A few months ago, I saw a tweet circulating that completely triggered my ego. The tweet implied that most freelancers have an unspoken privilege that they don’t talk about. That they are able to freelance because of a trust fund, or a cushion, or parents who paid for college.
Even though the tweet didn’t apply to me, I was triggered thinking that someone might think that freelancing has been a walk in the park because of some behind the scenes privilege. These emotions felt particularly intense because I had just finished looking at my income breakdowns for the past two years. Reflecting on how little money I made in the beginning, how much debt I was in, and how hard it was for me to put myself out there enough to get new clients, made me feel a sense of pride that I was able to overcome some financially and emotionally stressful times.
It made me realize that there really isn’t much transparency around what it looks like to “make it” as a freelancer. Especially with no cushion to fall back on.
This isn’t one of those articles where I’m going to break down how I make 10k every month using vague and oversimplified advice like “reach out to your network.” I don’t make 10k/month (yet), but I have been able to effectively replace my corporate salary.
Instead, I want to describe what my journey was like going from a corporate drone to broke “digital nomad” until I finally replaced my corporate income through freelancing.
I’ll start by saying that it absolutely takes a certain level of privilege to take the risks involved with starting an entirely new career path with no backup plan or cushion to fall back on.
I have no children, no dependents, and a good set of marketable skills thanks to the privilege of things like having access to education and a computer. My passport itself makes me more privileged than most of the world, just because of where I was born. I pretty much only have to worry about myself and I can be selfish with my time and energy, which has made it much easier for me to take big leaps when the risk of failure is high.
I had a house and a middle-class family and a car. My parent’s provided for me up until I went to college, and even then would throw me spending money. They had their own financial burdens and I had no college fund, so I took out loans because that’s what everyone did. Five years, and two degrees later, I had a master’s degree, $50,000+ in student loan debt and a stack of rejection letters because I had too much education and virtually no corporate job experience.
When I was unemployed (more on that later), I moved back in with my parents, no questions asked. I never had to worry about where my next meal came from. I was grateful but knew deep down that this type of comfort and privilege would lead to complacency. Throughout my childhood, I struggled with mental health but never experienced real, physical struggle. A voice inside me told me that my comfort zone was holding me back. But for a long time, I refused to believe it and nestled myself back into my cozy bubble.
Growing up, I excelled in school. Not because I was smarter than anyone, but because my parents made me. They threatened me, so I studied. When I got good grades, I was rewarded. It was a simple system to understand.
It wasn’t until recently that I realized just how mediocre I was as a teen and young adult. My minimal success was highlighted by the fact that a lot of the people around me were okay with mediocrity. I just happened to have parents that forced me to care a little bit more. But overall, I did nothing mindblowing. My grades were good and I was the quiet, nice girl which made teachers like me and give me special privileges.
Doing well in school instilled within me a false sense of confidence. I was a big fish in a small pond, until I wasn’t. I was used to getting what I wanted, and I was used to being good at what I did. This was mostly due to the fact that I lived in a bubble, and aimed small. When I started to get waitlisted at big universities I wanted to go to, I felt like there must be a mistake. I was always told how smart I was, and never even considered that there were other people, who had higher competition, working harder than me.
In other words, I felt entitled to great things, because I put in the bare minimum amount of work it took to stand out among my peers. When I couldn’t get the opportunities I wanted, I played it off like I didn’t care. I settled on a school, and later a job, under the guise that they were intentional decisions when really, I had been rejected from everything else. My ego was too fragile to admit defeat, so I let go of my ambitions and started aiming lower.
Failure and more failure
I got my first full-time marketing job, one week after I graduated from college. I didn’t even apply. A colleague from my part-time university job, referred me to an open role at a company her husband worked for. I did one interview, and a few days later they hired me. After three years and the harsh realization that there was zero room for growth at this company, I handed in my two-week notice. Later that year, I traveled to Europe for three months and spent six weeks on a cross country road trip.
I wanted to be a travel blogger and took my shot at freelance travel writing. I landed an opportunity with a company that paid me $.03/word. I rationalized that if I could just write 70,000 words for them per month, then I could make enough money to start my life over. But the thing about travel blogging is that you have to actually go places and do things worth writing about. So for the first few months, I milked every minute of every trip I took to have enough content to keep travel writing. It wasn’t sustainable, for obvious reasons.
Four months after I quit my job, I ran out of money, stopped writing travel articles, and started writing cover letters in search of a new job. After deciding I wanted another full-time job, I got one relatively quickly. It was another marketing job in my home town which seemed like a great opportunity at the time. I felt very lucky and fortunate to find something so quickly.
Fast forward 2.5 years later, I found myself back where I started. In a job, I hated, with no room for growth. I tell people that I quit, but the truth is that I was ousted. It was obvious that I didn’t want to be there. Most days, I was too depressed to give a damn about what anybody said to me, and spent most of my time at my desk, headphones in, doing what I needed to do. It shouldn’t have come as a surprise that they didn’t want me there anymore. Then, one day, the HR manager called me into her office and gave me an ultimatum. Quit, or be terminated on the grounds that I wasn’t a “cultural fit” for their organization. So I quit.
I knew at that point that working in an office was not for me. From that moment, I vowed to myself to do whatever it took to make enough money so that I never had to work a 9–5 ever again.
My first goal was to land a remote job. I had such an easy time finding full-time jobs in the past, that I assumed it would be just as easy this time around. Remote work wasn’t a huge trend yet, but the competition was still fierce.
In the 6 months after leaving my job, I applied to over 300 remote positions. At 26, I was living with my parents again, sending email after email, oozing desperation. I just couldn’t understand what was happening. I was so used to being rewarded for doing the bare minimum, I didn’t realize how many people out there were out working me, outperforming me and pursuing growth. I had settled into the idea that having a master’s degree and a few years of experience at irrelevant organizations somehow gave me an edge.
