Entrepreneurship in the Digital Age is a Lonely Journey

By Emily Gough

Entrepreneurship in the online world is an increasingly popular choice of work, but the part that we often aren’t prepared for is the loneliness that accompanies it.

The research indicates that entrepreneurship comes with a unique set of stressors and can often feel isolating. It’s not the side of venturing out on your own that is usually discussed; instead, it’s all about the glamourous visions we have of Instagramming while poolside on a beach, being able to keep whatever hours we like and not having to answer to a boss.

Yet in some ways, loneliness defines the journey of entrepreneurship. You’re choosing to embark upon a quest to solve a problem for a particular market in unique way with an idea that came from your head, automatically making things very personal in a way that others might not be able to understand.

The people in your life with so-called “normal” jobs are unlikely to fully comprehend the unique demands and issues that accompany building a business, and many entrepreneurs are known to fully immerse themselves in their work in a way that seeps into their personal lives, often to an arguably unhealthy level.

Plus, when it comes to our personal relationships, at the end of the day it can seem more exhausting to begin trying to explain what you do than to simply reply with a one or two sentence response of how your day went. Let’s face it, trying to describe to your well meaning 90-year old grandmother how someone on the other side of the world that you’ve never met paid you for a service delivered via the Internet can be both hilarious and frustratingly difficult.

Even loved ones who have a greater comprehension of the online space often still don’t fully understand what it means to be a digital entrepreneur. So instead, you withdraw from these kinds of conversations, answer questions as minimally and generally as possible, and quickly change the discussion to avoid feeling awkward.

On top of all of that, as an entrepreneur all of the responsibility is on you. Even if you have a team and people invested in you and your business, you’re the one ultimately calling the shots and relying on yourself. That can be a heavy weight to bear, and taking it on alone makes it even more difficult.

The good news is that there are things you can do to offset the powerful effects of loneliness, and the health of your mind, body and business will all benefit.

Connecting with Like-Minded Individuals Online

The best part about the online world is that there have never been more options to connect with people online. Facebook groups, forums, digital meet-ups, and masterminding are a handful of ways you can cultivate a sense of community with people who are dealing with the same types of issues or experiences as you are on either a personal or a professional level.

If you can’t seem to find a community that fits your needs, the option is always there to start a conversation yourself if you’re willing to get a little vulnerable about sharing what you’re experiencing, and it’s extremely likely that someone else is feeling exactly the same way and would love to connect as much as you would.

Attending In-Person Events

While the term “networking” has always made this introvert cringe, it’s really about simply connecting with others, and there’s nothing that builds those powerful relationships like meeting people in real life. Anytime I’ve ever attended an event, I push myself outside of my comfort zone to talk to people I don’t know and always end up leaving with a few new friends, a fresh perspective, and a renewed sense of purpose.

There’s something very grounding about connecting with others, and it helps you to feel seen, heard and understood. At the end of the day, that’s all any of us really want.

Coworking Spaces

When I made the switch from 11 years in the corporate world to working from home alone, I was surprised to find myself craving face time with other human beings. As an introvert I had assumed that spending most of my time alone would be the ideal fit, but quickly realized that human interaction is still important.

With co-working spaces starting to pop up all over the place, it’s a perfect option to work amongst others and get the interaction you might be craving while allowing you the freedom to run your own show. It also gives you the chance to meet new people in an office-type setting without the strict rules of the corporate world.

Bonus side effects: swapping out the uniform of yoga pants and messy buns for real clothes, in my personal experience, can lead to a bit of a boost in both confidence and productivity.

Limit Social Media

This seems counter-intuitive since I already mentioned connecting with like-minded people online can break us out of isolation, but there’s a fine line. Often when we’re loneliest, we reach for social media out of habit to feel even slightly more connected to other humans, but too much can make us even more lonely.

Getting likes or comments online can give the perception of support from others, but the feeling can be an empty one because most of us still try to present our best side to social media and the public eye. We want to be perceived a certain way, and curate our images and captions carefully, yet often we have no idea what’s really going on in people’s lives behind the scenes. Because we see friends and acquaintances popping up in our news feed, we feel like we already know what’s going on with them and might not be as likely to pick up the phone and actually call and talk to one another. And chances are, they’re thinking the same about you.

Taking time away from social media and setting boundaries around usage can improve emotional well-being and give you the necessary time, space and motivation to connect with people in real life.

Seek Help

The first step is even acknowledging that you need help, which can be the hardest part for those entrepreneurs that feel like we can do it all. The second hardest part is actually asking for that help, because it requires a level of vulnerability that we often try to avoid, even though this is the part where the best connections are often forged.

There are different kinds of help, and it’s going to vary depending on the situation and what’s going on in your life.

If you’re struggling with depression, anxiety, and perpetual loneliness, talk to a mental health professional. Working with a therapist can offer you clarity and an unbiased perspective that is invaluable, along with specific tools and strategies to build more support into your everyday life to keep things like perpetual loneliness at bay.

You might also need to call a friend to vent, hire a coach to work through some challenges in your business, or make a daily date with your partner to decompress after a long day. Sometimes simply speaking out loud to someone rather than ruminating in your head can offer a new perspective that wouldn’t otherwise be possible.


No one is meant to go through life alone. Connection is what we need to not just survive but to thrive, and being an entrepreneur doesn’t have to be synonymous with loneliness. Part of the joy of being an entrepreneur is that you have the choice to design you own life, and the journey will be a lot more fun when you open yourself up to inviting others to share the process with you.

Owner at Emily Gough Coaching, host of the Room to Grow Podcast & teaching entrepreneurs to build impact-driven podcasts, businesses & relationships.