I quit my job in January.
After years of slogging it in the restaurant industry, waiting for the “perfect opportunity” to actually do something fulfilling, I decided over the course of an hour-long meeting with my bosses to quit.
It took me a while to get to the point where quitting my job was the right move.
But at this point, nine months and thousands of dollars earned later, I’m glad I did.
How did I get here?
I never planned on staying in restaurants for long.
I was going to be an entrepreneur, starting with a Tim Ferriss style content business, then perhaps move on to bigger things.
But after setting up a few websites and writing a handful of blog posts over the course of a couple of years, I gave up (at least for a while) and got a “regular job.”
After landing my first job at prestigious Waffle House, I worked in a few other restaurant jobs, eventually making my way to a local restaurant startup that sells spicy-fried Nashville Hot Chicken.
On the whole, my restaurant career was a good experience – I learned a lot of things I needed to personally and professionally.
But after four years in the industry, I’d just about maxed out the value I could get from those jobs.
By the time January rolled around, I was ignoring all the signs that it was time to leave.
I’d set my dreams of fulfillment aside for a decent paycheck and a mildly stimulating job – which wasn’t enough to sustain me any longer.
The “startup” part meant I got to go beyond typical restaurant work (cook something, clean everything, repeat) and engage in more thoughtful pursuits like creating inventory and training systems.
But I was bored.
I’d fallen into a routine of just getting by.
Waiting for the ever elusive “something.”
So when I called for a meeting with the owner after getting back from a reflective Christmas vacation, I figured I’d find one or two new projects to work on.
That would be enough for me to just keep at it while I started working on something more personal and fulfilling.
But that meeting took an unexpected turn.
After the first five minutes of pleasantries, rather than moving on to discuss my continuing role in the company, it was politely suggested that maybe it was time for me to leave.
I say politely, I wasn’t exactly pushed out; I probably could have stayed if I really wanted to.
But I think they saw something I’d been ignoring: while I was contributing, I wasn’t invested.
Fortunately, I had enough self-knowledge to face the fear and facts: I was bored, I was waiting, and I didn’t want to deal with the challenges of moving on to something new.
So I accepted their offer despite my reservations.
They were right, it was time for me to do something else.
Nine months later, I’ve become a freelance writer/copywriter/content marketer (still figuring out what exactly I should label myself).
I’ve got a few regular clients, earn around $50 an hour, and, to put it mildly, am doing quite well.
Really, I’m glad I’m here.
And I still want more.
And I know I can get it.
I began these past few months knowing a few things about who I was and what I’d need to actually make it on my own.
I’ve developed systems of habits and tools that let me make steady progress – from fast food to freelancer and beyond.
So I figured I’d share some of the principles I’ve used to get this far.
Perhaps they can help you make it as a freelancer too.
Guidelines for Getting Things Done
I’m a big fan of principles, by which I mean ideas I use to make decisions and to remind myself why I do what I do when the inevitable self-doubt creeps in.
While there are tons of these I try to apply in work and life, three really stand out as being the most helpful on my journey from fast food to $50 an hour.
Use Systems to Make Progress
Starting out I knew who I wanted to be – the kind of person who can run their own business and support themselves outside of the omnipresent “regular job.”
I knew to become that person I’d need to do a few things I wasn’t comfortable with.
And from experience, I knew the best method for getting comfortable with the uncomfortable is to make a habit out of doing that thing.
Take writing for example.
After two weeks or so of searching for my next source of income, I landed on “freelance copywriting” as the thing to at least get me started on this new path.
Based on years of feedback from my English teachers, I figured I had at least an above average writing ability.
Combined with my daily journaling habit, I believed I could at least do the writing.
But was that writing worth paying for?
And could I write about specific topics I might have to research (as opposed to the “whatever’s on my mind” style of my journaling)?
Only one way to find out: try to get paid to write.
And write as much as possible while doing so.
To start, I looked for ways to make money online as a copywriter.
Ways that didn’t require a website of my own and years of growing an audience (that strategy hadn’t worked out so well before).
I eventually found what some might call a “content mill” known as Textbroker.
Despite the relatively low pay and lack of incentive to write good content, I actually appreciate the site – though I’d never write there again.
Basically, it’s a platform where people who want content written post jobs and offer to pay anywhere from $1-8 for a 500-1000-word piece.
To give you some perspective, in those days it would take me at least two hours to research and write 500 words.
These days if I’m on fire, I can crank out 1000 good, well-researched words in three hours.
So the pay wasn’t much.
In fact, I could make more money at Waffle House (though I’ll never work there again either).
But I didn’t care.
I knew I couldn’t make a living at that rate, and I knew I wanted to make $100 an hour, but I wasn’t there yet, and that was fine.
I needed to start, and to get started I knew I need a system, a set of tools and habits that I could rely on to consistently make progress toward that $100 an hour.
So I looked for four things:
- A way to build a portfolio.
- A way to get paid for writing without needing to spend time searching for clients and getting hired.
- A way to find topics to write about without needing to develop them myself.
- A way to find enough jobs and topics to write every day.
And Textbroker offered all this.
