The reality of living a freelance life

When I started out on my freelance journey, I was not sure where it would lead. Would I try my hand at freelancing to make money, while in pursuit of a new full-time job? Would I become a full-time freelancer, but still work a 9-5 schedule? Would I become a go-to resource for an agency or company?

The reality is, I could not have predicted the path ahead.

One of my first Instagram posts as a freelancer
QUITE different than my life today (though I did walk a dog today, too)

My journey as a freelancer

When I quit my full-time job, I was tired. I needed a break. I had been working for over ten years in a fast-paced environment and felt really…burnt out. Tired. Exhausted. Depleted. I had taken a three week break the previous fall to sort out my thoughts and thought that might help. I was actually at a breaking point then. But ultimately, and unfortunately, I spent much of those three weeks totally stressed about my life. What was I doing? How had I gotten to this point?

What I look back now and realize is: I was afraid to make a change. I was fearful that I wouldn’t have enough money if I quit my job. I was terrified that I wouldn’t be able to afford my crazy/expensive San Francisco rent. I didn’t think I could pay my bills while basically unemployed and living in one of the most expensive cities in the world.

(FYI: I was right. Moving to a less expensive city did reduce nearly all of those anxieties, but that is not the point of this post. Can you imagine if I had just lived in a cheaper city? All of this could’ve been totally avoided! What a boring movie that would have been.)

I also had become really comfortable with my life. I STILL love my old coworkers. They are like family to me and have totally shaped who I am as a person. When you work in an agency environment, there really is nothing better than the friendships you form.

I, of course, also really enjoyed a lot of the benefits and perks that came along with working at a big company. I loved that people in other industries knew the clients I worked on and my agency was so well respected. College students used to tell me it was their dream job to work there. It was amazing that I could visit virtually any city in the world and have an office to visit with local colleagues to befriend.

I was also deathly afraid that my job was actually my identity.

Finding myself without a label

When I finally decided to take the leap and quit, it was because I had the full support of my family. I called my parents and they recommended I take a break from work to figure things out. So, I did just that. I immediately found myself without a label. “Where do you work?” people would ask or “what do you do?” and I’d come up blank.

I was becoming one of those people that I used to judge (what a bitch!). The people that quit their “real jobs” in search of meaning. And man….did that feel really good. I took a long vacation and truly enjoyed it. I didn’t have the dread that came with remembering that while I was on the beach, I was also missing that big presentation, or coming back to a major pitch…and thousands of e-mails. I was just…living.

A slight detour on my confidence journey

This elation lasted for quite some time until one day my bubble was burst. I am sure you are thinking: duh. because she went back to reality and had to WORK. Not quite. I actually love working. In this case, it was because I let the judgment of other people impact me.

I immediately returned from vacation and started planning. I was reading books about starting a business (thanks, Dad!), got a few part-time paying jobs (most notably: dog sat for a famous Instagram dog), started doing project work for people in my network (including my old agency!) and got right to work.

There I was, just happily cruising along with my optimistic mindset and loving life. Then I hit a few pretty memorable bumps. It started with a critical comment here or there, a doubt from someone I’d meet, a “why would you ever quit such a secure job?,” a “no one is going to hire you at that salary to be a freelancer” comment. I remember someone telling me that my fantasy lifestyle I was building was not possible. It was deflating (obviously) and I started to doubt whether I had made the wrong choice.

What I should have done

Right away, I should have created a strategy map, complete with talking points and goals. While I had some of this in my brain, I had never been challenged about it. So how would I have known to do this? I had spent a decade of my life jumping for clients and other people. I had never actually focused on my own life’s success outside of my job.

Being challenged and called out in this way was one of the best things that happened to me. I learned how to articulate what I stood for, what I was searching for, what I needed to succeed and how to be proud and confident. I also learned to align myself with people that wanted me to succeed. I am damn good at my job. I can type that today and truly believe it. Hell yes.

So, now what?

I recently attended a retreat with Bold Woman Brands, where I led a few branding workshops. I shared some of these stories with the women I met as we talked about the life of freelancing, and how hard it can be sometimes.

I also have been journaling on a daily basis as part of my Artist’s Way journey. Through both of these experiences, I realized that I feel called to share more about my journey with others. If I can help someone else stay on track to fully realize their path, that will feel like success to me. More than money, more than promotions, more than titles…I care about helping people succeed.

Onward and upward!

Published by Cait Fitzpatrick

Cait is a digital nomad (branding and marketing), and can be contacted at Follow her travels and inspiration on Instagram @freelancefitz.

Leave a comment

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

%d bloggers like this: