10 Pieces of Advice from 10 Years of Freelancing

When I made my first sale as a freelancer, I was super excited. I was working nights as an editor at a newspaper and had big dreams that someday maybe I’d be able to freelance full-time, actually get to see my husband occasionally, maybe even be at home with a kid if we ever chose to have one.

Husband, who has always supported my crazy whims more than I give him credit for, took that first check, for $50, made a color copy and framed it for me. It hangs right above the light switch in my office (above that, a pic of husband and the girl from when she was about a year old).

Which explains why recently I knocked it off the wall. And when I picked it up, I noticed the date on the check.

December 3, 2003.

Which means in some capacity or another, I’ve been getting paid for freelance work for 10 years. I’ve gone from writing for free (way too much) to slugging out keyword articles for a couple of bucks each to ghostwriting ebooks and emails, working for About, writing my own books, quitting my day job, making more than I did with a day job (and a lot less) and deciding to have that kid after all. And sending her to school at age 2 because I didn’t feel like I could take either job seriously trying to do both at once.

I’ve learned a lot over the years, and here are some of the things I wish I could tell myself from back then. Some of them I still need to hear. Maybe you do, too.

1. Stop Writing for Free.

Right now. I mean it. Stop. If someone has paid you for your words, you are worthy of being paid for your words. So don’t work for free.

Write for yourself, for passion, for friends you like and causes you believe in, but chiefly, write for other people only when they pay you.

2. Blog Your Passions.

If you don’t already have a blog, start one. It’s great writing practice, gives you something to show prospective clients and editors, and is just a fun outlet for sharing your passions and learning more about the kinds of things you want to write about.

3. Treat it Like a Business.

I’ve never had a great record keeping system (I tried to use QuickBooks once and did it so wrong my accountant laughed at me and downgraded me to a spreadsheet) and I never keep track of payments and expenses while they’re happening.

And then every year I get super frustrated at tax time and wish I kept better records. I’ll do a better job for a few months and then slide back into not doing it. Set yourself up right from the get go and you’ll have a much easier time.

4. Learn Everything You Can.

About the topics you want to write about. About business. About freelancing. About life. Everything is potential fodder for blogging, personal essays and articles. Soak in what you can, as much as you can. Even if it doesn’t seem connected to your work.

This goes back to the age-old advice that writers need to be readers first. Read anything and everything that interests you. Keep book lists and have goals. Keep it fun, but input as much as you can.

5. Know that Things Will Change.

My first bio references a Yahoo email account and a Geocities website. Over the years I had a Blogger blog, a WordPress.org blog and my own self-hosted WordPress blog. I don’t think WordPress is going away, but technology will keep changing.

When I started no one was on Facebook; Twitter didn’t exist. People didn’t know about your writing on the web unless you told them personally or they somehow happened upon it in search. Things have changed a lot in 10 years, and they will change more.

In my time the financial situation for freelancers has changed a lot as well. When I started full-time freelancing I pretty easily made as much money as I made in my full-time day job (as an editor at a university press, so I was not making a lot). These days I probably do work less, and I’m focused more on craft writing and my own blog, but I make a lot less — even with long-term clients — than I used to. That’s the danger of being paid in page views and working in a world where people expect everything for free.

I’m sure it’s still possible to make a decent living as a freelancer, I just wouldn’t say I’m doing it right now.

6. Be Willing to Try Different Things.

When I was first starting out I had what I called “the year of yes,” in which I accepted just about every freelance writing gig people would pay me for (followed quickly by “the year of no,” in which I shrunk back to a few core clients). I wouldn’t necessarily recommend that, but don’t be afraid to do work in different genres and styles than may be part of your plan.

I never really expected to write about craft for a living, but it’s a great thing.

Be open to offers, to writing about things you only kind of know, to writing about what you want to know.

7. Don’t Go Full-Time Too Soon.

I’m a big fan of plans and knowing what I’m getting into, and shifting to full-time freelancing was a very calculated move for me. I took a lot of work while I still had a day job and figured out how I could replace most of my income before I decided to leave.

I also got a book deal that I could not have completed if I had a day job at the time. I’m not suggesting that’s going to happen for you.

And you may not need that level of comfort with things, but at least have a plan and know when you’re going to be ready to go if that’s something you even want.

8. Keep it Fun.

Yes, freelancing is a business. Yes, it is work. And work is not always fun, even for people who love their jobs. There are things I have to do (mostly related to email and website maintenance) that I hate to do and will put off as long as possible.

But there are parts that are really fun, too. Some days I just need to focus on the fun parts and remember that those fun parts exist. You just can’t completely ignore the less-fun parts all the time.

9. Find Your Tribe.

The word tribe is way overused in the online world, but it’s so important to know people who do what you do, understand what you do, have a similar passion and can support you in what you do.

This is kind of a crazy thing to do with your life, but there are a lot of people doing it. And thanks to the Internet its easier to find them than ever.

I’ve only in the past few years found blogger friends in my own community and now I have a group of girls who I know understand me and have my back. And that is the best feeling in the world.

10. It Really is Pretty Damn Awesome.

I am so lucky to get to do what I do. I get to write a lot about topics I love, I get to create things and share them with other people. I get to write books and share stories and hang out with awesome people in person and online.

I have amazing colleagues all over the world and a wonderful husband here at home who has always supported my choices. That means a lot, and I don’t acknowledge it as often as I should.

This job, this way of life, is really amazingly cool. Try to remember that, even on the hard days, the worst day freelancing is better than the best day stuck in an office.