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  • Writer's pictureTom Foxley

Loneliness and Entrepreneurship: The Hidden Struggle of High-Performing Business Owners

Most of the entrepreneurs and business owners I work with are lonely.

They get up early, and never really switch off from their work. Their partner loves them but doesn’t really understand. Their mates have real jobs.

What’s more, what they’re pursuing is difficult, and what is difficult is inherently lonely.

You are bombarded with self-doubt and questioning, and that compounds the loneliness.

When you do something difficult with your life, loneliness will strike.

Which would be fine if it didn’t completely derail you from your goals by leaving you second guessing your choices.

Loneliness isn’t just a shitty way to feel though. Loneliness is an inhibitor of your goals.

The irony is, you and I, us seekers of freedom, desire independence, but that independence often sacrifices connection.

It’s great getting to spend my time however I wish, but there’s a price to pay.

It’s not about quantity

I heard Chris Williamson say “loneliness is the price you pay for a complex mind,” on a recent podcast.

And whilst that may ring true (and certainly feeds my superiority complex), I think there’s some more nuance to this.

Loneliness is not just the price you pay for a certain complexity of mind. Loneliness is the price you pay for living in a fashion the majority of society deems unwise, uncertain, and unconventional.

Whether you’re running a business, training for the special forces, or raising kids by yourself, the pursuit of a challenging goal is inherently isolating.

Overcoming loneliness isn’t as simple as it first appears though. I don’t know about you, but I could not soothe the loneliness that punctuates my life by socialising with the vast majority of people.

If I spend time with the average person, I only feel more isolated and less understood.

Carl Jung said, “Loneliness does not come from having no people about one, but from being unable to communicate the things that seem important to oneself, or from holding certain views which others find inadmissible.”

It’s not the physical connection to people that we crave, it’s communicating your authentic perspective and being understood.

“If you have lots of people around you—perhaps even a husband or wife, or a family, or a busy workplace—,” Johann Hari wrote, “but you don’t share anything that matters with them, then you’ll still be lonely.”

Today, I am going to share with you the strategies and perspectives which help my clients overcome their loneliness and get back to executing on their dreams.

The role of connection

Your nervous system craves connection to other human beings. Without it, you default to other states of behaviour.

You either become filled with anxiety and stress, bursting with the desire to fight against your confines - the hustle and grind, blinkered mentality.

Or you have the urge to flee from the situation you’re in - man, I just need to get away from it all.

Or you completely shut down - you become a recluse.

None of those states banishes loneliness or gets you back on track with your goals, consistently.

When you have had enough connection with others though, you can access the parts of your brain which are evolutionarily newer.

These bits are the parts which are made to engage in complex problems, think long term, and also understand others better.

So in terms of your physical body, when you are connected to others, you can do better work. You can progress. You can achieve.

You need connection to perform at your best.

The glorious thing about this physical connection is that the better you regulate your nervous system, the more capacity you have to connect with others.

So you can shortcut this process by taking care of your nervous system. Once more, sleep, hydration, play, and cutting your caffeine intake are primary tools.

Check what you’re doing is meaningful

The ache of loneliness is compounded by a lack of meaning. If what you are doing isn’t taking you closer to who you want to be, loneliness is not worth the price of admission.

When I’m working with a client, one of the first things we will work on is adjusting their vision of success to be more meaningful.

Often, they’ve lost sight of what they initially connected to, and started creating a lifestyle and a business which is only a means to an end. Their life serves a logical purpose, and not an authentic one.

As such, they’re not only lonely, they're unmotivated and uninspired too.

It’s cliche but worth repeating: meaning is found in the process, and it’s to the process you must turn your attention.

Meaningful living fills the cavities where loneliness seeks.

My clients follow a simple rule: “if I fail in my ultimate ambition, will the process I’m taking be a reward enough in itself?”

Where to find connection

I’ve always struggled finding friends, and had to work hard to find people who I actually wanted to spend time with.

I played at being someone else for a long time. I developed a persona - a mask - that created surface level connections.

Whilst the mask helped me exchange pleasantries, it perpetuated the loneliness I felt, as I was never saying what I truly felt and thought.

What’s more, people want to connect with the authentic and imperfect you. They don’t want a paper person - someone without depth. They want substance, and you have that in abundance.

My chronic loneliness ended when I moved to Canada. I found my tribe out there, and through doing so, I discovered an obvious but effective rule to find others worth spending time with:

Do things you love doing in an environment where other people also do those things.

Mountains and adventure are my jam. When I moved to Canada, that’s what basically everyone loved doing, and it made it easy to connect.

This gave my life meaning, made the sacrifices worthwhile, and soothed the part of me which craved connection.

Now, I seek that in a small scale fashion. I choose to have golf lessons instead of going to the range solo. I go to CrossFit classes instead of training alone.

If you can’t solve your problem, change your environment.


Before I sign off, it’s important to note one thing. We often take for granted the connection we already have. I know personally that when I feel at my loneliest, I actually have sources of connection around me, I just want more.

By creating conscious connections with those you already know, you not only solve the problem you’re facing, but simultaneously reinforce the neural pathways that help you find more connection in the future.

Here’s how to overcome loneliness as a high performer:

  • The antidote to loneliness is feeling understood

  • Change your environment to spend time with those who share the same interests

  • Ensure that your vision and process is meaningful in itself

  • Press the right physiological levers to regulate your nervous system


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