Lessons From My Career Story
How many times in the course of a week are you asked the question, “So what do you do?”
I used to dread that question because I wasn’t exactly sure how to answer it while still being true to myself yet not sounding like a potential burden on society.
Now I love answering that question!
I have come to realize just how important it is to tell your story, especially when you are feeling uncertain about your future (and as you’re about to read I got really stuck a couple of times in my career).
In fact, I believe it’s one of the most important Life Skills That Matter.
Telling your true story is often one of the first actions I recommend people take when they want to work for themselves or design their lifestyle around more satisfying work.
What do you really want to do with your life going forward and how can your past help get you there?
Even telling yourself the story of your career up to this point in time can reveal patterns from your past experiences. It can help you make new connections, so you can see new possible paths for your work and life.
As you keep reading, I’ll share have many lessons (feel free to scroll toward the bottom) from my own story to help you learn how to better tell your story. (Sorry, this isn’t the short version, it’s the long one:)
A disclaimer: This is just my story. It’s not an endorsement of decisions I think you should make for your own career and life. After all, you are you and have your own unique story to tell. Use my story as an example of how to recognize patterns in your own career story.
So What Do I Do?
I’m a solopreneur business designer. I’ve been researching alternative ways of working for 20+ years now.
I am passionate about helping people work on their terms and in alignment with what makes them uniquely productive.
I want to relieve people of their anxieties about work. I suffered from chronic anxiety about work for the first 10 years of my career and got much better at managing it with the help of the Life Skills That Matter.
I believe everyone’s story deserves to be told, but everyone also owes it to themselves to discover their own authentic story.
I want to help you tell your story by making your work, work for you.
No matter how many different jobs or work experiences you’ve had, there is always one thread in your career that ties all of them together, no matter how disparate they may seem.
Whether you realize it or not there is a common motivation for why you choose the work you do.
For me, that has always been listening to stories about how other people lived their lives.
As a kid, I would read biographies of historical figures like Helen Keller, Albert Einstein, Eleanor Roosevelt and President Lincoln. My mother can tell you stories about how I could talk to just about anyone (still to the amazement of my father). People endlessly fascinate me. They are like fine wines to be appreciated and curated for their unique qualities.
My core motivation for work and the thread of my career has been to witness and share the stories of other people. I love helping people discover their own potential. I truly believe we all have a great untold story buried deep within us that needs to be shared.
My superpower is creating clarity from chaos. I help people like you see the patterns in your story. I show you the connections between your past experiences, so your unique purpose and source of motivation for work can be revealed to you. What’s your superpower?
Let’s see how the thread of my career led me to where I am today!
The Thread of My Career
I’ve been happily unemployable for 15+ years now. But it hasn’t always been that way. I’ve been stuck and got myself unstuck many times to transform myself from a compliant employee into an accidental (formerly reluctant) entrepreneur.
My journey to embrace the thread of my career has been a long and challenging one. In the end, it’s been totally worth it. I now live and work on my terms.
There are loads of experiences, stories and emotions I can share from my career over the past 20 years. Probably a more effective (and slightly shorter) way to describe my career is by highlighting its 5 phases:
1) Employee
2) Deeply Stuck
3) Reluctant Entrepreneur
4) Stuck (Again)
5) Purpose-Driven (Here and Now)
1) Employee: The First 5 Years of My Career
When I started my career I did what I thought I was “supposed to do.” I became an employee.
From the time I was 12, I thought I was going to be a lawyer. I attended a public high school in an affluent town in Connecticut (although my parents were not rich by any means) where the paths in life most discussed were the law, medicine or getting a white-collar job. At this point in my life and for years to come, I was listening to other people’s ideas about what I ought to do for work.
But then David Letterman changed the course of my life. On a whim, I applied for an internship on his show just before my senior year in college. I landed an interview, but didn’t get the internship. However, the experience did change the course of my life. (Has that ever happened to you?)
Applying for the internship gave me a glimpse of an unfamiliar world that changed my outlook on my career entirely. I questioned my career choice. Working around fascinating people in media and listening to their stories spoke to me in a way the law never did. (I’m so glad I didn’t ignore my inner voice that time!) Thanks, Dave.
