Why I Decided to Start Freelancing: 9 Indys Share Their “Independence Day” Stories

By Liz Alton, Contributor, on July 4, 2018

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There are a variety of different factors and scenarios that may encourage a traditional worker to start freelancing: This could be anything from a layoff to a bad boss, a unique market opportunity or a desire to travel the world. My own “Independence Day” is still fresh in my mind. After a round of company layoffs, I had the perfect opportunity to go solo. During that first day on my own, I felt a greater sense of freedom, trepidation and motivation than I had ever felt before. Even when I was working 80 hours a week, it was for businesses I truly believed in.

Sure, my early days involved constantly marketing myself and maintaining a tight cash flow. But now I have a steady stream of fantastic clients, including Fortune 500 companies and creative agencies. Today, it still feels like there are endless possibilities. Every hour I’ve spent on client work, marketing and administrative tasks has been worth it.

Curious about how and why other indys made the leap? Well, I decided to ask them. Here’s a closer look at nine fellow freelancers’ journeys to independence.

Making More Money and Enjoying More Freedom

For many freelancers, the siren song of freedom and flexibility draws them to go independent. “During the summer of 2009, I had one of those cliché ‘a-ha’ moments,” explains freelance writer, Angela Tague. “I realized I was making more money hour-for-hour from my weekend freelance work than at the newspaper office, which often included 12-hour days and little room for professional advancement. A few weeks later, my mother-in-law was diagnosed with cancer and my decision was made. I became a full-time freelance journalist and content marketing writer, tapping away at my keyboard from the cancer center lobby. My first few weeks into the freelance life brought me exactly what I had hoped for: flexibility to be with family, a boost in income and the ability to express my personal creativity more often.”

“In August 2018, it will be nine years since I made the leap, and I’m thankful for that decision every single day,” Tague continues. “My weekend side hustle has blossomed into a full-time career — complete with inspiring, entrepreneurial-minded colleagues, personally rewarding partnerships with clients and a malleable schedule to accommodate life’s challenges. For those thinking of making the switch, trust your gut instinct. If you have a financial road map in place, viable work ready to tackle and a whisper of confidence in yourself, go for it!”

Using In-Demand Skills to Choose Great Projects

Recognizing that your skills meet a specific market need can help you build the confidence to make the leap. Personally, my transition into full-time writing happened just as content marketing was exploding. Others have discovered that the tech field is an area where freelancers are in high demand — and that can give professionals the courage to go it alone.

Mark Alton, a healthcare analytics consultant, honed in on a gap in the market and made it his own. “The moment I decided to freelance was after leaving a role with a very difficult boss,” he says. “Healthcare analytics are an in-demand skill, and many companies need strategic support, data visualization and system administrator roles on a less-than-full-time basis.”

Keep an eye on new developments in your industry, and don’t be afraid to take action when the timing seems right. “When you see an opportunity in the market and you have skills to meet the demand, it’s worth taking a look at whether making that leap is right for you,” says Alton. “I’ve been able to be selective and work with great companies that I’m excited to support every day.”

Creating and Selling Your Own Products

When you work a traditional 9-to-5, you’re always busy creating for other people. Freelancing can give you the time and opportunity to make your own visions a reality. For Jody Halsted, a freelance publisher and podcaster, the transition to the freelance lifestyle was simple. “I had been a contract employee since my early 20s, and it was easy to just change my status from ’employee for hire’ to freelancer,” she explains. “As a freelancer, I was able to follow my own passions. Instead of creating around the products of others, I was promoting my own.”

Of course, you’ll have to work hard — especially in the beginning — to get the work and recognition you deserve. “It took a couple years of promoting my expertise before I became well-known enough for people to find me with a quick web search,” says Halsted. “I have a client list that spans the globe, and it’s still a thrill every time I receive an email for services or see that someone has purchased one of my books. Never underestimate your expertise. Someone, somewhere, needs advice that you can offer: Put yourself in the position to provide it.”

Getting Value and Recognition for Your Hard Work

Personally, one of the most rewarding aspects of freelancing — and one of the underlying reasons why I went out on my own — is the ability to capture the value of my own hard work. Since I was already putting in very long hours, I trusted that I had the energy and commitment to make a freelance business a reality.

In speaking with peers, I discovered that many of them felt the same way. “The moment I knew I should go freelance was when I realized I was being seriously undervalued and underpaid by the design agency I worked for,” says Matt Green, a freelance designer. “I was working myself to death, while they got all the praise and recognition. I quit my job and not long after started setting up my own business.”

Of course, the early days of freelancing can be difficult. “My first day, I expected clients to start pouring in from my website without much effort from me,” explains Green. “In reality, every day became an endless slog of contacting local businesses and going to networking events just to make them aware I existed at all. Things are starting to take off for me now. I don’t regret starting as a freelancer at all, and I’ve learned a lot since I started down this path. Is it hard work? Yes. But now I’m working for myself — for my true value — and getting recognition for it.”

Using Winning Strategies to Build a Profitable Business

Seeing the success of your ideas and strategies in the marketplace can also ignite the spark to go indy — which is exactly what happened for Allison Amos, a freelance strategist. “The moment I knew I should freelance was when my strategy outperformed my boss’s,” she explains. “I realized that I had the ability to build effective marketing strategies while having the freedom I was looking for.”

Amos came away from her experience with an important lesson. “Sit down and define what you’re really good at, and then stick to that as you grow your business,” she urges. “A laser focus will help you get involved with the right clients and build a profitable business — without losing your mind.”

