This year marks 30 years since I launched my career upon my graduation from Providence College. I've worked for myself for 26 of them, in ways I never thought were possible and on career paths that didn't exist when I started.
Along the way, I've done a lot of things I was told you're not supposed to do:
I resigned from my first job the day I was promoted, to take a job that paid less and had fewer benefits, because it made my heart sing.
I've been offered work several times without ever producing a resume.
I walked away from a successful business because I saw its industry declining and wanted to leave on my own terms.
When a client wanted to hire me as an employee, I proposed a consulting relationship instead, and they agreed.
I traded my video marketing expertise for a free apartment in Seville for 10 weeks.
I lived and worked out of a bag traveling the world for two years.
I gave up a six-figure consulting gig to care for my elderly parents.
Have a question about why or how I did any of the above? Ask Me
None of this was luck. In fact, it drives me nuts when I hear someone say, “You’re lucky to have a job.” That mindset says you are waiting to be chosen instead of creating work that works for you.
And none of it required being a special kind of person. I discovered ways of working I was never taught were possible, and each one came from a skill you can learn and practice.
I'll share the many ways I've made my work, work for me, what each one taught me, and how those lessons became the way I coach people today.
How It Started, and When It Didn’t Work
When I started my career, I did what I thought I was "supposed to do." I became an employee and did my best to fit into the system.
Well into college, I thought I'd be a lawyer. Then I almost landed an internship with The Late Show with David Letterman, and it bumped me onto a path in media. My first job was at Edelman Public Relations, writing communication strategies for healthcare companies (including Viagra, if you can believe it). As a history major with a love of storytelling, I moved to CBS News within a year, then to CNBC as an Associate Producer, and then into the new world of the internet at ThirdAge.com.
On Election Day in 2000, the system kicked me out. I was laid off in the Dot-Com Bust. Little did I know it was the biggest favor it ever did for me!
That layoff started my rebellion against everything I'd been taught about work.
I'll admit I was lost for a few years. I freelanced, went back to CBS News to help cover the 9/11 attacks, and earned an MBA in media management at Fordham University. Then I started consulting local radio and TV stations on their digital strategies. That grew into a video training business that I sold in 2012, when I saw the inevitable decline of broadcasting.
Eventually, I let go of my remaining broadcast consulting clients to start Life Skills That Matter to teach people how to make their work, work for them, as I had done for myself.
Even when I was trying to make my work, work for me, it didn’t always work.
After getting laid off, it took me almost a year to secure paid work. It was a freelance gig. Freelancing was something I never considered before because I was conditioned to think it was an unstable way of working. As it turns out, it was the best-paying work I’d had up until that point in my career, and it gave me greater time freedom!
After business school in 2004, I struggled to make ends meet for about a year. I was hired by the New York Broadcasters Association to write a book celebrating their 50th anniversary. They paid me $20,000 to write it, and that helped keep me afloat. That project eventually launched my broadcast consulting business, and I was earning six figures two years later.
After I wound down my broadcast consulting business in 2016, it took a couple of years before Life Skills That Matter started generating revenue. Fortunately, I planned wisely and had savings to sustain me.
More recently, I paused Life Skills That Matter twice in the past five years: first in 2021, because I felt burned out and needed to regain clarity about the work I wanted to do, and again from 2024 to 2026, after my father passed away. During that time, I focused on my local economic development projects in North Adams, where I currently live.
Looking back, what got me through each of these hard stretches was knowing what I needed to live on and planning for it. That’s a big reason “enough” became the first of my core principles.
I'm not a fan of resumes, so I won't walk you through every job. If you prefer the chronological version, it's on my LinkedIn profile.
How I Made My Work, Work for Me
After years of reflection on my career, I’ve observed five core principles that have guided me time and again to be able to work on my terms no matter what I was working on or who I was working for.
define what “enough” means for you
When I launched my on-demand sales training video archive for the local broadcast industry in 2008, within a couple of years it was generating well over half a million dollars annually. It was way more money than I had ever made, but I also asked myself, “Do I really need this much money?”
