Growing up as a kid in Detroit in the 1980’s and 90’s I dreamed about being several things: a sportscaster or sportswriter, a DJ (someone on the radio, think Wolfman Jack), an actor. As I got a little older some of these things lost their luster or I never seriously pursued the paths it would’ve taken to do any of these professions.

Probably like many kids and adolescents I had adults trying to entice or pique my curiosity with “realistic” life paths along the way. “Randy you could be a doctor!”, “how would you like to be a teacher?” or my great grandma, whom we called Oma, had me ticketed to be a Catholic priest! In high school my guidance counselor half-heartedly recommended I be a salesperson of some sort, which ironically, came the closest to where I find myself today.

Through happenstance I found myself being a Medicare broker in my mid-30’s in 2010. Like most of things I did to earn a living to that point in life it wasn’t the most intentional of paths. It just sort-of happened and I happened to be good at it.

Recently one of my colleagues told me a stat that sort of startled me. Within the first two years of getting their insurance license 92% of health insurance agents fail, i.e. leave the business and go back to working a regular job. Within the niche of selling Medicare, it’s right along those lines as well with a whopping 7-8% of those who start this line of work making it to Year 3!

So here I am in Year 14 of my career as a Medicare broker, and I wondered “Why me?” What was it about me that allowed me to not only survive, but thrive in this industry? Then it came to me that just about every job I’ve ever had until now was good training for working for myself and being a Medicare expert. As a person of faith, it became apparent to me that maybe I was led down this path and meant to be Mr. Nice Guy Medicare Advisor.

Growing up in Detroit my family were blue-collar and not wealthy by any means. This meant if I wanted to get anything more than the basics, I had to go earn money at an early age. The summer before my eighth-grade year I got up at an unholy hour to help my Dad on his newspaper delivery route to earn $3 or $4 per day. And once school started back, I’d help him on Sunday mornings for $5. Even in 1988 this wasn’t much money. Still, it showed me how hard my dad was working to make a living.

The following year I was old enough to start caddying at the local country club, Plum Hollow in Southfield, MI which was about 2 miles from where I grew up in Northwest Detroit. My uncles had been caddies there a decade or so prior to me. Also, one of my best friends and his sister already were lugging golf bags there, so I had an in.

The first year was rough as there were plenty of times I’d show up and either not get out or wait for hours before getting picked. Still, the pay was so far-and-away better than what my dad paid and the work so much easier (relatively speaking) that I was glad to do it.

What I came to realize was that it was a natural weeding-out process in a sense. Once you were an experienced caddie (they had ranks, and it took a year to go from newbie to captain and still another year and a certain number of rounds to become an honor caddie) golfers would request you or if the caddie-master knew you were good they’d set you up with the better paying golfers and get you out quickly. The rookie caddies (labeled ‘slashes’ by their more experienced peers) had to pay their dues. If you were a ‘slash’ life was much more difficult. But if you could weather-the-storm and come out the other side, you had it made, relatively speaking.

My second season as a caddie I got very fortunate and hooked on with a guy named Mr. Dan McDonald and became his permanent caddie for much of the next 5-6 years. There was a kid who was a senior in high school named Brad who was his caddie who was about to age out of the program, and I wisely ingratiated myself to him.

Pretty quickly we had an arrangement that he’d let me know when he was playing next and if I could be there, I’d caddy for him. Mr. McD, as I called him then, was a guy who owned a heating-and-cooling business and was a self-made guy who reminded me of many of the strong Catholic men I’d met growing up at church and going to a Catholic school, including my own grandfather. But he had a multi-faceted personality and big heart and taught me many things directly and indirectly.

For those who’ve read the Robert Kiyosaki book “Rich Dad, Poor Dad”, he would’ve been my “rich” Dad. During the prime golf playing months in Southeastern Michigan (April through October) and especially on summer breaks, I’d see Mr. McD more than my real father seemingly. Through him I got to see several things that were absent in my own life. He and his wife Mary had a fun, yet serious, marriage. My own parents were not aligned, to put it kindly.

He also was a successful businessman a good model for an adolescent like me. He made owning your own business and working for yourself look obtainable and not a struggle.

Through the years (I was his caddie for six golf seasons) he imparted a ton of wisdom both in terms of explicit words and mainly in his deeds. He treated me like one would treat their own kid (respectfully of course) and even when he was hard on me, it was clear it was because he cared. He was just an excellent human being, and he did this for multiple caddies over his time. I was very lucky to be one of them.

The next occupation was being a busboy and waiter. Once I got a car, I was mobile and able to work after school. That’s the rub, once you have transportation it made it necessary to work to pay for said transportation. So firstly, I worked at the same country club I caddied at my senior year of high school once the weather turned (September and October).

My very first day on the job I was quickly introduced to the world of foodservice and christened the occasion by spilling about six fully loaded glasses of water on one of the guests due to not being able to balance a full-tray on my first day. Talk about being thrown from the fire into the frying pan immediately! I didn’t have much time to process the trauma as I immediately had to figure out how to get food out to guests and then remove the plates once they were done with them. At 17 this was an entirely new concept to me.

