My Backwards Approach to Becoming a Self-Employed Freelancer

An accidental entrepreneur: that’s an accurate description of myself, and the situation I was in earlier this year.

I didn’t know what it meant to have a side hustle before I started blogging a little over a year ago. It sounds obvious, but I didn’t know anyone pursuing one.

I didn’t know a thing about blogging, or the community surrounding it. If you had told me you could make money writing online, I wouldn’t have believed you.

The word “entrepreneur” conjured up images of strict business attire, start-ups, and millionaires. Little did I know there was a push for solopreneurs; individuals starting and running their own small businesses, often online.

Thankfully, as I made my way through the blogosphere, I discovered that making a living online is possible — many of my peers were taking advantage of these opportunities. But I never thought it would be the path for me.

Yet, that was the path I found myself wandering down earlier this year — I left my job, and decided to navigate through this mysterious world of freelance writing.

Deciding to Freelance Full-Time

My boyfriend and I knew we would never be able to have the life we wanted in our current location, as the cost of living was too high. Our goal was to find a job that would relocate us to a place where our money went further.

My boyfriend was able to find such a job, and within a year, he would be eligible for a promotion. Relocation was necessary to achieve that; it was our one-way ticket out.

We started stashing away extra money to prepare, while still paying down our student loans. We had no idea exactly when this relocation would happen, or where we would end up. This made it impossible for me to start a job search beforehand. All we could do was wait and save.

In the midst of this, I saw many fellow bloggers making the switch to self-employment. It planted the seed in my head. By the beginning of 2020, I thought freelancing was a possibility for me.

I didn’t have much to lose: upon graduating college the only jobs I could find were administrative, which paid anywhere from $9 – $12 an hour. I saw people making more a month from side income than I did from my regular job! And I noticed there were lots opportunities out there, I just had to open my mind to them.

I wasn’t receiving any special benefits at work, other than a steady paycheck, and I am lucky to be on my parents’ health insurance plan.

I decided I wanted to give self-employment my complete focus. So I created a bare bones budget, and realized I easily had over a year’s worth of living expenses saved up.

If any time was perfect to try freelancing, it was now.

With that said, I am giving myself six months to earn $1,500-$2,000 a month, or it’s back to the cubicle trenches for me. I’ll be outlining my journey here on Careful Cents in hopes of showing you the steps you need to take if you plan on doing the same.

Creating a Plan Before Leaving

Conventional advice is to continue balancing your side business with your regular job, until your side income meets or exceeds your regular income, at which point, you can start making the transition. I fully believe in that advice!

However, sometimes you don’t have the luxury of taking your time. For example, Carrie had to quit her job months earlier than she planned to, in order to move to a new state for the summer and care for a sick family member.

This is when you can make the leap before you’re ready and still succeed! I don’t recommend this path to anyone other than those who have hefty savings, determination, and a good back-up plan in case things go south. I’m not encouraging you to go out there and quit your job to pursue what you love. You need a plan. I was planning this move for a year, and the amount I saved enabled me to make this decision, but it’s not one I took lightly.

Success doesn’t happen overnight, and that is why I want to be open about the struggles I’ve faced since I started this journey. There are a lot of challenges that come with jumping into something, as opposed to working your way in. I’ll be highlighting some of those struggles in future posts.

Launching a Freelance Career

The first struggle you’ll likely face when making the switch to self-employment is the decision to freelance in the first place. There are a lot of “what-if’s” that can plague you. But the bottom line is — what if you don’t take this chance?

I knew I wouldn’t get a better opportunity than the one I had staring at me, and in a manner that is uncharacteristic of me, I grabbed the bull by the horns and dove in. I knew I would regret not taking this chance when I had it.

Self-employment isn’t for everyone, but by sharing some things to consider, hopefully you’ll begin to see whether or not it’s the correct choice for you. Here are 4 vital questions to ask yourself in order to determine whether or not you’re cut out to be your own boss.

1. Can you make failure your friend? Lovely thought, right? But it’s a necessary question to ask yourself. As a solopreneur your business runs entirely off of your actions or inaction. As a beginner, failure is guaranteed in one aspect or another. No one is immune to it. The best thing to keep in mind is that failure propels you forward. It’s a lesson to learn that will help you in the long run.
2. Is your passion enough to carry you? You might think being your own boss is awesome. While it can be, you’ll be making all the decisions and taking all the risks for your business. Are you prepared to handle that? Some days, you might get up and wonder where your motivation went. Your passion for your work has to be enough to get you through those days. You need to have a “why” that you can refer back to.
3. What do you have to do to prepare? Unlike me, you might have quite a lot to lose when making the transition to solopreneur. If you have a 401(k) at your job, health benefits, insurance, etc., it could be a harder choice, but not an impossible one. Figure out the actions you should take to prepare for these losses. The easiest is to have a savings buffer!
4. Can you work from home, and alone, productively? You might think the answer is yes, but you’d be surprised. I thought working from home would be a breeze as I’m a disciplined and focused employee. But that when I was working for someone else. Working for yourself is a different beast. Being told what to do and deciding what to work on are not the same; it requires a different mindset. Find time to fully dedicate yourself to working as you would if you were totally self-employed, and see how it goes.