That led me to explore how to calculate the cost of my desired lifestyle, including saving for the future. When most people start earning more, they start spending more and become trapped in a lavish lifestyle that often requires them to work more and more to sustain it. That didn’t sound like the freedom I desired.
I realized the less I wanted materially, the more I could do with my time. I chose living simply even when I was earning a lot of money to buy back my time by investing it. I define “wealth” as the number of days you don’t have to work to sustain your lifestyle.
The lesson: Freedom starts with knowing your numbers. Decide what "enough" looks like before someone else decides for you.
In my coaching: I help clients calculate the true cost of the life they want, so they can reverse engineer their career to determine how much they really need to work to support their desired lifestyle.
Ask yourself: How many days could you live without working based on your current lifestyle?
self-reflect regularly
I majored in history in college and always loved reading biographies. One of the habits I observed over and over again when reading about these accomplished folks throughout the ages was their habit of self-reflection. Whether they journaled, wrote plans or talked it out with someone, they regularly reflected on their thoughts, behaviors, actions and habits to gain insights into themselves.
I first started journaling as a self-reflection practice about a year after I was laid off and have continued the practice on and off again based on my season of life. I typically journal a lot when I’m feeling stuck or in a transition.
Journaling has helped me see patterns in my thoughts and actions in ways I would have otherwise missed. It provides me with a more honest perspective of myself than staying trapped in my head, so I can confidently move forward.
The lesson: You can't design work around yourself until you know yourself for yourself.
In my coaching: Reflection is the first practice in my Clarity in Action methodology, and the one clients return to whenever their work or life changes or they get stuck.
Ask yourself: What pattern keeps showing up in your work that you've never written down, but you know is holding you back?
be open to all possibilities
I believe so many opportunities have come my way throughout my career because I’m open to all possibilities. Most people get stuck because they are either unwilling to consider all possible opportunities or they are unaware of them.
The human brain is curious by nature, but can also get stuck in fear mode when it thinks it's protecting you, even from emotional harm. When I’m stuck, I make a list of all possible options, even the ones I judge and think I would never consider. What I have learned is that when you consider all your options, you start seeing new options you might have never otherwise arrived upon.
Most people kill off opportunities by never testing their assumptions. I’ve made a habit of “just asking” or trying experiments.
After working for CBS News for just six months, I asked my boss for a month-long leave of absence, so I could work for CBS Sports at the 1998 Olympics in Nagano. She said yes.
When a friend of mine asked if I wanted to start a podcast with him, I tried it out. That led to the production of 500+ episodes across two podcasts and gave birth to Life Skills That Matter.
After living in big cities most of my adult life, I accidentally stumbled upon North Adams, MA, when playing Airbnb roulette while I was living out of a bag during the pandemic. I was seeking a more affordable and slower pace of life with access to nature and creative communities. It was exactly what I was looking for, but didn’t know existed! I’ve lived here since 2021.
Again, I’m not a fan of resumes. I’m a fan of showing your body of work no matter what it is you do. Your work speaks for itself and tells a much more exciting story than your resume ever will.
There are so many times that I just started doing the work before even getting paid.
I created a newsletter about the future of TV news that led to several unpaid speaking gigs before I started getting hired as a paid consultant.
I wrote a book in 2005 about how to land a job in media and wasn’t paid until I finished the book.
The lesson: Most limits are untested assumptions. Ask, experiment and start doing the work before anyone gives you permission.
In my coaching: Experimentation is the second practice in Clarity in Action. Clients design small, low-risk experiments before committing to a big change.
Ask yourself: What's one assumption you’ve recently made in your work without testing it?
build community around your career
Always Be Connecting. Building connections has been central to the resilience I have built for my career.
