Lessons Learned From a Year of Freelancing – Part 1

It’s been one year since I quit the security of my full time job, set out to travel Europe and had no idea what would be waiting for me when I returned. With a bit of luck and a lot of connections, I’ve been able to make freelancing a full time position but not without learning quite a few lessons (and mistakes) along the way.

What most people don’t know (and honestly, I didn’t realize either until a few months ago), was that this lifestyle was just waiting for me and every experience I have had thus far, was setting me up to succeed as a freelancer:

  1. I’ve always been an independent person, #onlychild
  2. While I have the utmost respect for those above me, I like working for myself, calling my own shots (and schedule) and learning from my own mistakes
  3. Although office life (and friends and endless snacks) are great, I have a hard time focusing with too much going on around me

So how did this whole thing come about? I made the jump.

Lesson #1: Make the jump and a lot of connections.

There’s something terrifyingly thrilling about going against the grain and doing something that people are shocked by for me. And in this moment, I was doing it times two: I was quitting my job to travel and had this little heard of plan to freelance. I didn’t know anyone that lived this lifestyle unless you counted those random people on Instagram who made it appear easy so you can imagine I got a lot of weird looks and “are you sure?’s” when I explained what I was planning on doing.

To be completely honest, I had no idea how to even start being a freelancer. I had worked at an agency where the clients just were and then when I worked on the client side, I just had to do my job. There was no acquirement or learning how to pitch myself to get more business. This was a whole new ball game.

I also had thought freelancing would be a short-term thing. I knew I would be eventually moving to a new city to join my then boyfriend turned husband once he got back from deployment and didn’t see a point in finding a full-time position until I was there.

In other words, this was what I thought would be a temporary situation. So making the jump into freelance was relatively easy. I didn’t enjoy where I was currently working, I had plans to meet Michael in Europe at some point and I was fulfilling a dream of travel that I hadn’t fully gotten the opportunity to do until then. My real jump at this point, was leaving the security of a full-time job to travel, and freelancing just happened to evolve from there.

It’s necessary to call out that there were a million reasons to not make the jump in this situation, however something was calling to me to do it. There is never going to be a perfect time to make big changes in life so when you hear something inside of you urging it to make it happen, listen. Life always has a funny way of working out if you just put yourself out there to let it take its course.

Don’t do it all willy nilly though. Be smart. Have some savings – at least 3 full months of necessary expenses: rent/mortgage, electric, gas, water, groceries, and a little extra in case you got sick or in an accident.

So how did I start freelancing?

About a month and a half prior to leaving for Europe, an old co-worker reached out about doing some social media advertising for his friend. Knowing I wouldn’t have an income pretty soon, I eagerly took on the hours even though the pay was half what I was used to (yes, I’m going to talk money here so get comfortable with it because this shouldn’t be a taboo topic) and the hours were going to be minimal – I didn’t care because it was an extra $300 a month that I got to spend in Europe!

Then, on my second to last day in the office, a running acquaintance reached out about my plans for post-Europe, explaining there was an opportunity for part-time work and wanted to know if I’d be interested. I had the chance to take on this client ASAP – I didn’t. And I’m proud of that choice. Europe was meant to be my trip. My time to explore and eat and drink and enjoy life. I didn’t have a need for immediate cash since I had spent the past year eagerly saving for this so I chose myself.

These first two clients were acquired through making great connections. However, when I had first met them, I didn’t befriend them because I wanted to work with them, our friendships evolved on a personal level and then turned business. It’s important to remember that anyone you cross paths with could potentially aide you in the future so no being a sassy b (unless they truly deserve it).

I think it’s also important to note that freelancing was never my dream – I had always imagined myself being a powerhouse director of marketing at a large agency or Fortune 500 company. It’s an unconventional role to take on that just happened to fall into my lap. While no two stories are the same, I want to share the lessons (and mistakes) I learned along the way to inspire that person who isn’t loving their 9-5 or the adventurer that wants to travel full-time but needs some supplemental income to know that with some time, patience and hard work, freelancing can evolve into something great.


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