When I think back to all the things I could have done to get to this lifestyle sooner, well, I made all the mistakes. I graduated with a pretty useless marketing degree in 2007 (Twitter, FB, and Instagram were barely blips back then), got a crap job working as a Marketing Assistant, and quickly became disenchanted with the 9-5 life.
In the first of many career changes, I moved to Florida and became a middle school teacher. Though I enjoyed it at first (and lasted 7 years in an industry where many trained teachers don’t make it past 3) the bureaucracy in teaching really wears you down. On top of that, I was stuck in one place. It’s really hard to make teaching into a remote job and while there are virtual schools, you’re pretty much stuck with most of the same problems of teaching in-person — and possibly even less pay.
I felt stuck because I didn’t know what else I could do. I wanted remote work but doubted myself because I didn’t feel like I had “real skills” that translated well on paper. In my head, I was “just a middle school teacher.” I couldn’t understand how to make my teaching skills seem important in a business environment.
What a difference several years makes — I now firmly believe that teachers can do almost anything they want when it comes to freelancing! So many educator skills translate well to business. (Project management is my sweet spot, but back to my story…)
Off to coding bootcamp
Taking stock of my options back in 2015, I figured that tech skills were the most remote-friendly. Programming bootcamps were becoming really popular at the time and I like the idea of making a quick career transition as I couldn’t stomach the idea of going back to a regular university, nor taking years to make a change.
I decided to dig myself further in the hole — because when you have debt, what’s more debt right? I shelled out $10,000 for a 9-week course and went all-in on this new direction.
So challenging, but also so much fun going through the fire with the other students!
It was one of the most challenging times of my life but I did well at the school — my group even ended up creating the winning web application at the end. After all of that though, I had major impostor syndrome and chickened out of trying to get a real “dev job.”
I’d quickly realized that the school’s teaching was at best mediocre, leaving massive gaps in our education and to make it all worse, I realized I didn’t have a great disposition for coding all day.
So now there I was, bummed at myself for shelling out all that money, a little bitter at the crap education our cohort had gotten, realizing I didn’t want to code all day, and wondering what on earth I was going to do now.
Bouncing around from job to job
The code school realized the potential of having me (a former teacher and former student of theirs) work with them to improve their curriculum so they hired me as an instructional assistant shortly after I graduated.
After working with them for about 5 months, I had a heart to heart with myself and asked, “Did you really mean to leave one teaching job for another? Is this getting you any closer to remote?” The sad truth was that it wasn’t so I knew I had to leave.
As annoyed as I was to have spent all that money only to not become a developer, the experience did help me. I was able to parlay the experience into getting a job as a technical writer for a company that knew of me through my group’s winning presentation at code school.
That place was a messy startup, a “total shit show,” is the way most of us who worked there described it. The company began sinking into more and more of a mess and showed signs of going under. I had nothing to lose so I put together a proposal asking to work from home. Just as it was on the verge of getting approved, the parent company stepped in and changed a lot of the rules — one of them being, no more working from home.
Hitting what I thought was rock bottom
I quit on a Wednesday, packed up my stuff and drove 18 hours back to Ohio. Yep, that’s how bad things had officially gotten. I left the beach and moved back to Ohio for a bit — a major blow to the “dream life” I was trying to build.
I decided there was only one way to get where I wanted to go — and that was to do what everyone had told me was impossible — to make the jump to remote work directly. If I was ever going to live the life I dreamed of, finding remote work was crucial. I spent my days scanning the internet, looking on remote job boards, and spending hours on detailed applications — often just to get a rejection a few days later. It was soul-crushing, depressing, and every day was a seesaw between, “I can do this,” and, “I should just give up now.”
Finally getting a remote job
One day I was scrolling the pages of a personal finance blog that I’d followed for a while and found an opening for a copy editor. For years I’d been the go-to person among family and friends for checking over resumes, fleshing out cover letters, and proofreading college entrance essays. This was something that came naturally to me and I knew that if this company would look beyond my resume, (I was still doubting how “middle school teacher” represented me on paper,) I could make something of this.
I took enormous care with my application, the test project they gave me, and in preparing for the 3 rounds of interviews. It paid off because I beat out 336 other applicants to finally land work as a copy editor for a fully-remote company!
It seemed like my dream was finally coming true. It had taken me less than two months to land remote work and I was elated. The job paid even less than teaching, but I figured I was smart and would be able to grow quickly.
