Making The Move to Freelancing Full-Time with Julia Halperin
At some point, many professionals ask themselves: “Should I go off on my own?” Maybe you’re tired of the grind of working for someone else, or you’ve started to imagine what life could look like if you were self-employed or running your own business.
On this episode of The Glass Sessions, we sit down with Julia Halperin - a full-time freelance writer, editor, and content strategist whose bylines include The New York Times and Cultured Magazine. Before launching her freelance career, Julia was a senior leader at top arts publications and most recently served as Executive Director at Artnet.
She shares her story of leaving a high-profile leadership role to build a thriving freelance career, the mindset shifts that helped her succeed, and the lessons she learned along the way. Whether you’re seriously considering self-employment or just curious about what it takes, Julia’s insights will help you understand both the opportunities and challenges of making the leap.
Where to start if you’re considering a move to self-employment:
Gaining clarity on how you want to spend your time
Before you make a move, reflect on what energizes you vs. what drains you.
Try our Time Audit Exercise to get clarity:
Log your day: start and end times, meetings, breaks, and tasks.
In the notes section, score each activity (1–10) based on how engaged you felt.
Track for a week and look for patterns.
Ask yourself:
Which activities light me up?
Who do I enjoy working with?
What do I want to avoid in the future?
What would my ideal workday look like?
Then consider: can you find that balance in your current role, in the same role at another company, or would self-employment give you more control?
Understand your risk tolerance
If you skew toward a low risk tolerance,
Start small. Freelance or consult on the side (check your employment agreement first).
Talk to people who have already made the jump - learn from their stories.
Partner with freelancers who have overflow work.
If you’re more of a high-risk, high-reward persona, you can still de-risk your jump by:
Saving enough to cover living expenses while you build.
Setting milestones and checkpoints to track progress.
Leave your company on good terms - don’t burn bridges.
Build a realistic daily schedule and stick to it.
You’ve decided to make the jump to self-employment. Now what?
Do the mindset work
Leaving a job you’ve been successful in isn’t just a professional shift, it’s a personal one.
You may feel like you’re grieving a loss: the team you led, the confidence of being in a known role, or even a piece of your identity.
It’s normal to feel unsettled, because our sense of self is often tied to our work.
Think of it as creating space for a new identity to grow.
You’ll now need to be intentional about:
Who you work with
How you spend your time
What your day-to-day looks like
Build your own accountability structures
The biggest difference in self-employment? No one is checking on you but you.
Make a daily schedule and review what you actually accomplished.
Set clear start and end times for your day (create “commute” rituals like a walk before and after work).
Don’t wait for motivation - plan tasks and do them regardless.
Tackle the hardest or most avoided task first thing.
When you’re your own boss, you also need to be your own cheerleader.
Finished a new client project? Celebrate.
Finally built that website page? Reward yourself.
Build small rewards into your routine, like a treat, a walk, or an afternoon off, to stay energized.
The economics of freelance or self-employment
Unlike a salaried role, you’ll need to set (and defend) your rates. Common models include:
Hourly: Charge for time, useful for ongoing or open-ended work.
Project-based: Set a flat fee for defined deliverables.
Per-word (for writers): Publications often pay $0.50-$2 per word.
Pro tip: If a client is late on payment, soften the ask with phrasing like:
“Just checking to make sure the system sent the invoice properly - I haven’t seen payment come through yet.”
You’ll also need to manage:
Taxes: Work with an accountant and set aside a percentage each month.
Benefits: Explore freelancer collectives like Opolis, which offer health insurance, retirement, and payroll support.
Building your network
Your network becomes even more important when you’re on your own.
Keep a contact spreadsheet: names, organizations, personal notes, last conversations.
Reach out after you make the jump to share what you’re working on.
Early on, say yes to most opportunities - it builds experience and connections.
Over time, learn to say no to protect quality.
Turning down work for the first time is a milestone worth celebrating.
Embrace the highs, the lows, and the in-betweens
Self-employment comes with cycles:
Some days, you’ll feel fully alive in your work.
Other days, you’ll wonder if you made the right decision.
And sometimes, you’ll just feel ambivalent.
All of it is normal. The key is to ride the waves, trust the process, and remember why you chose this path.
