Carolyn McHale’s unexpected leap to freelancing freedom and business ownership

Jan 13, 2017 · 5 min read

When the time comes to quit your job, sometimes you just know. Carolyn never planned to take the leap into freelancing, but an unexpected turn of events told her that it was time to make a life change. Shortly after quitting her job, she built her own business and quickly caught the travel bug. Read more about Carolyn’s freelancing journey below!

When I left my job to do my own thing, it was completely unplanned. I had worked for 4.5 years at a firm in Washington, DC doing print and web graphic design and loved my job. I had learned web design, which was still in its nascent stages, and was working on websites for the Country Music Awards, country artist Vince Gill and MCI Worldcom. I worked with a fantastic group of people in a profitable department.

One Friday before a long weekend, the web team went out for lunch together as a group and when we returned we were called into a meeting. All of the openly gay members of our team were let go right then and there, including my boss, the manager of the department. It was such a shocking experience, and left us rudderless. I returned from the long weekend and immediately put in my notice. The next day a co-worker put in her notice and we decided to go into business together. I was already doing freelance work on the side, but I entered into being a business owner and that partnership blind. I didn’t know anything about starting, or running, a business or how I was going to make it work. All I knew is that I couldn’t work at a place that didn’t respect the people that made it great.

Two weeks later I left on a three week rock climbing trip to Colorado, Wyoming, South Dakota and Kentucky. I had never experienced the landscape of the West, and I was hooked. I officially caught the travel bug! I knew that I had made the right decision in leaving my steady job because now I would have the freedom to travel. More importantly, I could also work with the kinds of clients I wanted to, on the kinds of projects that I wanted to.

What’s been your proudest personal moment so far?

Probably walking out of that job. I was the first domino — the rest of the team left within a month. I had coworkers in other departments come up to me and tell me that they were proud of me/us for taking a stand. People told me that I was brave, but I wasn’t. I was terrified of how I was going to pay my rent, but it felt so completely right that I knew it was what I needed to do.

I’ve had other achievements that were significant to me… Seeing for the first time one of my logos as a sign on the side of a building; winning the popular vote in a contest to design the helmet for gold medalist skier Lindsey Vonn to wear in the Vancouver Olympics; starting my business (again) by myself after I moved to Colorado.

But what might have topped the list was when a client sent me a photo of their tattoo, of the logo I had done for them a couple of weeks before. My jaw actually dropped!

How do you stay motivated and productive when flying solo?

I attend Meetup groups such as SheSays and Creative Mornings, which are great because they’re very community-driven as opposed to networking groups. I have formed strategic alliances with other designers, developers and creatives and collaborate with them as much as possible. I find that exchange of ideas and knowledge is vital in fighting stagnation. I also have work days in coffee shops with other creatives, and even folks who are just friends but who provide me good energy. Being around positive, supportive people motivates me. Working with respectful, appreciative clients is also extremely important.

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

For me it’s hardest not knowing when I’ll be paid, and therefore budgeting. I’m not especially interested or talented in finances, so learning how to manage money and cash flow was difficult for me. I’ve used Mint, The Muse and other resources, including an excellent accountant, to help me understand how to constantly improve my processes.

When I first went solo it was very hard for me to self-promote. I would meet people and not even tell them that I was a business owner. It felt hard and self-ingratiating to talk about me, my business, my design work. One day I had the realization that if I took my ego out of it and separated myself from my work that it was much easier. Once I realized that my work wasn’t me — but was a business, a product — I could promote myself in the same way that I would for any other business I believed in. This epiphany helped in general in regards to my work and dealing with clients, criticism and rejection. Now I can be passionate about the work I do, yet not wounded if its criticized.

What advice would you have for others taking the leap?

Starting your business is like having a baby–there never really is a good time for it to happen. All of the stars are not going to align before you are ready — you will not have as much time, money, experience or connections as you’d like when you take the leap. However, once you do take that step you will be surprised by the resources and support you have. Tell others what you’re doing and how they can help you. You’ll be surprised how willing people are to help, but they will be better able to assist if you tell them specifically what you need — don’t make it hard for people to help you!

When I became self-employed someone recommended that I read a book called “The E-Myth Revisited” by Michael Gerber. What resonated with me from that book was that we all become entrepreneurs because we love to do something (e.g. design). While maybe we have skills in other areas (management or entrepreneurship), we don’t have skills in all of them, which can cause stress and failure. This book helped me understand how to deal with the areas of business ownership that I wasn’t as experienced or skilled at in order to have a healthy business.

Lastly, remember that you aren’t the fire department — you don’t have to take every call! Although it’s hard at first, being able to say no to a project that doesn’t feel authentic or good is really empowering.

Where can we find you?

You can connect with me through my CloudPeeps profile!

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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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Freedom Creators

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