Freelance Like a Boss: 6 Tips for Emerging Writers 1



I’ve been freelancing for about a decade. It started as a side gig to make my full-time job seem more bearable. I told myself that if I could get paid to write essays about dating a girl who wanted to be Harry Potter, then sitting in a cubicle 40 hours a week would be fine. Better than fine! Because I was writing! Living the dream.

I was also quite tired. It’s hard to have two jobs. Or seven.

Now I freelance full-time and it’s still hard, but it’s also weird and magical and I don’t think I could go back to a “real” job even if I wanted to.

Put another way:

Every day I’m … 

Getting to this place in my career has been a long and windy journey, and along the way, I’ve learned a few things to make freelance life more stable, more interesting, and less crazy-making. Here are the top six tips that have helped me freelance like a boss. Because I am the boss. Literally. So I basically had no choice. Except I do because I am a benevolent boss. You should see my vacation hours. And how much time I devote to watching The Bachelor.

Get Organized

Have a basic plan for your day/week. Even if your not freelancing full-time, create a game plan for how much time you can spend on projects. Let’s say you can devote five hours a week to freelancing. Your plan could be as simple as:

“Spend two hours creating content, two hours promoting it, one hour on strategy/brainstorming.”

Or it can be more involved, with calendars and spreadsheets and such. I am not an organized person by nature, so I prefer to keep it loosey-goosey, but to each their own.

Having a plan in place will help you to stay focused on your goals, give you a sense of purpose, and prevent those panicky moments of “AM I DOING THE RIGHT THING???”

Say Yes

When I was first getting started, I took a lot of jobs that weren’t super exciting or interesting to me because no one knew who I was, and I hadn’t established myself in the fields I wanted to write in. So I said yes to just about everything—reviewing weird performance art? Yep. Writing about sex toys FOR FREE? Yes. Copyediting eBay listings about subwoofers? ZZZZZ yes.

Saying yes to unglamorous or lower-paying jobs helped me to hone several skills, such as:

  • Learning how to negotiate with people
  • Becoming a faster and more efficient worker
  • Gaining contacts that might help me down the road
  • And, perhaps most importantly, it forced me to write regularly and to get outside my comfort zone

Would I do any of this stuff now? Probably not. But I still see my early freelancing years as invaluable. (They also make good stories, and in the case of the sex toy gig, led to me getting my first advice column.)

Ask for Help

This is probably the hardest piece of advice for a lot of people. But no one becomes successful entirely on their own. We all need help, and we should all practice asking for it.

What does this look like?

It’s not begging, so get that thought out of your mind.

Asking for help doesn’t have to be a big to-do. It can be simple, such as asking if a contact knows an email address for an editor at a publication you want to write for. It can be putting a call out on social media if you have a specific request. It can be doing a favor for someone influential, in hopes they’ll pay it forward. It can be asking for advice from someone more established than you.

Remember, too, that most people WANT to help. It’s human nature. The key to not feeling like a douche about it is to give as much as you get, and to be respectful of people’s time and efforts.

If you want to delve deeper into this, I’d recommend Amanda Palmer’s book The Art of Asking, which is part memoir, part learn-how-to-ask-for-help manifesto. Or if you only have 12 minutes to spare, you could watch her TED talk for the Cliff’s Notes version:

Tell Yourself You Can Do It

The biggest obstacle I’ve come up against in regard to freelancing is not looming deadlines, hustling for jobs, or dealing with demanding clients—it’s myself. Especially when first starting out, it’s so easy to say, “I can’t do this! I’m not qualified! I’m not good enough.”

And, you know, it might even be somewhat true. But you should do it anyway. The only way to dispel the false notions we have about ourselves and our abilities is to test them. You do that by showing up, by doing the work, and by failing over and over again until eventually that failing becomes “experience.”

It’s fine to not know what you’re doing. It’s great, even.

Now, I’m not saying you should lie and tell a potential employer that you are a trained astrophysicist to get a job or anything, but I am saying that you should believe in yourself more than you do. If you don’t show up for you, no one else will.

To that end, challenge yourself and what you think you’re capable of. Don’t let niggling fears and anxieties stop you. Expanding our skill sets and our minds is how we grow.

Do What Interests You

What excites you? What burning problems do you want to solve? What do you think about constantly?

Factor your passions into your freelancing, because if you’re not excited about what you’re working on, it’s going to be difficult to stay motivated and on track when obstacles arise.

This doesn’t mean every gig you take will be your ultimate dream job—as I said earlier, sometimes we have to do un-fun tasks because they are there and someone is paying us for them—but also don’t lose sight of what you really really want to be doing.

Even focusing an hour a week on a side project or passion can help give you the added fuel to get through the crap stew of the rest of the week.

And Last but Not Least …

As Dory from Finding Nemo eloquently put it, when you’re feeling stuck, sometimes you have to “just keep swimming.”

Freelancing is about living life on your own terms. And all the highs and lows that come along with that. No job is without its challenges, but sometimes you have to just keep swimming, even if you’re unsure or doubtful or feeling down on yourself.

Reading the inspiring words of others helps me when I’m feeling stuck. Try:

Cheryl Strayed’s “Write like a Motherfucker” column

Ask Polly’s advice to writers

or Anne Lamott’s excellent book Bird by Bird

I’ll leave you with a quote from Strayed, in fact, because she is the most excellent:

The kindest thing I can do for you is to tell you to get your ass on the floor. I know it’s hard to write, darling. But it’s harder not to. The only way you’ll find out if you “have it in you” is to get to work and see if you do. The only way to override your “limitations, insecurities, jealousies, and ineptitude” is to produce. You have limitations. You are in some ways inept. This is true of every writer. … You will feel insecure and jealous. How much power you give those feelings is entirely up to you.

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