I’ve been happily unemployable for eight years now. It hasn’t always been this way for me. I’ve been stuck and got myself unstuck many times over to transform myself from compliant employee into accidental entrepreneur.
There are loads of experiences, stories and emotions I can share from my career over the past 18 years. Probably a more effective (and shorter) way to describe my career is by highlighting its 3 phases: 1) Employee 2) Deeply Stuck 3) Happily Unemployable
Employee: The first 5 years of my career
When I started my career I did what I thought I was “suppose to” do. I became an employee. After graduating from Providence College in 1996, I landed a job at Edelman Public Relations in New York City.
Most of us have build our careers based on that mindset. You aren’t working for your own ideals, but rather for someone else’s ideals. We work to be accepted by family, friends and society. We are afraid of failure. We’re even more afraid of failing in front of our peers. It scares us so much, we’d rather do what we’re “suppose to do” in life, rather than strike out on our own.
I was taught to be an “employee” and not an “entrepreneur”. My saving grace was my endless desire for new experiences.
During the launch phase of my media career, I swung from opportunity to opportunity. I felt in control and got any job I wanted. The first three years of my career were driven by acquiring new skills and responsibilities while working at Edelman Public Relations and CBS News Sunday Morning. Then I decided I wanted to be paid more, so I headed to CNBC and doubled my salary.
I lasted five months at CNBC, my shortest stint ever. The job delivered on my goals for more money and the title I coveted, but I lacked passion for the work. I barely knew a stock from a bond at that point. As an associate producer I booked three guests a day. Money is important, but I discovered passion for my work was a key ingredient to a sustainable source of income.
As realization set in that I needed to leave CNBC, I heard my old boss at CBS News took at job at ThirdAge.com, a dot-com partly owned by CBS at the time. Everyone was jumping into the dot-com frenzy of the late 90s, so I followed suit.
It was my first experience at a startup.The work was exciting, my co-workers were great, I traveled to San Francisco once a month and the money was decent. After just 11 months I was laid off as part of the fallout from the dot-com bust of 2000. I had no idea at the time it would be my last work experience as an employee.
Deeply Stuck: Reluctantly becoming an entrepreneur
Election Day 2000 was the day I was laid off. My career was stopped in its tracks. It would become one of the most pivotal events in my life. Everything I thought about work, money and how to live was about to be challenged. Thankfully, I went through this experience early in my career.
My old friend and colleague Jim Sheridan told me I “got knocked off my hamster wheel.” Man did I ever. As I continued to seek employment over the next five years, I would reluctantly transform myself into an entrepreneur. Here were the incremental steps I took:
After collecting unemployment for three months, I finally got a freelance job in Greenwich, CT producing an interactive CD-ROM for a pharmaceutical company.
I never freelanced before. Prior to getting laid off I would have never considered it, but I was so desperate to work I leapt at the chance. Those three months without work gave my idle mind lots of time to think. I believe that’s when the seeds of entrepreneurship were sown into my thoughts.
Freelancing was my first entrepreneurial experience and I didn’t like it one bit. It paid well, I was good at it and I was left alone, but I couldn’t handle the pressure. Honesty, I was afraid of working an entirely different way. Afterall, I was taught to be an employee my entire life and there is a certain comfort in that way of thinking. Freelancing felt too unreliable as a method of generating income.
2. Business School
Freelancing might have turned me off from the idea of working for myself, but it sparked my interest in the business side of media. Back then, the only path I saw for acquiring business knowledge and skills was by getting my MBA. After some temping gigs and a two-month stint freelancing at CBS News after the attacks of September 11th, I was enrolled in the Business School at Fordham University to study media management in January of 2002.
3. Managing My First Web Business
The business theory being taught to me in the classroom wasn’t enough to satisfy the entrepreneurial instincts bubbling up from deep inside me, so I took on an internship managing a website called TVSpy.com. At the time, it was owned by the career website Vault.com and focused on the television news industry, something I knew a lot about.
In under a year I turned myself from intern into the General Manager of TVSpy.com. It taught me the most crucial skill in business: how to sell. (Ironically, it’s something you’ll never learn in business school.)
In three years I doubled the website’s revenue from $150,000 to $300,000. I never sold a thing before in my life! Previously, I stuck up my nose at sales. It conjured up images of a car salesman or an insurance broker cranking out cold calls all day long trying to get people to buy something they probably didn’t need. No thanks.
Fortunately TVSpy would change my perspective on sales as I came to understand that the best sales people find problems and then sell the solutions to solve them. Now that was my kind of sales!
