Trading grad school for entrepreneurship: David Hathaway’s Freedom Creator Story

Dec 30, 2016 · 4 min read

We’re thrilled to introduce David Hathaway as our latest Freedom Creator. David decided to take the leap into freelancing while he was working on his masters degree in social work. Once he was introduced to the startup world he knew he wanted to make a major life change, quit school, and become an entrepreneur himself. Learn more about his story below!

How and why did you get into freelancing?

I got into freelancing more recently than perhaps some. For the last 6 years I my career focus was on social work and therapy — I was working on my masters degree to become a clinical therapist. Halfway through grad school I met Carrie Jones. She told me about the community, the startup world, and encouraged me to get involved. At the time I was unfamiliar with the world of startups and business — I didn’t even have a Twitter or Instagram profile.

I began toying with the idea of becoming an entrepreneur and thinking about my life in a different way. By July 2015 I decided to make that change. I taught myself everything I needed to know as I went along. I went to meetup groups, pitched every job I could find, and worked my ass off. While working full time and going to grad school I took on 5 new freelance clients. Over the next several months I was able to quit my job, decided to drop out of school, and built an entirely new career for myself.

What’s been your proudest personal moment so far?

My proudest moment has probably the moment I left my full-time job and started working from home. The freedom I felt was like nothing I had ever experienced. For the first time I felt as if I was in complete control of my life — and as though I had discovered some secret to happiness. I just couldn’t believe that every day I could just wake up and go wherever I wanted to work and set my own schedule. It felt like a dream that couldn’t last, yet here I am a year and half later still a freelancer and doing just fine!

How do you stay motivated and productive when flying solo?

Fear. No seriously, I am scared of losing this amazing life I have. Also, I really care about doing well. If I’ve learned one thing, it’s that if you want something bad enough and keep trying harder than everyone else, you can achieve it. I’ve talked to many many people who want to become freelancers, and the people who are still stuck at their 9–5 jobs right now are the ones who show no initiative in moving forward. They are waiting for it to happen for them, rather than making it happen through work and time. I encourage them, show them how to take the steps just like I did, but without a craving for it, nothing happens.

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

Being alone, and not having enough external input. Yes, building relationships is a core part of being able to work independently, but at the same time, its hard to grow and come up with new ideas in a bubble. I read, talk to people as much as possible, stay in communication in any way, and most often — take a step back to breathe and be mindful. Sometimes the best way to learn something new is to do nothing for half an hour with your eyes closed — the solution will come to you.

What advice would you have for others taking the leap?

If you truly want to be a freelancer, then start “working like a freelancer.” That means when other people “clock out” you are still hustling. Yes, you get to set your own schedule, but part of that also means doing tough work to get yourself where you want to be. Sometimes that doesn’t mean starting with your entrepreneurial project, sometimes that means working for 20 other people so you gain credibility.

Get to know your strengths, and play them up. I have two strengths: being clever, and being positive. I am not always right, but I always show up with a giant smile on my face eager to learn. Everyone loves someone who loves to learn and adapt. As a freelancer you will always be expected to learn new skills. What people really look for is who you are as a person and how you can communicate, navigate, and negotiate.

Where can we find you?

You can connect with me through !

If you’d like to share your Freedom Creator story, submit your responses 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.


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CloudPeeps empowers freelancers and businesses to do to their best work. Enjoy freedom to work the way you want, wherever you are. ☕️

Freedom Creators

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