The Long And Sometimes Windy Road To Financial Independence – Vol. 2

As promised, Mr. Mad Money Monster is stopping by today to share the next installment in his wildly entertaining trek towards financial independence. So sit back, take it easy, and enjoy the ride. Take it away, Mr. Mad Money Monster!

It would be interesting to see a financial blog dedicated to the amount of time we waste and squander.

I had a friend who once said we shouldn’t be born until we are 30 because it’s at that age that we actually start to do things that make sense. Well, for many of us anyway. It’s not a one size fits all axiom. But, I certainly would’ve benefited from a later birth, especially financially.

I’d love to see a blog dedicated to, “If I had a dime for every time…” or “If I knew then what I know now…” Wouldn’t that be an interesting theme? I think so.

Mindset Is Everything


In my previous post, I relayed the story about my mother’s never-endFinancial Independence | Financial Freedom | Financial Road | Frugality | Financial Journey via @MadMoneyMonstering quest for practical frugality without ever building real wealth. But she did invest. She invested everything in one basket. She invested everything she had in me and my brother.

The sentimental side of me still exists and I like to think she left me incredible wealth in all she taught me and in the memories she gave me. She invested into her children,  and it’s this kind of thinking that allows me to sleep better at night.

So we shift from my mother’s finances and my earlier childhood to my memorable and totally expensive teenage years. I often talk about how my mother stressed the importance of financial independence. In fact, you could say she harassed me, at least that’s how I felt as a kid.

The millennial generation gets a mostly undeserved rap for their excuses and reliance on parental support. The anxiety-ridden, coddled generation of basement dwellers has become a quick cliche. While it’s certainly not remotely true of the entire generation, my story stands far apart from any coddling or helicopter parenting.

Note: We love basement dwelling around here…as long as you’re paying down debt, planning your future, and building wealth. 

“If You Think For One Minute…”


“You better have money for car insurance,” my mother started harping around the dinner table by the time I was leaving eighth grade. “Don’t think you are going on our insurance because we can’t pay for that. So you better start working.” Once my freshman year started, it seemed like this talk was a nightly thing around the dinner table.

So, work I did. I worked as a lawn care kid, biking out to the wealthy, old-money neighborhoods beyond Glenbrook Golf Course. I mowed lawns, raked leaves, weeded beds and weed whacked. All at the strapping age of eleven. I brought the money home and handed it over to my mother. She put it away toward the omnipresent “car insurance fund.” This was 1981 and I wouldn’t be legally allowed to drive by myself until 1983.

I did yard work almost year-round and when the snow came I shoveled driveways by hand for sometimes a whopping five bucks a pop. All the money that came home was added to the insurance fund.

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Dating Is Expensive


Now, in between work and school, I had girlfriends. A lot of them. I discovered just how fun a pretty girl could be by eighth grade, and that meant dates. I had my first real date November 1980. I took a tall, blonde cutie in my eighth-grade class to see the Bob Newhart, Gilda Radner comedy, “First Family.” Before the main event, we were dropped off at the mall. I took her to a sumptuous meal of Sicilian pizza and soda at a mall restaurant, dropped some quarters at the Time Out video game arcade, and then got our tickets and popcorn. It was my first expensive make out session.

I don’t remember much about the movie.

However, my mother reminded me that I had a budget and that dates take away from what I could bank. She gave me that tacit look when the next insurance deposit was a little lighter. My first girlfriend also cost me a Christmas present, flowers, dance expenses, more movies tickets, and more trips to the mall food court.

All said I got through eighth grade without too much grief. I was working and the money was commensurate with my age. Ninth grade raised the stakes and the dinner convos turned toward “you better start thinking of a job upgrade” kind of context. “You can’t be putting away enough money on just lawn work. Start thinking about getting a real job!”

Young Financial Determination


phone - financial independence

My very own phone. It cost me a lot of money with long distance calls.

Toni was one of my close friends and one of the most admired of our school beauties. She was a teenage Cher, but with more attitude. Toni was a waitress at a local diner and she was also putting away money, only she was saving for an actual car, not just insurance. Damn…I didn’t think about that. I was focusing on the insurance but never gave serious thought to my own car. I just assumed I would drive one of my parents’ cars and pay my share of the insurance.

Toni did not think that way. She wanted her own car and she put in long hours at the diner starting at the age of 14. By our sophomore year, she had almost one thousand dollars for that car. That was really impressive for 1982. She got me a job as a dishwasher at the diner the summer of 1982. I hated it. I was in the back with guys decades older than I was. I was “the kid” and the only reason I was tolerated was that I had Toni’s seal of approval.