I liked the people on my team and the work I did at first but it wasn’t rocket science and after a few months I could do my job on auto-pilot. I was bored but kept it at bay by traveling on short weekend jaunts to new cities. When it came to the money I was still not breaking even, but seduced by the “I can work from anywhere” part of my job I ignored that I wasn’t making much of a dent in paying off my debt.
I soon began to realize that I was “remote” but still tied to a 9-5. The company was OK, but it was a far cry different from what I’d assumed before starting there. My conversations about my growth and development with my boss encouraged me to “stay put and be content and learn the ins and outs where I was at.”
I started to feel like I’d never be happy with someone else controlling how much I made or determining how valuable I was to the company by setting a dollar sign on my head. I kept meaning to start my own business and I had this little itch at the back of my neck, this little voice telling me that it wasn’t safe to be complacent, that I was floundering again, drifting, unhappy but not doing anything about it.
The smart thing to do, the safe thing to do would’ve been to start then, while I had a job, and use my free time to start a side business. I knew this at my core but there is a dangerous intoxicant present when you get a steady paycheck at the end of every pay period. It’s called, “I’ll do it tomorrow.”
I finally got to a point where I couldn’t ignore the itch any longer and I decided that after one last trip (house sitting in LA for a friend for two weeks) I’d bite the bullet, come home, stop traveling for 6 months and really get serious about building some kind of side business!
Hitting the real rock bottom
Life decided to make sure I was serious because on the last day of the two-week house-sitting trip, I got laid off along with about 30% of the company. I had my suspicions starting a week before it happened but still, it was sudden. I felt betrayed, pissed, and scared, but also fired up and grateful that this was going to force me into finally doing something I’d been too scared to do on my own.
The evening before the official layoff. Numb inside but putting on a brave face …
First up came a tough look at the numbers. I was 32 years old and had virtually nothing in savings — only in retirement funds I couldn’t easily access. I could blame this on being an American — culturally, we’re terrible savers — or blame it on being a teacher and not making shit most of my career, but at the end of the day, I knew it was purely my own fault.
I had around $5,500 in credit card debt — a number that was destined to climb again as I faced this latest drama life had thrown at me. My car was beyond upside down, I still owed about $9,000 on it, and I was also paying minimums on around $15,000 in student loan debts — both from the marketing degree that I’d never used and the programming bootcamp.
They say diamonds are forged under extreme pressure
The first month was pure hell mentally. I’m not going to lie. I had decided, “Screw remote companies and working for anyone else.” Forever betrayed, I didn’t want to hear one more talking head tell me, “We’re a family, we’re a team, everyone here is integral to our success,” only to gleefully (ok maybe that’s a bit exaggerated) kick me to the curb a few months later. I felt like I could trust no one but myself, so it was time to bet the farm on me. I would start freelancing. I would work for myself.
Weeks were spent engaged in this hideously constant mental battle of waking up and thinking “I’m going to figure out how to do this on my own,” to by the end of the day, depressed, “No more, I’m giving up, I don’t know how to do this, I’ve got to go and look for jobs.”
The next day I’d start out looking for jobs, get depressed by sending a few applications out into the evil black hole of the internet and decide, “No way, I can’t do this, I have to make it work on my own.”
I started studying how to freelance online. I read every blog post I could get my hands on, studied how to send pitches and struggled to make my “unused marketing major, turned middle school teacher, turned code school graduate and instructional assistant, turned technical writer, turned copy editor” experience somehow work for me.
In the moment, living through it, it seemed like a year of ups and downs. Anxiety can take any difficult time and make it feel like an eternity but in reality, only 3 weeks after getting laid off, I got a successful response to a pitch. I was stunned. Not only had I gotten a client, but from her feedback I’d apparently done a really good job on my pitch. Was this the beginning of things finally coming together? I worked with that client for a few weeks on a couple of very small projects and was amazed at how it only took one successful job to think “I can do this.”
All of the blogs I read on freelancing said to specialize or niche down, but I found that to be limiting especially on online freelancing sites where there was a ton of work available. With my background dabbling in careers that weren’t exactly cohesive and my lack of in-demand skills, I wasn’t sure how to position myself or what exactly I could offer.
I knew I didn’t want to be a copy editor forever. I was good at it but my life’s passion wasn’t chasing down grammar and formatting mistakes and checking to make sure that links worked. That did nothing for my creative side. So I bumbled around for a while, keeping my profile on freelancing sites somewhat vague, and instead, putting a lot of work into customizing each pitch that I sent out.
