Seven Lessons I Learned from Working an Assortment of Odd Jobs

I’ve worked in an office for over a decade, but I learned far more when I was being paid by the hour


Next month, I will enter my third year at my (mostly) dream job in finance for a Fortune 100 company. The path I took to get here was anything but the fast track. I paid my dues in offices and organizations with much less glamour and money while also working towards an MBA, but I always noticed that it was my experiences in the odd jobs before my career in corporate finance — and the intangibles that I picked up along the way — that really propelled me here.

From May, 1996, when I received my first paycheck as a 16 year-old, until October 2002 when I fell into my first gig in finance, I worked an assortment of jobs at a hodgepodge of places: a miniature golf course, a bank, an ice delivery truck, an SAT prep organization, a college admissions office as a tour guide, even a sidewalk hot dog cart. With the benefit of hindsight and age — I turn 35 this weekend — I can look back and appreciate these jobs and what they instilled in me, even if I never want to work at any of them ever again.

7. Unofficial Career Planning

Like apprenticeship and collaboration, most networking and career planning comes about informally and organically. I was able to meet a wide range of people from a variety of backgrounds — including several multimillionaires — simply by showing up to work and interacting with those around me. Some of these conversations led to something tangible like a reference or letter of recommendation, but more often they showed me different career paths and helped me to realize what I did — and did not — want to do, much more than any classroom lesson. I can’t count the number of times someone said to me, “I wish I had stayed in school,” or “Don’t make the mistakes I made.” One of the guys with whom I used to ride in the truck would question me about my college experience incessantly, wondering if it were like the way it is portrayed in movies and he would often wistfully say, “I wish I had been able to go to college,” before climbing out of the cab and hauling a hand truck around. I was never close to dropping out of school, but those moments helped remind me why I was in school and kept me focused on graduating so that I wouldn’t have to go back to the truck. (In fairness, I was lucky that the recession and student loan crisis has not affected me all that much. Someone else may have a different experience.)

6. There are many forms of payment

We have not lived in an actual bartering system for centuries, but that doesn’t mean that every ounce of work is rewarded with only currency. We work to make money and we use money to buy things, so why not bypass the middle step and work to obtain things? This wasn’t the plan — I almost always worked for a paycheck — but there were some nice side benefits. At the hot dog cart, I was paid in meatball and cheese sandwiches and soft pretzels in lieu of cash; as a deliveryman, the nicer guys on our route offered us free drinks; and the mini-golf course allowed myself and a guest to play for free, saving me a few bucks on many dates and platonic outings.

Even today, my salary does not encompass all of the rewards that I bring home on an annual basis. When asked if I would ever leave finance to write full-time, I say that not only do I need a much, much wider readership, but that there aren’t that many writers that bring home what I do, particularly when one includes healthcare costs, 401(k) matches, profit sharing, product discounts, and tuition reimbursement. My respectable salary is x, but my full compensation is x + y + z. Remembering that helps me stay both grounded and realistic.

5. Find where your personal line is drawn

For several years, I taught an SAT prep course to mostly disinterested and snotty high school students. I was not very good at it. Actually, I’m pretty sure I was awful. Anyway, during my training to become an instructor, one of the directives was as follows: when asked what you scored on the SAT, always answer “1600.” (This was before the grading was changed to accommodate whiny millennials. Kidding.) They told us that it would help our credibility as instructors and it would give them something to strive for.

I understand the thinking behind this, but it was still terrible advice, not only because no one believed us, but because it was so disingenuous. Obviously, a Saturday morning class and a book of practice tests alone can’t get you a perfect score and the idea that I would claim that they could actually turned me off from the entire enterprise. A major part of capitalism involves lying, or at least exaggerating. I get that and I’ve been a part of it in a variety of ways throughout my career. I know that every organization needs to market itself and much of that marketing involves overinflating the product or service being pushed, but students are not merchandise and teaching is not like other occupations. At least, it shouldn’t be. Selling an impossible dream to kids that just wanted a better test score so that they could get into a decent college still doesn’t sit right with me, even after more than a decade.

4. Don’t judge anyone’s occupation

Growing up in the outer suburbs in a large house in which my father commuted into the city on a train every day Mad Men-style, I was a little bit naive about how things worked in the real world. I wasn’t rich and the majority of my friends’ parents had incomes that were comparable or slightly below that of my own folks, but early on I developed a kind of disdain for those that worked in blue-collar or physically demanding jobs. This was not instilled in me by my mother and father. I don’t know where or how I came to this notion — perhaps it was just the general atmosphere of the greed of the Reagan ‘80s — but it took root early and informed many of my views and, dare I say, prejudices as an adolescent. I wasn’t rude or insulting to these people, but I did think I was somehow above them. I see that clearly now.

It’s a cliché, but driving a delivery truck and fetching drinks for my classmates gave me the perspective that I had lacked as a kid. These jobs were not only hard, but many people were doing them not out of laziness or incompetence, but more because of a lack of opportunity that I had not only been given, but that I had also taken for granted. Recently, though, times have started to change again. My friends that are plumbers and painters are doing better than many of my peers that wear business casual and carry a briefcase every day, probably because, like me, they can’t really fix much around the house. Ironically, as Americans steadily moved into cubicles and became overeducated, the need for handymen and contractors has increased. In this world of high unemployment and globalization, there’s no job that is too demeaning, particularly when they’re more lucrative and important than many white-collar jobs.

