeling what someone else feels. It doesn't really kind of encompass anymore what is meant or what makes it understandable. So warm accompaniment accompaniment means that you refrain from giving any advice, not trying to fix anything. You're not trying to tell them about your experience. You're not saying, "Oh, this reminds me of my time when I was sick." You're not trying to do anything but ideally, and this is from a practice that I also really enjoy called Nonviolent Communication, you just offer back what you're hearing. And that can be as simple as reflecting back the exact words and And that's not always the right thing for people. But if you're just getting started, you know, just saying, if you were doing this with me, Matt, you know, you say like, I had such a hard day at work. For me to just say, wow, it sounds like it's been a really hard day for you. That is the kind of warm accompaniment to be, I'm right there with you without being carried away by your experience. And so reflecting back what you heard somebody say, noticing whether you can be present. You know, if you get carried away and you might say like, "So I also had such a hard day at work and your day was so hard," now we're not co-regulating.

So I shouldn't try to match it.

Right.

Should I say, "I know how you feel"?

So "I know how you feel" is sympathizing with another person. It is not warmly accompanying their experience. When someone is having a hard time, what is important to them is to understand, for the nervous system to understand, that what they're feeling is okay. And I think that's what you're trying to say when you say, "I know how you feel." But more important, I think, is to offer up the reflection with warmth so they can see, "Yes, that's what I'm feeling, and this person is not triggered by this, so I guess it must be okay and my body can relax a little bit." What are some other examples of warm reflection? The main way we used to communicate as mammals is through the tone of voice. And there's a term in neuroscience called prosody that means the emotional content that your voice carries. And there's thousands of nuances that we have in our voices to communicate how we are feeling without the informational, the data of the words we're saying. So the most important thing that you can do is just to— the way you say, "Mm," or the way you say, "Aha," or the way you say, "I get it," the emotional content of your voice is the most important signal of safety. And we want to do that with kind of the resonance of our voice. And the best way I know how to do this is purely by understanding that you can stay present. To cultivate that yourself, right? It's hard. It's gonna be hard for you if you don't know how to—

It's hard to listen.

Right?

Right.

It's hard to listen if you haven't had enough listening from yourself for yourself or from somebody else for yourself so you can hold space. So that is, you know, the long-term practice. But looking into needs and feelings guesses from the Nonviolent Communication framework is a really wonderful, specific thing you can do to say, Are you feeling really upset because there wasn't enough understanding in this meeting? So that now the person has a chance to either say, yeah, you're getting me, and can expand or can clarify what their experience is and accompany that warmly and can say, no, I'm not upset because I wanted understanding. I'm really upset because there's no harmony in this company.

Aha.

It's not about understanding, it's about harmony. Right? And so now the closer, the more precise we can get to experiences, the more likely our nervous system can discharge it and let go of it.

And the classic book on nonviolent communication is by Marshall Rosenberg.

Marshall Rosenberg, yeah, exactly.

Well, I would particularly recommend it to anyone who's a manager, because I think one of the most important things you can do as a manager is listen to people, right, and really hear them. And that's very difficult, I think, especially if you're a new manager. There's a temptation to make it about you, right?

When you're a manager and you haven't done— all of a sudden you work with people, right? And you haven't done your own inner work and your own inner training, it's going to be hard to hold space for people, which to a lot of people is a first when they first become managers.

And that's a lot of what I've been thinking about as well, is people who are becoming managers for the first time in distributed organizations. Lots of people who are freelancers, but when you start to get to managing 50, 100 people, in a distributed fashion. There's just not that much out there about it.

Totally.

You've written about something called the Loneliness Spiral. Can you introduce that for the audience?

The Loneliness Spiral is associated with the fact that we have, as mammals, evolved to be in groups. We are very unfit to survive alone. When we are alone for too long of a stretch of time, many people report to feel a feeling that they name "I feel lonely." And that feeling is simply our nervous system's alarm system to say, "Hey, hey, you know, if you spend too much time alone, you're not going to survive in this world. Go make some friends. Go be with family. Go be with other humans." And we need that kind of physical touch, really in-the-same-room kind of interaction for that, often for that feeling to dissipate. The problem with the loneliness spiral is not that we feel lonely. The problem is that oftentimes when we feel lonely, we feel scared at the same time. And actually, when I feel lonely, what I want to do is go out and meet friends. But if I feel scared, now I start doing things because I'm not able to hold that emotion very well in my body. I end up maybe sitting on the couch, eating more potato chips because that kind of fills me up. And then watching some YouTube videos.

It can distract you though.

Right. No, exactly. So that can distract you, but it's not taking care of the underlying root cause. The thing that happens over time, if it's not being acted on, parts of our brain— an author called Stephen Porges, he wrote a book called The Polyvagal Theory. He calls these part of our nervous system the social engagement circuits. If they are not exercised, like a muscle through regular social engagements, through regular social contact. And this is one of my concerns with remote work. If that's not exercised, it atrophies.

So we're talking right now. Sounds pretty good. Like you could be right next to me. Does this also get activated by video calls, like by phone calls, those sorts of things? It does. FaceTime? It does. That's good news.

That is good news for remote work.

Because then I can connect with someone anywhere in the world.

