The Biggest Break I Ever Got
Why Chasing Your Dream Is Overrated
I had just graduated from college and spent the first year of adulthood driving around the country playing music in a band. We’d performed in churches, schools, and prisons—sometimes for hundreds of people, often for only a handful. It was fun and frustrating in different ways, but I was grateful for the opportunity to travel, play music, and have a “gap year.”
Now, the year of adventure was over, and I needed a job.
A relationship had brought me to Nashville, but I hadn’t made any major plans beyond getting there. After spending $1100 on a 1990 Buick Century, I was left with just $100 in savings. A friend from college offered to let me sleep in his dining room if I covered just under half the rent. My $350 share felt astronomical, but I had no other option.
Every night, I blew up my partially collapsed, inflatable mattress and fell asleep surrounded by piles of books and thrift store clothes, my barely-used cell phone buried somewhere in one of the piles.
When TJ Maxx told me I was overqualified to work retail and that I would probably just move on once something better came along, I assured them that they were correct. In spite of my honesty, I landed a job working at a call center in a small town outside the city. Driving to an office a few days a week to make fifty phone calls before lunch and another fifty before dinner got old quickly.
Within a month of getting the job, I started looking elsewhere for employment.
I did not have a computer, so I checked my email once a week at the local Circuit City, using one of their display computers to connect with the world. A series of hail-Mary emails to strangers on the Internet fell on deaf ears until one day I received a reply from a man named
.“I see you’re a writer,” the nonprofit founder wrote in reply to my request for advice. He was remarking on my college job as an English tutor—the only “previous employment” I could list on my resume. It was a small detail, almost a footnote in a life otherwise filled with chaotic changes in direction. He could just as easily have “seen” that I was a musician, a Spanish speaker, or a religion and philosophy major.
Instead, he saw “writer.” And that felt significant.
We struck up a correspondence that eventually led to him offering me a contract gig to help his organization start an online magazine. I had no idea how to do that but said “yes” anyway. It sounded fun and interesting and sure beat selling music subscriptions to strangers on the phone all day. After a few months, the part-time project turned into a full-time position, and I was able to leave the call center.
The job—working as marketing manager to help recruit young people for short-term mission trips—was one I was thoroughly unqualified for. Nonetheless, Seth took me under his wing, sending me books and blog posts to read, certain I had potential not only as a writer but as a leader. My Bachelor of Arts degree from a liberal arts school in the Midwest, though interesting to me while I was earning it, had not proved all that useful when it came to finding a job. So I threw myself into this work, growing with the opportunities that came with it.
Within a year, I had become the Director of Marketing, a promotion of which I was casually informed over lunch. “You know, you’re the marketing director,” my boss said in between bites of salad. “Right?” I nodded in agreement and ordered new business cards the next day.
Seth was a quick-start visionary who didn’t care much for bureaucratic formalities like job titles and descriptions. If I wanted one of those, I had to write it myself. To this day, whenever I hire someone, I have them write out their job description and then tweak it accordingly. I learned from Seth that the point of a job was what you did, not what people called you.
Admittedly, though, I liked the look of “director” on a business card.
For nearly seven years, I worked for Seth Barnes, doing what he asked me to do, often when I didn’t understand what he was asking.
Early on, he requested a report tracking “conversion rates” for recent emails we’d sent, and I had no idea what he was talking about. It took me an entire day to build the spreadsheet before sending him what I thought he was asking for. Within five minutes of receiving it, he returned the report with several corrections, and I spent the weekend fixing it.
I never knew what I was getting into or if I was doing it right. Most of the time, I made up what I was supposed to be doing and waited for someone to tell me otherwise. Often, no one did. I learned there was more than one “right” way to do a thing.
Not all the work was fun, of course, but there was an inherent challenge in the job that held my attention. I wanted to prove myself. This was more than ego or pride, I think. I wanted to feel like I had a place somewhere, like I was an individual with unique gifts to offer and people actually wanted those gifts. This job gave me that.
Becoming a professional marketer wasn’t something I’d hoped or planned for. It certainly wasn’t what I expected when studying the philosophy of Thomas Aquinas in college or reading Don Quijote in the original Spanish. But it was an opportunity, a chance to find a deeper identity at a time when I had no idea who I was or what I could be.
