The Top 3 Habit Changes That Kickstarted My Freelance Career

No deadline you set yourself for “making it” is enough, one freelancer finds. You’ve got to change what you do every day—then stick with it.

The Top 3 Habit Changes That Kickstarted My Freelance Career
[Photo: Mike Wilson ]

Two years into my “freelance career,” I was making a whopping $10,000 a year–barely enough to qualify as a hobby, let alone a career. Oh, and I still lived with my parents.


Worse, I knew why. Despite putting consistent effort into my writing, I wasn’t fully committed to turning it into a sustainable, self-sufficient career. Because back at Mom’s, an organic, gluten-free dinner was served at promptly 6 p.m. every day, no matter how much or little I worked. I had everything I needed without having to lift a finger. Comfort kept me complacent.

These days, I’m proud to say I’m no longer living off my parents’ good graces. In the year-plus that I’ve been fully independent as a writer, I’ve been hired as the lead writer for national ad campaigns, worked with multinational companies, and built a sustainable coaching business to supplement my writing income. But it took a few major habit changes to finally overcome my failure to launch. Here’s how I did it.

Related: How I Managed To Save Money On A $25,000 Salary In New York City

1. I Moved Out And Set A Deadline For Making It

Sometimes all you need is a good deadline to whip your butt into gear. I set mine at two months–because that’s about how long I’d have before the money I’d saved for living expenses would run dry. I rented a little place in Albuquerque, New Mexico, and told myself I had to push myself every day in order to grow my client list. Otherwise I’d starve or get evicted, whichever came first.

Necessity really is the mother of invention, it turns out. If you don’t have any material reason to hustle, perform at your peak, and succeed, well, you won’t. The comfort of living at my parents’ house, demoralizing as it might’ve felt at the time, was still proving a crutch. Back at home I spent one day every two weeks looking for new clients. And even then, sometimes I’d merely think, “Huh, it’d sure be nice to write for them”–I wouldn’t even send a query!


That kind of laziness wasn’t doing me any favors. So in my first month solo, I sent out more queries than I had in my first two years trying to hack it as a freelancer–because I had to eat. Pitching at that volume helped me become a professional, a mind-set shift that doesn’t always come naturally to first-time independent workers. I learned to think like an editor, scan for opportunities like a business owner, and schedule my time like a manager. Within three months, my success rate went from landing one in every 20 or so pitches to nearly one in three.

If you think you’re not ready to move out, no one is! I had a really short runway when I finally hit the ground running. But that was enough to push me to work like a dog and get my cash flow . . . flowing.

2. I Hit The Books

Building a thriving freelance career is an exercise in confidence building. Forcing yourself to go independent–whether that’s quitting your day job for good or moving out of your parents’ house–will give you a baseline to start out with, but to really thrive, you’ll need daily doses of vitamin K: knowledge. It’s the ultimate confidence booster.

There were many times when I felt helpless in those first few days and weeks in my new Albuquerque apartment. But that feeling began to retreat the more I learned about my craft. And when I cemented the habit of reading daily about how to write better, I finally developed the skills and confidence I needed to land gigs from big magazines and global companies.

These days, I shoot for 30 minutes to an hour a day of lessons from successful writers. I do my best to learn from their mistakes and their biggest breakthroughs alike. And I come out of each session with better techniques to sell and execute more articles. My personal writing bible is Writing Tools, the 2008 strategic guidebook for writers by Roy Peter Clark. After taking notes on that baby in my first month after going solo, I finally started to feel like I was going from wannabe to bona fide pro.


3. I Keep My Energy Up (Hint: It Takes Work)

Writing well takes energy–hell, doing any kind of sustained work at a high quality takes energy, especially when you don’t have a manager forcing you to do it. Before I found success as a freelancer, my energy levels dictated my day; I simply wouldn’t produce much if I felt tired. But since now that isn’t really an option, it’s got to be the other way around: my workflow needs to dictate my energy.

So there are a few habits I’ve adopted to help me keep my energy levels up. First, I exercise right when I wake up. If I don’t get my blood pumping first thing in the morning, I tend to feel bad and do nothing; it’s not just a physical booster, it’s also a mood booster. I’ve become disciplined about working out, no matter how I feel upon waking up. It kickstarts my confidence and gives me the energy to smash some keys.

But one early-morning session usually isn’t enough to carry me through the entire workday. I make sure to break away from my desk every 30-45 minutes to do some squats or pushups, or just go for a quick walk. These little spurts of exercise keep my body fresh and my mind sharp.

Second, I need good, nutritious food. When I was a rookie, I’d wake up and write first thing in the morning. But my brain was starved of glucose, and more often than not, I’d feel like fainting by the time I’d reached the end of my draft. That wasn’t sustainable, and the results weren’t sellable. So now, after exercising and before sitting down to crank out my first piece of the day, I fill up the tank with a bunch of healthy fats and proteins: yogurt, almond butter, eggs, cheese, protein shakes, coconut oil, macadamia nuts–the list goes on. This gives me a slow burn of energy to stay focused and on task throughout the day.

Related: What Happened When I Gave Up Gluten, Sugar, Dairy, And Coffee


Third, I meditate. Before picking up this habit, I’d often stress myself out, lose focus, and burn out by worrying over stupid things. By 3 p.m. I’d crash because my thoughts were running wild and killing my focus.

So now I take 30 minutes in the afternoon to do nothing. I lie down. I focus on my breathing–slow and from the belly. I center my thoughts on gratitude and opportunity. And I visualize kicking so much ass that my right foot sometimes even begins to throb a little (the power of a vivid imagination!). This one habit maintains my energy, sure. But meditation also helps feed the creativity I need to draw on continuously in order to work.

Freelancing definitely isn’t for everybody. It takes serious self-motivation, discipline, and confidence, which themselves take some habit changes in order to develop. But once I’d managed to retool my daily behaviors, I found myself in a self-sustaining cycle–with enough cash on hand to make a third month’s rent, then a fourth’s, and on and on.

Daniel Dowling is the founder of, where he shares action steps and inspiration for millennials and their employers. You can find more of his work on Entrepreneur, MindBodyGreen, and

About the author

Dan Dowling is a writer and coach who helps everyone from students to CEOs master self-improvement at In addition to writing for Fast Company, he also contributes to Entrepreneur and MindBodyGreen.