After graduating from Providence College in 1996, I landed a job at Edelman Public Relations in New York City.
Most of us build our careers based on that mindset. Get a job, any job. You have bills to pay once you’ve graduated.
However, you aren’t necessarily working for your own ideals, but rather for someone else’s. We work to be accepted by family, friends and society. We are afraid of failure, especially of failing before our peers. It scares us so much, we’d rather do what we’re “supposed to do” in life 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 and inspirational stories about people who blazed their own paths.
During the launch phase of my media career, I swung from opportunity to opportunity. I deluded myself into thinking I had complete control over my career because I got any job I wanted during those first 5 years.
The first 3 years of my career were driven by acquiring new skills and responsibilities while working at Edelman Public Relations and CBS News Sunday Morning.
I learned a ton about journalism from some of the best storytellers in the world at CBS News. Even though I was the “low man on the totem pole,” I created lots of opportunities to get myself out into the field to help produce stories. The highlight of my time working at CBS was helping to cover the 1998 Winter Olympic Games onsite in Nagano, Japan. It was a blast!
After two years at CBS, I realized I wasn’t learning as much as before and I wanted to be paid more, so I headed to CNBC for a promotion and doubled my salary.
I lasted 5 months at CNBC. It was my shortest working stint ever. The job delivered on my goals for more money and secured the title I coveted, but I lacked passion for the subject matter. I barely knew a stock from a bond at that point. As an associate producer I booked 3 guests a day, so at least I got to share some cool stories.
Money is important, but I discovered a passion for my work was the key ingredient for a sustainable source of income over the long term.
As the realization set in that I needed to leave CNBC, I heard my old boss at CBS News took a 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. Then 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 one of my last work experiences as an employee.
2) Deeply Stuck for 5 Years
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.
We all assume our career trajectory is a linear progression rising from left to right until we retire (whatever that means). Reality has shown me that it looks more like a stock market chart with lots of ups and downs. I was not prepared for that reality. No one told me I would experience “stuck” moments in my career.
My old friend and colleague James Sheridan told me I “got knocked off my hamster wheel.” Man did I ever. As I continued to seek employment over the next 5 years, I would reluctantly transform myself into an entrepreneur.
I may have felt stuck, but I took continuous, productive action to keep growing. Looking back it was my natural path, but I was unable to see it at the time. Here were the incremental steps I took to become self-employed:
a) Freelancer
After collecting unemployment for 3 months, I finally got a freelance job in Greenwich, CT, producing an interactive CD-ROM for a pharmaceutical company.
I had never freelanced before. Prior to getting laid off, I would have never considered it, but I was so desperate for work I leaped at the chance. Those 3 months without work gave my idle mind lots of time to think. I believe that’s when the seeds of entrepreneurship were sown in 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 in an entirely different way. After all, 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.
b) 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 2-month stint freelancing at CBS News after the attacks of September 11th, I enrolled in the Business School at Fordham University to study media management in January of 2002.
c) Managing My First Web Business
The business theory taught to me in the classroom wasn’t enough to satisfy the entrepreneurial instincts bubbling up from deep inside me.
I took on an internship managing a website called TVSpy.com to complement my business studies. 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 2 years I doubled the website’s revenue from $150,000 to $300,000. I had 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. I came to understand that the best salespeople find problems to solve and then sell solutions to solve them. Now that was my kind of sale!
d) Digital Ad Sales Expert & Trainer
While at TVSpy I had the opportunity to start my own weekly email newsletter about future business opportunities in local television.
I got to tell stories again. I interviewed industry experts and proposed my own new sales ideas. Writing was fun and I enjoyed engaging with 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 to share some of my ideas about the future of TV news.
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 as a digital sales trainer at his firm.
He didn’t offer me a job per se, 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 and getting paid to do it was a blast, but after 3 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 5 years of inching closer and closer toward entrepreneurship, I completed my transformation. I finally had the confidence to strike out on my own.
3) Reluctant Entrepreneur
As you might have learned by now, I did not set out to be an entrepreneur. It was never a dream I had or an option I even considered until changing economic realities kept nudging me down this path.
