Is Freelancing Really Equitable?
The reality of freelancing + fresh opportunities
When I first started freelancing, I kept seeing the same kind of story over and over again:
“I quit my job with six months of savings and finally went all in on myself.”
It was inspiring, but it also made me pause.
Because when I got laid off, I didn’t have six months of savings. I didn’t have a spouse covering rent, or parents I could move back in with. I had bills due, a laptop, and a stubborn belief that I could figure it out.
That experience taught me something I think a lot of “freedom economy” conversations skip over:
Freelancing isn’t equally risky for everyone.
Privilege Makes the Leap Softer
Let’s name it. The ability to start a business without worrying about your next paycheck is a form of privilege.
Maybe it’s:
A partner covering household expenses
Family support or a financial cushion
A job that paid enough to save in advance
No dependents, debt, or health care needs to manage
These safety nets make risk-taking feel easier, because it is. If you have time and money to experiment, you can weather slow starts, client dry spells, or failed offers.
But if you’re building from a place of urgency, layoffs, underpaid jobs, burnout, the stakes are different. You don’t just need to “follow your passion.” You need income. Quickly.
That’s not a lack of ambition. That’s the economic reality most freelancers face.
Entrepreneurship Isn’t Equitable, But It Can Be Strategic
I want to be honest about something: I didn’t start freelancing because I felt free. I started because I felt cornered.
But even without a safety net, I learned that you can build stability in layers. You can de-risk entrepreneurship by creating structure around your skills.
You can turn freelancing into something that doesn’t rely on privilege, but on systems.
Here’s how to start.
Ever notice how every freelancer group chat eventually devolves into a “what the heck do we do about health insurance?” thread? 😅
You’re not alone, and it actually doesn’t have to be this way.
We won’t pretend that we’re the experts on Health Insurance, so instead, we’ve partnered with the experts at Solo Health Collective to break it all down in a no-BS, easy-to-understand workshop just for freelancers. Bring all your questions and on November 12th for our free workshop.
Get ahead by booking a free call with Solo Health Collective Today to explore your options. #partner
Step 1: Separate Security from Creativity
When you’re starting out, not every client has to be dreamy. Not every project needs to “light you up.”
Your first goal is income stability, not brand alignment.
I had one client that paid me $1k/month for social media content, not my dream gig, but it bought me breathing room to pursue bigger, better opportunities.
Ask yourself: What service can I offer right now that businesses already need and are willing to pay for? That becomes your baseline income stream.
Step 2: Build a “Safety Stack”
Since most of us don’t start with family wealth or long-term savings, we have to create our own version of a cushion.
Here’s the framework I used to make freelancing less risky:
Anchor Client: 1 retainer client that covers baseline expenses (ideally 40–60% of your income).
Project Work: 1–2 fixed-scope packages for cash injections.
Quick Wins: 1:1 sessions, templates, or audits for flexible income.
Even if one client drops off, the others keep the lights on.
Step 3: Build Your “Pipeline Confidence”
The scariest part of freelancing isn’t not having clients, it’s not knowing where the next one is coming from.
To fix that, I built a simple pipeline habit:
Every week, send 3 emails or DMs to potential clients.
Every week, post one piece of content showcasing your work.
Every week, follow up with anyone who said “maybe later.”
Within a month, I went from “no leads” to a waitlist. The consistency created confidence, and confidence is what replaces privilege when you don’t have a cushion.
Step 4: Redefine “Risk”
The truth is, traditional employment isn’t risk-free either. I learned that when I was laid off.
Freelancing just changes the kind of risk you manage: from being dependent on one employer, to managing multiple income sources you control.
And when you think about it that way, freelancing can actually be less risky, because you’re never one layoff away from zero income again.
Step 5: Build Equity Through Access
If you’re in a position of privilege, use it to make freelancing more equitable for others:
Refer newer freelancers when you’re overbooked.
Share resources, templates, and client leads freely.
Normalize transparent pricing so others can charge fairly.
Mentor someone just one step behind you.
Because freelancing isn’t just an individual pursuit, it’s a collective ecosystem. The more we lift each other up, the more sustainable it becomes for everyone.
Freelancing is easier if you start with a safety net, that’s true. But it’s possible for anyone willing to build their own version of one.
Start small. Create structure. Focus on consistency over courage.
You don’t need privilege to succeed. You just need a plan and persistence.
👩🏽💻 Upcoming workshops in the membership: Nov 5th supercharge your social with AI toolmates, Nov 6th morning flow and mindful start, Nov 12th Healthcare plans and Nov 21 office hours with Creative People’s recruitment team. To watch all of these for free, use code FFSUBSTACK at checkout for one month free trial.
💖 This Thursday (30th October), Kylie from Solo Health Collective will be hosting an Ask Me Anything about health care plans for freelancers ahead of open enrollment. Join our membership here.
✨ Your 2026 glow-up starts here: Join Solo Summit by Lettuce, a free one-day event for freelancers and founders ready to scale with strategies to keep more of what you earn. #partner
📚 My latest read! Let me know in the comments what I should be reading next.
👩🏽💻 A client is looking for a copywriter, focusing on Paid Social (Meta & TikTok). Start Date: ASAP
Rate: $35.00 per hour
This is what I needed to read today!
I am so sick of seeing people who don't have to think about income or finance posting on LinkedIn about going freelance -- which for these people is effectively a fancy way of saying they're unemployed -- and how amazing it is.
I've been freelance before, it has plenty of pros, and some cons, but it's really bloody hard and not enough people are honest about it.
THANK YOU for this newsletter and being clear-eyed about the realities of freelancing when you don't have those cushions like 6 months of savings and a spouse covering bills and housing. This is like a breath of fresh air.