Kate Kendall
Jun 28, 2016 · 4 min read

We’re in the process of launching a new publication on Medium called Freedom Creators. The purpose of Freedom Creators is to showcase stories from the freelance, remote work, lifestyle design, and creative communities. We’ll not only feature some of the incredible folks from the CloudPeeps community but also many others who have taken this path. To kick it off, I thought I’d put my hat in the ring. :)

Working at Outsite in Santa Cruz, hiking in Banff, Canada, and Airbnb roof deck views on the Amalfi Coast.

How and why did you get into freelancing?

Back in May 2010, I was working in Melbourne as a digital director at a magazine publishing company. I was 25 and had the dream job with the big title but something was missing. Each morning, I’d look up at my bedroom ceiling and think about moving to San Francisco. One day, my friend Eddie (a fellow FC) said to me: “If you never go, you’ll never know.” The next day, I booked flights, quit my job and started an adventure in becoming untethered. I’d built up a financial buffer to see me through the transition but from there, I started freelancing to figure out what I wanted to do.

Entrepreneurship can feel like a choice, but often it’s not — some creatives and founders make the worst employees and can only cope by being their own boss.

What’s been your proudest personal moment so far?

When I first quit my job, I had nothing ahead of me. It took about three months before I started working with my first client — a natural language flight-search startup. The feeling of the unknown — not knowing where you’ll get your next paycheck from is crazily scary. I was lucky that I was unattached at the time and realize that taking risks can be a luxury. Now, six years later, I’m super proud that I’m still going. In that time, I’ve created two companies, numerous offline communities, and now get to focus on empowering other freelancers to take the leap. I regularly get caught up in what’s next, forgetting the journey’s progress to date but it feels pretty good to still be roaming free.

How do you stay motivated and productive when flying solo?

It’s funny as we often brag about escaping the 9-to-5 to work whatever schedule we like. However, I’ve found working a consistent workweek the key to success when WFH or for/by yourself. I used to work all the time: 100-hour weeks and every weekend. Then, I got a bad case of burnout so when I started CloudPeeps, vowed to have healthier working habits.

Communicating with my team via Slack and having morning standup calls really helps get my day started. Going to barre, yoga, indoor soccer and city hikes keeps my physical health up. I’ve also just started using a standing desk (it’s cardboard and only cost $30) and 100% recommend it.

Really, it’s all about routine, planning, and switching off as much as possible to reset.

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

For me, it’s a combination of things. The uncertainty around the future: will I have a home? Where will I live? How will I look after a family? What will I do if I get sick? What about retirement planning? I’m at that life stage when these things start to matter more but I then remember that these things were still there when I worked for someone else: the fear was more about keeping the job though!

The other thing is the relentless grind: as an indie worker, you have to make things happen if you want them to happen. A lot of things depend on your own performance, clarity, stamina and energy. You can’t float off into the distance, or cruise and still collect a paycheck.

What advice would you have for others taking the leap?

Do it from a place of strength, build as much of a financial buffer as possible, find your first client or PT job before taking the plunge, network and surround yourself with supportive freelancers in the same boat, and don’t analyze too much!

Where can we find you?

On my CloudPeeps storefront, my blog, Twitter, Snapchat (kate-kendall), Facebook and IRL at a Freelance Friday coworking meetup near you.

If you’d like to share your Freedom Creator story, follow the above question format then submit it to the publication for review. 👊

Freedom Creators

Freedom Creators is a Medium publication dedicated to stories from the freelance, remote work, lifestyle design, and creative communities. Curated by CloudPeeps.

Kate Kendall

Written by

Tech entrepreneur and advisor passionate about the indie way. Founded Indie Labs, CloudPeeps, The Fetch and more. Helping female founders via Atto.vc. 💪

Freedom Creators

Freedom Creators is a Medium publication dedicated to stories from the freelance, remote work, lifestyle design, and creative communities. Curated by CloudPeeps.

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