I kept my dishwashing job and still did yard work in the wealthier neighborhoods. The money increased but I was also dating more. The older I got the more complicated and expensive the dates got. I started upgrading my appearance and that meant haircuts with styling. And that meant tipping the stylist. Toni took me to the mall and told the stylist to give me the feathered hairstyle. It was so cool. But, that also meant hair care products and, of course, it took another bite out of what I was able to give to my mom.

“You’re going to have to do better,” I was told at my nightly dinner table grilling. “You’re going to fall short, and if you think for one second we are paying for your insurance you got another thing coming.  Do you realize what it’s going to do to our rate to add you to our policy?!”

The nightly grilling was a lot to take. I became anxious about money and still feel residual effects today.

Do You Want Fries With That?


I eventually left the diner, disappointing Toni, and did what I will bet a number of you reading this have done–I went to work at McDonald’s. Spring, 1983, I got the polyester brown uniform and paper crew hat and I became part of the Golden Arches Empire. Do you want fries with that?

It’s here that I have to state that I always loved movies. They were my escape from some pretty heavy unpleasantness in my early childhood. I was eight years old when I saw the original “Jaws” in 1975 and I left that theater knowing I wanted to make movies as a career. The mall across the highway from McDonald’s had a Music Makers theater multiplex. It had five theaters and it was the social hub of my town. That’s where I really wanted to be.

“You will not quit McDonald’s until you have another job to replace it,” my mother declared after I floated the idea of working at the theater one night at the dinner table. “You will have your learner’s permit in September and you’re thinking of quitting your job NOW?” It was summer 1983 and I was turning 16 in September in my junior year.

My very first work day at McDonald’s started at 4 AM. I got up, packed my uniform in my backpack and I biked the almost ten miles to the restaurant up on route 611. It was dark and early so the traffic along Route 209 wasn’t so bad.

When I arrived, one of the managers, had a giant blacktop brush and a number of parking lot sealer buckets waiting for me. My job was to seal the parking lot before the breakfast crowd started to arrive. I had to start with the drive-through and work my way out. I was in a T-shirt and shorts and by the time noon crept up I was speckled with black sealer on my legs that started to burn in the afternoon sun.

It went downhill from there. I worked with one guy who would spit on special drive-through orders no matter how many times I reported it. I biked to and from work almost every shift. I took my official corporate check home and signed it over to my mom. I did have one benefit–my meals were free, and that cut down on dating expenses.

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Dating Is Still Expensive


Financial Independence | Financial Freedom | Financial Road | Frugality | Financial Journey via @MadMoneyMonsterThrough all my high school adventures and part-time jobs, I continued to date. And it never got cheaper. I eventually broke up with a girl who lived about thirty miles from me. Aside from our expensive dates, phone calls were long distance back then and my mother saw our phone bill skyrocket during that love affair.

Our phone romances were often interrupted by my mom or dad picking up an extension and reminding me it was time to “wind it up.” That set me back sometimes 40 bucks a month, with one record bill hitting 80 dollars. I had to hand over two paychecks to cover that bill. I needed to make more money. My lifestyle was inflating before my very eyes. My only solution was to make more money.

One afternoon lunch break served as an exploratory mission to the movie theater across the highway. I walked over, went to the box office, asked for an application and filled it out. What the hell, I had to try, right? It was my lucky day, the cynical, sarcastic manager came down from his upstairs office and asked me when I could start. “Right away,” I replied.

He asked if I could work weekends and even holidays, including Christmas and if I was 16. I lied and said yes.


Switching Careers


The money was better. Free movies. Free movie posters. Most of all it was a social upgrade. A mall job was cool. I worked hard between my sophomore and junior year to totally revamp my image. My social makeover resulted in my election as class president and THAT is a whole other story on finances and wealth building for another time.

The whole thing was serendipitous. It started to rain while I interviewed for my theater job. When I got back to McDonald’s the rain brought several buses in for feeding. All hell had broken loose and I was screamed at as soon as I punched back in. I manned the ketchup and mustard squirting caulk guns. The assistant, polyester-suited manager snatched one of the guns from me and showed me how it was done. I was just too damned slow, she told me.

I looked at her frenzy in amazement. And laughed. This was so stupid. She flipped and asked me what was so funny, didn’t I see all those people out there waiting to be fed? “They don’t look like they’re starving to me,” I flipped back. I took off my hat, dropped it to the floor and walked out. I quit. I biked home in the rain. McDonald’s was the only job I ever walked out of.

“You did what?!” my mother asked. I repeated that I just got hired at the mall movie theater and that I started in a few days, that Friday in fact. It was a no lose situation. “You better hope so,” she huffed. “Because you’re turning 16 in less than two months and if you think for one…”

Almost Sweet 16


birthday present - financial independence

My sweet birthday ride.