After a few weeks of sending pitches to strangers on online freelance sites, I realized that I should get more strategic about what I was doing. I belonged to several freelancing, small business, and online business Facebook groups. I also followed a number of bloggers in the space and knew that small business owners are typically extremely busy, trying to do all the things and wear all the hats — CEO, marketing, sales, HR, product design, content, etc.
Why was I pitching to the hundreds of thousands of companies of all sizes on “the internet” through 3rd party freelance sites when I could be going directly to the source? I made a list of people I wanted to reach out to. They all ran online businesses (so remote work-friendly) and as far as I could tell they were successful enough to pay (key 1) and they were small enough to likely need some additional help in order to continue scaling their business (key 2).
I sent pitches to 9 people. It was absolutely terrifying pressing send on those emails. Rejection is scary, even over email and I worried about completely insignificant things. What would these people think of me? Was I presumptuous to think I could help them? Would they laugh and think my proposal pathetic? Would they talk to others in the Facebook group, “You’ll never guess what this idiot girl emailed me…” It was bizarre but I’m human and those thoughts and many more ran through my head.
But then the responses started coming in almost immediately. All 9 people responded! 6 said, “Let’s talk” and the other 3 said, “Thanks but I don’t have a need at this time.” (Click here to get the script that generated these results.)
I was floored! I realized that these people were all dealing with various business problems and stresses, and all I had to do was understand what they needed, and help them solve the issue. Fortunately, with my messy career path and jumping into things without any training, I was confident in my ability to kick ass at hustling. So that’s what I did.
What my life is like now
I wrote this post from my desk in front of the massive floor-to-ceiling window of a 9th floor Airbnb in Quito, Ecuador.
My life is 100X better than when I was working a traditional 9-5 job. I live a location-independent life, traveling to different countries when I like. I’m learning Spanish and making incredible friends and connections all over the world.
I decide who I want to work with, when I want to take on more clients, and I have consistently worked less but made more. Even at the very beginning when I started freelancing, I made the same income as at my previous job but working just 10 hours a week.
I also decide when I want to work. None of my clients require me to lock in for 9-5. I also don’t ask permission to work in a different time zone, take a day off, or go on vacation. I can sleep off a hangover after indulging too hard in a new city’s nightlife, or take off in the middle of the day to go to lunch with a friend. I can toss up an airplane emoji and a “Travel day, back online tomorrow!” on my Slack away message and hop on a flight to transition countries without ever having to make sure it’s approved.
This is all possible because early on I realized the value of finding high-quality and long-term clients. I specifically work with people who are good human beings and have good values on a personal level. I need to be able to agree with how they treat their customers, their other employees or contractors, and how they run their business. I work with people who are honest, kind, and out to provide value to their customers, not the kind who will do whatever just put a buck in their pocket.
My clients give me a ton of responsibility and value me, my ideas, my work, and are happy to show that value in how they pay me. They treat me as an equal or even defer to my expertise in a way no boss ever did and there are no power struggles, backstabbing or ladder climbing; instead, an environment of mutual respect and teamwork to meet our goals.
Due to purposely working with this type of client, I’ve been lucky enough to never experience the typical “shitty freelancing life” I’ve heard so much about. Clients from hell, clients who don’t pay, clients who increase the scope of a project on you. Or the “starving artist” part of freelancing where you’re constantly chasing after new work. I have never had to seek clients after that first initial round of email pitches! The shortest client I’ve worked for was around 3 months. The longest client is four years and counting.
There’s a common misconception that a 9-5 job is dependable and freelancing is risky. Fortunately, I got laid off from my last 9-5 which taught me that there is nothing truly stable about a “regular job.” Stability comes in having money coming in from different sources and that’s what I’ve got with my clients. I know that if any client project wraps up I can start by reaching back out to others I’ve worked with in the past. They’ll surely have work or know someone else who does.
It’s not just the multiple income streams that contribute to my feeling of stability, but the amount of money as well. I made $96,000 in my first full year of freelancing and paid off all my debt. Now, paychecks go to enjoying life, padding my retirement and savings, or giving it away.
I started this site because I want to help you grow in your freelancing career. It took me a long time to go from leaving my teaching career to where I am now. But it doesn’t have to be that way — I was learning (and making every mistake in the book) as I went. You can use what I’ve learned to make that same journey 10X as fast. And I hope you will because the freedom and quality of life that this lifestyle brings are unmatched.
If you want more freelancing help, get my 22-page free guide. It’s called Your Freelancing Roadmap: Discover the 9 simple steps that lead to a six-figure income.