4. Digital Ad Sales Expert & Trainer
While at TVSpy I had the opportunity to start my own weekly newsletter about future business opportunities in local television. I interviewed industry experts and proposed my own new sales ideas. Writing was fun and I enjoyed engaging the community I served. Little did I know, that same newsletter was actually laying the groundwork for the next phase of my career as a sales trainer.
In the fall of 2003 I was contacted by the Freedom Broadcast company to speak at their annual executive conference in West Palm Beach about some of the ideas I had been writing about. They owned a handful of TV stations throughout the U.S. I was so flattered, I did it for free. It would be my last unpaid speaking gig.
As I finished business school I was still strongly considering employment opportunities until Graeme Newell, another contributor from TVSpy, asked if I wanted to team up with him. He didn’t offer me a job per say, but rather a revenue sharing opportunity. He would sell my digital sales trainings to his clients for a commission and I was free to find my own clients. I waded a little deeper into the entrepreneurial waters.
Traveling around the country speaking on something I was passionate about was a blast, but after three years it took its toll. It was time to find a way to make money from my expertise without having to leave my house. After five years of inching closer and closer toward entrepreneurship I completed my transformation. I finally had the confidence to strike out on my own.
Happily Unemployable: Building my first business
Just before the economic meltdown in the fall of 2008, I started my first business, LocalBroadcastSales.com (LBS). It was profitable on day one and I never relied on debt to build it. Most people weren’t starting businesses at the beginning of the Great Recession, but somehow that wasn’t a distraction for me, but rather an opportunity.
In five years I built an archive of 600+ video training modules with over 30 trainers. It became a lower cost sales training alternative for broadcasters. Rather than fly someone like me in for a day of training, they could access our archive of sales trainings every day of the year for almost the same cost or less.
At its height LBS generated $500,000 in annual sales. I actually generated less revenue from many of my clients than if they hired me for a day of in-person training because of the compensation structure I had with my trainers and the expense of producing video. However, my hourly rate increased compared with selling in-person trainings because I eliminated my travel time and was able to sell the same trainings over and over again.
Building my first business was exciting and I learned a ton. It was also around this time that I met Chris Wilson. He was one of the first to recognize my desire for something more from my work.
I was thankful for the amazing opportunity LBS provided me, but by year three I knew it wasn’t going to be a sustainable source of income over the long term. My passion for broadcasting and digital advertising sales waned. I no longer wanted to serve the traditional employee mindset, but rather those with an entrepreneurial one.
I knew I didn’t just need an exit strategy from LBS, but for my entire broadcast career path. It took me three years, but I was fortunate enough to sell LBS to one of my trainers in 2012. It was time to start helping others get unstuck.
Takeaways From My Story
After selling LBS it took me another year and lots of conversations with my UnStuckable business partner Chris Wilson to completely pull myself out of broadcasting. No matter how many times I’ve been stuck and got myself stuck, more often than not, I need help getting unstuck. Thank you Chris!
As I begin my new journey to build the UnStuckable community with Chris, here’s what I’ve learned about building a meaningful and sustainable source of income to build the lifestyle that’s right for me:
1) Build on your past experiences, don’t throw them away.
When people are looking for change in their career or life it’s often very tempting to throw away your past. It seems easier to build a new identity when you don’t have to compete with the old one. The trick is learning how to apply them to a new vision and confidently explain their enormous value. I’m still using the content production skills I learned at CBS News and will use my training skills for UnStuckable.
2) There are other ingredients besides money and meaning for a sustainable career.
Once I built a successful company, I thought it would be the pinnacle of my career, but I became unhappy. As they say, be careful what you wish for! I realized that not only did I enjoy the freedom of being an entrepreneur, but I needed to have passion for the work. I also need to be passionate about the people I’m going to be working with every day to have a sustainable source of income.
3) Never stop learning and challenging yourself.
The second I feel like I’m starting to coast in my career, I know it’s time to reassess and learn something new. Our economy is changing too quickly now for me to rest on the laurels of my college degree from 20 years ago and my MBA from 10 years ago. There are so many new ways to teach yourself and acquire new skills thanks to the miracle of the web.
4) Know your story.
Your resumé is not the story of your career. The last time I updated my resumé was 10 years ago. I no longer have one and will never again. The titles on your resumé don’t define who you are. Create your own label. Define yourself. Understanding the story of your career allows you to be honest about your failures and what you can learn from them to build an UnStuckable life.
5) Be aware of when you are getting stuck.
Half the battle for building an UnStuckable life is being aware of when you are stuck. Sometimes they are small moments and sometimes they are life changing events. My warning sign for when I’m getting stuck is when I have recurring negative thoughts about something in particular or when I’m feeling a little too comfortable.
Chris and I are on a mission to help people recognize when they are stuck. We want to work with you to identify the most effective habits for getting unstuck and building an UnStuckable life.