Freelancing Can Be Lonely. Here’s How To Find Community—And a Mentor
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Freelancing Can Be Lonely. Here’s How To Find Community—And a Mentor

Maybe you love your colleagues, maybe you enjoy the structure of an office, maybe you love knowing exactly when you’ll get paid. And yet, the pull to go freelance is strong. Maybe you want to be your own boss, maybe you want to set your own hours and maybe you want to make more money. This week on Girlboss, we’re taking the leap into the world of freelancing with helpful tips, inspiration and stories of real women who did the thing. Freelance, baby! 

My first (and only) freelancing experience lasted all of 2 weeks. I was in between jobs, so I was forced to work from home all day—a concept that was practically foreign in 2018 (if only baby me knew what was coming)—and it was awful. Not because of the invoices (more on that here) or the lack of structure in my day, but because of how isolating it was. I would push myself to work at a coffee shop some days, even if it was just for a few hours, but other days, I would wake up, roll over, grab my laptop and work from bed until it got dark outside.

No matter how many stories I filed or emails I answered, I still felt like it was an unproductive day. I longed for the moments where I could go into a place of work, be surrounded by the buzz of my colleagues as they quietly typed away on their laptops and hear the chatter of their weekend plans fill the air. At the time, I was living with my family, which helped with the loneliness, but they didn’t really get what I was going through. I wish I had someone to talk to, who was going through what I was going through. If only baby Victoria had this guide to help her back then, maybe her freelance career would have lasted more than 2 weeks.

Anyone who has gone out on their own has probably grappled with these feelings. We chatted with three women who know exactly how it feels: Rachel Kelly, former founder of a virtual coworking community, Jasmine Williams, content marketing consultant and freelance coach and Alison Grade, author of The Freelance Bible. They share their tips for overcoming loneliness, building a community and finding a mentor as a freelancer. If you remember one thing from this story, let it be this: Just because you work for yourself doesn’t mean you have to be by yourself.

Harness the power of virtual community

“Community and community space doesn’t need to be this thing that happens in real life,” says Kelly. “There’s something really amazing that happens when you have a support system to connect with online too.” Of anyone, Kelly would know. Make Lemonade was originally a physical coworking space in Toronto until August 2021, when she decided to move the business online and launch the The Get Sh*t Done Club, a 12-month business foundations community. Kelly offers regular community calls, workshops, a private Slack group, supportive onboarding and more to support small business owners and help them grow. The community currently has 80 active members. “Being able to connect with other people who are going through the same thing as you is so important—and there’s a lot of great connections and community spaces like that,” adds Kelly. Some of our faves include Facebook freelance groups like 1…2…Freelance: A Community for Creative Freelancers, Freelancing Females, Digital Nomad Girls and Click-worthy Creatives. There are also a ton of startup organizations like Women Who Freelance, IFundWomen, Young Entrepreneur Council, Business In The Streets, Freelancing Gems and that are amazing resources for freelancers. On a global scale, Freelance Business Month in Belgium is the biggest worldwide event for freelancers. And lastly, check your area for city-specific Facebook freelance groups and organizations that are bringing fellow freelancers together.

Hold yourself accountable

It’s easy to isolate yourself in your home and go even a few days without talking to another human being—especially if you live alone. Throw in a global pandemic, and no wonder you’ve resorted to solely talking to your plants and fur baby (which is perfectly acceptable, BTW). “When I do start to feel lonely, I have to make much more of an effort to reach out to people,” says Williams. Maintaining relationships is so important for the success of your business, but “it’s something that people don’t always prioritize because it’s hard to see that ROI,” adds Williams. It’s not like buying a new laptop or redesigning your website, where you see the immediate benefit to your business. “Community is something people should invest in too because, at least for me, it’s been a big reason why I stuck with it and why I’m at where I’m at now. The community helped keep me going.” Kelly agrees. “It’s given me a sense of belonging and more of an understanding of what my worth is, and also it’s helped me flex my skills—[something] that I don’t think I would have gotten in a traditional job or learned in school.”

Don’t be afraid to be vulnerable

Oftentimes, these digital communities have thousands of members, where you can get lost in a sea of notifications. Real, meaningful connections are often made one on one, so don’t be afraid to reach out to individuals whose work you really admire. Kelly suggests saying something like: “You’re really great at this. I’m really struggling with this. Could I buy you a coffee? Do you have some time to talk about this? I really value your support.” She adds: “Make it so simple. Make it really easy for them to say yes.” Oftentimes, these interactions lead to mentor-like relationships: Individuals who have been in your shoes and are just a few years ahead of you in their careers make the perfect people to go to for advice. “Go to the person who does the work that you want to do and is someone whose work you’re inspired by,” says Grade. If anything, you’ll foster your own little community of freelancers and entrepreneurs that you can turn to. Isn’t that mentorship in its own way, too?Another thing to remember: “It’s quite easy to cut yourself off from people because you think you’re in competition,” says Grade, especially if you work in the same industry. “Not seeing people as competition but as collaboration is really healthy.” These are the folks who you’ll lean on when you have a family emergency or you’re out sick and need help getting a project out the door for a client.

Celebrate your wins out loud

Whether it’s a huge win (“I just scored my dream client”), a medium win (“I reorganized my Google Drive”) or a small win (“I put on pants today” or “I made a healthy lunch”), everything deserves to be celebrated. And as much as your mom or BFF will cheer you on, there’s something different about a fellow freelancer who just gets it. “There is so much research that proves when you actually take the time to celebrate your wins, you can move towards goals that you thought were too hard. It’s this good addiction. There’s something that happens in your brain that makes you want to be celebrating yourself more,” says Kelly. 

Switch up your environment

“The beauty of freelancing is you can just do what suits you, and some days it’s just under the duvet, in your pajamas,” says Grade. “I definitely find just sitting in a coffee shop is really nice [too], just to watch the world go by and see real life happening.” This is easier said than done in a pandemic, but it can be as simple as inviting a friend out for coffee, taking a walk around the block, working from a fellow freelancer friend’s house or going to a physical coworking space (if and when they are opened). Or even simpler: Working one day from your couch, another day from your bed, the kitchen island or dining room table. You’ll notice how big of a difference this makes to your mental health.

Join a formal mentorship program

Mentorship can be super informal, where you have casual coffee chats with people you admire (as mentioned above), or it can be more formal. There are plenty of mentorship programs that will set you up with those who can help you with any area of your business. A lot of university programs offer this, as do other freelancers. For example, celebrity ghost writer (such a cool job) Pauleanna Reid runs the New Girl on the Block mentorship program, and Williams herself has a 6-week mentorship program for freelancers. “You don’t know what you don’t know,” says Williams. “That can be the real value of mentorship: it can help you realize you have questions you didn’t even know you had. A good mentor should really help you fill those gaps.” 

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