Earlier this week, we uncovered the top ten freelance trends of 2017. If nothing else, let the one thing you take away be that it’s an exciting (and increasingly profitable) time to be a freelancer. More and more people are opting for creative, independent work. They’re collaborating with fellow indie workers to work on projects they’re passionate about. They’re making their own schedules and living lives that are meaningful to them, whatever that looks like for each person.

We’re so inspired by the members of the CloudPeeps community, as they’re truly defining and creating their own freedom. We wanted to learn more about their journies – to dive deep into their stories. So we launched a new Medium publication called Freedom Creators, celebrating independent work with stories from the freelance, remote work, lifestyle design, and creative communities.


Having interviewed several creatives, we’ve learned about what inspired them to pursue independent work and how they stay motivated. We’ve learned what challenges they’ve faced and advice they’d like to bestow on aspiring freedom creators. Here are just a few of our favorite insights.

Breaking into freelancing

Everyone’s journey into full-time freelancing is different. We love hearing the unique stories behind why each freedom creator has chosen independent work.

“The switch happens slowly and also very fast. There was a time when I felt like I would never be getting enough projects to support myself, and all the sudden I had multiple deadlines a week! The idea of doing the same exact thing in the same exact place everyday gave me unspeakable anxiety. I wanted to find more flexibility for myself while doing something I truly enjoyed.” – Sunny Eckerle, Freelance Illustrator

“I started taking on more side projects for fun and came to realize that it was this work that left me feeling alive.” — Krista Gray, Branding and Community Specialist

Staying motivated

Maintaining motivation is a challenge for just about anyone in any job or profession. Some of the freedom creators we spoke to found that working with other people helps motivate them.

“I try to set up side projects that allow me to build small teams and work with the people I admire. I usually run Kickstarter projects that enable me to hire great people and pay them for their work.” – Monika Kanokova, author of This Year Will Be Different — A Guide for Freelancers and My Creative (Side) Business

Monika Kanokova

Others are the exact opposite.

“It’s easier for me to be motivated when flying solo because I always feel like I’m able to do good work and keep the client happy. I’m always at my best when I have the freedom to design my own workday and work from wherever I choose.” – Dani Bradford, Adventure Traveler

And others who find listening to their own bodies to be most effective.

“I try to keep a routine for myself without being so rigid as to kill the best part about working for yourself — flexibility! It’s important to understand how you work best.” – Sunny Eckerle

The challenges of indie work

Getting started in any career can be challenging, especially when building your own business. The freedom creators we interviewed have been honest and forthcoming with the challenges they face and how they’re overcoming them.

“The biggest challenge is self-doubt, hands down. It can be very hard to stay motivated and confident without team energy or the occasional kudos.” – Krista Gray

“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.” – Tessa Greenleaf, Matching Specialist for CloudPeeps

“Since leaving the corporate world, pushing through any self-doubt and standing by my prices and services, even when I really need more clients, has been a regular challenge but one that I feel I’m getting stronger with over time.” – Kat Loughrey, Freelance Social Media Strategist

Advice from experienced freedom creators

Freedom creators are passionate about what they do. They’ve found happiness in designing the lifestyles that work for them and want to see others do the same. With that, here are just some of the nuggests of advice we’ve gathered from the creatives interviewed.

“Don’t just work “in” your business, but also “on” your business. Initiate side projects and use these to show to people what you really want to be hired for.” – Monika Kanokova

“Work hard, always be open to opportunities that come your way, and think critically every day about the work you want to be doing, and the kind of life you want.” – Dani Bradford

“I’ll also share one of my favorite sayings which is ‘Start before you’re ready.’ It’s important to have your ducks in a row and to make sure you can realistically support yourself with freelance, but I also believe if you wait until you feel totally prepared, you’ll never actually go for it. It can be very scary and uncertain, but if you push yourself and work hard you’ll be surprised at what you can accomplish and what comes your way.” – Sunny Eckerle

“Start small. Moonlight. Don’t jump with no plan. Don’t pressure your creativity to support you. Learn the skills, put in the work, track your metrics, and be humble. Nobody likes an asshat.” – Dusti Arab, CEO of ThinkCharm.com

Dusti Arab

“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.” – Tessa Greenleaf

“Plan your vendor expenses, draw up a business plan, and project how many client accounts you need for your ideal monthly revenue as a freelancer.” – Noelle Bell, CEO of Buzzworthy Social Media

“Stay as healthy (physically and mentally) as possible, as there is no one else to carry the slack, and build strong routines that benefit you and your goals on a long-term basis.” – Kat Loughrey

Do you have a freedom story to tell?

We’d love to share it! To be featured on Freedom Creators, fill out this form and we’ll let you know when your story will be published!

Are you more into short-form content? We’re always up for featuring Peeps on our social media channels. Comment below to get more involved in the community.