Loneliness at the Top: 8 Tips to Help You Stop Feeling Isolated as an Entrepreneur

Woman entrepreneur feeling isolated

You’re up late. The rest of the house or office building is dark. Even during the day, you mostly work alone. 

You have coffee dates or mastermind group meetings, but most of them are virtual and when you click “leave meeting,” you’re alone in your office again.

You’ve had a real win in your biz, hard-won and long-fought-for. You tell your beloved and they say, “That’s nice dear,” when what you want is for someone to recognize how much this means and pop the metaphorical bottle of champagne for you.

Or you’re feeling the stresses of being the one who wears all the hats and carries all the responsibility, but none of the other parents at pick-up time, not even your bestie, gets what you’re going through.

Loneliness is a real threat to your mental and emotional well-being. And when you’re not your best and feeling isolated, it’s hard to bring what’s needed to your business.

The human brain sees loneliness as a threat as serious as the threat of physical harm. When you feel very isolated and lonely, your nervous system engages a threat response , and when the loneliness is ongoing, the result is continuous, low-grade chronic stress that leads to adverse physical and mental consequences.

Loneliness is a major risk factor to mental health–not only for business owners but for everyone. It’s linked to depression, poor sleep quality, impaired executive function and cognitive decline. But business owners are more likely to feel lonely than their employed counterparts.

If you’re a business owner and you’re feeling isolated and lonely, you’re in good company. The Harvard Business Review found that half of CEOs report experiencing feelings of loneliness. Many first-time CEOs said that these feelings negatively affect their performance. 

Why business owners are lonely

Entrepreneurs are isolated because there are simply fewer business owners around–and even fewer women business owners. It’s much easier to find someone with a difficult work situation or micro-managing boss with whom to commiserate. It’s harder for us to find someone who gets us.

Also, the more that we are impacted by systems of oppression, the fewer entrepreneurs there are who share our experience. The value of peer support, validation and perspective is unparalleled, and yet it’s hard to access.

It’s lonely “at the top.” Leaders have emotional reactions related to the people they lead: clients, employees, contractors. etc. It’s not appropriate (and in fact it’s harmful to the relationship) to expose these people to the raw emotions that come up for us about their behaviour…but emotions do come up!

As business owners, we do a lot of emotional labour to manage all this, yet we can experience loneliness because there are few places to be transparent about this work, and even fewer people who can hold space for us, so we carry the emotional weight alone.

Often associates or employees have resentments about leaders (often for good reason, let’s be honest), and haven’t worked out their relationships with power. They can make assumptions about you as a leader based on previous experience, or based on their beliefs about people in positions of power. (Whether you like it or not, power is inherent in your role.) As a result, they respond to you in ways that reflect their assumptions, not your behaviour or intent. This can be hard to take and can also bring up a lot of feelings.

People in your audience, as well as employees or contractors, may have you on a pedestal. This can make it challenging when your humanity comes to the fore. This is distressing and can generate  feelings of loneliness.

If we don’t know any other business owners, it can feel like no-one gets us. We lack connection with people who validate and understand us, and when we don’t have that, it contributes to the sense of isolation. Most people are risk-averse, but we business owners embrace risk and are frequently taking leaps into the unknown. 

What we need is someone who can say to us, “Yes, of course it’s scary. This is a big leap. I know you have what it takes to do this and I’m here to cheer you on.” rather than “Maybe you shouldn’t you give up the security of a regular paycheck and a pension.”

Sometimes we are literally lonely  because we’re just too busy or too pooped to socialize—that is, outside of networking where you have to be always on and it’s part of your job.

Another isolating factor is the desire for impression management. It’s hard to trust that disclosing your vulnerability when you’re having a bad day won’t deter people from doing business with you. In addition, it’s hard to find the right place where you can really let your hair down with people who get you, your fellow entrepreneurs.

But what if someone does figure out you’re “not OK?” Entrepreneurs are leaders and public figures who can’t be seen to have problems, so we may believe we have to hide them. As a result, we can experience shame when we are exposed in a way that’s not consistent with the carefully curated representation we’ve been working to convey (not to mislead but to enable potential clients to trust us).

