My Backwards Approach to Being a Self-Employed Freelancer in 6 Months

backwards approach to freelancing

This post is from new Careful Cents contributor Erin, who owns the blog Journey to Saving. Over six months she’s documented her backwards journey to self-employment.

An accidental freelancer: 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 go full-time freelance

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 2014, 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 freelancer 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 freelancer. 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.

By sharing my experiences here, I hope to inspire others to take this leap — even if it’s with a backwards approach. The biggest takeaway is knowing that it’s possible.

People are succeeding day after day; 53 million Americans are currently freelancers. Why not you?

3 Reasons Freelancing is More Secure Than a Full-Time Job (#FinCon14 Recap)
3 Ways to Save For Retirement as a Self-Employed Entrepreneur


  1. Tania says:

    I think many people underestimate the commitment that goes into self-employment. Often, they believe that leaving their jobs will allow them to cut down their hours, working when they want (or not when they don’t), not realising that you’ll probably be working far more hours and much harder for yourself than you ever did for an employer.

    • Erin says:

      Very, very true Tania. I know I fell into that trap a little myself. Often times, freelancers like to highlight the best parts of the job, and not the worst. I’m learning the hard way!

      • Lisa says:

        Amen Tania and Erin!

        People seem so afraid to talk about the challenges and only talk about the dreamy part of entrepreneurship…which gives false pretences.

        Don’t get me wrong, I’ve been an entrepreneur since 16y.o …it’s all I know and I love it. BUT…it comes with grind and hustle.

        Can’t wait to see how your journey unfolds.

        All the best!

  2. Kirsten says:

    Can’t wait to read more about your journey here, Erin. Love your writing!

    I’m with us on the working from home. You have to be very disciplined and while I do great at work, there’s people watching! I’m also scared if out on weight by snacking all day 😉

    • Erin says:

      Thanks Kirsten! Surprisingly, I’ve found that I snack less at home than I did at work. Then again, my last job had too much downtime, and I’m prone to snacking when bored. It’s really nice to be able to make meals for myself, though.

  3. Kassandra says:

    I will definitely be following your journey Erin and cheering you onward. I always say that self-employment is not for the faint of heart but for the brave in spirit.

  4. Corina says:

    Hi Erin,

    First of all congrats for the bold move! It´s not easy to do it and to write about it.

    I used to be scared of the idea of not having a steady pay check. Now, as I am working on making my way into the freelance world, I realize it´s what I really want. I still have a fulltime job, but everyday I am anxious to get home to work on my side hustle. It´s a long road till getting paid as well as on my fulltime job, but I love working for myself.

    If a year ago, I was scared of the idea of freelancing, now it´s the other way around.

    Thanks you for sharing your experience and looking forward to hear about your progress. 🙂

    • Erin says:

      Thank you Corina! I’m so glad to hear that you’ve opened up to the idea of freelancing. It *is* scary not to have a steady paycheck, which is why I’m very thankful to have my savings. I don’t think I could have done it otherwise.

      I wish you the best of luck in getting your freelance income up there, but at the very least, you’re enjoying the journey to getting there, and that’s what it’s about. I’m sure you’ll be well prepared when the time comes. =)

  5. Kayla says:

    I tried to comment once already, but it said my name looked like spam 🙁 Anyhow, Erin I’m so excited to hear more about your freelance efforts and what you learn along the way. I too am just breaking into freelancing and I have a lot to learn!

    • Erin says:

      Thanks Kayla! I think it has something to do with the “@” symbol when you go to comment. If you have questions on anything specific you’d like to see me write about, shoot it over! =)

  6. debs says:

    You’ve really stepped up your game, Erin, so I’m sure this will be really helpful. Plus, you are a great writer and have technical expertise, so no doubt you can do this!

  7. Great advice, Erin! And, so awesome that you’re making it work! I never thought I’d enjoy writing my blog (and the blog world) as much as I do. It has definitely planted the seed of freelancing in my brain too… I’m still working my full-time job, but I’d love to start adding freelance gigs on the side.

    • Erin says:

      Thanks, Mrs. FW! You are an excellent writer if I do say so myself (and with how fast your blog is growing, I have no doubt others agree). I’d love to see more of your work out there!

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