How to Stay Connected in a Distributed World

When Buffer co-founder Leo Widrich reached his breaking point, his company was pulling in millions in annual revenue. He’d achieved his dreams of profitability and financial security, and he’d built a dedicated team working together toward a common goal. His team was distributed, a point of pride for the company. But Leo was lonely, unfulfilled, and felt ill-equipped to cope with the ups and downs of life. 

Distributed Podcast: Hear Matt Mullenweg in conversation with Leo Widrich. Read the transcript.

The Silicon Valley startup model has generated massive economic growth in the U.S., but the odds are still against the average startup. Nine out of ten will fail, including many who’ve received millions in VC funding. The environment can be a psychological minefield. Startup founders and employees feel pressure to work around the clock and “crush it” until they reach the next funding round, sales goal, buyout, or IPO. There’s always an upcoming milestone after which things will become “normal,” everyone will be able to relax, find a reasonable work-life balance, and focus on the long-term goals of the company. But for many that moment never seems to arrive. Instead, startuppers find themselves working their lives away. 

It’s a recipe for burnout, and Leo was feeling it. Even startup founders who are successful by any conventional metric can hit a wall where they are utterly exhausted, unable to cope with the pressures of running a business, neglecting their personal or family lives, and wondering what it’s all for. 

After reaching his breaking point at Buffer, Leo spent two years in a Buddhist monastery “doing deep inner training” and “pausing to reconnect” with himself. Fortunately Leo was able to emerge from the other side of his burnout with a new outlook on life, and now he wants to share that outlook with other founders and executives. 

Today Leo practices emotional resilience. The term is so important to him that it’s the name of his coaching business, where he counsels other founders and executives. When Leo left Buffer, he hadn’t set out to become a personal coach, but his experience at the Buddhist retreat changed the course of his life. 

I was living in New York, and there is a monastery called Blue Cliff Monastery in upstate New York that I wanted to check out. I went there for a few retreats, to see what this life is like, that seems the exact opposite from the rapid-fire startup life, where these Buddhist monks and nuns were living, going so slowly, [with] barely any agenda…

Widrich discovered Buddhism in the writings of Vietnamese monk and activist Thích Nhất Hạnh, one of the most widely-published modern Buddhist activists. Hanh’s approach incorporates various strains of Buddhist thought and adds ideas from Western psychology. Leo takes this teaching a step further through the integration of Western management training and self-help literature. Now he wants to share the methods of emotional resilience he’s been developing since his exit from Buffer to help others avoid the burnout he experienced. 

Making Connections in a Distributed World

Distributed work is such a new phenomenon that even companies that have embraced it are still codifying best practices for employee wellness. There’s still a lot we don’t know about what it takes to foster mental and emotional well-being in a telecommuting context. This year, Buffer’s “State of Remote Work” report, based on thousands of interviews, revealed that almost half of the remote workers surveyed noted that their biggest struggle is wellness-related. Twenty-two percent can’t unplug after work, nineteen percent feel lonely, and eight percent have difficulty staying motivated. 

It’s not easy to maintain emotional wellness at any workplace, but the stresses that distributed employees must overcome are unique and not commonly addressed by the scads of traditional-workplace psychology books released each year. Perhaps the primary challenge is finding and maintaining human connection. Leo recognizes the hurdles these employees face more than most personal coaches because he founded and helped run a distributed company. 

The main way we communicate as mammals is through the tone of voice. And there is a term in neuroscience called prosody that means the emotional content that your voice carries. And there are thousands of nuances that we have in our voices to communicate how we are feeling without the information or the data of the words we are saying… The way you say, “Mmm,” or the way you say “Uh huh,” 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 the resonance of our voice. 

On distributed teams, high-fidelity vocal conversations you might see around the office can only happen over video chat. Video chat technology represents a key tool for distributed teams, but the default often remains fast, asynchronous text chat or email. As a result, sometimes wires are crossed, messages are misconstrued, and feelings get hurt, which can lead to distributed workers feeling disconnected from their teams. 

