When Your Path Feels Unclear, Just Hold On
Advertising or journalism? I had to pick a college major, and my folks nudged me toward "job stability". I took their advice, became an ad exec, then hated my choice. But then...well...woah...
As a sophomore at the University of Illinois in the 1990s, I was at a crossroads.
I’d been accepted into the University’s (then-named) College of Communications and had to declare a major. Would it be advertising or journalism?
I didn’t yet understand how important it was to listen to my gut back then, but deep inside, I’d often imagine my grown-up self as “on assignment” and changing the whole goddamned world. Still, imposter syndrome tamped down those visions, I think. Did real people like me actually get paid to do jobs like that? I mean, c’mon.
I knew very little about journalism or advertising, so I turned to my parents for advice.
My mom was then a teacher-turned-technical writer. My stepfather had a computer science background and an MBA from the University of Chicago. My biological father was an attorney.
My bio dad’s advice was, as usual, emotionally driven, a bit flowery, and rather impractical. “Follow your heart, Princess!” It sounded lovely, but at 19, I didn’t really know what my heart needed for its future.
My heart loved three things: people, creative writing, and storytelling. None of us knew at the time I was dyslexic, but (perhaps as a result?) I was, without a doubt, a tenacious, high achiever. I had excellent grades but often worked longer and harder than my peers to complete the same assignments. Was my driven nature better suited for journalism or advertising? The pressure to decide felt suffocating. What were these career paths really like, anyway? What if I picked the wrong “door”? Would I be trapped forever in a miserable job? What if I couldn’t support myself?
What if I failed?
I appreciated how direct my mom and stepdad seemed. Even with a journalism degree from a great school, they said, the industry may be tough to break into.
That’s true, I said, cracking my knuckles.
How will you support yourself in the cutthroat world of reporting? they asked.
This was 1987, before the explosion of online and digital journalism. There were no hyperlocal news outlets back then. As I understood things, you’d cut your chops in local journalism and rise through the ranks by being scrappy and assertive with a take-no-prisoners attitude. Believe me, I’d watched enough of Lou Grant and The Mary Tyler Moore Show to understand that journalism was NOT for the weak.
Even WITHIN journalism, there were choices to be made. Print? Broadcast? Holy cow, this felt like way too much pressure for a teenager.
Broadcast journalism seemed WAY too competitive, yet finding success in print also felt unrealistic. Though magazines often paid writers thousands of dollars per article, landing a paid gig like that seemed as likely as hitting a home run.
Why was my confidence about journalistic success so low?
I think my parents sensed that I appreciated civility, certainty, and dependability — or at the very least, they wanted all those things for me — and guided me to seriously consider advertising.
During this decision-making time, I remember one stress dream in particular. I was on a print assignment in a dark alley with a flashlight, digging through dumpsters, searching for “evidence” for a breaking story, only to come up with nothing — then cursing myself for choosing the wrong career path as rats scurried across my feet. And yes, I’m very aware that all the signs were pointing toward me being a fiction writer, but let’s not go there right now.
Though I felt pulled toward a career in journalism, advertising (and what very little I even knew of it) seemed the more stable industry.
In those days, advertising — with its Madison Avenue mentality and Hollywood production quality — was definitely a hot and thriving “thing”. Advertising salaries were generally better and more dependable than journalists’ take home pay, and the work in advertising itself seemed far more exciting. Visions of the “lonely life” of a writer gave me chills, whereas getting paid (and paid well) to be creative and write advertising copy with other interesting people about cool new products sounded like… an absolute blast.
And so, I dutifully earned a Bachelor of Science in Advertising (barely making it through my statistics courses), applied for a job at legendary Chicago agency Leo Burnett, and actually got it. I felt like I’d made it big, and at the same time, and immediately felt like a complete fraud.
At Leo Burnett, I wasn’t in the creative department. I was hired into the Client Service “track”, which meant they started me out in the Media Department selling ads until I proved myself. Then, I’d “graduate” out of the media “pit” to a position as an Assistant Account Executive, working directly with the creative and media departments as well as the clients themselves. There’d be no jingle writing, no brainstorming copy. There’d be lots of numbers, lots of late nights, and constant travel to thrilling locations like… Battle Creek, Michigan.
My starting ad agency salary in 1990 was significantly more than most of my college friends’. After I was hired, my best friend, who’d attended Northwestern’s Medill School of Journalism, struggled for months to find a job. She eventually landed one in P.R. for a salary lower than mine. My parents, it seems, had been right; advertising was the right path to take.