Diving in When Opportunity Strikes

In my own experience, freelancing has involved a constant process of learning and reinvention — and the other freelancers I spoke with agreed. “I spent 23 years in the Air Force as a communications and information officer,” explains Stacy M. Clements, a web and cybersecurity consultant. “I started freelancing with web development on the side, while still in the Air Force. One day I was chatting with a store manager who was interested in building a website, and out of the blue he asked, ‘Would you make a website for me? I would pay you to do it.’ Voila — a freelancer was born!”

After retiring from the military, Clements decided to freelance full-time. Throughout the process, she came to the conclusion that continuing to develop your skills and expertise is key to growth. “The reality is that as I developed my technical skills, I realized that I needed to focus more on learning skills like marketing,” explains Clements. “What I really wanted to do was help small businesses succeed, and simply providing a ‘set of hands’ doesn’t always help to meet those goals. I’m now focused more on being a strategic partner with technical skills to help implement the business vision, rather than being just a ‘webmaster.'”

“I’ve realized it’s okay to shift the services I offer as I continue to develop both my technical and my business skills,” explains Clements. “The key is to ‘know your why’ and stay focused on that goal. The great thing about freelancing is that you can focus on your why, your way.”

Bringing Your Skills to a Bigger Playing Field

Having a unique skill set and perspective can create the opportunity to develop an unexpected business. Meaghan Hurn, a freelance consulting chef, realized her uncommon abilities made her services valuable to numerous businesses — not just one. “My moment came to me while I was a luxury chef in Arizona,” she says. “I was working with the GM to create menus and culinary experiences for our guests, and while I was sitting there telling him why what I’d proposed works, I knew that I needed to venture out on my own and start showing other GMs and business owners these ideas and creations. I have a unique ability to tune in well with guests and what they want.”

“At the end of that meeting, I walked out of his office and into my own,” Hurn explains. “I had already built up clients that would hire me to be their private chef while they were in town, so that got me through the rough patches of getting area restaurants to understand why hiring me is actually beneficial for them. It was a hard sell in the beginning. Now I have so many restaurant owners who see the benefit of a consulting chef and hire our services.”

Consider your unique skill sets and how they can be leveraged to improve your clients’ day-to-day operations. “My unique ability to read people has been able to help high-end luxury restaurants gain their competitive edge back,” says Hurn. “The local family restaurants in my area have gone from ‘same old, same old’ to ‘wow!’ The best part for me is [that] I see [the] immediate results [of] my hard work, and I know I’m making a difference in that business owner’s life.”

Using Unique Knowledge to Fill a Market Need

In some cases, you don’t need direct professional experience to launch an exciting business. Sometimes, your idea can stem from a personal experience, or knowledge you’ve accumulated in your daily life. That’s how it happened for Alina Adams, a school consultant in New York City. “Applying for a child to enter kindergarten in NYC (yes, even your local, zoned [school]) is a full-time job — and I did it three times!” she explains. “As a result, other parents started coming to me for advice. So I gave out advice. Then they invited other parents, and it turned into a workshop. Preschools began offering to pay me to give a workshop.”

Those workshops blossomed into something much larger, turning her personal experiences into a full-fledged business. “Parents at those workshops begged me to write a book so they could have all my information in one place,” Adams continues. “In April 2015, I published the book parents had been clamoring for, Getting Into NYC Kindergarten, and now I regularly go to schools, religious organizations and other businesses, giving talks to help people navigate the draconian NYC school application system.”

Throughout your freelance journey, be sure to think about how you can leverage new products and services that build off of your current offerings. “Because so many people wanted to talk about their particular situation after reading the book or attending a workshop, I began offering private consultations, which turned out to be the most lucrative part of the process, and now it’s a full-time business,” says Adams. “I do my consults over the phone or in person during the day, and am still available to do school drop-off, pick-up, attend any parent activities and get my kids to their after-school classes without it causing a disruption; most parents who need my services are free the exact same hours I am! Plus, I really feel like I am helping people, and I am still using my writing and production skills, just in a different way.”

Making a Living Doing What You Love

Sometimes a part-time freelancing experiment turns into a full-time business. “I didn’t start freelancing with the intent of doing it full time — I just wanted to make a little extra money doing something I loved,” says freelance copy editor and proofreader, Barbra Harper. “Then I needed to supplement my income when I had to have surgery and go on medical leave from my job. When my medical leave was exhausted, I could no longer travel to my job every day, so I requested that I be allowed to split my working hours between home and the office. My request was denied. That was [when] I decided to continue doing what I love — copy editing and proofreading — on a full-time [freelance] basis. Truthfully, it was scary. I’d been working mostly one-off jobs through a freelancing platform, so I didn’t have a list of steady clients or a stable income. I learned to specialize, and I started finding writers and agencies in those niches who needed my expertise.”

Harper’s hard work and persistence paid off. “Today, I have anchor clients who keep me supplied with work I love and an income that’s significantly higher than what I made in my 25+ years working in offices,” she says. “And I work part-time hours, so I have time to spend with my family and enjoy life. I only wish I’d started my freelance journey earlier!”

Lessons Learned From Freelancers

Of course, there’s no single “right” way to start the freelance journey. But the experiences of freelancers across different fields can reveal some important tips and strategies on how to go it alone:

  • Look for opportunities to break out on your own, especially when your skills are in-demand.
  • Take the time to differentiate yourself by focusing on your biggest strengths.
  • Don’t be afraid of hard work and experimenting as you go.

The early days of freelancing can require relentless marketing and networking to get your name out there. And you may experience some bumps along your road to success as an independent worker. But, at the end of the day, the payoff of freedom, flexibility and building your own business from the ground up is worth every minute. Stay focused and look to your challenges as learning opportunities. Before you know it, you’ll be well-equipped to take your freelance business to the next level.

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