Compounding this problem is what Leo calls the “loneliness spiral,” which occurs when remote employees don’t make a strong effort to maintain meaningful work relationships. 

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 a feeling that they name “I feel lonely.” And that feeling is simply our nervous system’s alarm system to say “Hey if you spend too much time alone you’re not gonna survive in this world. Go make some friends, go be [with your] family, go be with other humans.” And we need that physical touch, really in a same-room interaction for that, often for that feeling to dissipate. 

In a loneliness spiral, a feeling of standard-issue loneliness is amplified by fear. We begin to think that we deserve to feel bad, or that we aren’t deserving of meaningful relationships. So instead we turn to coping mechanisms that distract us from loneliness and fear, leaving them to metastasize. 

It can take a long time for these problems to amplify to the point of burnout. For Leo, it took six years for his lifestyle to catch up with him. 

Building Buffer, Building to a Breakdown

In 2010, Leo was just another aspiring business school student. His friend and future co-founder Joel Gascoigne came up with the idea for Buffer in his Birmingham, U.K., bedroom after using Twitter for about a year and a half. His followers were engaging with his content, so he wanted to partially automate his activity. He tried a few existing tools that required him to attach a time and date to each tweet, but he wanted something simpler — for example, tell an app to post five times a day and let it do the rest. He created a simple tool called Buffer and shared it with his modest Twitter following in November 2010. Three days later he had his first paying customer. 

Joel iterated on the project across many mini-launches, enabling the company to generate continual press. Leo’s content-marketing sensibilities helped take Buffer to the next level. Leo dropped out of college to invest all his energy in Buffer after hitting what he calls “ramen profitability” at $1,000 in revenue per month. Leo wrote constantly about the company’s progress on the Buffer blog, guest-blogged at friends’ sites, and penned articles about social media management at various news outlets, keeping the site in the headlines and on the radar of tech and media leaders — people who could not only help Buffer build an audience, but also become potential customers themselves. 

When Buffer hit 20,000 users in July 2011, the co-founders uprooted their lives and moved to San Francisco. They took 150 meetings with investors, 18 of whom believed in the company enough to invest. They raised $450,000 to turn Buffer into a more comprehensive social media management tool that enabled customers to post on LinkedIn, Facebook, Twitter, and eventually other platforms. 

Although momentum was building in San Francisco, Joel is from the U.K. and Leo hails from Austria. It turned out that securing U.S. visas was not as easy as they thought it’d be, which meant they wouldn’t be able to stay in the Bay Area. They relocated first to Hong Kong in January 2012, then six months later to Tel Aviv after more visa troubles. These woes resolved by mid-2013, and the company officially relocated back to San Francisco. But this experience drove the founders to embrace a distributed model so they’d never have to let their talent acquisition suffer from geopolitical or bureaucratic bottlenecks. Around that time their team had grown to 10 people, with employees joining from the U.K., Australia, Hong Kong, and the U.S. They instituted regular team meetups to cultivate shared mission and friendship. 

They continued to iterate on their product with updates to the tool’s scheduling options, and drew in more customers through thoughtful content marketing. In 2013 they launched a new Buffer blog called Open, which narrates their “journey as a remote, transparent company trying to create a happier workplace culture.” In addition to its distributed status, Buffer made a name for itself for being transparent. They made details like revenue, salaries, equity, fundraising, and diversity numbers, as well as prices and product roadmaps, fully available to the public. When Leo decided to leave Buffer, he explained his decision in a blog post

Over the last few years, and particularly the last 6 months, we noticed that slowly some differences were emerging between how Joel would approach execution and how I would in various instances. When we discussed topics like new product offerings, the spectrum of nurturing versus performance for bringing on new team members, being customer-centric versus team-centric, we were more often than not starting to fall on differing parts of the spectrum.

But the differences in management style and their divergent aspirations for the company weren’t the entire story. Today Leo describes his state of mind at the time in starker terms:

I started to feel like I was hitting a wall. This thing that I always dreamt of, to have a profitable company, to be financially secure, to have a team… I felt that having that success, having some of that financial security — it left me unfulfilled in a lot of other areas. — in the sense of deep lasting connection and also a lack of emotional resilience to deal with the ups and downs that startup life comes with.