I had an exciting job, an awesome salary with incredible benefits (insurance, matching 401K, annual bonuses, tons of paid time off, access to a health club, 3-hour lunches, taxi reimbursement, and an endless supply of Diet Coke in the break rooms). I tried every day to push past my insecurities and forget about how much I missed writing and convince myself that making $22k at 22 years old meant that I’d really MADE IT!
Or so I thought.
I ABSOLUTELY sucked at my job. Though I LOVED my peers, I was horrible at the work, which involved (wait for it…) statistics and NUMBERS. Only later would I learn I have dyscalculia — similar to dyslexia, but with numbers.
I pulled so many all-nighters and cried so many tears trying to make my brain make sense of my assignments, always falling behind everyone as we bought advertising spots for our company’s iconic “critters” like Tony the Tiger, The Jolly Green Giant, Toucan Sam, and Snap, Crackle & Pop.
I left Leo Burnett in 1994 and landed at DDB Needham, another Chicago agency, where I worked as an Account Executive managing ads for packaged goods. The work — less media buying and far more business writing and client hand-holding — was so much better than in my previous position, so I thought I’d found my professional home. I told myself that Burnett just hadn’t been the right fit for me, and that Needham’s more relaxed and approachable vibe was what I’d needed all along. It was here that I made more lifelong friends and began to find my voice as a businesswoman.
Needham, at the time, had some of the worlds’ biggest brands, including Budweiser and General Mills, and I travelled constantly to my clients’ offices and to TV commercial shoots in L.A. I wore control-top pantyhose underneath my amazing suits, attended lots of big parties and promotions, and spent endless non-work hours with my office girlfriends watching Beverly Hills 90210 and Melrose Place while drinking wine and laughing our asses off.
With these friends, I felt like I was part of an exclusive club of FUN, which made the dreariness and empty feelings I had about the actual job that much more tolerable. With them, I went on my first “girls’ weekend” (followed by many more) and opened up about my deepest feelings. I didn’t love the work itself, but I loved the people I worked with and the stories we shared and the memories we made.
Creative writing, it seemed, was the only thing still missing in my life. Professionally, I was deeply unfulfilled, and I couldn’t “happy” myself no matter what I did. It was during that time I began struggling with insomnia and eventually started taking an antidepressant (Prozac). I also began considering life outside the agency bubble, wondering What else is out there? How do people even navigate a non-agency life?
Before I could summon the courage to quit my job, I was gently “let go” from Needham. Leaving with my tail between my legs left me deeply ashamed and depressed.
Thankfully, I found another job immediately, working a woman out of her home, a lady who’d previously worked at Needham who then become a sales rep for TV commercial directors. It was there that I honed my sales and customer service skills while dipping my toe into bookkeeping and accounting. My new boss kept asking me when I planned to have children (I was newly married), and insisted that if I ever got pregnant, she’d let me bring my baby to work. At one point she even handed me something I’d never heard of — an ovulation predictor kit — and urged me to start trying for a baby.
This woman’s home was in the Lincoln Park neighborhood of Chicago, and her husband lived in Florida, where he owned and managed an orange grove. The longer I worked for her, the more she left me alone to run her business while she travelled to visit her husband. I spent most of my time working out of her walk-out-basement in Lincoln Park by myself — a rare, remote working setup way back in 1995. At one point, when her son was a senior in high school applying to colleges, my boss asked me to edit — then write — his admissions essays. The kid got into his #1 school, and I got two bottles of wine and her favorite recipe for minestrone soup.
One day, with tears in her eyes, my boss handed me a “final” check and told me it was my last day. Though she barely offered an explanation, I was almost relieved to have a reason to leave that role. I’d lost my soul working for her, toiling every day in her basement only to return to my own garden (a.k.a. basement) apartment in Lakeview. I literally and figuratively needed to rise above my circumstances, but I didn’t yet know how. When she let me go, I was free (if not forced) to start looking around.
I don’t recall who, but someone suggested I contact a job placement service, and it was there that I took a quick typing test and completed an interview and found myself placed immediately as a recruiting coordinator at Deloitte & Touche Consulting. Not only did that job pay better than any position I’d ever had, but it also sent me all over the country as I managed recruiting programs at schools including Harvard, Yale, Princeton, Stanford, USC, Duke/UNC, the University of Chicago.
Initially, I was intimidated. Who was I, little old me, with my bachelor’s degree in advertising from a state school, to work with these brilliant, cream-of-the-crop MBA candidates?