When clients post jobs, you just write and submit the piece they’re looking for, then the client decides to accept or reject your submission.
If your piece is accepted, roughly $5 will be headed your way(!).
There was enough work that I could find at least one piece to write every day.
And because I just submitted work and didn’t have to be hired first, I had the chance to prove my writing was worth paying for.
Without needing any sales skills.
If they didn’t accept my submission, I still had another piece for my portfolio.
And that was my system.
The habit of writing every day and the website where I could find topics to write about.
Together they helped me build a portfolio and prove my writing was worth paying at least $5 for.
Iterate on Your Success
I knew I needed to work on building systems for a couple of reasons.
One, I didn’t quite trust myself.
It was just too easy to put off important tasks I didn’t want to do.
There’s always another show to watch or game to play.
So I needed to build some structure for myself; habits that I could commit to doing every day to reduce my anxiety about starting and continuing this new and productive work.
Part of that anxiety came from a habit of spending all my free time entertaining myself.
Another part of that anxiety came from not knowing if I could commit to reaching a goal like earning $100 an hour long enough to actually get there.
By working on systems, I could focus on starting small and incrementally grow from there.
Without feeling like I was failing to reach a goal I couldn’t really control.
I could spend two hours a day writing.
I couldn’t control how much I made, or whether I got hired.
So I found a way to get better without needing those things to feel competent.
And that same way let me gradually build capacity by testing my limits and consistently raising the bar.
That’s where iteration came in – the idea of working towards one goal for a period of time, then moving to another goal that builds on the first, and so on.
At this point, I knew a few more things:
- I’d gotten into the habit of writing every day, so I knew I could take an idea or topic and write 500 words on it in 2-3 hours.
- I’d proven my writing was worth at least $5, but I wanted to make more.
- And earning more meant finding another platform with a greater earning potential.
This is where Upwork came in.
I’d heard of it years ago (before my failed blogging attempts) but decided freelancing wasn’t for me.
During the search that lead me to Textbroker, I came across Upwork but put it in my “ideas for later” pile.
When I was starting out, I didn’t want to need to earn clients.
I just wanted to prove I could write well enough to get paid while building a portfolio.
Having accomplished that with Textbroker, I knew it was time to iterate.
I took my writing habit, the knowledge I could get paid with it, and the portfolio I’d built and added a new, more profitable layer: getting hired by clients that would pay more than $2.50 an hour.
So I setup my Upwork profile and got started.
I built on my daily writing habit by adding a daily prospecting habit: finding jobs that interested me, writing proposals and submitting them to potential clients.
I was hesitant at first.
The fear of rejection was strong, even though that rejection just meant getting no response from a relatively anonymous digital communication.
And unlike over at Textbroker, where if a something I wrote was rejected I’d still have a portfolio piece, I couldn’t reuse a proposal to get more work (don’t send out boilerplate proposals!).
So I didn’t have that “second prize” excuse to cope with the rejection.
On top of that, now I was trying to convince someone to commit more than just a couple of bucks.
Which raised another uncomfortable question: even if I could earn some money from writing, could I earn enough to actually make a living?
It was tough dealing with so many unknowns.
But using the principle I’ll get to in a minute, I eventually got hired.
This time $25 for four hours of work.
Which might seem like a Textbroker level of success, but it was worth so much more than that.
I’d gotten hired.
Now I knew I could do that too.
And I got public feedback I could use to get the next client.
Perhaps I could make it as a freelancer after all.
Just Keep Going
Underlying both of these principles is the one I really needed to work on.
The one that has been hardest for me to use before.
The one most likely to determine my success in becoming the person I want to be.
You could call it tenacity, persistence, or endurance.
But I call it the principle of “Just keep going.”
I stole the phrase from Brian Clarke, who offers that support it at the end of his Unemployable podcast.
Despite my reservations about the idea of mantras (do they actually work? I don’t know) I’ve made it one of mine, something I say to myself in times of desperation and triumph alike.
When I wake up and don’t feel like writing:
It’s only two hours, just keep going.
When I’m afraid to write and submit proposals:
It’s not about this being the one that leads to the job, it’s about sending out enough quality proposals to win by numbers. Just keep going.
And when I’m unsure what to do next:
Should I apply for this job or that one?
Should I increase my rate?
How do I keep growing?
Just keep going.
I’m playing a long game, a game of consistent progress in a general direction I want to move.
It’s not so much about what I get done every day, and it’s not so much about achieving a particular goal by a particular deadline.
It’s about putting in the work, feeling satisfied with making even a little bit of progress every day, and trusting that I’ll not only consistently get better this way, I’ll be able to figure out what the next move is when the time comes to shift my priorities.
Making It As a Freelancer
All this said, there are loads of other tricks and tactics I used to go from fast food to $50 an hour the past few months.
It’s really the culmination of some hard learned lessons spread over the course of a few years.
And these principles might not be what you need to make it as a freelancer.
But my hope is that I’ve at least helped you come up with some ideas that can lead you there.
I at least feel confident in suggesting that if you keep trying, working, and moving, you’ll figure it out eventually.
And when you find yourself on the path from where you are to where you want to be, just keep going.
Also published on Medium.
