20 Years, 20 Lessons: Takeaways from Life as a Freelancer
Updated: Jan 26
When I began my first job fresh out of grad school as the editor of a publication for K–12 students, I kept a printout of editor's marks taped to my wall. The production team assumed the printout was for their benefit, but it was actually for me—I had little idea what all those
squiggles and lines and symbols meant. I had to learn—and fast.
Many classes, a maze of experiences, and a whopping two-plus decades later, I'm still learning—part of what I love about being a freelancer. Here are some takeaways from these past many moons, gleaned through uplifting successes, self-sabotaging failures, and simply trying to adapt to the ever-changing professional landscape:
1. Say "Yes" As Much as Possible: Asked to write about something you know little about? Give it a try. Most jobs require research and a bit of scrambling. You'll be surprised by what you can tackle. Once you say "no," doors often close, so do what you can to keep jobs coming your way.
2. ...But Know When to Say "No": Not accepting a job isn’t ideal, but sometimes it's just not a fit, or you're simply overbooked. If you must decline a job, do so with diplomacy, and be gracious about it. Even better, recommend someone you know who might be more well-suited to the task and subject matter.
3. Follow Through: Being proactive is imperative in the world of freelancing since the nature of this type of work is learning how to get jobs (ideally ongoing or intermittent ones) and maintain rapport with your clients. Getting a lead is great, but unless you follow through by reaching out, nothing will materialize. It's up to you to make it happen.
4. Be A Squeaky Wheel, But Not a Nag: Since many freelancers work off-site, it's important to check in every now and then, or simply let your clients know you're available. Just don't badger them, especially if your client lets you know they've brought the work in-house or don't respond after more than one query.
5. Ask Thoughtful Questions: Before you begin the job, learn what your client is seeking (rather than simply assume). Take the time at the onset to discover what your clients' goals are, and actively listen. If there are existing documents, ask to see them to gain a sense of the look, style, or tone of their brand. Otherwise, ask for examples of what they like, which helps provide a starting point—much easier than working tabula rasa.
6. Challenge Your Comfort Zone: In order to make a real go of it as a freelancer, it's important to be open to projects that involve unfamiliar subject matter, or a style of writing or editing you haven't done before. Rather than turn your back to it, welcome the job as a learning opportunity. It's amazing what you can get the hang of when you simply give it a try.
7. Keep Good Records: Since being a freelancer is akin to running an independent business, you're responsible for keeping track of your hours, billing your clients, and making sure you get paid. Jot down your work hours each day, attributing which hours you worked for each client, and what you accomplished that day.
8. Do Your Homework: Before you meet with your potential client, research the people you'll be meeting with, along with the company, its story and mission. You'll know the right questions to ask, save valuable time, and be a much more appealing candidate than someone who comes in unprepared.
9. Deadlines Matter: If something is due in a week, submit it no later than the due date—or even better—early. Clients want the work, not excuses, and if you’d like to keep getting jobs, make sure you adhere to their deadlines.
10. Pace Yourself: If you're juggling more than one job, it's easy to get overwhelmed, especially if you don't pace yourself. Make a spreadsheet, write down your tasks and when they're due—whatever works—and then figure out how much you need to get done per day, per week, etc. Planning helps you gain a sense of accomplishment and reduces stress, especially as deadlines approach.
11. Get Organized: Keep track of files, paperwork, invoices, etc. in a way that makes sense to you. Your job will be far more manageable with some kind of system in place. Plus, it's far more peaceful working at a desk with ample space than one buried beneath haphazard piles.
12. See People: Freelancing can be isolating, so make sure you take time to see colleagues, attend meetings, and get together with friends, even for a brief walk or tea, to help you maintain a sense of community and connection. These gatherings are remarkably restorative, and help you return to work feeling more grounded and energized.
13. Create Realistic Expectations: Some clients give you plenty of time to complete an assignment, while others want it by yesterday. If a job can be finished quickly, great, but if it's going to take longer, be clear about what's involved, and how fast your turnaround can be.
14. Build a Portfolio: Use whatever you have to create a portfolio, and build it up from there. Clients like to see samples of work, and having a few examples readily at hand is helpful, even if you're just starting out. (Unpublished work is fine, too, as are older pieces—simply delete the date where possible.)
15. Keep Learning: With modern technology keeping us on our toes, it's important to stay relevant and not become a dinosaur devoid of applicable skills. Classes, seminars, or online tutorials on topics of interest help open your eyes to trends and market demands, and offer up an opportunity to practice new formats and skills.
16. Treat Each Client as a Priority: Even if you're juggling a handful of clients simultaneously, give each one your complete attention while communicating without mentioning other demands on your time. Truth be told, they're not concerned with your other commitments, as long as you get the job done—well and on time.
17. Don't Burn Bridges: It's a surprisingly small world, and you never know when you might happen upon someone again. Try to maintain your professional demeanor whenever possible, even if you've had a less than pleasant experience. You just might cross paths with that person down the road.
18. Network: Much of my work has materialized through connections— knowing someone or someone-who-knows-someone. Begin by getting together with friends or colleagues and brainstorming. Far more than online applications, personal connections and recommendations are what ultimately open doors.
19. Just Do the Best You Can: When I get anxious about a challenging assignment or am still in the "proving ground" mode with a new client, I recite the mantra, "Do the best you can do. That's all you can do." Somehow this helps me let go of my inner critic and get to work.
20. Express Gratitude: The words "thank you" are powerful. Remember to thank your clients, especially when inquiring about potential assignments and when submitting invoices. The holidays are also an ideal time to express your appreciation through hand-written cards, which convey far more warmth than emails or texts. After all, your clients enable you to continue doing the work you enjoy, which is a gift in itself.
Elisse Gabriel is a Bay Area–based writer, editor, and founder of Red Balloon Creative Content (www.redballooncreativecontent.com). Feel free to reach out to her at firstname.lastname@example.org for any content creation, copywriting, editing, or consulting needs.