I believe there will be more and more “reluctant entrepreneurs” like me in the coming years due to unforeseen changes in our economy. I may have pursued entrepreneurship reluctantly, but I have absolutely no regrets about my decision. I am now happily and proudly unemployable.
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. On the contrary, it was an opportunity.
In 5 years I built an archive of 600+ video training modules with over 30 trainers and managed 4 employees. These modules 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 $600,000 in annual sales. My hourly rate also 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.
I eventually ran the business so efficiently that I put in an average of 30 hours a week and was able to run my business from Seville, Spain, for 4 months.
Building my first business was exciting, and I learned a ton. I was thankful for the amazing opportunity LBS provided me, but by year 3 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 had waned.
I realized the core of my training was around personal transformation and strategies for managing change. I no longer wanted to serve the traditional employee mindset, but rather those with a more entrepreneurial one.
I knew I didn’t just need an exit strategy from LBS, but for my entire broadcast career path. I was fortunate enough to sell LBS to one of my trainers in 2012 (it would still take me another 3 years to call it quits on broadcasting altogether).
It was time to start helping others get unstuck and help them design their lifestyles around unconventional possibilities.
4) Stuck (Again)
Feeling stuck for 5 years is tough. Once I got myself unstuck, I thought I knew everything I needed to avoid becoming stuck again. Oops! I was totally wrong.
As I get older, I realize that life is never going to stop challenging you. Sometimes you might not feel up to the challenge, but if you face it, you’ll learn a ton about yourself.
Not only would I feel stuck, but I experienced depression for the first time in my life. If you’ve never experienced before, it’s a whole other level of feeling deeply stuck. Here’s how I think I fell into it…and how I got myself out of it:
a) Comfort Zone
Once I sold LBS at the end of 2012, I didn’t have a clear plan about what I would do next. I was drawn to helping people transform their careers, but I didn’t know what that would “look like” yet.
For the next year, I did what a lot of people who aren’t sure about their next step do: I retreated into my comfort zone. I continued doing in-person sales trainings for broadcasters and even took on more clients than I had in the previous 5 years running LBS.
b) UnStuckable
Around this time I was having on-again, off-again conversations with my friend Chris Wilson about working together. We started doing some research and experiments with podcasting in the fall of 2013. We eventually launched a podcast called UnStuckable, which focused on how people got unstuck in their careers and transformed themselves.
It was both an exciting and draining experience. Four weeks after we launched UnStuckable in April 2014 it shot up into the Top 100 podcasts on iTunes!
Even 2 years later, it was still one of the top 150 career podcasts on iTunes. Clearly, we were onto something, but we didn’t have a business plan. That turned out to be a big problem.
Chris was still working full time at this job, while I was working full time on UnStuckable. I was cranking out 5 podcasts a week and still managing some broadcast sales training projects. By the summer of 2014 a variety of forces in my life conspired at once to send me into my first-ever depression.
c) Depressed
Depression is a funny thing. It kind of sneaks up on you. It takes you into its grip and you don’t know how bad you were until you’ve come through it. At least that’s how it worked for me.
So what caused it? Three primary events.
First, my mom had a stroke in February 2014. She was very lucky. Physically she is fine, but she lost most of her short-term memory. She has always been one of my most important confidants.
The experience has been one of the most significant losses of my life.
Second, I turned 40 in July 2014. Honestly, the number didn’t bother me, but I wasn’t prepared for my “midlife passage”. I had no idea the changes men go through physically, mentally and hormonally until it started happening to me (probably in my late 30s).
I know our society jokes about the “midlife crisis,” but now having gone through it, I think it’s time we had a more productive conversation about it to help reduce the associated anxiety that inevitably goes with it!
Third, Chris and I struggled to align our work styles, needs, values and expectations. We are both talented in our own right, but we couldn’t get into a workflow together for our project.
I think we would both agree that we spent more time trying to figure out how to work with each other than turning UnStuckable into a business. That’s never a good thing.
d) Purge
My breakthrough moment came when my sister visited me in August 2014 while I was vacationing in Cape Cod. She got me to have a good cry about our my mom. It was the emotional release I needed. It was the bottom of my depression.
After that I resorted to one of my favorite life skills, purging. Almost nothing else gets me moving forward again like letting go.
