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Leaping from Full-Time Employee to Freelancer

Corporate was Good to me

I loved my career as a full-time employee. I was able to develop my skills, gain experience, and build my network with the support of incredible people and companies. I also loved that company benefits like a 401(k) match that allowed me to build wealth from my early twenties. There wasn’t anything wrong with my career path. I successfully found companies that gave me the autonomy to grow and flourish in my career. It was also that autonomy that introduced me to a number of awesome freelancers.

As I learned more about freelancing, I had a great network of people to ask the real questions:

  • Are you happy with your choice to freelance?

  • What are the best parts?

  • What are the worst parts?

I continued to be more interested in the idea of freelancing but I wanted to make sure it wasn’t a “grass-is-always-greener” situation. I worked for an agency that hired many independent contractors/freelancers. I started to have conversations with my manager about what it could look like for me to go freelance. I was itching for a change of pace and a change of scenery.

Simultaneously, my little sister was graduating from college and looking at different cities to start her career. We started talking about moving to Denver (I was living in Chicago at the time). It seemed like the freelancing stars were aligning for me:

  • I had a new adventure to look forward to with the move to Denver

  • I had the support of other freelancers and my manager

  • I had saved up money in my Freedom Fund to take the risk

  • and I had a plan for revenue from day 1.

It was time to take the leap. If you want to read more about my leap, check out my blog, “3 Things That Made My Transition To Freelance Easier” at

I took this leap about five years ago and I’m grateful that I did. It was the right move for me. Since going freelance:

  • I met my husband! He was my first date when I moved to Denver. He has an entrepreneurial spirit and is the best partner in all our ventures. He encourages me to take risks and work on my abundance mindset.

  • We spent over a year traveling the country in our Airstream. I needed to be close to an airport to get to important client meetings and he needed solid wi-fi. Other than that, we could be anywhere. We spent two weeks on the ocean in Malibu, and a summer playing in the Colorado mountains.

  • I improved my relationship with money and increased my business acumen. While working at the agency, I learned about P&L’s and profitability. To take those skills and apply them to my own business was exciting and motivating.

  • I’ve taken dog walks in the middle of the day, choose to do deep thinking work on Sundays (like writing this blog), and have more time to visit with family and friends.

To make sure I share the trolls under the bridge as much I share the sunshine and the rainbows, my three biggest challenges with freelance have been:

  • Predictable income. I had to make changes in my life to allow for variable income. One primary change is, whatever the opposite of lifestyle creep would be. I made choices in my life to reduce my living expenses, stop mindless spending, and get clear on my values.

  • Being the “me” in team. I miss being on a team and leading a team. I have built my business, The Pledgettes, in a way to grow by adding a team and constant collaboration. I miss bouncing ideas off coworkers and being in the trenches with other smart people. I plan to get back to teamwork as The Pledgettes continues to grow.

  • The CEO of Everything. In addition to the communication strategy work I do as a freelancer, I’m also the accounting department, sales department, operations department, and every other department under the sun. As a full-time employee, I was able to spend the majority of my time on my work. As a freelancer, I did the work and then had to do all the administrative work to support that. I know some freelancers bring on a Virtual Assistant to support them in the admin work and allow them to focus more on their creative work.

Finally, just remember that just like every opportunity in your career, it doesn’t need to be permanent. If you take the leap to Freelance and decide it isn’t for you, you can absolutely get back into full-time work. Understand your risk, the potential benefits, and make the best decision for you!

Wishing you success in developing the career and life you want!

Jenn Uhen is the Founder of The Pledgettes, a community for women to talk about more. For more information, check out and to get connected with Jenn, find her on LinkedIn.


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