I first wrote about Buffer, and its co-founders Joel Gascoigne and Leo Widrich, nearly seven years ago. Over the years, I talked to Leo about Buffer's quest for transparency. And the company's foray into self-management. And how, after becoming profitable and banking nearly $1 million in cash, the company raised $3.5 million in capital. 

By any standard, Buffer was extremely successful. And so were Joel and Leo.

Then Leo decided to leave Buffer and start a new venture. 

And, then, when that business was thriving, he decided to live in a monastery in the woods.

Balance sheets, P&L statements, bottom lines: Numbers are important, but they only tell a small slice of an entrepreneur's story. The emotional journey every entrepreneur takes is even more fascinating.

Why did Leo decide to spend months in a remote Buddhist monastery and return, as he says, "maybe not much wiser, but slightly more emotionally resilient in my approach to life and the world"? 

Let's find out.

You crafted an extremely successful entrepreneurial career. Give me some context for why you decided to make such a drastic change.

A little over eight years ago, I started a very promising project with a friend. That project became Buffer, which became one of the most successful and well-known brands in the niche of social media marketing software.

Today, the company is making close to $20 million a year and continues to grow.

But for me personally, something happened along the way. About five or six years into working on the company, as we got more and more successful, almost the opposite seemed to be true for me. 

Slowly but surely as the years carried on, the light breeze of excitement I felt from working on the company of my dreams started feeling like wading through mud. Every step became heavier and more difficult than the one before.

And the most frustrating part was that I couldn't figure out why. Why wasn't my level of happiness and aliveness growing alongside the growth of the company, the people we hired, and the success we were having? 

That's not an uncommon phenomenon. Many people love the start but not necessarily the "middle."

After mulling it over for months and running into some misalignment about the future of the company, I turned to what I thought was the right next step: to leave and set out on a new venture, one where I'd rediscover my lightness and sense of well-being that I had had in earlier years.

In a way, it was an effort to recreate the feelings and sensations I had early on at Buffer.

For a few months, it seemed to work. Together with a small team, I worked on building a product that had strong meaning for me.

But, after a short amount of time, that, too, left me feeling stuck and frustrated. The experience wasn't living up to the idea I had in my head. And I was just tired and disillusioned about what to do next. 

Which made me feel like I was at a major crossroads in my life.

Just as the realization settled in that this also was clearly not the thing that I wanted to keep doing, a large company approached us to buy the product and the early team for a few million dollars.

It seemed almost too good to be true. I had been working for just a few months on something that I was already not enjoying as much, and now I could sell it -- and save face from any fears of failure I was starting to have.

Sounds like an easy decision.

But, actually, it wasn't. My head was spinning. I found myself coming up with arguments why I wouldn't want to sell.

A year earlier, I had done a kind of strange "self-finding" workshop that had opened with the question, "What do you see yourself doing in five years?" Even though I wanted to roll my eyes until they vanished in the back of my skull, I went along with it.

So, a year later, I opened my notebook and read what I had written the previous year during the exercise: "Live in the woods and lie on the grass by a quiet lake."

Startups can be all-consuming. Was the problem mainly that you were burned out? 

Yes, a part of me did feel very tired and exhausted. But more than that, I felt like I was stuck and frozen, and that my life was no longer in flow.

I had a routine that was almost set in stone. There was so little meaning to my life and my endeavors. There was no flexibility, no spontaneity.

With that came a deep unhappiness and despair, even though I had achieved some measure of financial security.

Also, I had the sense that my whole life happened on a certain plane that seemed very narrow. There wasn't enough expansiveness, aliveness, vulnerability, and trust that things would work out. Everything had basically tightened up. 

That sounds extremely painful. So what happened next? Did you just drop it all?

In a way, I did. I left everything behind. I desperately wanted to have a makeover.

There was a Buddhist monastery in the woods of New York I had visited a number of times before. I went there to seek refuge, and lived with monks and nuns for a while just to see what would happen next -- and if my sense of well-being might improve in some way.

I remain very grateful to them. It was a gentle yet also a fairly rigid regime of early morning meditation, chopping wood ...

At first, I thought I'd go for a month. But I kept extending my stay. In all, I spent almost two years in that sort of setting, and today I still live close to the monastery in a small apartment near the woods.

Clearly, the experience grew on you. What did you learn? And how did that change your perspective?

It was one of the most transformative periods I've ever experienced. My whole body, or more, my whole nervous system seems to have turned itself inside out since then.

I thought I had been everywhere up to that point: traveling the world, achieving some financial success, and even tasting some amount of fame.

Yet it turned out there was one place I hadn't been, which was turning the focus toward the inside.

One of the reasons many people like to stay busy is so they don't have time to be introspective. I've done that. Probably still do.

At first, what I found was very painful, like discovering a house that I had lived in for 27 years but hadn't tended to or even visited. If you imagine what a house like that would look like, you have a pretty good idea of my inner world at that point. 

