THE FREELANCE LONELY HEARTS CLUB

The decision to start freelancing is usually primarily driven by time and money, but there is an emotional component that’s worth much more than an afterthought. 

In becoming solopreneurs, we leave behind a built-in network of people to collaborate, commiserate, and share memes with. When the communal water cooler and coffee maker disappear and nothing comes in to take their place, we’re left alone with our own thoughts (for better or for worse). A shocking 54% of freelancers report that their mental health wasn’t something they considered when making their decision to fly solo — so it’s no wonder that so many of us are startled when isolation creeps in. 

Even if you were never a fan of group projects, working in a bubble has creative and logistical costs. External input challenges our assumptions and sparks ideas we wouldn’t otherwise have. Feedback from people we respect makes our work better. Casual conversations lead to introductions and opportunities. 

If you’re feeling the effects of freelance isolation, it may be time to think differently about what collaboration can look like for the self-employed. Your support network doesn’t have to be made of people in surrounding cubicles (in fact, it doesn’t even need to be made of people in surrounding time zones). Let’s talk about who you need in your corner to build a balanced sounding board, and start assembling your dream team. 

The Cheerleader

Do you have an enthusiasm enthusiast in your life? Everyone deserves someone who fully believes in their potential, celebrates their successes, and encourages them to aim high. 

Your cheerleader doesn’t have to be someone who shares your role or works in your industry to radically affirm your awesomeness. Look for someone who tends to imagine things going right — they’ll be essential during the times when you’re fixated on what can go wrong. 

The Skeptic

If you’re worried that listening exclusively to the cheerleader in your life will end with you giving up your career to sell elderberry syrup out of a camper van, don’t worry — the skeptic will put you in check. 

Who do you know that has an eye for the blind spots in a plan and a talent for pointing them out in a (hopefully) un-jerk-like way? This person is an invaluable resource for gut-checking decisions and anticipating problems before they have a chance to snowball. 

The person in your network who has a reputation for being a bit of a Debbie Downer may be a calculated realist. Trust your skeptic to keep you grounded and well-informed of risks so you can allocate your time and resources in more strategic ways. 

The Sage 

When you think about your collection of professional contacts, is there anyone who seems to really have it all figured out? Your sage is a mentor figure — typically someone further along in their self-employment journey who has successfully done what you’re currently trying to do. 

This person can offer a longer view of the challenges inherent to solopreneurship. Buy them a coffee and find out what they wish they’d known when they were at your growth stage. 

The Pro

Being an office of one doesn’t mean you have to be an expert in everything. The time you spend trying to teach yourself tax law, attempting to draft your own contracts, or struggling to unjam the paper shredder takes away from the time you have available to do the work you set out to do. 

Finding a pro (or more than one, depending on your needs) lets you make better use of your own abilities and spend less time muddling through the overwhelming parts of business ownership. CPAs, bookkeepers, attorneys, investment brokers, and a whole world of other professional experts are waiting to take things off your plate. Find the ones you trust, and make peace with letting certain things exist outside of your expertise. 

The Connector

That person who seems to already know everybody at the networking event isn’t just friendly — they are proactive, organized, and intuitive. Connectors have an ear to the ground and a head for the details, making them an essential part of any freelance community. 

Connectors help people, ideas, and opportunities find each other in an isolating world. The next time you have to pass on a project, find your connector and let them help you recommend a replacement. They help us remember that, even though we all work for ourselves, we can still succeed as a community, 

The Crush 

Who do you admire, and why are you keeping it a secret?

Your business crush is someone whose work, ambition, or life philosophy resonates with you. You may feel inspired by them, or even seek to be a little bit like them. Whether your crush is a favorite TED Talk presenter or the featured speaker at an upcoming conference, you don’t have to know them personally to benefit from their role in your support system. 

Of course, if you do get an opportunity to tell them how cool they are, take it. Even very successful solopreneurs don’t always realize the impact of their work on other self-employed folks, and the good energy you put into the world is good for us all. 

As freelancers, community isn’t something we’ll stumble into — we build it intentionally, brick by brick. Think about which roles are already filled in your network and who is missing. 

Together, we do better work and build better businesses. Send that friendly email, LinkedIn request, or virtual coffee invite, and nurture the relationships that make you feel supported and seen.