Sometimes you win, sometimes you lose

wins and losses.jpg

Wins and losses from my first month freelancing full-time

It’s been about one month since I said sayonara to my comfortable fulltime job with benefits to diving off the deep end into full-time freelance work.

Why did I leave stability for potential craziness?

You ready for a little story time?

A few years ago, I got my first taste of remote work. Up until then I had been traveling and working abroad teaching English in a tiny micro-country called Andorra on a Fulbright (10 bazillion brownie points if you know where that is).

After my time was up I moved to the East Coast off of Cape Cod to try and figure out what I wanted to do. I lived in my aunt and uncle’s cottage that had no internet and television with dreams of writing and reading by the water. Well, that sort of happened.

I mostly was lonely as all hell and felt lost.

yeah this wasn't me

yeah this wasn't me

Fast forward a year and I found myself a job working for a Spanish startup from my bedroom in Ohio. It was a dream life. I could wake up, make coffee, and not ever have to worry about commuting. As someone who kind of hates driving, this was wonderful.

I spent a year learning the ins and outs of social media marketing, management, and content marketing. After realizing I couldn’t sustain myself much longer on that measly salary I was getting, I found myself a desk job at a breakfast restaurant franchise. For two years I did basically all of their digital marketing.

I was a jack-of-all-trades for that company. I did blog writing, email marketing, social media management, ad strategy and implementation, copywriting, budgeting, minor website development, PR, local store marketing…I think that might be it…

Frankly, I got burnt out.


It was too much. And the whole point of me getting into the digital marketing world was so that I could do it in my own time and from anywhere. So why was I chained to this desk wearing nice clothes? It didn’t make sense.

I started side hustling copywriting and brand strategy to get my feet wet and see if I could really make the leap to full-time freelancer. Turns out I could.

I quit my cushy full-time stable job for freedom, for traveling, and for my mental health. For knowing that if I’m ever crazy busy, it’s a busy I chose, not one that someone chose for me.

I quit for empowerment.

Here are some of my wins and losses in my first month out in the world as a solo entrepreneur.


I’m crazy organized

To be honest, most of the big decisions I’ve made in my life have been by following my gut. Even when I start talking myself out of something I still always go with my initial gut feeling. This transition was a bit different.

I was and am so damn organized. You won’t even believe the research and spreadsheets and goal setting and projections I’ve done. I didn’t want to just throw myself into it willy-nilly because, well, I need to pay my bills and eat food. I even joined the Unreal Collective, an accountability group to help people take their passion projects to full-time projects to keep me on track.  

all the spreadsheets

all the spreadsheets

Before I completely quit I made sure I had at least half of my income already coming in, which yes, meant I was working 60+ hours a week for a time, but it also meant that when the time came I only had to make up 50% of my income and not 100%. That equals way fewer panic attacks.

For the first time ever I really want to do this right. Being my own boss in this field has been a dream of mine ever since I was introduced to it, so I want to give it my absolute best shot.


Development of processes, forms, checklists

To build upon this “whoa you won’t even believe how together I’ve got my shit” point, I’m also feeling really confident in the processes I’ve created. I’ve gotten a ton of inspiration from other copywriters, but I’ve worked really hard to make them my own.

let's do this

I’ve also put together checklists for myself. Because my memory sometimes works like a sieve (see all the tools I use to help me with this problem), having a list that I always have to refer to makes me feel more confident and makes me feel more professional. Even if you are the total expert in your field, make yourself a checklist. Why? Listen to the science behind it in this awesome Hidden Brain episode.

Networking actually works

Networking is completely exhausting for me. There is so much handshaking and so much business card giving and so much smiling all the time. My face always hurts afterward. What’s been the best thing is a realization that it really works for me.

People need writers. They need people who can take their ideas and put them into a readable and emotional hook. There was one networking event I went to in January that brought me 3, count ‘em 3, new clients. And that’s just the direct interactions, not counting the referrals. Totally worth the sweaty palms, but maybe only once a month from now on.



Time for side projects

I’m a person who always has a million dreams that I’m working towards. My dream this past month has been a crazy renovation project to create a home office and weaving studio in our tiny Cape Cod style home. As what always happens with home renovation projects, it’s taking way longer and costing more than expected.

It also means that I don’t have a desk of my own for awhile, but I’m ok with that. Working freelance allows me to build my schedule the way that makes the most sense for me and ensures I still have energy at the end of the day to bust down some walls, do some drywall works, and refinish some floors.


Learning how to be ok with failure

This might be weird that it’s in the “wins” pile, but hear me out. I was always an “A” student, and the first time I got a “B” I had a total freak out. My whole identity was shattered! Who was I? Why did I even matter!?!?!?

The best thing about being a freelancer is that it’s teaching me to fail. I’ve done some stupid things. I’ve printed business cards that had font so small you can barely read them, I’ve sent the wrong email to someone, I’ve forgotten it was January and not December, I’ve not priced myself properly. The list could go on. But hey, I’ve learned from each and every one of those mess ups and I couldn’t be more grateful.

I’m totally writing more on this later, as I think this is the most important lesson of them all.



Too much time drinking coffee- holy goodness

caffiene and weird human overload

caffiene and weird human overload

Part of starting out as a freelancer is making all those connections. Above I said networking actually works for me, which is awesome, but I also have to take into account that more networking means even more coffee dates.

Sometimes those coffee dates turn into a total waste of my time. Either the other person just wants me to buy life insurance or they think it’s a date. Why, men, when you meet a woman at a networking event that is decidedly focused on business, you think us getting coffee to discuss our work equals an actual date? Sigh.

Some of the coffee dates are super productive and I make awesome connections. The reason why this is in the loss column is because damnnnnnn. I cannot keep drinking this much coffee. Or tea. Or hot water, for that matter. I need to get better at determining who is worth my time and who isn’t. It’s hard because my gentle warm heart wants to make everyone happy.


Figuring out how to balance work when you lose someone

In my first month as a freelancer emergency struck. I lost a dear friend of mine. I was deep in grief but still had client work, still had emails to write, still had research to do. All of that was wholly impossible.

The benefit of working for someone else is that you can just send in a notice saying you’ll be out for a few days for an emergency and the team will cover for you. When you work for yourself, who will cover for you?

I had to forgive myself for not working that week. It was ok. My clients totally understood. But dang was that hard to write all those emails. It was pulling the band-aid off my grief each time.

I don’t think freelancers talk about enough so keep your weather eye on the horizon for more on this later.


Health insurance

herbal medicine is better than witchcraft

herbal medicine is better than witchcraft

Gods. Health insurance. What a nightmare. The biggest hang-up for me in quitting my fulltime job was what to do about this major piece. It’s not cheap. Health insurance could be the cost of an entire client, and that totally blows.

I’m on an Affordable Care Act plan (Obamacare), but it’s total calamity insurance. I’m talking $9,000 deductible and I have to pay the full amount each time I go to the doctors. Here I am with my fingers crossed that my appendix doesn’t burst or I stay healthy. I'm doing everything possible to stay healthy, including a fantastic cocktail of exercise, herbal teas and remedies, and a steady sleep schedule.


Dependability of a steady paycheck

This is just part of being a freelance entrepreneur. There is a mad wild high when you send off 5 invoices at once, but a mad wild low when you haven’t sent any in a while because everything is in proposal or finishing stage.

Just comes with the trade. I’ll get used to it.

The final skinny

I love what I do. It’s been a month and I’ve learned so dang much. I wouldn’t trade it for the world. Even if in 3 months, by pure terrible happenstance, this doesn’t work out, at least I gave it my all.