What No One Tells You About Going Freelance After 50
How I Left Corporate, Found Freedom, and Built a New Career on My Own Terms
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Let me start by saying this: Going freelance after 50 isn’t easy—but it’s absolutely worth it. I didn’t plan to be self-employed. I had a long, stable career in corporate sales leadership. I knew how to manage quotas, lead teams, and close big deals. But I didn’t know how to be my own boss—until I had to figure it out.
Like many, my journey started with a layoff. That “corporate restructuring” turned my life upside down—but it also turned out to be the catalyst for the most fulfilling chapter of my career so far.
So if you’re over 50 and wondering whether it’s too late to go freelance, I’m here to tell you: It’s not too late. But there are a few things I wish someone had told me when I started.
Here’s what I’ve learned—and what I think every midlife freelancer should know.
1. You’re Not Starting Over—You’re Starting From Experience
It’s easy to feel like a beginner again when you leave corporate life. But here’s the truth: You’re not starting from scratch. You’re starting with 20+ years of real-world experience, resilience, and a professional network that still matters.
I leveraged mine to build my first freelance client pipeline—including my own family business, where I helped grow a $1.7M sales funnel in 90 days. That experience gave me the confidence to land my first contract with a digital agency.
💡 Tip: Start with your existing contacts. Let people know you’re available for consulting or contract work. The quiet network often brings the best leads.
2. You’ll Wear Every Hat—So Learn the Business Side Fast
Freelancing means you are the product, the service, the marketer, the bookkeeper, and the tech support.
Some tools I’ve found helpful:
Notion for project management
Google Workspace for proposals and organization
Wave or FreshBooks for invoicing and expenses
ChatGPT for brainstorming content, sales pitches, and strategy (and so much more) It can truly be a Virtual Assistant once you really lean in.
If you’ve been in leadership, these skills might feel familiar—but they’re different when you’re running a one-woman show.
🔗 Recommended Reading: The Freelancer’s Bible by Sara Horowitz and the LinkedIn Freelancer Playbook (Affiliate Links)
3. Health Insurance Is a Beast—But You Can Tame It
One of the scariest parts of going freelance in your 50s is losing employer-sponsored health insurance. I know it was for me.
We ended up using Health Market Consultants (a free service I wrote about here) to explore our options. They helped us navigate private plans and choose one that fit our needs and budget.
👩⚕️ Tip: If you or your spouse are self-employed, look into:
ACA Marketplace plans
Health Share Ministries (if eligible)
HSAs for tax savings
COBRA (for a limited time)
4. Motivation Isn’t Always a Given—Build a Routine Anyway
In corporate life, your calendar is dictated for you. As a freelancer, it’s all on you. That sounds like freedom—and it is—but it can also be paralyzing.
What’s helped me stay motivated:
Starting my day with intention-setting (read about that here)
Creating a “theme day” system (ex: Monday = client outreach, Tuesday = content, Friday = admin)
Co-working virtually or in local cafes for a change of scenery
🎧 Try: Listening to podcasts like The Accidental Creative or Being Freelance for midweek motivation.
5. Your Value Isn’t Defined by a Job Title
This one’s personal.
After decades in corporate sales, I was used to introducing myself with my title. VP. Director. Sales Leader. Those titles felt like proof that I had earned my place.
But in the freelance world, no one cares about your old title—they care about the value you bring today.
It took time, but I reframed my self-worth. I am not my last job. I am my skills, my work ethic, and my ideas. That mindset shift has made all the difference.
Final Thoughts: Freelance Freedom Is Real—But You Have to Define It
Going freelance after 50 isn’t a fallback. It’s a bold choice. It’s a commitment to designing your own life, your own schedule, and your own definition of success.
You may have to unlearn some corporate conditioning. You may have to try things that scare you. But you’ll also wake up with more purpose, creativity, and freedom than you’ve felt in years.
If you’re considering this path, I hope my journey helps you take the leap—with eyes wide open and heart fully in it.
📚 Reading Recommendation:
The Simple Path to Wealth by JL Collins (Kindle Unlimited)
A smart, jargon-free book for financial independence. Read it here (affiliate link)
🛠️ Tools I Use & Recommend:
DrinkMate Sparkling Water Maker – Because hydration is part of my productivity ritual.
YNAB (You Need a Budget) – The best budgeting app for freelancers.
Personal Capital – For tracking your net worth and retirement goals.
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