Tessa Greenleaf on knowing when it’s time to make a change and take a career risk

For this week’s Freedom Creators story, we couldn’t be more excited to feature our own matching specialist, Tessa Greenleaf. Tessa was one of our very first Peeps and members of the CloudPeeps HQ team. She specializes in helping businesses define their goals and find the best freelancer to fulfill them. She even goes a step further to help them structure the job.

She’s able to pull this know-how from her own experience as a freelancer, as well as working closely with Peeps for the past two years. Learn more about Tessa’s journey and what has brought her to CP below!

How and why did you get into freelancing?

I was about two years into my first full-time job after college when I realized that I was bored. My job was purely that: a job. My work each day was completely consistent, and I simply wasn’t being challenged. I kept telling myself that was a normal feeling, and that having a secure job with amazing benefits was what everyone looked for — but it wasn’t enough.

“The real turning point for me was when I realized I could translate my writing skills into social media work.”

I knew I had to do something else with my time, so I started doing editing and copywriting work on the side. At the time, I wasn’t really earning any money but it was nice to get my hands dirty in other types of work. My degree was in English Literature, so I always loved writing and editing. Getting back into that was fun.

The real turning point for me was when I realized I could translate my writing skills into social media work. I found CloudPeeps in early 2014 and landed my first client through them not long after I joined the community. That was when I realized there was a real shift happening in the workforce, and that freelance work was something that could really change lives (including my own).

What’s been your proudest personal moment so far?

Since moving out to San Francisco, I’ve taken advantage of all the outdoor activities this part of the country has to offer. My proudest moment was hiking to the top of Alta Peak in Sequoia National Park.

At 11,207 feet elevation it was the tallest mountain I’ve hiked so far. There was a point where the altitude started to hit me and I didn’t think I would be able to catch my next breath, let along hike another mile straight up. It took everything in me to convince myself to keep going. When I made it to the top it was the greatest feeling of accomplishment I’ve ever felt.

How do you stay motivated and productive when flying solo?

The name of the game is having a routine. After working a typical office 9–5 for years I knew that the way I was most productive was by structuring my day. Even though I work solo most days of the week, I still map out portions of my day for specific tasks. That helps me keep organized and on top of my own schedule.

“The name of the game is having a routine.”

What’s the hardest part about being an indie worker?

Working alone can also become very isolating very quickly. It’s important for me to go into a coworking space at least a couple times a week. I find it motivating to connect with other people and be in an environment where we’re all working at the same time — even if we’re working on other projects.

What advice do you have for others taking the leap?

Don’t make emotional decisions with your career. There were plenty of days when I was ready to walk straight out of my office full stop and not look back — but I didn’t. Even though I wasn’t in a job where I was happy and challenged, I knew that I needed to make the best of that opportunity for as long as possible.

“Don’t make emotional decisions with your career.”

I inserted myself into situations around the office where I could gain new experience working on different projects. That gave me the opportunity to build my resume and skills set and set me up for success in new roles.

Where can we find you?

You can connect with me through my CloudPeeps Storefront!

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