Anyhow, I was part of a crew of other busboys (several also caddies like me) so I learned the value of teamwork and having to serve under the waiters and waitresses whom it was my job to assist. You know, basic stuff they really don’t teach you in school.

I left the country club and wound up taking a job at a family restaurant near my home in the winter as there wasn’t enough hours at the country club to make it worth my while post-Christmas and I needed money consistently.

They hired me as a busboy too, but within a week they determined I had the personality to be a waiter instead. This was my first experience in the workplace of promotion, which was a vaguely gratifying feeling, along with a bit of a pay-bump.

If you’ve never waited on the public let me, tell you: it’s a bit of an education. You’ll meet all kinds of people, and you can tell much about others from how they treat the ones who serve them. Good, bad and ugly.

Me being a people-pleaser already, I also had it beaten into me at Catholic school to be submissive and conscientious, so being a waiter was a mixed bag for me. Once I got good at it, I had many folks who would come in and request me to wait on them, which was great. What wasn’t so great was those who were jerks to me and I didn’t have the life-experience to realize the problem was almost always them and not me. On the plus side, it did give me the life-experience to deal with all different types of folks and really connected with many of the customers whom I got to know.

Throughout my 20’s I was a waiter at family restaurants, the Ritz Carlton, Macaroni Grille, and a few other fine-dining restaurants. It taught me people skills, coping skills and how to work hard. All-in-all a definite net positive.

When I was 23, I started dating a girl who I worked with at the family restaurant with who actually set me on a course of the Monday through Friday, 9-to-5 type job that is the backbone of our white-collar American society. She was the first person to get me to seriously question the direction of my life in the restaurant industry and through her friends got me to be a file-clerk at a mid-size accounting agency where I’d have a salary (a crappy one, but hey, I was young 😊), some medical benefits and have the weekends to myself for the first time since childhood.

There were some stark differences between this slice of corporate America and the restaurant business. Instead of being tipped, where effort and attitude typically correlated to better pay, here you had to ingratiate yourself to management to have an easier path as a worker. My manager, Jeanie, was quite the character, but not a fun or easy manager to work under. I quickly figured out that a bad manager could make a job that wasn’t that bad feel like it was akin to forced labor. Me, being someone who likes to give people the benefit-of-the-doubt, especially those in authority positions at that age, it took me awhile to work out an exit strategy, in the form of another promotion.

While doing my job better than any of the other file clerks within weeks, I got to know the manager of the secretaries (administrative assistants for those who prefer that term), a nice lady named Lori, and befriended many of the accountants with my positive outlook and can-do attitude.

Without getting too much in-the-weeds of interoffice politics of this firm, I found an opportunity to become an administrative assistant quickly and not have to deal with Jeanie but be supervised by Lori instead and get a pay raise. At this point I got see how a job that wasn’t glamorous was made fun by someone who was your advocate in Lori. While I had no formal training in being an administrative assistant she taught me specifically what I needed to know and trusted that I’d grow into the role and give it my all, which I did.

Being an administrative assistant taught me how to navigate a more professional environment and how to organize my time and energy way more efficiently, as I was thrown into the deep end during tax season at this accounting firm. I also learned many of the tricks and ways to conduct yourself I use today to conduct myself in a professional manner, but also to work with others. Key was keeping the schedule for several accountants and how to run an appointment in terms of setting it up. In hindsight this was great to learn as I’ve been setting up my own appointments for 14 years now.

After a year plus there, I was fired for a dumb prank that went awry. As horrible as it felt being let go, it served as a springboard to my next work experience, which, is my favorite, other than working for myself. Through a connection of my friend Jeff Hupp, I was hired as an administrative assistant for J. Walter Thompson in downtown Detroit to the Regional Advertising Force department of JWT.

The RAF team wrote, directed and produced all the Ford ads locally and nationally through our department. It was a great place to work, even when I was there at the time and in hindsight. The guys who interviewed and ultimately decided to hire me were John Kmiecik and Jim VanderEyk. They oversaw the copywriters, art directors and producers who were all integral to the creation of the ads we all see on TV. Naturally, I knew next-to-nothing about advertising, but they saw in me a fellow creative (I produced my own local cable TV show with my best friend) who had just enough experience to be able to work with the eclectic bunch of people who constituted their team. In fact, one of the chief reasons they went with me was the nature of the dumb prank that got me fired from the accounting firm and my forthright honesty about it. Talk about taking lemons and making some sweet lemonade!

For a little over six years, I assisted them in facilitating the running of the nuts-and-bolts of the department. Booking travel, processing expense reports, answering phones for the managers, scheduling meetings, and other necessary administrative tasks.

Over the years I met some of the coolest, most remarkable people I’ve ever known and am friends remotely (via Facebook mostly) with to this day. Everybody from Elmore Leonard’s song Bill to my fellow administrative assistants, to folks in the accounting department (what is it with me and accountants?). I was blessed to work with excellent folks in an environment that fostered my personal creativity while showcasing my blend of humor and hard-working professionalism to an, on-the-face-of-it, pretty unglamorous job. But they made me feel honored and fulfilled all the years I did it. If I ever wrote a TV show that’s like “The Office”-meets- “Mad Men” it’d be based on the excellent work experience I had there!

