4 Ways to Avoid the Lonely Pitfalls of Entrepreneurship

4 Ways to Avoid the Lonely Pitfalls of Entrepreneurship

A Corona in one hand. Sunscreen in the other. Your laptop sitting in front of you with the waves as your backdrop. This is the life of the jetsetting, beer sipping, surf riding, stress squashing entrepreneur. Or at least that’s the story that has been sold to us. We envision days of the 4-hour workweek, doing what we want, when we want, with no boss or coworkers to bother us. But is it reality?

In the not-so-distant past, I was living this lifestyle, hopping from Colorado to Hawaii to Nicaragua, running my business from my laptop. During my downtime in Denver, I’d rented an office for myself, vowing it would be my place of work when I wasn’t exploring the world. And it worked for a little bit. Having a private office of my own seemed like an escape at the beginning. It gave me a reason to get out of the house and out of the coffee shops. And in some narcissistic way, just knowing that my company had an address stroked my ego. But It didn’t take me long to realize that this lifestyle wasn’t sustainable.

It evolved (or devolved…) into working from coffee shops again for the sheer benefit of being around the energy of other humans as my office sat vacant, collecting a check from me every month. I had become what many many entrepreneurs suffer from as they fight to build their companies – the loneliest guy in the room. In the chase for freedom, we often forget that we can’t do it alone. Not only that, but we shouldn’t want to do it alone. We’re social beings. It’s in our nature. The pursuit of the sun-drenched days working from paradise don’t take into account the very essence of what makes us human – the connection to those around us. Thankfully I learned this early on, and found 4 key ways to avoid these lonely pitfalls of entrepreneurship in the future.


If happiness is a house, community is the foundation. It’s wired into our DNA to have a group of people to share life with, and that includes our businesses. The best investment you can make as an entrepreneur is into the community that you surround yourself with. Whether that’s a local meetup, a community workspace, or a coffee shop frequented by entrepreneurs, find a group of people with similar passions and surround yourself with them as often as possible. This human interaction creates the most energizing positive friction available and can lead to partnerships, new hires, customers, and friendships.


Imagine a jumbled mess of parts in front of you. When assembled, they’re a car, but right now they’re simply disparate pieces of engine, chassis, steering column, interior, and more. Building a business without someone to help guide you isn’t terribly different than trying to assemble this car without an instruction manual. You might eventually figure it out on your own, but why waste so much time when there are people out willing and able to guide you? If you don’t have access to resources like this, seek out guidance and mentorship on your own. There are leaders and organization in every city that have a wealth of knowledge to pass on. Go give them someone to pass it to.


You are not your business. Your business is not you. When you’re feeling lonely as an entrepreneur, it can seem as if you and your business are one and the same. It winds up defining your worth and who you are. When we let this happen, we let our happiness be dictated by something that is largely out of our control. It’s to find hobbies and interests outside of work. Yes, we’re an entrepreneur, but we’re also a mother, a father, a biker, a skier, a friend, a tea connoisseur, an aspiring chef, or anything else we desire. Our business is a part of us, but it is not us. And knowing the difference is essential to keeping the loneliness of entrepreneurship at bay.


It can be extremely tough to achieve #3 (redefining yourself) if we’re constantly connected to our businesses. The unending emails and growing to-do list will never give us space to breathe if we don’t set boundaries. Give yourself blocks of time everyday in which you’re completely disconnected from your business. Grab beers with friends. Read a good book. Get a workout in. Whatever it is that allows you to take a step back from the entrepreneur grind, make it happen. Set your boundaries and stick to them. You’ll help yourself detach from the stress, redefine who you are, connect with others, and invigorate your mind when it’s time to get back to business.

Loneliness is one of the least talked about aspects of being an entrepreneur. It takes vulnerability to admit it, but the sooner we do, the sooner we can dive head first into building a community and life that supports and elevates our business. These 4 tactics have helped me get out of the rut and #levelup my personal and professional life. What have you done to keep loneliness in check? Let me know in the comments or give me a shout on Twitter.


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