What helped me overcome my imposter syndrome was that these students were just as — if not more — unsure and insecure as me. Turns out I, not they, had a job and insurance and security. I got so see them up close as the human beings they were — with runs in their stockings and sweat running down their uneven sideburns and panic in their shaking hands as they waited for their turns to interview. I read their emails asking repeatedly when the job decisions would be made — and if they might have a fighting chance.
I came to see that even the *best* education and the *best* upbringing won’t guarantee a thing when you’re being interviewed by a cranky VP who stayed out way too late the night before because he’s going through a horrible divorce, and that his mood will likely determine whether you get a job that day or not. I came to see that so much in life is truly out of our control, and that what matters most is authentic and compassionate connection.
I left that job after I had my first child in 1997. By then, I’d also enrolled in grad school on a scholarship to earn a Master’s in Teaching. Though I briefly returned to work after my maternity leave, I knew I couldn’t juggle work AND motherhood AND my pursuit of an advanced degree. I was so fortunate to have a spouse with a decent salary that allowed me to stay home until I’d earned my Master’s and returned to work, but I’ll also take credit where credit is due; my salaries had contributed to his advanced degrees.
When I finally walked across the stage to receive my Master’s diploma, I waved to my family which, by then, included three children — ages 5, 3, and two months.
For the next 10 years, I taught and developed classroom curricula. I loved that work and appreciated how it afforded me the ability to be present during my kids’ youngest years.
And then, in 2008 when I turned 40, I decided it was finally time to launch my writing career. I could no longer ignore the ache in my belly to be an author, and I’d never let go of my dream to somehow change the world. Something about turning 40, perhaps, gave me a confidence boost (or was it a kick in the ass?) to say, “You’re not getting any younger, so for God’s sake, follow your heart.”
Just like when I was 19 years old, I wasn’t sure where things would go. But now, I had confidence and a stronger sense of self. Unlike when I was 19 years old, the uncertainty felt exciting, rather than overwhelming.
I started by blogging about how clueless I was about launching a writing career. When my blog was seen by a hyperlocal news editor, I was immediately offered a job as a reporter for an online news outlet.
My first paid gig as an actual writer! I was now officially a journalist.
Within a year, I had a weekly, paid opinion column, which led to more opinion columns at bigger outlets and with more exposure and better pay. One of those columns led to my first book deal — a and that book comes out later this year, 33 years after I graduated college with a degree in advertising.
Believe me, there’ve been many times I’ve questioned whether I should have saved myself decades of heartache and insecurity and just gone straight into journalism in college.
The answer is absolutely no.
At 19, I wasn’t yet ready to take a blind leap into journalism. I don’t think I had the fortitude to handle the industry itself or the self-confidence to navigate its pending, epic changes. By the time I finally stepped into the profession, at the age of 40, I’d acquired invaluable life experience and confidence that helped me fully embrace my opportunities.
I’d stepped into journalism at a time when news was literally shifting — from being a “product” to a “service”. At the time, I was young mom with an earnest desire to make a name for myself by connecting with others and sharing authentic feelings. If ever there was a time for the internet to train a spotlight on my heart, this was it. Timing is everything, and you can bet I didn’t waste this chance. I was far more prepared to juggle the feedback than I’d been at 19 — especially the less than favorable comments — and far more able to appreciate how much this window of opportunity meant.
I’m certain that my parents were right when they encouraged me toward a career in advertising. I know that they had my best interests at heart. I also know I did the right thing by giving the ad life a fair shot. In doing so…
• …I had the privilege and opportunity to learn what I’m NOT good at.
• …I acquired business management skills that I now use to run my own businesses as an author and writing coach.
• …I now know what it feels like to fail and then pick up the pieces. As such, I believe I’ve gained a greater sense of tenacity and even empathy than I’d have otherwise known.
• …I was forced to be a self-starter and learn how to change direction when my “path” no longer served me.
• …I ultimately ended up learning journalism through boots-on-the-ground, scrappy, fumbly, in-the-moment work, rather than from a textbook in a classroom.
• …I deeply, deeply appreciate what I now do, which includes a combination of advertising AND journalism. These days, I research, write, report, market, promote, project manage, speak publicly, and serve my clients. I’m using every skill I’ve picked up along the journey.
• …I know I’m making small, meaningful contributions that help to change the world.
And so, if you’re unsure about which next step to take, listen to your heart, believe in yourself, try new things, and always, ALWAYS believe in the the power of change. Nothing is permanent, and if things don’t initially fall into place, rest assured that you have it in you to change the direction of your life.
Have you ever been at a crossroads, unsure which path to take? Which one did you choose, and how did it turn out? What did you learn from your experience? Would you change anything?
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