So for the first time in my life I really tended to my "inner house." I opened rooms I had never been to. I wiped off the dust. I cleared out and healed things that were rotting and hadn't received any attention.

Even before going to the monastery, I had been meditating for more than five years. But I discovered that wasn't something that had gone very deep. Even though I had thought it had. 

I also learned a lot about how trauma works and lives in the body, especially with experiences that seemed "normal" to me before; for example, like a parent not paying full attention when I was crying as a child. I ended up studying a lot of that: how neuroscience shows that emotional trauma stays forever with us, stuck in our bodies, until the point that we attend to it with kindness and empathy.

I tried different therapy modalities. I found talk therapy very unhelpful. Eventually I landed on a method called somatic experiencing that is growing in popularity. It's an approach that relies on the scientific evidence of emotional difficulty and how it lives in the body, and how it can be gently released from the body. 

What impact did all the changes you went through have on your professional journey?

It definitely changed everything about how I wanted to live my life, and how I wanted to contribute to the world. A part of me felt the need to change gears completely.

I learned more about meditation practices and started teaching. I studied nonviolent communication as a modality and underwent some training in somatic experiencing, the body-based psychotherapy method I mentioned earlier.

My dream is to pass on what I learned in a way that is accessible to people. I'm not sure many are interested in taking two years off to live in the woods. [He laughs.]

But my hope is that a lot of people want to get a little more access to their inner world, to feel more emotionally resilient to deal with their lives, and, ultimately, to bring more happiness into their lives. 

That really became my focus when I emerged from that intense time of inner healing. I've been working with dozens of founders, entrepreneurs, and professionals since then in one-to-one sessions to offer them the kind of empathy and support around tending to their emotions that I craved. 

What are some of the most important things you've learned since then that you can share with other entrepreneurs and professionals?

First, I should acknowledge just how much of a privilege going off for a couple of years or more to tend to my inner world has been for me. I understand that is not accessible to most people. That's why I want to make those kinds of healing experiences available to everyone -- even and especially those who have important jobs and companies they can't just put on hold like I did.

Although, I do think there are times that is a good idea.

The most important thing I recommend to anyone for whom this resonates is to build a true support network -- especially on the emotional level, but also on the business level. That can come in the form of therapy, or coaching, or regular meetings with a trusted friend.

I used to be very averse to that, basically thinking it's not cool to allow yourself to be supported by others in that way.

I'm embarrassed to admit I still feel that way, even though I know I shouldn't.

I think very differently about it today, both from my personal experience and my professional experience training as a body-based therapist in somatic experiencing.

As mammals, we've evolved to co-regulate our emotions and feelings. We're not really meant to be as independent as the Western world often believes. 

It took me a long time to understand that, and to allow that support to come into my life. Ideally, you can find someone you trust on a gut level whom you can be vulnerable with and have regular sit-downs when you feel stuck in your life.

There are few things more powerful than that for building a healthy and happy emotional and, by extension, professional life. 

I also recommend reading and learning about the importance of our emotional world, how to regulate emotions, and how well-being happens in our bodies from a neuro-biological perspective. Two books I really recommend are In an Unspoken Voice by Peter Levine and Your Resonant Self by Sarah Peyton.

A lot of self-help focuses on action, on how to push through, how to "win," how to move, break through, and achieve. I get that that is an important aspect. Yet I also feel there is not enough emphasis on learning how to hold space so that life, your emotions, and your body can unfold and be heard in the way they want to. There needs to be a lot more balance between the action-oriented mind and the empathic, space-holding, emotionally attuned mind. Only when the two are integrated can true healing, meaning, and happiness emerge. 

You sound like you're in a much better place, but what do you still struggle with?

Finding that balance I just referred to is still very hard for me. It's hard to go from on to off when I work on or do something. That habit of go, go, go is ingrained in me.

The other day over lunch my girlfriend said, "I don't think you're really here. Is your mind still on that client?" I had to nod sheepishly.

It's an ongoing challenge to live in that in-between space, where I do the things I want to do, but then leave them and step back and do other things. Or just rest. 

Along the way, I had unconsciously decided that I only matter when I'm always working and achieving. Unraveling that, and letting it go, has been hard. 

That's an important point: Integrating what I'll call mindfulness with the desire to achieve certain things is really hard.

To be honest, it's been fairly hard. Writing and talking about marketing software was a lot easier. [He laughs.]

That's why I've made building emotional resilience a centerpiece of my life, both for myself and for others. I want to share that with the world by being the support person to entrepreneurs and professionals that I wish I'd had.

And also by offering tips and insights on what it means to get more in touch with our inner worlds to build emotional strength and resilience, in part by writing and opening up about my journey and experience. I'd like everyone to have easy access to that sort of wisdom of the body and of the latest findings of neuroscience around emotional resilience.

Published on: Feb 26, 2019
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