Three years ago I was a technical project manager at a startup. I managed a team of computer programmers and I made a lot of money. I appeared to be living the life. But I was miserable. One day, sitting in front of my computer in a meeting I was supposed to be running, I thought to myself “I can’t do this anymore,” and something inside me broke.
I made the terrifying and tough decision to quit my job and pursue a completely different career. I became a nanny. While the baby napped I finished a college degree online. And then when college was done I had a crazy idea. Maybe I would start to write again. Just to kill some time while the baby napped.
So I started a blog. I started writing every day and people were actually reading it. They told me they connected with what I wrote. That I was really good at telling a story. I don’t know why I believed them, but I did. So I kept writing.
Then I finally got the courage to submit a pitch to a digital magazine. And it got accepted. One of the first pitches I ever sent was approved. And published. It doesn’t usually go that way. I’m really lucky. A few weeks later, that site published another piece I wrote. And I began to believe that i could really do this. I could be a writer. It didn’t happen quickly and it wasn’t easy, but I just kept trying.
Then The Tempest found me. One of their fellows tweeted at me to offer me a writing position. When I read the email I actually cried. It was finally happening for real. I began writing for The Tempest a few times a month. I built a portfolio.
I still had a full time job and writing full time was still a dream. When The Tempest opened their Fellowship program again I jumped at the opportunity. I applied, crossed my fingers and prayed. When I got accepted I cried again. I was one step closer to my dream.
The fellowship is one of the best things that’s ever happened for me. It gave me incentive to write at least five times a week. I got direct access to the editors and learned about the publishing process. I learned about editing pieces for publications and became a go to assistant editor for the website’s CEO, who personally mentored me. I learned what it really meant to be a writer and editor for a digital media outlet.
When my full time, seasonal job ended I decided to take the plunge and apply to freelance writing jobs. I had applied to some of these places before, but they’d never even emailed me back to say no. But with the fellowship at The Tempest on my resume, I finally started hearing yes.
Today, I am a full time, paid freelance writer. I write for two paying sites at least five times a week and I’m published multiple times per week. I never thought I’d be able to make writing work as a full time job. I always thought it’d be a side hustle and I’d always have to work a “real job” to support myself, but that’s not true today. I’m literally living the dream.
But it’s a lot of hard work. Freelancing is only about 25% writing. It’s 75% hustle. It’s taken a lot of trial and error to figure out how to make it sustainable. Here’s what I’ve learned so far that’s helped me a lot.
You’re going to get rejected, a lot, but do not give up:
When I first started pitching, I would send out pitches three or four times a week to multiple sites, and I got rejected all the time. I got really discouraged until I talked to other writers and found out that this is totally normal. Everyone gets rejected a lot. Media outlets want to see a portfolio before they accept pitches, so until you build a portfolio you’ll get rejected a lot.
The best way to build a portfolio is to accept a fellowship or internship. You’ll be doing a lot of unpaid writing, but the mentoring and portfolio building will pay off in the end.
Time Management is everything:
Going from working on a structured environment to working for yourself is tough. I often think “well I make my own schedule so I’m actually pretty open.” Then I over schedule myself with things that aren’t work and I’m scrambling to get an article done late at night.
Figure out when you work best, then clear out that section of your day. Treat it like an actual work schedule, not flexible time.
Keeping track of your pipeline is essential:
In order to make actual money writing you have to do A LOT of writing. I write 8-10 articles per week. If I over-commit and miss a deadline, I risk losing consistent work because I’ll be seen as unreliable. So, I have to keep close track of what articles are due when and what I need to do in order to get them written.
I use a website called Trello to map out my pipeline. Every article I get assigned goes on a “task board” as a task and each task has a due date. The tasks are organized in columns by when they’re due: today, tomorrow, or this week. This allows me to organize what needs to be worked on now, next, and later.
Find a system that works for you and keep a close eye on that pipeline.
Always have a pitch or four in your back pocket
You won’t necessarily be assigned articles, so you’ll have to be coming up with your own ideas. Make sure you can always deliver an idea and an angle in a pitch whenever you’re asked. If you take too long to put together a good pitch, you’ll miss the opportunity. Editors move on fast.
Always be on the lookout for new opportunities
Even if you’re lucky enough to land consistent freelance work with one company, it likely won’t be enough money. Some sites even cap how many articles you can write per week or per month so there will be a top end of what you can earn with them.
This means you’ll need to be writing for multiple sites consistently. Bookmark a bunch of job boards and check them regularly.
Always believe that you are worth the money
The gig economy makes it really easy for digital media outlets to pay writers very little. There’s always someone willing to write for less than you and there’s always someone willing to write for free. This means that you will need to insist on being paid.
Sometimes it’s really awkward to ask for money or ask for more money, but the key is remembering that you are absolutely worth it. Your writing is valuable. Your writing is important. You deserve to be paid. If you don’t believe this now, that’s fine. I didn’t when I started either. But say it to yourself over and over until you believe it and next time someone asks you to work for free, say no and pitch the same thing to someone who will pay you.
Being a freelance writer is hard. It’s a lot of work and it can be really stressful. But if you are a writer at heart it’s also an amazing adventure. There’s nothing better than seeing your work published and hearing someone say, “I loved that piece you wrote.”
You can make this dream come true. So get your fingers on that keyboard and go live the dream.