How Financial Cowardice Lead Me To Financial Slavery

I was 16 years old when I got my first real job.

I grew up in the small factory town of Marion, IN., about an hour north of Indianapolis.  Like most kids I worked for neighbors pulling weeds, mowing lawns, and washing cars.

Eventually, my parents grew weary of my irregular employment (or lack of) and got me a job as a busboy at their favorite restaurant, The Icehouse.

The Icehouse was the most popular restaurant in town, and its motto was: Food, Fun, and Firewater (firewater is alcohol). 

Part of the appeal was its owner, Steve, who drove a Crimson-red Jeep Cherokee Limited with gold spoke wheels, and a vanity license plate bearing his nickname: The Iceman.

And at every lunch and dinner service, 7 days a week, The Iceman would greet every single customer, ensuring their meals were satisfactory, and refilling their drinks as needed.

He would stroll through the restaurant humming the phrase, “Only in America” a nod to the fact anyone, even a factory worker like him, could achieve their dream in America.   

The Icehouse was a precursor to what we know today as Applebee’s, or Chili’s, or Friday’s. Normal dishes were bedazzled with tastier ingredients and catchy entree names, and there were fun appetizers like jalapeño poppers and mozzarella sticks. And the atmosphere was warm and inviting with nostalgic signs and TV’s everywhere.  

Everybody wanted to eat at the The Icehouse.  Politicians, judges, business owners, bankers, lawyers, doctors, visiting celebrities, dignitaries, shady characters, gamblers, athletes, coaches, drunks, shift workers, the elderly, prom dates, and people having affairs. 

My Aunt Melanie met her second husband, Gary, at The Icehouse.  He was a traveling salesman.

I didn’t really enjoy busing tables or washing dishes or cleaning ashtrays.  And I wasn’t making much money, I actually made more money washing cars for my parents’ friends.  

But it was a cool place to be, and the Iceman was a charismatic leader who inspired me to work hard and hustle.  And I enjoyed the cast of characters I worked with, the waitresses, cooks, bartenders — all of us commiserating over cigarettes in the break room.

Every Friday night, around 10pm when dinner service ended, a DJ would start the weekend with a cheesy 80’s dance tune, and then The Icehouse would morph into the hottest dance club in town. And I would go home.

I tried working at a few other restaurants in college, but I never experienced the same pride or camaraderie I felt at The Icehouse.  The other restaurants were more like manual labor, and drudgery, led by disgruntled people. There was no “cool” factor.  

So, I decided then I would never work in a job that didn’t interest me.  I would never sell anonymous industrial widgets, or become some boring lawyer, or grind away at a repetitive factory job. No offense to anyone in these jobs, they just weren’t for me.

By college I developed an interest in journalism, and I started looking into writing for my college newspaper, The Ball State Daily News.  If I had a knack for anything academic, it was reading and writing.  I don’t claim to be some great writer, but I can spell and put a few sentences together. Things like grammar and English always came easier to me than math and science.

And I loved newspapers.  To me they were institutions of truth and service to their communities.  As a kid I would start each day with a bowl of sugary cereal and a crisp copy of the Chronicle Tribune, a beacon of local news, information, and entertainment for our sleepy town.

Landing a job for the school newspaper was not easy.  Ball State had a robust journalism program and competition was fierce for student jobs.  Truth was, I never summoned up enough courage to apply.  While I was convincing myself I would never get hired — at the same moment — I found out they were also hiring students to sell advertising in the paper.

I stumbled upon the highest paying student job on campus, paying 100% commission to sell ad space to local businesses. 

To me, selling ads in the lone school paper seemed easy. And that may be the secret to sales success — sell for a monopoly.

Ball State is based in Muncie, IN., and it is by far the largest economic force in an economically depressed region of the state. And if you ran a business in Muncie, it was smart to advertise in the only school newspaper. This was back in the early ’90’s before internet and social media.  Everybody read the campus newspaper.

Selling advertising was fun, it was mindless, and certainly more lucrative than being a journalist.  I reasoned, if I don’t write for a newspaper, I can still support journalism by selling ads — which pays for the journalism.  But even more pressing was graduation; the business side of newspapers was a more lucrative and stable career path.

This is the moment in my life when I sold out, where I chose the commercial path in life, opting for what paid more money and offered the most security instead of pursuing a passion.  I wasn’t a financial slave yet, because I wasn’t in debt. But I was a financial coward.  

More than anything, I was compelled by security. Something I lacked psychologically throughout my childhood, because my parents lived beyond their means. I was a sophomore, and it was about this time my parents got divorced, largely due to their financial problems. 

Rather than pursuing my interest, I became programmed to pursue money. The possibility of being poor terrified me.

My parents instilled this terror in me when I was young, because they were also terrified of being poor.  And the root of their terror was not in actually being poor, but what their friends would think of them if they were poor.  Which is dumb, because their lawyer and doctor friends wouldn’t be “friends” with a poor version of my parents.  

I remember between the ages of 10 and 15, I was a horrible student. To say I goofed off in high school would be an understatement.  I spent most of my time inventing new ways to cheat. Once, when my elderly Spanish teacher left the classroom for a moment, I strode up to her grade-book and changed my test score from 68 to 88.  It didn’t work.

And when I brought home successively bad report cards, my dad would take me for long scenic rides through the poorest neighborhoods in town, reminding me where I was heading.

Selling ads for my college newspaper led to a sales job at the largest newspaper in Indiana, The Indianapolis Star

Being the new guy, I was assigned the worst territory full of industrial warehousing and strip bars.  But I hustled and developed a lot of new accounts.  Most of the salespeople I worked with sat at their desks and waited for the phone to ring.

Newspapers had virtual monopolies on local news at this time, they were at their peak of influence, and staggeringly profitable.  The Star alone took in over $150M in annual revenues in the early ’90’s. More than all of the local radio and TV Stations combined.     

I kept on hustling, earning two Salesperson of the Year awards, and eventually graduated to more lucrative territories.  By my mid-twenties I was earning more money than most of my friends, Problem was, I had no clue what to do with it.  And this is where my dismal personal financial skills started putting me on a path towards financial slavery.  

With more success and security at work, I started buying things I couldn’t afford, and adopting habits — like gambling — pushing me beyond my financial means.  I would justify this behavior by reassuring myself I’ll keep making more and more money.  

I was rebelling, in a way, for choosing a career that wasn’t all that fulfilling. If I didn’t have the courage to become a journalist, at least I can spend some money and have fun!

And from there I never looked back.  My career path became a continual pursuit of security and money in the evolving landscape of advertising and media.  When newspapers began to show signs of strain in the early 2000’s, I transitioned to selling radio, and then to local TV.

Over the next 5 years, I would make every mistake possible in personal finance. I borrowed money from banks, credit unions, friends and family.  I used credit cards like they were free money, leased cars I couldn’t afford, and spent excessively on food and booze.    

I never saved money, never budgeted, cashed out my 401k, bought a house when I was cash poor, and paid massive amounts of interest and bank fees. Oh, and I gambled, a lot.  

By age 32, I was a quarter million dollars in debt with no savings to show for it.  

I had become a full-on financial slave. Owing money … paying interest … and continually living beyond my means.  Oh, and I had a career in Advertising Sales that I didn’t really like.  Which meant I was a financial coward, too.  But now I was trapped.  

So, on a cold snowy Christmas morning in 2005, driving to Detroit to see family, I listened to an audio book by Dave Ramsey called The Total Money Makeover, and it would change my life forever.