Every rejection was a punch to the gut and a blow to my ego.
When I did eventually land a few clients, they pushed back, ghosted me, and laughed in my face when I told them my rates. I cried, swallowed my pride, Googled “how to deal with rejection” and carried on.
I still get rejected on a weekly basis. Whether it’s from clients or publications I want to write for, my inbox is full of people telling me I’m not the right fit. But through a constant mindfulness and gratitude practice, I’m finally able to maintain composure and not completely shut down at the idea that one person doesn’t want me.
Every rejection was a punch to the gut and a blow to my ego.
After my failed job search, I decided to give freelancing a shot. At the time, I had no savings, a negative bank account, more than $20,000 in credit card debt and over $50,000 in student loans. In 2018, I bought a one-way ticket to Bali for $500 on my credit card and maxed out my cash withdrawal on another credit card.
I checked a bag and packed a carry-on full of ramen noodles, granola bars, and other cheap non-perishable snacks because I was afraid I wouldn’t be able to afford food. For a while, I shared a room with a friend to save money, lived in places that I hated, and said no to every weekend plan because I had no money. My student loans went into default. My credit score dropped over 100 points.
I stayed up late and woke up early and sent 10 emails a day (that’s not even an exaggeration) until I found clients that agreed to pay me the bare minimum of what I could live off of. I used my credit cards to pay for coaching and online courses to learn new skills to help me market myself more. I paid coaches to help me through the mindset blocks that I told me I would never be self-sufficient, or that I didn’t deserve to be paid what I was worth.
I did this for a full year before I really started feeling a small sense of security in my finances. Luckily, Bali is pretty affordable when you’re living on US wages, one of the main reasons why so many “digital nomads” set up camp there.
Let’s talk numbers…
In my first full year of freelancing, I made $16,000.
I can count on one hand the months where I earned more than $1,000. When I first sat down and did my finances and realized how little money I earned, I felt defeated. But the more I reflected on this number, the defeat morphed into pride.
This was money that I poured my blood sweat and tears into earning. I hustled to find clients, took nearly every opportunity that came my way and made this money with no handouts or outside help. None of it was guaranteed to me, and I had to fight for every penny.
I currently earn between $3,000–5,000/month. I have one client that takes up the majority of my time and pays me the majority of my income. The rest of my earnings come from contributing articles and blog posts to a handful of marketing and business publications. A very small amount, ($100–200) comes from the Medium partner program. And an even smaller amount ($50–100) comes from a few new affiliate marketing projects I’m working on.
I’m about 50% of the way towards paying off my credit card debt. The student loans are another story, but slow progress is still progress.
I know that my earning potential is unlimited, which now gives me the confidence to be more picky about the work I do, and how I spend my time.
For the past few months, I’ve been focused less on new client acquisition and more on nurturing my current relationships while I figure out what lies ahead. I’m in a position where I feel very fortunate to be able to limit my client work in pursuit of more creative projects that don’t earn me money (yet), but that I know will pave the way for more opportunities later on.
Taking risks is not for the faint of heart. But once you push past the discomfort and inevitability of failure, serious growth happens. Past versions of me refused to recognize my immense level of privilege I had (and still have). I sank into the role of the victim and blamed everyone around me for my lack of success.
My ego stopped me from ever asking for help or showing signs of weakness. I had to forget everything I thought I knew about how to navigate life and start from scratch. I’m not saying that freelancing is the hardest thing in the world. In the grand scheme of the world, my struggles don’t even really count as real struggles. I’m alive. I’m healthy. I have a roof over my head and a family that has my back no matter what. I live on a beautiful island. I literally get paid to write on the internet. I am living a dream life.
Before this journey, I would have a panic attack before every email. I was timid and afraid to talk about money or debt. I felt like I had to compete with everyone around me, and would resent other people’s success. I was arrogant and assumed I knew everything.
Now, I assert myself and ask for what I’m worth. If they can’t afford it, it’s not a fit. I send cold emails in my sleep. I pay for courses and coaching and am constantly learning new things about business, writing, and marketing. I no longer rest on the idea that I have a master’s degree in marketing so I know more than people because I don’t. I celebrate other’s success and lift people up because there’s room out there for all of us.
I turn down offers that don’t align with my values. I no longer feel scarcity around finding clients or making money and try to live my life with a mindset of abundance.
It’s hard to see growth while it’s happening. But once you start reflecting on the things you used to feel and fear, and how much differently those things affect you, it becomes clear that growth was happening all along.
I’ll admit, part of the reason I was inspired to write this is that my ego threw a fit at the idea that people might think that I got where I am because of outside help or some trust fund that doesn’t exist. I’m not at a point in my spiritual journey where I no longer care what people think, but I’m working on it.
There are things I wish I knew about successful freelancers and entrepreneurs, that most people don’t want to talk about. For a long time, I thought I was failing because my journey didn’t look the same as others. I compared myself to successful people and assumed that their path was straightforward. I thought I was doing things wrong and that I would never be able to achieve my goals because they were too ambitious.
For me, failure led to growth. Taking risks and falling on my face deflated my ego enough to force vulnerability. Teaching myself how to be vulnerable, let go of what I thought I had to be doing, and embrace what was happening in front of me forced me to see myself through a different lens.
I’ll be the first person to admit that it does take a certain level of privilege to take risks. But the more people are transparent about what they’ve gone through and how they made it work, the more attainable all of those unrealistic goals seem. Transparency into the process, including the good and the bad, can show other people that even though it will be really challenging at times, it can work. If they can do it, you can do it.