I just needed to clear lots of stuff out of my life to help myself heal. Stuff that was holding me back and stuff I probably should have dealt with long ago.
I spent the fall of 2014 decluttering all my possessions. I used the basic rule, “use it or lose it.” If it had no use or brought me no joy, I got rid of it.
The process of getting rid of physical stuff generated momentum to get rid of digital waste, obligations and relationships. Most importantly, I was long overdue for a declutter of my mental space.
I tackled my fears, re-evaluated my expectations and questioned my desires. The theme of my 2015 was “let go.” It was liberating and energizing!
In March 2015 Chris and I decided to end UnStuckable. I have no regrets and have UnStuckable to thank for laying the foundation of Life Skills That Matter.
I also decided to let go of my remaining broadcast sales projects to start the next phase of my career with a clean slate.
5) Purpose-Driven (Here and Now)
As they say, “it’s always darkest before the dawn.” Depression isn’t fun, but it forces you to stop, reflect and evaluate your life in a way we all never seem to make the time to do. I had fallen into one of the deepest valleys in my life, so here’s hoping I’m about to climb one of my biggest mountains.
Spending a year reflecting has helped me understand myself in a deeper way than ever before. I have a clear purpose. I found my pace in life. I clearly understand my work needs, so I can design a business in alignment with my work habits and the needs of the community I want to serve.
I’ve always wanted to build a business to help people, but at the same time it needed to financially sustain my family.
I’ve had a lot of ups and downs . . . lots of downs I wouldn’t wish on anybody, but that’s why I’m doing this. I believe teaching the Life Skills That Matter can help bring greater and deeper awareness to your work, saving you a lot of time, energy and emotional distress.
Takeaways From My Story
If you’ve read this far, thank you! After writing about my story, I discovered a few lessons I would now like to share with you.
1) Build on your past experiences, don’t throw them away.
When you are looking for a change in 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 your past identity to a new vision and confidently explain its enormous value. I’m still using the content production skills I learned at CBS News and will use my training skills for Life Skills That Matter.
2) There are other ingredients besides money to building a sustainable career.
Once I built a financially successful company, I thought it would be the pinnacle of my career, but to my surprise 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 also needed to have passion for the work. What motivates you to work?
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 13 years ago.
There are so many new ways to teach yourself and acquire new skills thanks to the miracle of the web. We all need to set regular learning goals for ourselves.
4) Know your story.
Your resumé is not the story of your career. The last time I updated my resumé was 13 years ago. I no longer have one and never will again.
The titles on your resumé don’t define who you are as an individual. Create your own label. Define yourself. Be able to clearly communicate your “superpower.” What is something you can do effortlessly, with joy and a sense of mastery?
Understanding the story of your career also allows you to be honest about your failures and what you can learn from them to build the lifestyle that works for you.
5) Be aware of when you are getting stuck.
Sometimes they are small moments and sometimes they are life changing events. Getting stuck shouldn’t be something to be avoided. Recognize it. You should never feel ashamed if you are feeling stuck. It’s your inner voice trying to tell you to take a new path. Listen to it.
My warning signs for when I’m getting stuck are recurring negative thoughts about something in particular or feeling a little too comfortable.
6) More of us will become reluctant entrepreneurs than we might think.
Only you can choose your path in life. Only you know if you are happier and more productive as an employee, careerpreneur, freelancer, solopreneur, entrepreneur or some other way of working.
I believe more and more of us need to wake up to the reality of working for yourself for two primary reasons:
a) Managing yourself is the future of all work, whether you work for someone else or yourself. If you have to manage yourself, why not own yourself and create work that works for you?
It’s sneaking up on us more and more as jobs are automated or outsourced. I believe more people will become reluctant entrepreneurs in the coming years.
I’ve been there, and I want to help you make a productive transition.
b) We’re all seeking inner peace (I know I am!) and one of the most effective ways to reduce your anxiety, to feel like you are enough and to live life at your pace is by designing work in alignment with your values, needs and abilities.
Tell Me Your Story
Enough about me! Now it’s your turn to tell me your story.
Send me a question about how I can help you make your work, work for you. What have you always wanted to do? How would you like to work?
Remember, it’s possible!
Stephen