5 Things I Did Before Quitting My Day Job

For almost a year I was a proud weekend CEO, a side hustler, and an after-hours business owner. Whatever you want to call it — it was pretty exhausting (in the most inspiring way)!

Quitting my 9–5 job was always that light at the end of the tunnel, making the late nights and busy Saturdays worth it. As my copywriting business gained steam, the light got closer and closer. Then one day it arrived.

I took the leap in March 2016, and I haven’t looked back since.

I absolutely do not have a dramatic Monster Boss story, in which I got to tell my tyrannical overlord to go jump in a lake. Nope, I worked at a Washington, DC-area nonprofit filled with the most positive, hardworking, and lovely people I could possibly imagine. And I knew I’d miss them like crazy!

But I remember several years ago sitting on the couch and typing the term “passive income” into Google. I made what turned out to be the life-changing decision to start following Pat Flynn and his podcast, Smart Passive Income.

Following Pat opened my eyes to this great big world of online business.

Later, I learned another name that would change the game for me: Marie Forleo! I’m sure you’ve heard of her. I still remember moving the not-small amount of money over from my savings account to my checking account, paying the tuition and signing up for Marie Forleo’s B-School. My palms were sweating. Was I insane? Maybe a little.

Thankfully, I made my investment back during my first week of business.

It’s still pretty surreal to be out on my own. On my first day as a full-time business owner, I couldn’t shake the feeling that an “adult” was going to show up and tell me to go to work! (And keep in mind I was 31 years old and very much an adult! So this really didn’t make any sense).

But you know what? It didn’t take long to get used to it. Creating my own schedule. Prioritizing what I believe is most important. Living the dream!

Today, I wanted to share with you 5 things I did before making The Big Leap to self-employment.

#1. I saved up a little under a year’s worth of living expenses.

The amount you have in savings before you strike out on your own will simply correlate with the amount of risk you want to take on. A year’s worth of living expenses just felt right to me.

I’m also blessed with several incredible retainer clients who more than cover my monthly expenses. The downside that comes with the freedom and exhilaration of being an entrepreneur is that these clients could decide to move on (or who knows, maybe I will). So it just made sense to have a chunk of change I’ve vowed not to touch, but that I know is there as a safety net.

#2. I’ve lowered my living expenses — at first!

Again, I was blessed to have a stable of incredible retainer clients, but I decided to offset my risk even more by moving to a place with lower rent. In the notoriously expensive Washington, DC area, that meant moving in with two roommates for the first couple of years.

Suddenly living with two other people took some getting used to, but I actually loved having the built-in community — especially since I was suddenly without the camaraderie of coworkers.

As it turned out, I liked my new neighborhood much better. There was an amazing pilates/yoga studio steps away from my new house. Taking any class I wanted smack in the middle of the day was an exhilarating novelty at the time... but I digress.

I’ve since moved into my own place, but dramatically lowering my living expenses while I found my full-time business footing alleviated so much of the pressure.

#3. I gave plenty of notice at my day job to ensure a positive break up.

I gave over two months’ notice at my day job. I learned so much from my amazing team at our Washington, DC-area nonprofit over the four years I’ve worked with them. I got choked up putting in my notice.

The work from home survival kit my colleagues gave me at my going away party.

I even finished up my conversation with my supervisor by saying, “I want to make this transition as smooth as possible, and it was really important for me to give you plenty of notice.” The more, the better! I had plenty of time to close out four years’ worth of projects.

Bonus: as I departed to embrace my life as a freelance writer, my coworkers gave me a thoughtful surprise party and an adorable Work-From-Home Survival Kit. I love them so much!

#4. I worked on my elevator pitch.

Here’s something I didn’t think about!

I’d kept it pretty quiet at work that I had this copywriting side hustle. I just didn’t want to seem distracted at work, or give the impression that my heart wasn’t in my full-time job (neither of which were true at all, anyway!).

But when I brought my secret business life out into the open, people who weren’t at all familiar with online business were excitedly asking me what I did in my business…

And I realized I didn’t have a lot of experience explaining what I do, from scratch.

Here’s what I came up with:

“I write the marketing materials for businesses, usually for their websites.”

Then if they wanted to delve deeper and ask me more questions about how I got started, how I find clients, etc., we could keep chatting.

#5. I carried around my business cards at work.

Now here’s where things got fun.

When I revealed I was leaping into my freelance writer life, plenty of my coworkers told me about their own secret-ish side businesses and asked me for my business card. They wanted to keep in touch and maybe hire me to write for them sometime.

So many fascinating conversations ensued! Did you know I had a (now-former) coworker who runs a therapy dog business? Or that another makes games for kids who want to learn about science? Neither did I!

The people I worked with turned out to be even more amazing than I’d ever realized.

Now I’d love to hear from YOU!

Are you a full-time business owner? Are you a side hustler who hopes to make the move to full-time someday? What’s standing in your way, and what plans are you putting in place as you plot your escape? Let me know in the comments!