Six lessons learned from five+ years of freelancing

I’m always a strong advocate for transparency in business. One of my least favorite things about the online business world is how it’s very easy to project a vision of everything being effortless. That’s not my business origin story, and it’s not really the sory of anyone I know.

This post is the opposite of that, showcasing my entire freelancing career from start to present day. No holds barred. Buckle up & grab some tea — it’s quite a ride, and not without a plot twist or three!

In 2009, I was a restless 20 year old, ready to get out of the rural area I’d grown up in.

So I moved to Austin, TX, with my then-husband and no jobs waiting for us. More accurately, we moved to Buda, a suburb. It sounds stupid to someone who grew up in a city environment, but when you’re from such a rural area, the concept of a suburb doesn’t really make much sense at all. It’s at least 15–30 minutes to everywhere when you live in the boonies, and there’s no public transportation, so you shrug and say “this’ll be fine!”

At this point, I knew I wanted to start freelancing, but had been planning on easing into it while working a day job. Enter the first plot twist: the day we got to our new place, the head gasket in my car pretty much exploded. It was a $1200 fix, which obviously we didn’t have just lying around. And we’d just moved to a suburb with no job opportunities within walking/biking distance and no public transportation. Womp womp.

He got a job outside the home, I threw myself into doing anything I could think of online to get money. (I mean, not anything — but you get the idea.) I started working for a few content mills (super low writing rates: $15 or less for 500 words). Luckily, I read and write/type so fast that it added up. It still wasn’t a lot, but over a few months, it helped.

The problem was that I wasn’t being publicly credited as the author of the things I was writing. As a result, I was working for content mills and didn’t see any way to stop working for content mills, because I still didn’t have a portfolio.

Lesson one: If you’re doing to do cheap work, do it with an endgame in mind.

Don’t just frantically do it to pay the bills, because that’s a fast path to burnout. In my case, I should have been doing work I was credited with and leveraging that into better work.

Not shockingly, I started to get incredibly burned out on writing. Around this same time, a friend of mine (who is actually one of my best friends to this day, so it’s funny that she’s a turning point in this story) posted a question on Twitter asking for organizational tips. I took it upon myself to send her a ridiculous 3,000 word email outlining my entire project planning process. Her reply was something like, “Woah, you know this isn’t normal right?! Not everyone does this! You should totally be a project manager!”

Project management? What’s that? Not everyone is this organized — really?!

Lesson two: What’s obvious to everyone else is not necessarily obvious to you.

I studied the ideas behind good project management for a few months, still writing in the meantime, and then basically pitched myself as an intern to a few online web design agencies. I’d work with them to learn the ropes and they’d get free work. Win-win. I turned out to be pretty good at it, and slowly transitioned over to doing freelance project management.

For the next couple of years, I had kind of a hodge-podge business model. I was doing freelance project management for online businesses, some consulting for solopreneurs, and classes/workshops on productivity/organization. I also did a little bit of admin work on the side, though I never advertised it — it was more of a fill-in-the-gaps thing.

[Somewhere in here, I also got broke my foot, moved three times in a year, and got divorced. My life is many things, but never boring.]

Business was always a struggle, though. The people that I was doing PM work for or selling it to knew they needed a project manager, but they often asked for a high-level admin assistant instead. What happened more than once was that I’d work with a very successful solopreneur, get them super organized, set up all of their systems, hire and onboard and train a VA and…essentially put myself out of a job. In between that and the fact that a lot of business owners either staunchly refuse to get organized, or actually get off on being disorganized and stressed out, it was just hard to sell. (I’ll note here that I do know people who make it work and who have successful service packages that do what I just described, so it’s not impossible. It was just really hard for me.)

Lesson three: Tactile, concrete things are easier to sell. Also, make sure your customers don’t just need what you’re selling, they actually want to buy it.

Everything hit the fan in late 2013. In addition to a seven-month-ish mental health saga (nervous breakdown, going on medication, having a bad reaction to the medication, going off medication — withdrawal, yipee!) that had worn me down, I lost my main project management retainer client. They went out of business unexpectedly and they’d been something like 75% of my income. I went into a depressed tailspin in a matter of weeks. I was absolutely exhausted, the winter season was always slower than normal for my work, and I did not have the get-up-and-go to replace that income.

Lesson four: Don’t put all, or even half, your eggs in one basket. It’s a recipe for disaster.

I decided it was time to take a break and get my first actual-fax grown-up job. And here we revisit lesson two. I kept applying to jobs that were oriented to the organization and admin side of things, and I was getting interviews. But inevitably in the interviews, people would ask me about why my marketing or creative background. In one phone interview, with a super nice HR manager I remember to this day, she flat-out said, “I love your personality, but I don’t think you’d be a good fit for this role, talents wise…do you mind if I ask why you aren’t applying to marketing positions?”

I hadn’t thought of myself as a marketer at all, but I tweaked my resume accordingly and got results. I started one place in December, but got another job offer in late December that seemed like a much better fit, so I switched to there, doing content and social media marketing.

The agency job was…interesting. I definitely don’t regret taking it, but I have enough stories from it that it’s going to be a chapter in my memoir someday. Think the Devil Wears Prada, but with more substance abuse issues. After the umpteenth insane incident (where I was berated for and interrogated about going to the doctor to get serious medical issues looked at, which is totally illegal and also just a jerk move) I started working on my escape plan. I started pitching freelance gigs like mad, hoping to build up a pipeline of clients ASAP so I could get away from the awful stressful/abusive environment. At this point, I was working a full time job, plus pitching 2–3 gigs a day during the work week and 4–5 a day on the weekends, plus keeping newsletters and semi-regular blog posts going at my site. I drank a lot of coffee, is all I can tell ya.

When I realized that I wanted to go back to full-time freelancing, I thought I’d probably go back to the PM/consulting/classes/products business model. On a whim, I started looking at marketing oriented gigs — because I did love most of what I was doing at the agency, just not necessarily everything else that came with having a full-time job. I came across some writing gigs. And I pitched them. And I started getting them. And I was somehow surprised. I left the day job in May of 2014.

Lesson five: Sometimes, getting a job is the right thing to do.

In fact, I learned a lot from getting a day job — enough that I wrote a whole post on the experience and the lessons I learned from it: Six reasons getting a job was the best thing I ever did for my business. Even though I had some people imply I was failing or quitting by getting a job, I don’t regret it one bit.

Although I also pitched/applied to several gigs that were more generally marketing oriented, the writing is what built up steam. I thought I’d be working 50/50 on marketing/writing, but after several months, it was all writing.

And here I am, over a year later, a full time freelance writer (although I do lots of things because I like to keep myself busy). The hilarious thing is that when I was doing project management type work, I was essentially doing it to subsidize my writing. What I wanted to do was spend the bulk of my days writing…but somehow (possibly because of that awful content mill experience) I just didn’t think that was possible.

Lesson five: Learn to shut up and take the money.

Work doesn’t have to be difficult and draining for you to get paid for it. You don’t have to spend ages convincing people that you’re worth what you charge. Sometimes, it really is as simple as saying “I’m a writer, here’s my samples, let’s talk” to get paying work.

One last lesson: Anyone who makes it seem as simple as 1, 2, 3, profit & easy freelance career is the exception, rather than the rule.

Most of the freelancers I know have stories just as crazy as mine, especially if they started young or were forced into it by necessity (or had to jump sooner than they thought they’d have to). If I could do it all over again, of course I’d get to a profitable, sustainable business faster — hindsight is 20/20, after all. In the meantime, though…at least it makes a good story, right?