5 Ways Entrepreneurs Can Conquer Loneliness and Feel More Connected

Entrepreneurs suffer from loneliness at alarming rates. It’s time to start talking about it.

Tony Hsieh, entrepreneur and founder of Zappos, seemingly had everything.

He was worth millions. He had a degree from Harvard, was surrounded by famous artists and entrepreneurs, and wrote a book, Delivering Happiness: A Path To Profits, Passion and Purpose.

So when news that Hsieh had died on November 27, 2020 from complications of smoke inhalation when a fire broke out in the home of a friend where he was staying, it came as a shock to many. 

As news trickled out during the days following his death, it became apparent that he had been struggling with alcohol and drug addiction, depression, and loneliness for quite some time. Mentally, he was in a downward spiral, and the pandemic had exacerbated Hsieh’s isolation and loneliness. In a Forbes article about Hsieh, apparently his friends and family had tried to intervene, to no avail.

Although the fire is still under investigation, there’s some indication that his drug addiction and destructive behavior caused the fire or contributed to Hsieh’s inability to escape it.

Entrepreneurs Are a Lonely Bunch

Loneliness has become an epidemic in America. The global health service company Cigna recently released results from a national survey exploring the impact of loneliness in the United States and found that almost half of Americans report feeling lonely.

The problem of isolation is even worse for entrepreneurs. Starting and growing a business, it turns out, can be extremely lonely. A recent study found that entrepreneurs who experience occupational loneliness are more likely to burn out. Another study showed that half of CEOs report feelings of loneliness in their role. 

“We’re told things like ‘fake it till you make it’ and ‘just keep pushing and you’ll get there,’” says Jay Clouse, an entrepreneur who recently became SPI’s Community Experience Director. “But it’s a really, really tough road. And we fear sharing the challenges because people will think if it’s not successful, then ‘I’m not going to pay attention to it or invest in it.’”

“We’re afraid to let people into the reality of what’s going on because we don’t want to undermine our own efforts,” says Jay.

The need for connectedness is a basic ingredient for psychological growth and well-being. But there are many forces that contribute to entrepreneurial isolation, including:

Other People Don’t Understand Entrepreneurs

Entrepreneurs are unique human beings. It takes a certain kind of person to take risks and chart their own path, and they may be constantly having to deal with the “doubters” and hand-wringing family members. Not everyone understands or condones their decisions. 

“Being an entrepreneur is not normal. It’s not what most people do,” says entrepreneur Jeff Gargas, who is the Co-Founder and COO of Teach Better Team.  “Because of that, most people don’t understand what it is actually like running a business. Most people don’t understand how your brain works. And when most people don’t understand you, how you think, what you do, and how you feel, it’s lonely.” 

Entrepreneurs Have to Make the Final Decisions

For entrepreneur Heather Newton, founder of Protospiel Online, the thing that stirs up the strongest feelings of loneliness is “the pressure of being the one that makes the final decision for anything that needs to happen in my business. Although I can ask for input from my trusted circle of friends, I know that the decision is ultimately mine, and that can feel scary and lonely — especially when the decision is big and hairy.”

There’s added pressure when you know your decisions will affect your employees and family. There may be a lot of people depending on you to make the right decisions and succeed. When you have the sole responsibility of making decisions that will affect others’ lives and livelihood, there’s no one to turn to for support. It’s only you.  

Entrepreneurs Typically Work Alone

“I used to travel alone as an equine photographer,” says Olie Moss, founder of Equine Photo School. “I would live alone far from friends and family. Life as a traveling entrepreneur is tough. I could at least call home and chat with my parents who are also entrepreneurs who understand the stress and struggle.”

The pandemic has made this issue much worse. Studies have found an “alarming” increase in loneliness since the arrival of COVID-19. More and more people are working from home—alone.

“I spend so much of my day(s) at my computer, working on project tasks, organization, etc.,” says Jeff Gargas. “Even with a team, most of my days are just me. I love when I have meetings, or someone interrupts my day because so often I have almost no contact.” 

Entrepreneurs Face Long Hours and Hard Realities 

It’s common knowledge that being an entrepreneur can mean long hours. Bringing your vision to life takes time and commitment. Studies have shown that twenty-five percent of founders work over sixty hours a week, which affects their physical and mental health. 

And it goes without saying that working sixty hours a week leaves little time for relationships. Beyond long hours, the financial stress of starting a business, and waiting months or even years to become profitable, can take a toll on your partner and family, leaving you even more vulnerable to isolation and loneliness. 

Entrepreneurs often have to face hard realities as well. “A lot of entrepreneurs have teams,” says Jay. “They’re leaders of organizations and they often find that they have to shield some of the hard realities from their team in order to protect the team’s psychological well-being. Also, your family probably doesn’t have a lot of experience with it and doesn’t understand. So who do you talk to?”

5 Ways to Fight Loneliness as an Entrepreneur

So what’s the solution? Here are a few tips that will help to keep you connected, happy, and healthy.

