Great Jobs: What I've Learned from the Best Jobs I've Held

I realized this year that, having found my first job while still in high school, I have now been in the workforce for more than two decades—and fortunate enough to have been able to find and hold employment for most of that period. Since those first forays into the world of work, I have held—as anyone who has looked at my profile page here at Vault will know—a variety of jobs in different industries, across three continents. While most would not fall into the neat categories that firms typically look for as part of their hiring process (I managed to graduate from college without knowing what an internship was), all have taught me something that my life and current career would be significantly less rich without. 

In looking back at my "career", then, there have been periods where I've earned more money than I needed or thought I was worth, and other times where I struggled along on minimum wage. Similarly, there were times where I felt valued and motivated, and some jobs where simply showing up seemed to take a Herculean effort, never mind the hours spend performing mindless drudgery once I actually got there. And some jobs have run the gamut from being great one month to terrible just a short time later—and vice versa. 

Oddly, it's not always the "best" jobs that have been the most enjoyable—which is the measure that I'm going to focus on for this post. Here, then, are the 3 best jobs I've held to date*:

3. Freelance journalist

Uncertain pay that requires you to hustle and get in people's faces all day long, sometimes driving for miles to talk to someone who really doesn't want you to be there. Pitching ideas you care about all day long, only to find that the one person who wants your services needs you to cover a village meeting on zoning requirements that will run for four hours, with a flat fee of $40 for the article payable on publication. 

Sounds like a dream, right? 

And yet: for someone making the transition into the world of media, with no background in it, there really couldn't have been a better proving ground. Having suspected that I wanted to work in media, and having glamorized the idea of being a reporter thanks to the collected misrepresentations of the movie and TV industries, the life of a local freelancer set me straight about how grueling and humdrum that life could really be. But it also allowed me to do the one thing that so much career advice suggests, rightly or wrongly: follow my passion. And, while that passion turns out to have been more as a consumer than a producer of news, I gained valuable experience in everything from pitching ideas to interviewing to writing copy—all skills that I still use on a daily basis.

The best part: Seeing my words in print for the first time was great, but definitely overshadowed by the first time I heard "oh, I saw your piece in the paper" from a complete stranger.

2. Bowling alley employee

There are jobs that are great because of the growth opportunities they offer, or the salary, or the contacts. Then there are jobs that are just fun, despite not offering any of those benefits—a trait that is often consistent with jobs that we know we're going to be leaving behind at some point.  Sure: my stint working in a bowling alley in college involved a lot of smelly shoes, the occasional disgruntled customer, and being forced to entertain kids' parties on a regular basis dressed in a dog suit that looked like it hadn't been cleaned in a decade. But it was also a job that came with very few real responsibilities, the ability to help people enjoy themselves, and a crew of colleagues that had a similarly short-term outlook on the position, which made for a fun working environment, and plenty of after-hours fun. Not to mention all the free bowling we could handle.

The best part: Watch me clean up this split.

1. ESL teacher

I'll make no bones about it: I had no desire to be a teacher, and decided to teach English language because it was the only way I could afford to see the world after graduating college. Prior to setting foot in the classroom for the first time, I was terrified of speaking to groups of more than three or four people. My knowledge of grammar was often deficient to that of my students (and likely still is), and I didn't truly grasp the reasons why people wanted to learn my language, or how difficult it was to do so. 

And yet the time I spent as an English teacher—almost three years, total, in Eastern Europe and Asia—is one of the most rewarding periods in my career, and life, to date. While I was able to fulfill some of my travel-related goals, I learned more about the world from the people in my classrooms than I did in all the sights I saw or places I visited. I don’t know that I ever became much of a teacher, but I did learn to see people as individuals with distinct hopes, ambitions and motivations, and to begin to conquer my fear of talking to them in groups. I also learned that my instincts were mostly correct: that while I was happy teaching adults, I was not cut out to spend my life trying to control classrooms full of children. Most useful to me in my career since, however, was the lesson that, if you're spending the majority of time doing something you don't like, then the place you're doing it doesn't matter. That realization helped to shift my focus from following my passion for travel to one that I've already touched on: media.

The best part: That moment when you see a student grasping something you've taught, and knowing they'll never forget it.

*Note: present job excluded, because you don't always know what you've learned in a role until after you've left it. Also because my boss might be reading this! 

What are the best jobs you've had, and why? Let us know in the comments below, or on Facebook or Twitter.