The Bootstrap Fallacy: Inspiration for “Green-Lights”

It happened a couple of times. The first time was annoying. The second time was downright frustrating.


Do you travel the same way to work every day? My school is only about six miles from my home. There are a couple of ways to get there. While I vary my route from time to time, no matter the path, there will be several intersections with traffic lights.

As I reflect on it, there are a few that I can count on turning red, but those I have devised either turning right or checking email on my phone. Eliminating down time, I don’t feel a hint of pain, waiting for the light to turn. One or two pauses in the hurry to work doesn’t hurt. For the most part, I am usually traveling in the direction that affords most traffic lights to be green, most of the time. 

One morning in the spring of 2019, I was on my way to work, and every single traffic light was turning red right just as I got to it. Was someone messing with me? Although I had plenty of time to get to school without being late, the annoyance of being held up was acute. Having already checked my email (several times), I felt the vacuum of down time; wasted time; robbed time! These lights were stealing my productivity from me. Just the kind of thing to make me see red.

It wasn’t more than a couple of weeks later that the same thing happened again! I’ve been driving these roads for nine years, and never had this many red lights to sit through. What was going on? It was like the planets aligned, and they hated me! 

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What if your whole life felt like one red light after another?

During one of these red lights, it hit me: This feeling of frustration is what some people feel all of the time! While I generally expect things to go just fine for me, there are people who experience trials and conflict at every single intersection of life. This got me thinking about how ignorant people like me are. I use the word ignorant in the literal, “Not knowing” sense. And, I am the guy coasting down the green-lit road. What if this tiny feeling of frustration that I experienced for only a moment, and then it was over, and I had a great day, was a prolonged, every-single-day, all-day-long feeling?

What if I teach students who experience this feeling? Everything they try to do is wrong. Even if it isn’t true, they might feel like they can ONLY make mistakes! What if they come from a household where nothing is ever good enough? What about the families who can’t get a break? Would a child that comes to school from such a family see life differently than one whose family is financially successful? I think so. What about health?

I almost understood my ignorance once before. When I was in college, I ran my own College Pro Painting business, and it was extremely successful. I won a medal, even… “Rookie of the Year”! 

I remember this like it was yesterday: Before winning the medal, during the height of my most successful time of the summer, when I had several crews pumping out high-quality, prosperous production, I was finishing up the evening’s estimates and feeling good about landing several of them. A couple realizations swept over me. 

The first one came from my reflecting on all that I had done. The summer before this one I had risen from a first-time painter to goal-driven, successful foreman on a painting crew. My leadership was so powerful that I pushed my tiny crew of three to shatter our manager’s expectations time and time again; To the point where he practically begged his boss to interview me for a managerial position the next year.

This boss did give me a go. The interview process was severe, but I got hired. Next, I underwent several weekend training sessions that taught me how to run my own business. 

Now, I was driving around an old Dodge cargo van that I had paid for with my own money; money that I had gotten as deposits on painting work that would be completed that summer. This was my first vehicle! Before beginning the marketing season, that spring, I didn’t have more than a couple hundred dollars in my bank account. I was selling clothing at a retail store in the King of Prussia Mall a couple times a week for minimum wage, plus commission that barely covered my travel expenses. 

This was my junior year of college. I was 20 years old. I had been dating a girl whom I whole-heartedly expected to marry for about a year and a half. The week before finals she dumped me. She did NOT say, “It isn’t you; it’s me.” She had been preparing to tour with a drama team during the summer that I would be pioneering this painting business. The leader of that team was very funny, popular, and attractive. “Bye, Matt.” 

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This devastated me. I don’t remember if it came before or after the breakup, but at some point this girl had said to me, “I’m afraid you won’t be successful.” Where this came from, I don’t have a clue. I had hit the ground running, and HAD already experienced quite a bit of success, booking more work early on than anyone else in the district.

Being dumped made it pretty awkward to borrow my ex’s car to do estimates. I began borrowing a friend’s old jalopy. Uncle Buck’s car had nothing on this rolling, sputtering, brown boat of a car! But, this did not dissuade customers from agreeing to have me and my painting crews paint the outside of their houses! Eventually, I saved up enough in deposits to buy my van. I used deposit money to buy painting equipment and put advertisements for college students looking for summer work in the local newspapers. (They were paper back then!) Deposit money was used to pay for direct mailing that the corporate painting umbrella company College Pro Painting put together and mailed for me. All I had to do was tell the company how many bundles and where to send them, then pay for it. 

