Lessons Learned From a Year of Freelancing – FAQ

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.

FAQ.

What made you make the switch?

I don’t think it was something I actually thought about – I was unhappy at my job, I wanted to travel and Mike was deployed so I used his deployment as an excuse to quit and “visit” him. I also knew that at some point I’d be moving to be with him so I figured I could fill the time gap between traveling and moving with some freelance work. When I moved to Virginia and realized the position I wanted didn’t exist here, I knew I had to make this work. Added bonus that now it can come anywhere with me even if the Navy does move us to Timbuktu.

What is your favorite part?

Being able to make my own hours, 100%. I can work when I know I concentrate the best and can make room during the day for personal things I love: working out, Lu walks, lunch with friends, etc.

What is your least favorite part?

Not having a place to go every weekday – sometimes it makes me feel a little frumpy (not brushing your teeth until 2pm does that to ya) and dare I say, useless? I’ve learned that even though you can easily stay in bed until 10am, it helps to stay consistent and get up at 6 or 7am, walk across the hall and get straight to work.

How do you get clients?

I’ve been pretty lucky that I acquired all of my clients organically through connections. If that isn’t working for you, check out your favorite small town brands & shops and see what they have got going on. Pitch yourself and see where things go. Also, send me your name and expertise and I’ll be sure to recommend you if I hear of a good fit 🙂

What do you need to get started?

Honestly, I had nothing. I learned it as I went. My first client sent over a contract so I saved that and re-wrote it as things went on. I had no portfolio, just old documents & reports from my time at Resolution & RAM. Hell, I still re-organize my computer & Google Drive folders to this day. So don’t stress about having it all figured out before you start, this whole thing is a learning process.

However, one day, I hope to have a website and business cards to feel a bit more professional.

What do you wish someone had told you before you started?

“When you’re in a dark place, you sometimes tend to think you’ve been buried. Perhaps you’ve been planted. Bloom.”

Aka you’re gonna fucking make it.

What keeps you up at night?

Finances. It’s scary not having a stable job or steady paycheck that comes with benefits. I work my ass off to make sure I can support my family but sometimes clients just don’t want or can’t afford to keep you and will drop you at a moments notice. Unfortunately, this is just something that comes with the territory and why it’s so important to have an emergency fund prior to launching into full time freelancing.

Although, every once in a while it’s late night texts from clients because they have my personal number 🤦🏼‍♀️ However, big plans coming soon to squash that one (aka buying myself a work phone – hollaaaaa)

How has the shift from office life to WFH life been?

WOOF, it’s been rough! I prefer silence when I work so I was excited to get that when I switched but then I realized that in those moments I wanted to talk, the only one here to listen was Lu. And homegirl never answered. This is where I’ve decided that I need to just not be negative and focus on the positive spin.

Why have you not LLC’d your business?

This is a bit of a personal battle – I had visited our accountant late 2018 and he told me it wouldn’t be wise considering the military lifestyle. Each time we cross state lines, I would need to re-register myself and screw going out of the country because that’ll f you real hard. It kind of hurts my soul because I would love to follow in my parents footsteps and have a real business of my own but it’s not in the cards right now. Meanwhile, I’ll just be pretending it is for now.

How do you handle insurance?

Another personal win, #NavyWife. HOWEVER, last year pre-wedding, I was totally insuranceless *cue every medical professional having a heart attack reading this.* I got quoted over $1000 a month to have basic insurance and that was something I couldn’t afford. Catastrophic is another option and was about $350 a month but I clearly like to live life on the edge. However, if I had been in a position where I didn’t have guaranteed insurance being mine in a few months, I would have gone the catastrophic route because I’m a relatively healthy human.

What about savings?

Not having a 401k anymore is weird guys!!! You forget how much can build in just a year without you even realizing it’s missing from your paycheck. The first couple of months (okay, first 9) I wasn’t saving anything. I wasn’t making enough for that to be feasible and I simplified my life A LOT – no more manicures, I wasn’t traveling, we didn’t go out, I cooked every single meal at home – we were on a spend embargo. As I’ve slowly built everything up, I’ve been able to start setting a small percentage off to the side each month and this keeps gradually increasing. So don’t expect to be saving a ton that first year or so but eventually, you’ll get back up there.

Oh goodness, and taxes!?

LOL the bane of my existence. I’m lucky and my parents have an accountant to do all the math for me but that doesn’t mean I’m not stressing about it the rest of the year. You MUST set aside tax money each month. They are no longer automatically docked from your pay! So make it easy on yourself and do it slowly throughout the year rather than a lump sum come tax season. I looked up what taxes were in my area and save that percentage each month.

What kind of documentation do you use?

The things I use the most are: a contract that has evolved over the past year, pacing, content calendar, and reporting templates that have come with me from Resolution, a time tracker on Google Sheets (tracks daily, weekly and monthly hours + total client income & the amount needed for taxes) and an invoice template that I created. Everything else, you can create as you need.

Another thing I absolutely rely on that isn’t necessarily documentation but will help keep you sane are alarms. For the tasks I have to do every day (post to Instagram & Facebook) or week (share blog posts to Facebook & Twitter or schedule Tweets), I have re-occurring alarms. Without them, I’d definitely forget some of those tedious tasks.

I don’t do social media, how can I be a freelancer?

I think freelancing is available to anyone, I just happen to be in social media. Find what your avenue of work is and then start looking for clients or businesses that can benefit from what you’re providing. By definition, “a freelance job is one where a person works for themselves, rather than for a company. While freelancers do take on contract work for companies and organizations, they are ultimately self-employed.” So are you working for yourself already? If so, you’re technically a freelancer, just another name for it 😉


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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