I want to talk about something that nearly every freelancer has faced at some point, maybe even before officially diving into freelance life. It often starts with excitement. You’ve made the bold choice to pursue your own path. You share the news with friends and family. You get some love. Some support. Maybe even a few “I’ve always thought you were entrepreneurial” comments.
And then… you hit resistance.
Not always hostility, but uncertainty. Doubt. Concern. Questions like:
“What about paid vacation?”
“How will you get by without benefits?”
“What if you get sick?”
“Are you sure this is sustainable?”
Sound familiar?
The dreaded, unwanted, unsolicited career advice.
Our loved ones care deeply about us. If they’ve spent their entire lives in salaried positions, it’s natural for them to project those experiences—and fears—onto us. What we see as freedom, they sometimes see as instability. The disconnect can lead to strain, especially if they don’t understand how freelance revenue generation works or if they view entrepreneurship as a glorified side hustle.
So, how do we stay grounded in our career choice without alienating the people who just want us to succeed?
First, Let’s Talk About the Awkward Conversations
Ever tried explaining freelance life to someone who’s only ever had a 9-5 job?
They smile politely when you mention “flexible hours,” but their eyes glaze over once you dive into taxes, client acquisition, the lack of sick days, and how your business expenses are still your expenses because you are the business. Suddenly, you’re left in the corner of the family BBQ explaining deductions to the potato salad.
It’s OK. They still love you. They just don’t get it—yet.
Here are a few things that can help:
1. Come Prepared with Calm, Clear Responses
Anticipate the usual questions. Rather than arriving on the defensive, arm yourself with thoughtful counterpoints. Share stories about how you’ve handled difficult situations. Reassure them with real examples of how your business works and how you’re making it thrive.
2. Know That You’ll Need to Explain It More Than Once
Auntie might not remember your job title. Mom tells everyone “she works with computers,” even if you’re not a programmer, but because you carry around a laptop. That’s fine. Be ready to explain again, and again. It’s not a sign of disrespect—it’s just unfamiliar terrain for them.
3. Talk About Your Work with Pride and Transparency
Most people are fascinated when they hear about the behind-the-scenes. Talk about a client you helped, a campaign you brought to life, or a creative solution you implemented. When you share stories, you bring your world to life, and you build credibility.
4. Set Respectful Boundaries
You don’t need to justify your existence. Listen with respect, but expect the same in return. If someone is being particularly insistent or dismissive, it’s OK to disengage. Politely change the subject, or excuse yourself entirely. Your business is your business.
And Now, Let’s Loosen Up – Literally
As freelancers, we spend a lot of time at desks, in booths, or glued to our screens. That tension we feel in our bodies? It’s real, and it’s not helping our confidence or clarity.
This week, on the Freelance Fitness podcast, I’m coaching upper body mobility. No equipment needed. Just a place to stand and move freely.
This is your chance to reset—physically and mentally.
You’ve Got This.
Freelancing isn’t for everyone—but it is for you. And just like in mobility training, progress comes from consistency, clarity, and a willingness to stretch your limits.
You are strong. You are capable. And you don’t need anyone’s permission to pursue the life you’re building.
Now go shake out those shoulders and take on the rest of your day like the boss you are.
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