It’s easy to look back on these moments as some sort of cosmic plan to get where I was ultimately headed, but it didn’t feel like that at the time. By doing the work that was available instead of pining for some far and distant dream, I realized I could love a lot of things—not just the handful of experiences and interests I’d collected from my first couple decades of life.
Before you can have a dream, I think you first have to understand what’s possible, and this was my season of possibility.
The biggest break I ever got was not getting published. It was not meeting an acquisitions editor over sandwiches at a conference in Chicago. It was not even starting my blog or getting those first thousand subscribers.
The biggest break I ever got was the first time someone saw something in me that I could not see in myself. It was the belief of a mentor, the foresight of an almost-fatherly figure handing me a variety of tasks and projects in hopes that I might find some meaning and identity in it all. It was the patience of a boss who kept nudging me towards new challenges, helping me find my edges so that I could better understand what I was capable of doing and becoming.
After working with him for the greater part of a decade on a number of projects including a book, I met with Seth in person one day in 2013 and told him that it was time for me to move on. With his blessing and support, I’d started a side project that had blossomed into a full-time income. I told him everything on paper made sense, and the only hesitation I had was the fear that I might be disappointing him.
He said, graciously, “Jeff, I’m not disappointed. I’m proud. The truth is, I’ve been waiting for this conversation.”
I guess I had been, too. But as usual, he saw something before I did.
Postscript: I could say the rest is history, but really it was more of the same: a series of steps, one after the other, some large and some small, each building on what had come before.
My first few years of self-employment introduced new challenges, but in many ways I had been trained to deal with those. Like any beginner, I thought I knew more than I did, took on too much, and learned from my mistakes. But it was not as overwhelming as it could have been and mostly felt like just another chapter in the same story. I have those seven years of working with Seth to thank for that.
Granted, not everyone has such luck with a boss being so understanding and supportive. But I believe every job offers hidden lessons that can prepare a person for what’s to come. Personally, I think all our talk of “chasing your dreams” is overrated. It’s certainly important to find work you love and do what brings you a sense of meaning. But when you’re young or just starting out, you don’t always know what that is. And without extensive experience, how can you?
You need a chance to try things and learn what you could be good at, to become an apprentice. After all, a dream is just an idea, something you heard about somewhere or saw someone do once. And if you are waiting for that, who knows when it may come along? What’s more interesting is to work with what’s here now. What can you dig into today without consigning yourself to a lifetime of drudgery?
There is an art form to doing this that requires subtle navigation, but it’s worth learning. Every gig can be an invisible opportunity to leverage for something greater. My friend and client Dana Robinson refers to this as ”flyswatting,” arguing that when you humble yourself and do the work nobody else wants to do, you create an advantage for yourself. You can get close to a person of power or influence by helping them with the most menial of tasks. And that kind of proximity brings with it privilege. That was certainly the case for me, as I was able to see up close and personal what it looked like on a daily basis to run a large, international organization. It taught me a lot.
In Dana’s brand-new book The King’s Flyswatter, he explains how to do this. It’s a parable with practical applications and life lessons for how anyone can use their current work situation to create a better future for themselves. Our team had a blast collaborating with him on it, and I recommend getting it in the beautiful hardcover cloth-bound edition. But it’s available in other editions, as well (just make sure you grab the bonuses). You can even give your email address in exchange for a free audio copy.
Being a marketer at a nonprofit was my version of being a flyswatter. It was the apprenticeship I didn’t ask for but the one I needed. By doing the work that needed to be done, I learned valuable skills I was later able to apply in pursuit of other aspirations—what I eventually came to call my dream. But none of this would have been possible without that first “yes,” without a willingness to swat some flies. We all have to crawl before we can walk. And some of us have to swat flies before we can lead—or fix spreadsheets before we can write.
What a gracious and encouraging post this is, Jeff. The truth is, I was lucky to run into you. You were hungry and sharper than you realized. And together with the team that gathered around us, we changed a corner of the world. Those were good years.
The job-hunting experts like to stress “transferrable skills”. I had plenty of those from previous work in being a school director and talked myself into a management trainee job at a bank. I hated it, but the principle still remains: skills you hone in one job can contribute to your success in the next ones.