Lack of access to support is another factor that plays a role in isolation. Entrepreneurial poverty is a thing. Cash flow is the single biggest financial challenge in many small businesses. We aren’t all raking in the big buck. Research shows that 88% of women-owned businesses generate less than $100,000/year.

Not only do we struggle to pay for the help we need in our businesses (wouldn’t it be less stressful  if you could hire a VA and some marketing support?) but also the cash we take home is limited. In addition, most self-employed people don’t have health insurance.

How are business owners supposed to cover the cost of supports like therapy and massages? For stressed-out business owners these are far from luxuries. Even if you do have the cash for therapy, it’s a challenge to find a therapist who understands entrepreneurship and who can support you in addressing the psychological side of money in your business.

Tips to stop feeling isolated as an entrepreneur


First and foremost, finding a community is a must. There are many low-cost communities for entrepreneurs online and with some searching you will find one that fits your values and your budget.

Even networking in person is worth a try. You might have to look beyond your immediate area to find a group that’s a good fit but it’s worth the trouble.

In these communities, with time, you will find that one person or two who stands out from the crowd and with whom you might want to connect more deeply.

It’s important to find someone in whom you can confide, so that with some people in your life, you don’t have to worry about impression management.

Setting good boundaries

It’s important to establish good boundaries around what you will and won’t share and in what contexts. Work with a coach or therapist to identify where those boundaries are, and make sure there is at least one close and trusted person in your life with whom you can be totally transparent.

A trusted confidant

It helps mental and emotional well-being generally and defend against loneliness and isolation to have someone in whom to confide. Just like therapists need a therapist, leaders need someone with whom they can process their feelings about the people they lead. This is where leadership communities, trainers and coaches can be very beneficial.

Emotional Intelligence

Therapists can serve another important function for business owners: they can help them cultivate emotional intelligence. Leaders who are more attuned to their own emotions have less internally-generated stress and are more capable of having healthy relationships with their businesses. Attunement to the emotions of others means you are better equipped to form meaningful connections and build trust with your clients, employees and contractors.

Leadership training and community

Leadership training and community can also be helpful for addressing the isolation and loneliness you feel as a business owner. One resource is Brené Brown’s Dare to Lead trainings and the community of learners you will connect with in those programs. I’ve explored the 15 commitments of conscious leadership and the work of the Conscious Leadership Group and that might be a resource to explore as well.

Loneliness is different from alone

Alone time is necessary for mental health and creativity, both.

Cal Newport, the author of Deep work and Digital Minimalism says that deep work helps individuals work effectively.

The key to deep work is the elimination of distractions. Solitude is one way we can eliminate distractions. We may feel lonely in that solitude, of the keys to deep work and however Newport says, the loneliness felt in these moments of solitude is not necessary deleterious.”

Lyanda Lynn Haupt has a whole chapter on solitude in her book Rooted. She says, “Solitude in nature is an essential way of deepening… intimacy with our own minds.” 

Haupt makes an crucial point about solitude that distinguishes it from the loneliness many business owners feel. She makes it clear that solitude that has a positive spiritual impact when it is chosen. 

It’s important to have alone time. Haupt cites the work of Dr. Marcus Riley to say that solitude, without the need for the social pretenses (in other words, impression management), is both a relief and enriching. She quotes Riley as saying that when the need for social interactions and pretenses fall away away in solitude, our brains are allowed to roam free. 

It’s easy to see how this can benefit the business owner, who needs all of their brain power to think creatively and strategically about their business and its challenges and growth.

If you’ve had enough alone time and are looking for company, you might like to receive emails from someone who is likely to “get you”, then please sign up here for my newsletter.

About the author 

Shulamit Berlevtov  -  Shulamit (she/her) is the Entrepreneurs' Therapist. She is working passionately to mitigate the entrepreneurial mental health crisis through keynote speaking and educational workshops and by supporting women entrepreneurs 1:1 to care for their mental and emotional wellbeing and their money psychology in an era of relentless stressors that can make you want to lose your crap on the daily.

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