#1: Seek Out Connections

Finding people you can talk to, and developing true connections, is key, says Jay Clouse. 

He actively seeks out people who “get it.” When he first started his business, he went to a bunch of local meetups in Columbus, where he lives, and built a local community. 

“I just think it’s really important to talk about it. And as hard as it is, you need to be able to confide in someone—it could be a partner, a friend, a business partner. You need to tell somebody if you’re feeling this way or it’s going to fester and get worse. And it seems to build up and get harder the more time that you let pass.” 

During a particularly hard time in his entrepreneurial journey, Jay reached out to a friend, who was going through a similar situation, and the two met up for dinner once a week. “We didn’t actually talk about our businesses that much. We just knew that we were both in it. There was something about that, that comradery and connection, knowing that this person gets it and that they’re not asking how the business is going, because they know that I don’t really want to talk about that because it is challenging.”

For Heather Newton, she finds that attending conventions and meetups with others in her industry is helpful. “When we’re not in a pandemic, I attend several local and out-of-state board game conventions and other meetups for entrepreneurs and various types of creatives. Whenever I start feeling lonely, it’s nice to have a date on the calendar that I can look forward to as a chance to be with like-minded people.” 

But during the pandemic, Heather says, she participates in peer mastermind video calls, and keeps up with what her favorite communities are doing through online groups. “I try to be choosy and only put my time into online spaces with an encouraging, fun, and hopeful tone.”

#2: Create “Water-Cooler” Moments

Another way to create connections is by building in water-cooler moments throughout your day. 

If you were a regular employee working in an office, you’d have several opportunities to connect with people in the lunchroom or water cooler. But as an entrepreneur you’ve probably left those corporate cubicle days behind, for good reason. 

So instead, set up a Zoom call for you and your friends and colleagues to check in and chat. This could be a virtual lunch, happy hour, or coffee break

At SPI Media, we sometimes have virtual happy hour on Friday afternoons to chat about different topics (like our vinyl record collections), or play games together

#3: Be Vulnerable

There’s a certain amount of confidence that entrepreneurs must possess, and showing vulnerability can feel like the kiss of death for anyone who’s attempting to “fake it until you make it.” 

But being vulnerable is key to combating loneliness. Sharing your struggles and fears with your spouse, a mentor, or a trusted friend will foster true connection. 

“It’s really easy to get your identity wrapped up in the business that you’re building. And so if you’re admitting that the business has problems, that can feel very personal,” says Jay. 

“If you haven’t done the self-work to understand that you are not what you do, you are not the business, that’s a hard chasm to cross. And it does take humility, especially from that position of having your identity so wrapped up in the business to, to ask for help or to share the challenges or to admit that things aren’t going as well as you’d like, because it feels like you’re admitting your own flaws or exposing your own weaknesses. And that’s not the case, but it’s really easy to feel like it is.” 

#4: Keep Mental and Physical Health a Priority

Of course, getting enough sleep and exercise is common advice to help fight depression, stress, and feelings of loneliness. And drinking enough water and eating a healthy diet can help too. 

Writing down your feelings in a journal is a good idea as well. It can help you to clarify what you’re feeling, and help you realize what you need to do to find a solution. Sometimes, feelings of loneliness can be subconscious. Maybe you’re feeling angry or sad, but at the core of those feelings is your isolation. Writing down your feelings and coming face to face with them can help you to sort it all out.

And reaching out to a mental health professional is always a good idea, especially if you find that you’re taking steps to feel connected, but it’s not working. 

#5: Join a Membership Community

Online communities are also a great way to find other like-minded people and help fight loneliness. They allow you to have a regular place to “hang out” online, and (pre-pandemic), meet up with local members as well.

When Jay was first starting out, he found communities like Tropical MBA. And then he started his own online community, the Unreal Collective, which recently joined forces with SPI Pro.  “If you can’t find the community you’re looking for, you can build your own,” he says.

Here at SPI Media, we knew our audience members were looking for connections. When surveyed, “connecting with other entrepreneurs” was at the top of their list of reasons for joining an online community. That’s why we’re are taking steps within SPI Pro to help entrepreneurs feel less lonely. 

“We are really focused on making the community about connection,” says Jay, “to the degree that we hold frequent events so that we can connect people in real time over video. We want each member to be able to find at least one other person who they can trust and connect with as quickly as possible. We’re not giving you a digital space and saying ‘good luck.’ We’re welcoming you into that space and helping you get connected to other people, whether it’s through our events, whether it’s through our mastermind program, so you can continuously meet with other people on a weekly or monthly basis. Those are really, really big aspects to the SPI Pro membership.”

If you’re looking to connect with other entrepreneurs, check out SPI Pro. Or, if want to start your own membership community, check out the live training workshop below. Let’s fight loneliness—together.

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  • Karen Beattie

    Karen Beattie is a published author, editor, and SPI’s former senior content manager.

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