When I moved to North Adams and started exploring how to help develop its economy, I made a list of 60+ people related to economic development in the area and reached out to them. I landed a ton of meetings, which turned into several paid projects, launching my recent foray into economic development.
I landed my job at CBS News by cold calling shows on a daily basis until I finally got an interview.
When I started podcasting, I thought it was merely a way to share inspirational stories, but it soon taught me that it was a next-level networking opportunity. Eventually, I interviewed people like marketing guru Seth Godin, JetBlue founder David Neeleman and bestselling author David Allen.
In the Age of AI, I deeply believe building relationships has never been more crucial than right now. If you want opportunities, you need to connect with other humans to get them. Humans form emotional connections with each other and advocate for you in a way AI never will.
The lesson: Opportunities come through people, not AI. Build relationships before you need them, like after a layoff or a lost client, and keep them going after.
In my coaching: That's why my programs are built around small peer groups. People with a shared goal and no shared history push each other further than they'd go alone.
Ask yourself: Who are three people you could reach out to this week, just to learn from them?
manage your energy, not your time
I slowly eased the chronic anxiety that plagued me early in my career once I realized it was more important to protect my energy than to maximize my time.
From my own experience, interviewing 500+ entrepreneurs and executives, as well as reading hundreds of biographies, a typical human only has three to four hours per day to do their best mental work.
When I started consulting in 2005, I was still stuck in the 9-to-5 mindset. Within months, I realized I was finishing my to-do list in about three hours a day, without all the office distractions.
It took time to let go of the eight-hour day. Now I know my best pace: three or four hours of deep work, usually in the morning, with 20 or 30 minutes of meditation midday to refresh my brain.
The lesson: Your best work comes from protecting your energy, not from filling your hours.
In my coaching: I help clients map when they do their best thinking and what drains them, then redesign their schedule around it.
Ask yourself: When do you do your best work each day, and how do you currently protect your energy?
The Thread That Ties It All Together
When someone asks me, “What do you do?” I tell them the story I want them to truly know and not what I think they want to hear. Sharing a story about your accomplishments is so much more interesting than listing them. It creates interesting openings for conversation and connection with other humans.
I view my work opportunities through the lens of my career story and not whether or not I have the right skills or experiences. It gives me the freedom to repackage my skills and experiences to pursue opportunities that, on paper, I don’t seem qualified for.
As a kid, I read biographies of Helen Keller, Albert Einstein, Eleanor Roosevelt and President Lincoln. My mother can tell you how I'd talk to just about anyone, to the amazement of my introverted father. People endlessly fascinate me. They're like fine wines, each to be appreciated for their unique qualities.
PR, news, digital media, training, podcasting, author, consultant, coaching: every job I've chosen has been a way to witness and share other people's stories. That's the thread of my career. And somewhere along the way, I discovered my superpower: creating clarity from chaos.
No matter how many different jobs you've had, or how unrelated they seem, there's a thread in your career too. It's the reason you keep choosing the work you do. It's what makes you, you. Finding it is the first step to making your work, work for you.
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?
What This Means for You
I spent the first chunk of my career with chronic anxiety about work. Much of it came from trying to live up to other people's expectations. It got better as I learned to align my work with my values, needs and abilities, and to choose not just what I worked on but how, when, where and with whom.
I eventually became happily unemployable. That's my answer. Yours might look completely different: reshaping the job you have, changing careers, going independent, or making the most of your final decade of work. What matters is that you design it, instead of fitting yourself into someone else's system.
Work is changing faster than ever, and the assumptions behind what we were taught about careers no longer hold. That's why I believe the life skills that matter most now are knowing yourself, staying curious and connecting with others. Every lesson in this story is one of those skills in practice, and they're the foundation of how I coach.
If you want to make your work, work for you, start by reflecting on the story of your own career.
Not sure where to start? Take the free Career Clarity Assessment to see where you stand right now and your best next step.
Have a question about how I did any of this? Ask me.
Remember, it's possible!
Stephen