I started at the theater that Friday afternoon. I filled out my tax forms and other various paperwork, was shown around the projection booth, met the other employees, and, life was good. Just before the end of my matinee shift, the boss asked to see me. “Have a seat,” he said with his cigarette dangling over his straggly beard. “We have a problem.”

I was only 15 years old. Why didn’t I disclose that? Why did I lie? I was turning 16 in a few weeks and didn’t think it mattered. It did. He liked me and I made a good impression, aside from being a liar. He made me a deal, he would hold my job and I could return to work after my 16th birthday.

I felt acid reek into my belly. I felt like I had been roundhouse kicked in the gut.  My last McDonald’s paycheck was coming, but my mom had asked that morning, “when do you get paid from the theater?”

“After your birthday?!” she freaked. I told her it was a paperwork issue. What I didn’t tell her was that I lied to the manager. I told her I still had my last check from McDonald’s and that it was only a few weeks between paydays. My plan was to make up for it with extra lawn work and babysitting for a lady down the road. I did whatever it took. Even calling up old yard clients and asked if they needed anything extra to be done. I cleaned rain gutters, sealed more driveways (they were a lot smaller than the McDonald’s parking lot) and I babysat almost every weekend for the rest of the summer. She accepted my efforts.

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Happy Sweet 16!


I turned 16 years old that September. I was a healthy, good-looking teen and the president of his class. My parents surprised me with my own car. My biological father restored an old 1975 Ford Maverick. It was maroon and black, hood scoop and jacked up with mag wheels. It was badass and it was mine.

My friend Toni bought her very own car with her very own money. She had a choice between a trip to France with the high school French class or the car. She bought a gold, 1974 Datsun 280-Z. Sadly, it would prove to be a fateful purchase.

My theater boss kept his word and I returned to the theater after I became of age. As expected, my mother sat down with me and showed me the insurance paperwork. She had me sit with her at our kitchen table as she filled out the forms to add me to their policy. She explained the financial breakdowns to me and where my money was going. And, she accounted for every dime.

Then came a new speech.

“Don’t Be Stupid”


Mad Money Cat - financial independence

Mad Money Cat makes his own money. Passive money. #smartinvestor

“You’re 16 now. You have a lot of friends and you’re a social boy. You have some friends who like to raise a little bit of hell and I know you do, too.” We sat across from each other at the kitchen table. Just me and her. “You have your permit and in a few weeks, you’ll have your license. All I ask is never drive drunk. Call me from anywhere if you can’t drive. Don’t get into a car with someone who has been drinking or doing anything else. I would rather get a call from you at four in the morning than get the call to come to the morgue to identify your body.”

All those years of incessant pressure to work and perform to make money. Spending hot summer days landscaping, raking, washing dishes, flipping burgers…and it all came down to that moment. She was telling me to not be stupid.

I was her investment. She wasn’t diversified. She invested all she had into my brother and me. She was watching us mature and now she wanted to see what dividends we would bring.

Present Day


Fast forward to present day, here I am on the path to financial independence with my own family. My mother would be so proud to see how her no-nonsense teachings gave me the skills and discipline I need to focus on such a long-term financial goal. And even though she never built massive wealth, she taught me the importance of frugality and money management. She also taught me that hard work pays off.

Did I squander and waste my time and money during my teenage years? Sure. Did I also learn really valuable lessons? Sure. I learned it took time and energy to make money and so very little effort to spend it. I learned that lifestyle inflation is real and can happen at a very young age. And I also learned that meeting financial obligations and goals is a priority above all the fun stuff. So for that, thank you, Mom.

So, if I knew then what I know now…I’d already be rich! But, I’m not ashamed of my financial story and the journey is supposed to be half the fun anyway. And we’re definitely enjoying the journey.

What are your thoughts on no-nonsense parenting when it comes to frugality and money management? What have your parents taught you? Or, what are you teaching your kids?






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  • Tony Nov 4, 2017, 1:41 pm

    We were raised to be independent and were taught the value of money frequently and consistently.

    We are going to teach our kids money concepts early, starting at about the age of 3. Kids can learn early and it helps them to manage their money later in life.

    • Mad Money Monster Nov 4, 2017, 2:00 pm

      I couldn’t agree with you more. I started teaching my daughter about money at about the age of 3, too. I often joke that I was teaching her about saving before she could put two sentences together. It sounds like you have your parenting act together 😉

  • Steve Poling Oct 30, 2017, 3:40 pm

    i have a couple grown kids who are working out. my daughter turned me onto FIRE blogs and my son has an 80% debt-service rate. at dinner table from an early age, i was wont to ask them, “What did you do to stay off welfare today?”

    • Mad Money Monster Oct 30, 2017, 4:46 pm

      Sounds like you taught your children what they needed to know to be successful with money as adults. Congrats!

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