It's good news, and I wonder if you've noticed this with remote work, is that most calls are scheduled, right? We're not here to just catch up. You know, we're not here to just tap me on the shoulder and say, "Hey, Leo, how you doing?" by the water cooler, right? "How was that concert you went to last night?" So, the sort of social engagement that I'm talking about, the kind of almost intimacy that can develop, that happens most likely when things are unscheduled and spontaneous, are much harder to happen. We've experimented with this at Buffer. We tried to have book clubs and kind of social hangouts on Zoom and whatnot to kind of create that. And I think that's often what's needed beyond the scheduled meetings where there's kind of an agenda and you work through and the informational content really is the thing what it's all about and not the emotional content that really is the thing that trains our nervous systems to know, okay, I'm not alone, there's other humans, they care about me, I care about them, that kind of thing.

How about if I'm in a crowd? 'Cause I know personally sometimes I can feel very lonely even though I'm around a lot of people. Just going to a coffee shop, but is that gonna help anyway?

It's something, it's something, but you can still feel very lonely. And my view on that, from what I've learned about, you know, kind of our inner states, is that often that social engagement is activated only when we reveal something about ourselves, when we show something about our truth and about who we are. And that's sometimes not very likely to happen in a coffee shop. You may walk around a lot of other humans, but there is no heart-to-heart, or there is there's no kind of emotional connection. I think the CTO at Product Hunt, his name is Andreas Klinger, he had the great suggestion. He said like, "I think it's a good idea for remote workers wherever they live to find other remote workers and to start small offices together so they could develop a kind of a group cohesion even though they don't really work together." I love that.

A lot of folks listening to this are probably on one side or another of a one-on-one with a direct report or a manager. And so what would be some good questions or things for people to do when they're in those meetings?

The most important question, I think, for a manager is to ask the person how they're doing. It's colloquially so common to answer that with "fine." It's almost like a reflection.

Like, if you said, "How you doing?" I'd be like, "Yeah, good." Right. Or "fine." I wouldn't even think about it really.

Exactly.

Because it's very vulnerable to answer something not well.

Right. So it becomes a question, how can you give people a chance to open up? The number one way I know how to do that is to give space to the other person to resolve things themselves. As a manager, the best thing you can do is train yourself to hold space for yourself so you are not having a million things that you need to unload on to your employee, to keep making more room, to keep letting more things bubble up that can be resolved involved, do you feel— how do you feel about this? You know, what do you know? To keep it with open-ended questions and to let advice maybe only come in at the very end.

So, I mean, you co-founded one of the more prominent distributed companies. If you did another company, would you make it distributed again, or do you think that kind of in-person is more important?

I would probably not start distributed for a sapling to grow. I have this feeling that being in the same room together could be really, really vital, at least the first 2 people.

I would actually, I think, I would probably agree with that. WordPress, we were always distributed because it was open source, but for Automattic, the early folks, myself and Tony, who joined as the CEO a few months after it started, we would see each other quite frequently in San Francisco. I was more based there at the time.

So I think that early time, I think being together could be just extremely vital. And over time, I think I feel I would be still excited to to open that up and to make it fully remote, you know, as you go beyond 10 people. And I would— kind of remote work is a little bit like the Wild West, you know, has so many benefits, but there's so much that's not understood about the dynamics. I would probably be even more conscious about, first and foremost, my own coping strategies to being working alone a lot and setting myself up much better. Oftentimes the people that joined later don't they were way better set up than people that were wanting to have a job at the company. They already had their families set up, right? And they were happy to spend more time with their kids and at home. And, you know, oftentimes they were better set up than me as one of the founders too. Like, that's all over the place all the time.

So let's say we are doing a distributed company. We talked about some of the advice you'd have. Any other tips or things that you think, you know, from your experience folks in a distributed company, managers or founders, should think about?

Cultivating human-to-human connection as much as you can within the company. I had this one idea, I think what would be great is to have for these maybe distributed companies in particular to have a resident stress therapist, you know, that people could just go to and sit with for an hour and pour their heart out in relation to what's going on in the company so that they have some context, right? And then to meddle with the less productivity-related things when I believe productivity is always about emotional state anyways. When we are not productive, it's because the task at hand has some emotional charge that stops us from doing it. Either we are scared because of how people might receive this. A lot of people are scared of being successful and being seen because there's a lot of underlying trauma around actually being seen for what people do. So I think always the reason when someone doesn't want to do a task, there is some underlying emotional charge that's not being taken care of. And finding a way to get to that within a company with— through maybe a group activity, regular, like, structured or unstructured time where where people can interact with each other and to work with a manager or to have a stress therapist or something like that. So that those aspects of your life that are often where you get stuck, they can get unstuck.

I've been asking everyone, if you could imagine 20 years in the future, what percentage of jobs do you think are distributed or not at all?

Hmm. I would maybe say 30%.

30%. All right. I appreciate it. Well, Leo, thank you again so much for joining today. A lot of good tips, and you've given me a lot to think about.

Thank you so much for having me on, Matt. It's been a real pleasure.

That was Leo Widrick, and you can find him on Twitter at @LeoWid. That's L-E-O-W-I-D. Or at his personal site, powered by WordPress, leowid.com. If remote work is going to become the rule rather than the exception, we're going to need to come up with ways to cope emotionally with our new social environments. Maybe that looks like Maybe it's like regular team meetups. Maybe it means hanging out in virtual reality. Maybe it's coworking spaces with happy hours. Maybe if people feel less pressure to leave their hometowns to go work in employment hubs, they'll be able to maintain stronger ties with friends and family. The solution's gonna look like all these things and more. Whatever the future of work looks like, I'm glad that people like Leo are thinking about the psychological traps that might be easier to fall into when working from home. I know that the next time I start to feel a little lonely, I'll make plans to grab a matcha latte friend so my vagus nerve can get some exercise.