Also, in 2001 I became a certified handwriting expert, graphologist, and would moonlight working events by analyzing the cursive handwriting of strangers for “intellectual entertainment”. This was my first small business. Although I didn’t have enough time to do the graphology full-time, I worked for myself to get word out that I had the requisite skills to be hired by those who were interested in what I had to offer. It was an excellent “side hustle” and part-time, professional work that was a precursor to the job of Medicare broker. I would also analyze someone’s writing the way I analyze someone’s Medicare insurance today!

Come Thanksgiving 2006 my relationship with my longtime girlfriend ended at the exact time my best friend Dan Minard was visiting me after moving to Nashville, TN earlier that year to pursue his musician muse. I had long felt a feeling of stagnation and hated the colder climate of Southeastern Michigan and Dan presented the idea of moving to Tennessee to room with him and making a life change in the warmer environs of Nashville. He correctly pointed out that if I gave it a try and didn’t like the change that I could return to Michigan.

After sleeping on it overnight I felt the impulse to give it a shot. At that point I didn’t have a kid or a significant other to keep me there and if I didn’t do it now, it would more likely be never. I told him I’d give it 2 years and see how it went. If nothing else, it would be a memorable chapter in my life.

I had to wait until I got my tax return refund (that’s how poor I was), but on February 7^th, 2007^th me and my good friends Tim and Michelle Luttman moved me to Nashville, TN for the grand adventure.

I had no job lined up, but my sister Kathy at the time worked for a temp agency, Kelly Services, that had a Nashville office who set me up with my first assignment at Genworth Financial in their Medicare Supplement division as an agent helpline rep for their agents in the field throughout the U.S. Did I have any experience whatsoever in insurance, let alone Medicare? Absolutely none. But I proved to be a quick study and within a few weeks they offered me the job full-time, at a salary greater than what I made at JWT when I left!

Quickly, with the help of a few great ladies named Joan Maguire and Rose Faulkner, I learned enough about Medicare to be dangerous. As fate would have it, about three or four months into this new job, someone in the Agent Recruiter department got let go, opening a position where I’d be recruiting agents through the US to sell Genworth’s Medicare Supplement product. This position was a huge opportunity for me since I’d still have my same salary, but also, I’d get overrides on whatever my agents sold, which turned out to be some real money (at least to me at that point in life).

In the short run it was an opportunity to really improve my income, but in the long run I got to learn the Medicare business intimately and pick the brain of agents who were out there selling and making a living. I befriended many good people who were kind enough to tell me if I got my license, I might make a good agent myself one day.

Well under some initiative my bosses’ boss at Genworth had where we’d know what the agents we were recruiting were going through, my department of three (including me) were put into a week-long insurance school and then took our life and health license test to become licensed agents ourselves.

I passed and got my license in fall of 2008, which was fortuitous as when Genworth was undergoing financial strain and cost-cutting in January 2010, my entire department (again all 3 of us) was laid off. Eventually things got so bad for Genworth that they sold the whole Medicare Supplement division to Aetna. For the purposes of this story, I was unemployed that fateful day in 2010 with an uncertain future to say the least.

I had spoken to and theorized I could become an independent agent at some point, but I had just gotten married in May 2009, and we’d bought our first home in August of that year. My wife had a steady job and encouraged me, since I already had my license, to start talking to my agent buddies and figure out the best way to become an agent.

Quickly, I got licensed with as many Medicare companies as I could and began to buy leads. Due to all my prior experiences, it felt natural being a Medicare agent. Being a caddie and waiter taught me how to work with the public and many kinds of people, from many walks-of-life. Being an administrative assistant taught me how to do the basics of scheduling and how to act professionally. Working in advertising taught me the ins-and-outs of how to market myself. Being a handwriting expert taught me I could run one-man business and be a certified professional.  Finally, working as a direct agent recruiter put me in direct contact with the very people who were doing what I’ve been doing for the past 14 years and helped me save years of figuring out many things myself.

Combined with my determination to prove my former employers made a mistake, I committed myself to being the best Medicare agent I could be. The first 2 years were tough (remember that stat that said 92% of people in my industry quit in the first 24 months), but I hung in there and sold enough to get me to the next year until sometime in year 3 I caught a break and enrolled over 150 clients in one enrollment season. At that point I became established enough that I knew I’d be able to sustain myself enough to continue to do this.

Of all the jobs I’ve ever had, this is my favorite one. I have more control over my time and know that I’m truly helping people for a living. Like any profession it has it’s good points and bad points, but overall this one is the best combination of pay, job satisfaction, and autonomy. I don’t think most would glamorize or pick this line-of-work but in hindsight it took all the skills and previous experience of mine and combined it into the perfect role for me. As someone wiser than me put it: Joy isn’t getting everything you want, it’s enjoying what you create. On second thought, maybe I did come up with that one 😊!

Who would ever expect to go from this to a Medicare Advisor?!