The Freedom Economy gives entrepreneurs, freelancers, and other contract workers the ability to take control of their lives and enjoy the freedoms that come with flexibility. Before I thought of working for myself this is what my boss told me. “I’m sorry, Josh. It’s a mistake. If you walk away from the workforce, you’ll lose your marketability and you’ll be years behind where you could have been if you hadn’t.”

I can still see the look of skepticism and pity on my boss’s face when she delivered that warning. At the time, I had kids — twin girls, no less — on the way. My wife was transitioning to a new company and career. And we were selling our house in Boston and moving to Michigan. For my boss, the decision to leave a somewhat safe, reliable job with a company like CBS to join the Freedom Economy made no sense.

At the end of our meeting, she shrugged her shoulders, shook her head, gave me a half-hearted pat on the back, and walked away with a look that said: Go ahead. Kill your career. But don’t come running back to me when you’re desperate for a real job again.

The Very Real Benefits of Self-Employment and the Freedom Economy

Thankfully, I never had to. In fact, as it turned out, ditching that desk job to join the Freedom Economy was the best professional decision I’ve made.

Within a year, I had a few clients — including a Boston-based venture capital firm that pioneered content marketing in its industry — feeding me a steady flow of work. By 2013, I had hustled my way into gigs with HP, Rackspace, and a handful of other big, high-paying clients. And by the end of 2014, I had grown my one-man business to more than $120,000 in annual income.

More importantly, the flexibility of working for myself in today’s Freedom Economy had allowed me to spend those five years watching my kids grow up. I heard their first words. Saw their first steps. Took them to dance class. Shuttled them to the doctor. I was able to fit in work when I had gaps in family time, rather than the other way around.

Beyond that flexibility, the Freedom Economy offers other perks:

  1. Creative freedom: Instead of being told what to work on, I was able to decide which projects best aligned with my skills, expertise, and style. If a client’s project didn’t jive with what I wanted to do, I could politely decline and not worry about getting fired. More importantly, as my credibility grew with clients, I was often given the creative freedom to help shape their content strategy.
  2. A virtually limitless financial ceiling: When I was gainfully employed as a full-time journalist and copywriter, I was lucky to have a job — let alone get a 3% annual raise. As a freelance writer, I controlled my financial destiny. If I wanted to raise my rates (and I was confident it wouldn’t send my client base running for the hills), I could do that. If I wanted to hire a few other freelancers to take on work that I didn’t want (or have time) to do, I could do that.

As a result, I more than doubled my income in two years. And by 2015, I made as much in one year as I did in five years as a full-time copywriter at CBS.

  1. Enormous opportunities for personal and professional growth: One of the best parts about freelancing is the speed at which you’re exposed to new things — people, industries, ideas, etc. This creates an incredible opportunity to develop your knowledge and skills, and grow your network. When you work for a business, your social and professional circles are largely limited to that company.

Working for myself, I had the opportunity to travel to Boston, Austin, and San Francisco for work. I had a customer in London. And I once had a conference call with a client while he drank a beer on a beach in Brazil. All of those experiences and people helped me grow and develop at a rate that just isn’t possible in most corporate settings.

The Not-So-Pleasant Side of the Freedom Economy

With all of that said, freelancing isn’t always roses, butterflies, and sunshine. In fact, there were plenty of times when I wondered whether my old boss at CBS was right.

More specifically, there were three big downsides to freelancing:

  1. Flexibility comes with a big caveat: When I was getting started, turning down projects wasn’t an option. To build up a book of business, I needed to accept whatever gigs came my way (and under whatever terms the client set). There was no negotiating and, in many cases, I was underpaid for the amount of work projects required.

And then there were the Friday emails. Oh, the Friday emails.

Here’s the thing about freelancing: Ultimately, you’re a service provider, not an employee. So, if a client has a problem that needs to be solved or a project that needs to be completed, they expect it to be done on their terms. If it’s Friday at 5 p.m. and they need a project done by 10 a.m. Monday, you don’t negotiate. You either say “yes” or you walk away from the opportunity. This is particularly true when you’re just getting started and developing new client relationships.

  1. The IRS and the admin work: Oddly enough, I started college as a math major. But that dream ended the day I started Calculus 3. Needless to say, I’m no math whiz and I certainly didn’t start a freelance writing business to be an accountant. The reality, however, is that accounting — invoicing, expense reporting, tax filings, etc. — is a very big part of running a successful freelance business. I can’t tell you how many times I had to chase down a check that a client forgot to send, or worry about whether I was accurately tracking expenses.

The worst was the day I received a letter from the IRS in 2014 telling me I’d botched my 2013 tax return and owed thousands in back taxes, penalties, and interest. From that point on, I realized that while working for myself I would need to commit to spending a few hours each week on accounting and admin to ensure all my ducks were in a row.

  1. The downside to no commitment: As it turns out, showing up to work in your pajamas every day does get old.

Don’t get me wrong, I loved not having to shave every day. And I certainly didn’t miss my old 90-minute commute into Boston. But you do start to miss the water cooler conversations. You miss being part of a team. You miss having the opportunity to create a longer-term impact on one business, instead of being a short-term solution for a lot of very different businesses.

Truth is, this is one of the biggest reasons I ultimately decided to walk away from freelancing to take a job with a company full-time.

As a freelancer, you never truly feel like an integral part of anyone’s team — even when your clients go out of their way to integrate you into their organization. While I was fortunate to work with a handful of clients that treated me like part of their extended family, you still feel isolated. And, in the back of your mind, you always wonder if you’ll be the first one cut when the good times aren’t so good anymore.

The Ultimate Question: Would I Consider Working for Myself All Over Again?

So, considering the pros and cons, would I take the same leap into the Freedom Economy again? This one’s easy: Absolutely.

Truth is, if I’d stayed with CBS, I wouldn’t have hooked up with the Boston-based venture capital firm that allowed me to meet people from Uber and ProductHunt before both companies blew up. I wouldn’t know anything about B2B technology. And I certainly wouldn’t have my job now — a gig with a great, growing technology company that’s given me total freedom to help shape its future.

Just as important, I wouldn’t have been able to enjoy my kids’ most formative years. I might have missed their first words and steps. I wouldn’t have been able to coach their soccer team. And I don’t think I would have developed the same strong bond that I enjoy with them now.

So, would I do it all over again? You’re damn right I would. And, given the benefit of hindsight, I’m willing to bet my old boss at CBS wouldn’t be so opposed to the idea.

Discover whether diving into the Freedom Economy is right for you. Learn more about the gig economy at Spera.

Josh Zywien is a copywriter with Ambassador, a Detroit-based startup that makes referral marketing automation easy for brands like HP, SAP, and Zenefits. Prior to joining Ambassador, Josh was a freelance writer for five years and worked with brands like Magento, Experian, Rackspace, HP, MarketingProfs, and OpenView Venture Partners. You can find him on Twitter @JoshZywien.


Author Cristiano

More posts by Cristiano

Leave a Reply