I followed College Pro Painting’s training to a T, and added my own passion, coupled with persistent energy. It proved to be a recipe for success. In the afternoon, after classes, I would drive over to my “turf” and go door to door, asking people if they wanted a free estimate for exterior painting or “Would you mind if I placed a lawn sign on your lawn?” My pitch was simple and sincere: “Hi, my name is Matt, and I’m a college student trying to start my own painting business in your town.” This message was incredibly well-received. I was well-received. I was able to place lawn signs on the lawns of houses covered in vinyl siding that sat on main thoroughfares. Also, I was able to conduct and land all kinds of jobs. I hustled. I took any job; none was too small or big or difficult or easy. 

One last thing before I move on from this success-story: Two of the 20 or so people that I hired to work for me during that award-winning summer were college students who had painted the year before. Not only that, but they had worked for a College Pro Painting manager like me, so they knew the ropes. These two proved to be the spine of my business. The one with a little more spunk was made foreman of the crew, and I left his buddy on his crew. This last act was probably one of the best decisions I made that summer. You’d think that splitting them up, and making each a foreman of competing crews might have been more profitable. The camaraderie these two shared helped them absolutely love what they did that summer… That and the totally awesome bonus money that they earned! 

So, I’m sitting in my van in the middle of my successful summer thinking back on my humble beginnings, tragic rejection, and hard work. I’m finally feeling the emotional fruits of all of this success, and I think to myself…

If I can do this, anyone can. Why don’t more people start their own business and experience success the way I did?

Typing this thought makes me cough inside; Like, I feel like I am punching myself in the gut! My only consolation is the next thought came fast:

Wait a minute. NOT everyone CAN do this. 

When I thought this last idea, it was not with hubris. It was a realization that I was lucky. If I had bought this van I sat in with “my own money”, it was only after having been trained in how to acquire that money. Also, the people who entrusted this money to me believed that I would provide the painting that I promised. Would they trust anyone? No. 

Part of my drive that summer was due to proving my ex-girlfriend’s fears wrong. Does everyone have that going for them? Would I wish those painful feelings onto other people? Of course not.

Sure, the area where I ran my painting business was what the business called a “Pioneer Turf”, in that no College Pro Painting manager had worked there before, but College Pro Painting was far from a pioneer business! My customers had the assurance of me working for a company that had successfully trained and operated student-managed painting businesses for over 25 years! 

Lastly, having two guys who already knew how to paint and how the College Pro Painting system worked was gold! While they produced work, I trained other painters. I had them train painters. Success bred success, and everyone was happy to be working on a winning team.

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I may have had a couple of hiccups along the way, but my van and I had driven through green light after green light, picking up speed as we went.

Years after this college experience I heard the phrase “Pick yourself up by your bootstraps”. It seemed to make sense. Take what you’ve been given and make something of yourself. At the time, that’s what I thought I’d done. I did not understand that other people and situations and unearned personal talents/abilities were like a jetpack lifting me the moment I touched my boots

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Where are the bootstraps?

I’ve done a little research on this phrase. It is more than just a little ironic. It  was used as a put down, suggesting that someone was delusional, for how could you lift yourself from yourself? (Alvarez, 2015) Not only was it an insult, but originally to use the term “Bootstrapping” was to make fun of people who thought that others could be successful from nothing! 

I don’t think that it is classy to make fun of anyone. I will say that I felt a little silly, when I realized my own flawed thinking about personal success. When I sat through one of several red lights on my way to work that fateful morning mentioned at the beginning of this blog, all of this flooded my psyche. If it were even possible to “Lift yourself up by your bootstraps,” some people’s straps snap. Other people don’t even have boots! This got me thinking about a better metaphor: Traffic lights. 

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What have been your experiences with privilege and inequity?

Now that you know where the ideas for “Green Lights” came from, how might it be interpreted? What parallels to teaching and life can you make? Who is sitting at red lights? What can be done to help them? Will it hurt the person driving down the main road with all of the green lights? Is that appropriate? Who is the jaywalker? Who was driving the Ford Crown Vic that had an accident? The elderly person? I challenge you to look for literary easter eggs. What does it mean to you?

Sources:

Alvarez, S. (2015, April 7). Where does the phrase “pull yourself up by your bootstraps” actually come from? Retrieved January 5, 2020, from https://stateofopportunity.michiganradio.org/post/where-does-phrase-pull-yourself-your-bootstraps-actually-come.