What I Learned When I Was Burned Out

For most of my life, I associated burnout with a lack of self-discipline. I thought it happened to people who weren’t attuned to their needs, who pulled all-nighters, who didn’t exercise or eat well. As a physically healthy, reasonably successful entrepreneur, I assumed I wouldn’t ever burn out. I was very wrong.

I founded CircleUp, a technology-powered investment platform, in 2011 with Rory Eakin. The early years were challenging and thrilling, but in mid-2016, as I shared years later in this post, something changed for me. This was the period in which we realized that, to survive, CircleUp would need to pivot. Figuring that out was agonizingly stressful, and it prompted a round of layoffs, the first I’d ever had to navigate as CEO. Just after, we had to secure another financing round for the company and launch our first investment fund. And during all of this, I was juggling brutal personal problems: My wife and I were experiencing fertility issues, and I was diagnosed with cancer. My directors, cofounder, and a handful of close friends knew what was going on, but I kept it from everyone else, fearing the news would damage company morale during an already difficult period.

There were stretches of time when I felt lonely, terrified, depressed. I couldn’t sleep, couldn’t relax, and was constantly on edge. I began to have crippling headaches and blurred vision — unrelated to my cancer, several MRIs confirmed. Often, I put on a brave face to make sure the board, our investors, and employees felt comfortable. Sometimes, people could see I was struggling. At the end of 2017, one board member suggested I take a six-week sabbatical. But I kept trying to brush my feelings off as “typical founder/CEO exhaustion.” Persistence had been my superpower. I hadn’t yet realized that it was a double-edged sword.

Over the next few years, things calmed down professionally and personally. I had surgery to remove the malignant tumors. CircleUp’s financing and fund successfully closed, and we moved into post-pivot growth. My wife and I had our second, long-awaited child, and then a third. But the burnout was real. I got very little pleasure from our company’s wins, and quite a bit of pain from our losses. One day in fall 2019, my five-year-old daughter said to me: “Daddy, you always look so sad.” I knew then it was time to make a change.

A primer on burnout from our partners at Ascend, a job and life advice channel for young professionals.

That October I told the board I wanted to step down from the CEO role. I explained that while it would be a hard transition, I believed it was the right move for the company and for me. We agreed to a 12-month timetable, during which we would raise another round of financing and find my replacement. That, too, was difficult, because I had to show passion and energy despite being exhausted. And then the pandemic hit. The next few months were exceptionally hard, but through an incredible team effort, we raised the round, the new CEO took over in October 2020, and I transitioned to executive chairman.

I learned a great deal from this experience, and have tried to apply those lessons to decisions around mental health at CircleUp, particularly during the pandemic. Over time, and as a team, we have focused on a few key issues: belonging, vulnerability, empathy, sense of control, and external resources.

Belonging.

When I was CEO, I felt much more isolated than I had at other points in my life. I often asked myself: Can I be “friends” with teammates? Can I share my real feelings? CEOs are hardly alone in this — lots of people are lonely, especially now. At CircleUp, we’ve always tried to facilitate workplace bonding. Our initiatives have included small-group lunches (pre-Covid), a buddy program for new employees, and social events so that people can get to know one another. Lately we do Zoom happy hours, trivia events, and talent shows. We even do occasional in-person events for small groups — masked and socially distanced walks, for example. The point is to create space for employees to relate to each other as people, and hopefully to develop friendships and a feeling of community.

Vulnerability.

America’s tough-it-out business culture makes it hard to admit when you’re not excelling or even if you’re just feeling insecure. As I was burning out, I found it hard to trust and rely on others, which only made things worse. The team at CircleUp has worked hard to encourage more authenticity and vulnerability — and it truly is a collective effort. For example, over the past year senior executives have written to the entire company to address key events, from the Covid-19 outbreak to the racial justice protests to the storming of the U.S. Capitol. We want our employees to know they don’t have to process their emotions alone. The leadership team tries to lead by example, bringing their “whole self” to their roles and not only submitting to 360-degree reviews but also discussing the results with their teams, warts and all. While it’s often uncomfortable to share in this way, we find that it helps to build trust, encouraging more vulnerability from everyone.

Empathy.

When everyone is working on their own thing, it can be hard to empathize with people on different teams or at different levels. Remote work has exacerbated that. At CircleUp, we encourage leaders to model and talk about the importance of empathy. We also have team members present at regular (now virtual) get-togethers, so everyone knows what others are working on and why it matters to the organization. And in one-on-ones with their direct reports, managers routinely ask, “How are you doing?” and then “How are you really doing?” Empathy is part of how we talk internally about our entrepreneurs, too. CircleUp’s mission is to help startups thrive by giving them the capital and resources they need. So, when we discuss how they are performing, no matter the situation, we insist on using respectful and empathetic language.

Recognition.

Lack of recognition has been shown to be another driver of burnout. Sometimes people experiencing chronic stress don’t even notice they’ve achieved something good. Once when I was burned out, I got upset about some positive comments that a top venture capitalist had posted about CircleUp online. Rather than being excited that he liked us, I was frustrated that he didn’t know us better. We want to make sure everyone at CircleUp feels recognized, so we showcase people’s accomplishments at all-hands meetings and on our company website. On Slack we also celebrate wins big and small.

Control.

Entrepreneurship is an inherently risky business — you rarely feel in control of your fate. But even at startups, there are ways to make people feel somewhat in control. CircleUp runs on OKRs — objectives and key results — created for every team and employee and made public within our company. These are clear, transparent agreements between each person and their manager, and employees can choose how they achieve results, which we hope creates a sense of autonomy. We also encourage employees to block off hours on their calendar to do focused work, or even to spend time with their kids. We want to give people control over their schedules and prevent the back-to-back meetings that push work into the evening hours.

Outside help.

Depression affects about 7% of U.S. adults in a given year, and it can be connected to burnout. That means at a company with 60-plus employees (CircleUp’s size), at least a few people are battling or have battled this affliction. At my lowest points, when every single day was hard to get through, I suspect that I could have been clinically diagnosed as depressed, but I didn’t seek the help of a medical professional. At CircleUp, we try to help team members head off serious mental health issues. We offer periodic days off for wellness, a small stipend for mental health expenses, reimbursement for mental health apps, and leadership coaching so that managers learn not only to notice and relieve their own stress but also to see when employees are at risk, engage with them, and point them to outside resources when necessary.

. . .

Not every driver of burnout can be addressed in the workplace. Someone’s sleep pattern, exercise routine, personal relationships, and diet aren’t areas where a company can typically intervene. But there are a few things leaders can help with, such as managing workloads to create more free time, celebrating outside interests and hobbies, and providing healthy snacks or meals. More important, they can develop a workplace culture that prioritizes team members’ well-being. It’s up to all of us to recognize the risk of burnout and to build an environment that staves off its causes. The biggest mistake I made in managing my burnout was not reaching out to my board and team members for help. We should all aim to build organizations in which every employee — from the CEO to the frontline worker — feels comfortable seeking that kind of support when they need it.