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F50 Issue #37: Freelancers must never do this!
Published 13 days ago • 5 min read
F50 Issue #37: April 29, 2025
Never Freelance Alone: Five Benefits You Could Miss Out On
Remember Sophia Petrillo from The Golden Girls TV show? To start off, let’s enjoy a bit of storytelling, Sophia style.
Picture it — your home office, the year 2000.
You just upgraded your internet from dial-up to a brand-new cable modem. As you log in to your email, you’re thankful that you can now work from home. Not everyone gets a job as an administrator for an online business!
The trouble is, you feel so alone. No one else in your neighborhood works like this, and it’s tough to get in touch with your clients and colleagues. You wish you knew other freelancers who work from home, but you can’t find a group online, let alone in person.
Oh well, guess it’s time to settle in and start working. At least you can look forward to meeting your family for dinner tonight.
Now picture it — your home office, 2025.
You’ve upgraded your internet to a cable modem with Wi-Fi. As you sit outside on your deck, sipping coffee, you check your email and see that the Freelance After 50 Virtual Summit is starting in an hour. Next, you check into the Freelance After 50 Facebook group. It’s abuzz with new members. Some admit they’re a bit nervous about starting a freelance business. You quickly comment back, telling them you understand and encouraging them to hang in there.
You’re still working as an online administrator, but times have changed. You’re part of a freelance community, and you feel a lot less alone. You don’t know how you managed during the early years.
But never mind that—it’s time to grab another coffee before the Summit starts! * End scene *
Times have certainly changed for the better. One of our mottos at Freelance University is “Never freelance alone.” Gone are the days when you were the only one in your neighborhood who worked from home. Nowadays, many people do.
And gone are the days when you couldn’t find any supportive communities. A simple online search yields plenty of options to choose from.
Community has always been a huge part of Freelance University. Here’s how Craig describes it:
“One of our students a while back said, ‘Your community has been my light in the storm.” And what she meant as she unpacked it was that ‘I've been inundated with all this information about how to start a business, and I came here. And I found people that are just like me, that are brand new to this similar stage of life….’
“As much as we have all the education and classes, often people will come to our university for the courses, and then they stay for the community because the community is what helps you deal with some of those confidence issues.”
With that in mind, here are five things you could miss out on if you freelance alone.
Five Benefits of Belonging to a Freelance Community
1. Support
“They're dealing with the same things. And it's a safe place to talk about what you're dealing with. I mean, whether it's social media, like ‘I'm too afraid to go on social media in the beginning.’ And then they go on social media, and they get the rah-rah support of the community, and they build their confidence. And I think we need that.”
This is a quote from Colleen Kochannek during her presentation on Day 3 of the Virtual Summit. She discussed how to overcome imposter syndrome and build a freelance business.
Community is a big part of that because it provides emotional and mental health support that builds confidence. You can also tap into more formalized types of support, like mastermind groups (to help you overcome challenges) and mentoring relationships (guidance from more experienced freelancers).
2. Accountability
In addition to cheering you on, a community provides accountability so you’ll make the most of your success. Instead of just taking a bow, you’ll be motivated to keep challenging yourself. As Colleen Kochannek says,
“I'm a huge fan of getting the right support, the right classroom, the right community, the right network, all of those things, because you need that extra oomph behind you. You need those people pushing you along and cheering you along. Really holding you accountable to get you [to] move forward.”
Community members can give honest feedback on your business systems, pricing, and services. As they recognize your efforts, they may refer you to other clients for projects they’re unable to do. And sometimes, simply being part of a well-respected community gives you extra credibility.
3. Companionship
Sometimes you might miss a good old water cooler conversation. But the great thing about social media these days is you have a community at your fingertips, like the Freelance After 50 group. You can access it as easily as picking up your phone or sitting at your computer.
At Freelance University, our Student Group on Facebook brings freelancers together to talk about their businesses and the courses they’re taking. But it’s also a place where you can celebrate wins or just say hi. The people there understand what you’re going through and can lift your spirits if you’re feeling lonely or isolated.
4. Resources
“Your community is where your opportunity is going to be found. But the thing that makes that opportunity possible are the things that you are able to do. And technology just is a way of doing more. So I would encourage you to build your community, stay active and connected, and learn as much as you can about the technology that is going to help you do your job better.”
Franklin Taggart shared this advice on Day 3 of the Summit. His presentation discussed “How to Leverage Technology in Your Freelance Business.”
When you belong to a community, you can share informative articles, blog posts, podcast episodes, and other resources to help each other learn more. And you can gain access to learning opportunities like virtual summits, webinars, and workshops. Some communities may even share job boards and listings, so you can find new clients!
5. Collaboration
“If you want to go fast, go alone. If you want to go far, go together.”
— African Proverb
Finally, belonging to a freelance community gives you the option of collaborating with other freelancers. Maybe you’ll meet someone with complementary skills who can work on joint projects with you. Or maybe you’ll form a referral network with them so you can pass on work that you aren’t able to do yourself.
Whatever you do, you’ll go farther when you freelance alongside a community of like-minded people!
Insider Resources
On Day 3 of the Virtual Summit, Brian Clark gave a presentation on becoming a digital nomad after 50. He’s a “writer, traveler, and serial digital entrepreneur” who enjoys a location-independent career and an unretirement lifestyle.
If you’d like to read more about unretirement planning, check out his “Further” newsletter. It provides valuable resources and some Gen X nostalgia with a flashback music video at the end of every issue.
As the Further website says, “Start planning to live your best life now, not at some mythical retirement age.”
Looking for the best freelance careers after 50? In this video, we explore the top opportunities for midlife professionals who want flexibility, income, and fulfillment in 2025 and beyond
Discover how to leverage your experience and skills into a thriving freelance career—whether as a consultant, coordinator, or creative.
Plus, get access to The Top 25 Freelance Careers Guide for 2025 to help you find the perfect path! So, remember—never freelance alone! And as they say on The Golden Girls, “Thank you for being a friend!” We’re happy you’re part of the Freelance After 50 community, and we’re here to support you!
Craig & Kelly Cannings, Co-founders of Freelance University
Ready for an exciting new chapter in your life? Join 8000 subscribers who are pursuing a second-act freelancing career to gain the income, flexibility and freedom they desire!
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