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What I Wish I Knew Before Going Freelance Full-Time

I am often asked how I decided to “go freelance.” 

I didn’t “go.” 

I was kicked. 

One morning eight years ago, I woke up early, rented a car, and began driving from my home in North Carolina to a college campus in South Carolina. I had an assignment from my employer, a sports magazine, to write about a college football player there.

Half an hour into my ride, my boss called. He told me to turn around, go home, and come into the office that afternoon for a meeting. He would not tell me what the meeting was for, but he didn’t have to: I was going to be laid off. 

It was not a shock. The journalism industry in general was a mess. And this magazine in particular had been through numerous rounds of layoffs. I knew I would eventually get caught up in one, and finally, I did. 

I was ready emotionally, or as ready as I was going to be. Though I was sad to see it end, I was grateful for the 13 years I worked there. But I was not ready, at all, to “go freelance.” I knew how to write a magazine story, but that was it. I didn’t know how to find clients, or pitch, or invoice. I knew nothing of branding or business models or contract language.

I was terrified. As I drove to the office to meet my fate, and in the weeks that followed, I kept asking myself the same question: what the hell am I going to do now?

In the eight years since, I’ve made every mistake there is to make, some of them more than once. Some were inevitable. More were not. Here’s what I have learned since then that I wish I could have told myself before I became a freelancer.

The most important thing is who you know

It’s more important than the quality of my work, more important than my ideas, more important than my passion. More than 90 percent of my work has been for people I knew or with whom I shared a mutual friend. So if you’re working full-time at the moment but dream of going freelance, make sure that you are networking now with anyone and everyone who could potentially hire you in the future. 

More than 90 percent of my work has been for people I knew.

Time slows down after you submit a pitch

I had staff jobs at two newspapers and one magazine before I became a freelance writer. Editors at those places were required to respond in a timely manner if I proposed a story. If they didn’t, I could walk over to their desk or give them a call. In the freelance world, that’s not the case. 

The time between submission of a pitch and answer takes forever. Even after eight years, I still obsessively refresh my email after I send a pitch. Making matters worse is the industry, as a whole, handles this process terribly. I don’t like when my story ideas get rejected, but I can deal with it. I can’t stand pitches that go unanswered and I absolutely hate being ghosted. I know it’s not personal. I know “they” are wrong for treating anyone, me included, like that. I was wholly unprepared for how frustrating this would be…and still is.

Ask for more money

I needed more years than I care to admit to learn this. Two experiences stand out. 

While negotiating terms for an assignment for ESPN.com, I asked for an aggressive rate and generous expenses budget. I was stoked when they said yes to everything. I celebrated, by which I mean bragged about, the success in a phone call with a friend/mentor with decades of experience as a salesman. He told me flatly if they said "yes" to everything then I had not asked for enough.

“Force them to say no,” he said. 

I was angry at him at first for not celebrating with me. But he was right. 

The second lesson came at a writer’s conference. A freelancer I admire said every time she lands an assignment for a new client, she asks for 50 percent more so her base starts out higher. I talked about her comment with one of my editors. He told me to always ask him for more because he always says yes. 

I tried to play it cool. Inside I screamed “WHAT?!? WHY DIDN’T SOMEONE TELL ME THAT?!?”

WHY DIDN’T SOMEONE TELL ME THAT?!

Full disclosure, I almost never ask for 50 percent more. But since that conference, I have asked for more money far more frequently than I did before. My clients have said yes much more often than they said no. 

I know that many of you may be thinking, “What if I lose the client because I asked for more money?” Trust me, that fear prevented me from asking for more money for a long time. However, in my eight years as a freelancer I’ve never lost a client because I asked for more money. 

It’s OK to fire clients

Early in my freelance career, I met once a week with a mentor. Though we worked in different industries, I learned a lot from him as we ate lunch on his deck overlooking a wooded area. One day I arrived extremely frustrated with a client. Before I even told him about this, he launched into a story about similar frustrations. The client had become more trouble than it was worth, so he ended their relationship. 

This time I didn’t bother to try to play it cool. I said “WHAT?!? WHY DIDN’T SOMEONE TELL ME I COULD DO THAT?!?”

When you work for a company, you can’t fire your boss. That’s one of the greatest parts about being a freelancer: you can choose who you work for and who you work with. 

It’s never as bad as you think

Freelance work is rarely consistent. Some months I’m overwhelmed with clients. Other months I think my email must be broken because I’m getting no responses. I just have to remember that I will find other clients, land other deals, come up with more ideas … and all the while, the world will keep spinning. 

Mentors in other industries are more valuable than mentors in your line of work

As much as I like talking shop with other writers, I have learned far more about being a freelancer from friends and mentors who do something else for a living. (See Nos. 3 and 4 for examples.) I’ve learned about risk taking from pilots, dealing with difficult circumstances over which I have no control from a dog-mushing coach and the importance of authenticity from an ATV tour guide.

The grind never stops …

As in, never ever.

… so take advantage of the freedom this lifestyle provides 

At first I chained myself to my desk. But that made me miserable. Now I take long lunches when I can, stay for that extra cup of coffee with a friend I don’t see enough of and sneak off to the park with my kids. The work is still there when I get back. You became an indie for a reason, so make sure that you’re getting the enjoyment out of it that you hoped for when you joined the freelance world. 

Some of you, like me, were pushed into freelancing. Others of you quit your jobs to get into this challenging and exciting business. Whatever got you into it, I hope these lessons make your life as an indie more successful, more productive, and more enjoyable.


If you're new to freelancing or looking for ways to be more organized, make sure you always start with a strong contract. Check out Indy’s legally-sound contract templates to set yourself up for success.

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