5 Small Experiments to Test-Drive Self-Employment in Your 50s and Beyond
You Don’t Need the Whole Plan
If you’ve been climbing the career ladder for decades, the thought of pivoting toward self-employment can feel both exhilarating and overwhelming. Maybe you’ve hit a wall in your current role or simply feel the pull toward more meaningful, flexible work.
But where do you start—especially if you don’t yet know exactly what you want to do?
Here’s the good news: You don’t need a five-year plan or a fully baked business idea. You just need curiosity—and a willingness to experiment.
Small, low-risk experiments can give you the insight and confidence you need to explore self-employment before taking a bigger leap. Let’s look at how.
Shift Your Mindset: From Career Ladder to Curiosity Loop
Early in my career, I had a clear trajectory: designer to senior designer to creative director. Every role led to the next.
But self-employment doesn’t work like that. There’s no predefined ladder. Instead, it’s iterative. Messy. Experimental. And—if you let it—deeply fulfilling.
Think of your next chapter as a curiosity loop: try something, learn from it, and adjust. The goal isn’t to have all the answers. It’s to start asking better questions.
Reflection prompt:
What’s something you’ve always been curious about doing for work—but never gave yourself permission to explore?
5 Small Experiments to Try on Self-Employment
Each of these is low-cost, flexible, and designed to give you insight—not overwhelm.
1: Offer One Service to One Person
Pick a skill you enjoy—professional or personal—and offer it as a one-off service. Resume review. Closet organization. Custom playlist creation.
When I was facing repeated layoffs, I started offering UX consulting on a project basis. That one experiment turned into a 10-year freelance career.
Try this: List three skills people have asked you for help with. Which one could you offer as a microservice?
2: Teach Something You Know
Host a short, free (or low-cost) workshop online or in person. It could be a lunch & learn at a local library or a Zoom class for friends.
Teaching reveals two powerful things: what excites you, and what people want to learn from you.
Try this: Sketch out a 30-minute topic you’d enjoy sharing. What’s one small takeaway someone would get from attending?
3: Build a Tiny Offer
Take something you already use—a spreadsheet, template, or checklist—and package it into a downloadable product.
Try this: What’s a small tool or resource you could share online? How might it help someone else?
4: Shadow a Solopreneur
Know someone who works for themselves? Ask if you can tag along for a day or schedule a virtual “behind the scenes” chat.
Self-employment isn’t just about what you do—it’s how you manage your time, clients, and energy.
Try this: Reach out to a self-employed friend. Ask: "What’s a typical week look like for you—and what do you wish you knew when you started?"
5: Live Your Ideal Week
Take a week off (or simulate one on paper) and block out how you think your post-career life could look: time for projects, movement, rest, and connection.
You might be surprised by what energizes you—or what structure you crave.
Try this: Draft your “ideal week” on a calendar. What stands out? What’s missing?
Debrief: What Did You Learn?
Run one experiment at a time and give it your full attention.
Then, reflect:
What energized me?
What drained me?
What surprised me?
What do I want to explore more?
It’s not about performance. It’s about clarity.
Use Your Experience for What’s Next
You’ve built a life rich with skills, perspective, and resilience. These experiments aren’t a detour—they’re a way of tuning into what matters to you now.
Investing in yourself through small tests of curiosity is one of the most energizing things you can do.
If you’re already experimenting—or want help designing one that fits your skills and goals—I’d love to hear about it. Let’s talk through what’s working, what’s unclear, and what your next step could be. Book a free call and we’ll shape your next experiment together.
