Lessons Learned From a Year of Freelancing – Part 5

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.

Lesson #5: Find the positives and make the best out of the negatives.

I’m not even going to lie to you here, freelancing is a tough game. Before you can acquire one new client, you get turned down by 4. Once you have the security of a client, they can fire you at any moment for reasons only God knows. Not to mention you can’t be certain they’ll ACTUALLY pay you at the end of the month (yes, I have had to HUNT down a few checks).

When things get financially tough, it can be somewhat of a mindfuck. As I’ve mentioned, freelancing was never my endgame. I was doing it to fill some time prior to moving and had every intention of finding a full time, in-office position once in Virginia. I applied to no less than 100 places (when Virginia Beach started to fail me, I expanded my reach further and further – we’re talking DC, Raleigh, even NYC just to find a job I could LOVE) and heard back from 2. The first position decided to go a different route. And the second position, I was over-qualified, had more experience than my would-be boss and the pay was lower than low. I had also just lost one HUGE freelance client because they didn’t want a remote worker. So here I am, just married, just moved across the country to a new city, tons of bills and I only had a few freelance clients that couldn’t even cover the rent. So I started applying to every Starbucks in the area. I got offered the job, $9.14 an hour. That was a low blow. But we needed the money so I accepted. This was something that had to be done in order to make things work and sometimes you have to make those sacrifices.

I never ended up working at Starbucks because by the grace of God, a current client nearly doubled the hours they needed. Then I got an email from a previous client about additional work. THEN I saw a job listing on an Instagram post. Somehow, it all fell into place, I just needed to give it some space to allow for that to happen. I’m not saying this will always be your experience but sometimes you have to let things play out a bit before making more changes and I’m here to tell you that IT’S OKAY. You’re allowed to struggle through some low points. You’re allowed to pick up a side job as a cashier at your local grocery store to make ends meet. It’s okay to struggle because without it, you wouldn’t be able to appreciate the success at the end of it all half as much.

On top of all the financial games, working from home is a whole new skill most people don’t already have. Will you actually work when the couch and dog are calling your name to cuddle and binge watch the latest season of literally anything? Do you have a dedicated space to work that isn’t your bed or kitchen table? How organized are you? How do you set your boundaries and not end up posting to Instagram on your wedding day (yeah, I did that 🤷🏼‍♀️)? It takes some serious self control and discipline and that took me a few months to really master.

However, it can be really great at the same time. You have the ability to work from anywhere (as long as you have WiFi) and you get to create your own schedule – HOLLA.

I personally know that I work best from 7am-11am and 4pm-9pm so I do the majority of my projects during that time and leave the middle of the day to get through emails, phone calls, household chores and working out. Experiment with timing to find what works best for you.

Sure it can get boring working from the second bedroom of your tiny apartment, not seeing anyone except your dog for most of the day but that also means that when you’re on a call, you get to play fetch with her or if you have a break, you can take her on a walk. And when your husband gets a random day off, you’re able to join him without asking your boss for a personal day and make the most of your short time together because the Navy puts him through a grueling deployment schedule.

TBH, it took me a while to recognize all of the positives this position brought me and I think that’s something extremely important to remember no matter what situation you find yourself in. Your attitude will directly affect the situation – complain constantly and it’s going to suck, be positive and things will somehow work out.


I think it’s 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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