Fostering Empathy and Warm Accompaniment

Leo is quick to clarify that people seeking emotional wellness and mental health don’t necessarily need to go live in a monastery. Leo takes a cue from Thích Nhất Hạnh, who developed a school of thought called “Engaged Buddhism,” to explain how Buddhist teaching can help its adherents contribute to society in a positive way. 

You don’t need to go off for two years. But there needs to be some sense of regularity to coming inward… 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. 

But this inward focus doesn’t mean that Leo advocates a solitary pursuit of wellness. This is where his perspective can be valuable for remote workers. Support from others is key. 

The reason I think this is important is because the very idea to do things alone, especially for the likes of me, [is] only further perpetuating the way I see the world, that I need to be hyper independent, that I need to pull myself [up] by my own bootstraps, that it’s about strength and doing things alone…It’s not how we evolved, it’s not how our brains are wired… 

The individualism of Western capitalism isn’t well-suited for the cultivation of communal wellness and connection. But Leo says that these are so crucial that one needs to be intentional about finding support in one’s community. He recommends a scheme for this he calls “Empathy Buddies.” 

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 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 yourself.

In addition to this ancient wisdom, Leo brings insights from modern neuroscience to his wellness philosophy, like the concept of autoregulation, which he defines as a natural unconscious coping mechanism to deal with a deregulated state. This could mean binging on junk food when one feels anxious or avoiding interpersonal contact when one is struggling with low self-esteem. 

Leo’s solution to this destructive pattern is self-regulation, a mental tool which we can consciously build within ourselves. Essentially, when we are tempted to return to self-destructive behaviors, we can examine ourselves to determine what’s driving those urges. “The body always keeps the score of whatever we haven’t fully processed,” says Leo: we carry emotional hurt and frustration around with us, and these manifest in physical ways. The goal is to fully process this pain rather than dulling it with excessive work, food, drink, or some other short-term balm. We must ask ourselves, “Why am I feeling this way? Why do I feel hurt? Lonely? Misunderstood?” 

Again, Leo advises that this process can be enhanced when performed with a partner or a group. He advocates a practice called warm accompaniment, which is designed to help you help others through hard times. 

Warm accompaniment means that you refrain from giving any advice. You’re 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… you just offer back what you are hearing and that can be as simple as reflecting back the exact words. 

Organizational Solutions for Distributed Teams

One solution a lot of distributed companies try for countering employee loneliness is meetups, both at the team and company levels. These allow team members to get to know one another on a personal level and collaborate on projects that are well-suited to collocation. As teams grow in size, team bonding becomes more difficult, so ensuring frequent face time is something that most distributed companies (including Automattic) have made part of their company culture. 

But what can managers of remote employees do on a day-to-day basis to help employees feel more connected to their teams? Leo suggests that it can be as simple as asking the employee how they’re doing on a regular basis. Check-ins backed up by a genuine compassion for one’s teammates can help team members feel valued and connected to their colleagues beyond the work that has brought them together. 

Leo also recommends that managers deal with the noise and emotional dissonance in their own lives so that they can be equipped to listen well and perform warm accompaniment with workers who may be in emotional distress. 

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 onto your employee, to keep making more room, to keep letting more things bubble up that can be resolved … To [ask] open-ended questions and to let advice maybe only come in at the very end

Leo provides some great exercises and mental models for both managers and employees. At a higher level, it will be HR leaders in distributed companies who chart the course for the future of employee wellness on distributed teams. One suggestion Leo has for large distributed companies is to consider hiring an on-staff stress therapist to provide remote stress management coaching. 

The personal wellness frameworks Leo recommends are ones he typically teaches on a one-to-one coaching basis, but that doesn’t mean that distributed companies can’t introduce similar wellness practices, in addition to those derived from other schools of health and wellness. Perhaps new technological tools that we can’t yet imagine will one day help employees stay connected not just on a collaborative level, but on social and emotional ones as well. 

Illustration by Homestead Studio

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