3. Never leave on bad terms

This should go without saying, but I’ll say it anyway. You never know what will or will not happen in the future and while you may be positive that you’re walking out a job for the last time, there’s always a possibility that the future is not as kind as you had hoped (or expected). After all, the company you work for is not your friend and you may need to reverse course and come back to your old employer asking for a job. The way you exited is an important factor in whether you can return, almost as important as how good you were at the job itself.

Over my senior year winter break, I went back to slinging ice for a few weeks to give me a little more spending money for my final semester. On my last day before going back to school, I walked into the office of the dispatcher — the guy that planned every truck’s route and basically ran the day-to-day operations — and thanked him for the opportunity, something I always did before leaving. “Will we see you in the spring?” he asked. I responded by telling him that I was going to Cancun for spring break and after that I would be graduating, so this would be my last time climbing in and out of a truck. He wished me well and then mentioned that I was always welcome to return at any time. I told him I appreciated that, but walked out positive that I would never be back.

Of course, I enjoyed every second of senior year, never once giving thought to what I would do for work after graduation. I just knew someone with vision would hire me despite my lack of internship or apparent desire. I spent much of the summer in Portland, Oregon and came home to unemployment. After a few days of moping and blindly applying for jobs, I walked back into that dispatcher’s office and asked to come back. He said yes without hesitation. That job kept me afloat for a few weeks and, even after I was able to snag a temp job in an office in Center City, Philadelphia, I kept chucking ice on Saturdays. I did it for a little extra scratch, sure, but I think I also did it because I know they needed good people and since they had been so good to me, I wanted to help them out as well.

2. The customer is (almost) always an asshole

Mallrats (1995)

Kevin Smith, a man that worked in a convenience and video rental store, knew what he was talking about. Working with the public is a thankless endeavor that often involves getting yelled at for something with which you had nothing to do and having people treat you like their servants because they hate their lives and need to take it out on someone. Bruce Wayne doesn’t treat Alfred nearly as badly as most people treat waiters and cashiers.

My mother worked in a clothing store for a time and I remember going to visit her and watching as she had to constantly refold and stack clothes that customers had picked up, looked at, and then tossed back on the shelf with no regard or thought. It was a Sisyphean task and I remember feeling so badly for her. This was the woman that had raised me, and now she was forced to stand on her feet all day and straighten up after sloppy strangers. It made me both sad and angry.

I have my own stories. I’ve been yelled at and cursed out by customers for such egregious acts as accidentally handing someone the wrong color golf ball, not filling the ice box quickly enough, and not cleaning the entire campus thoroughly before a large tour.

There are exceptions, of course. As a bank teller, my drawer came up $400 short one day and I had no clue what happened. The head teller and I did everything we could to try and track it down, but it was gone. I felt horrible. The bank wasn’t going to collapse because of it and it’s not like it came out of my paycheck, but I was still responsible. A few days later, a woman walked up to me and laid four one-hundred bills down and said, “You gave me these by accident.” They were new bills so they were stuck to the other bills I had given her — we weren’t allowed to crinkle them in an attempt to separate them because some customers want crisp bills. She didn’t have to do that. She could have kept that money and no one would have ever known.

Not all customers are assholes. Just the vast majority of them.

1. The job could always be worse

There are few things worse than unemployment and, as I’ve said, I’ll never again look down on another’s line of work, not only because we all need to make a living, but because there are hundreds of jobs that so many of us don’t want to do. I know this because I’ve done a few of them. I delivered ice in the snow and literally worked for food and tried to convince kids that one test really could affect their futures. Those weren’t the worst, though. At the miniature golf course, those on the closing shift had an assortment of duties to do including making sure no teenagers were still on the course, shutting down the batting cages, emptying the trash, and cleaning the hot dog rollers, but they paled in comparison to cleaning the bathrooms. Cleaning a public restroom at the end of a hot summer day is like…………well, I can’t even come up with a simile. It’s awful. However, it also gives you some much needed perspective. Other tasks, once thought to be excruciating, were now manageable and we were eager to do them if only to avoid bathroom duty.

Today, some of the people around me sit in their ergonomically-designed chairs in our temperature-controlled office and carp about how tough they have it. Yes, there are stressful days and I’ve gone home with a splitting headache after getting chewed out by an executive, but I always try to remember how much worse it could be and how lucky I am to have the career I have and all of the things that it has allowed me to do and buy. Interestingly, I don’t think I would have this job — and I certainly wouldn’t be nearly as good at it — if I hadn’t had so many experiences in so many peculiar places of employment. They were disparate and seemed to have little in common, but they all taught me one thing above all others:

It could be so much worse.


Christopher Pierznik is the author of nine books, all of which can be purchased in Paperback and Kindle. He has written for a variety of other sites and works in finance. You can like his Facebook page here and follow him on Twitter here.