9 Jobs That Were the Most Important in My Life

9 Jobs That Were the Most Important in My Life

Jobs picI’ve had many different jobs in my life. The estimated number I came up with is about 20 jobs that I’ve had in my life. Those are the jobs that had titles that I could remember. The real number is probably different.

Out of those 20 jobs, there were 9 jobs that were the most important for me in my life. There were various reasons for why these jobs were important. I’ll attempt to point out the lesson I learned from each job along the way.

The Inspiration

I didn’t come up with the idea for this post on my own. The inspiration came from Ty over at Get Rich Quickish, who wrote a post called 23 Side Hustles I’ve Done in My Life.

Ty wrote about all the side hustles in his life. I’m changing it up a bit to discuss the jobs in my life that were the most important to me. Call it a way to get to know me better, Brian the massive debt to mogul guy.

I wrote extensively about my very first job as a Paperboy, where you can learn all about my start in the working world.

9 Important Jobs

These jobs weren’t about pay, necessarily, though I will try to include what I remember about pay. The jobs are in chronological order. I tried to be concise, but…well, you’ll see. Here are the 9 most important jobs to me with some lessons learned from them…

1. Paperboy
I started as a paperboy in the working world, delivering newspapers daily to customers around my neighborhood. I rode my bike with a milk crate on the handlebars to make my deliveries. It was a cool setup and a great gig. I learned about the importance of customer service, having a daily responsibility, how to handle money, and that $30 can buy a lot of baseball cards.

I earned about $30 per week, from what I recall. That was a king’s ransom to me in those days.

2. Mini-Golf Attendant
The next job with importance for me was working at a miniature golf place as an attendant. I would work afternoons and evenings, running the place by myself as a young teenager. I basically played cashier and tried to make sure the customers behaved themselves. This was a small place behind a Taco Bell. I would buy a small soda at Taco Bell and refill it for free throughout the night.

The owner was a tough cookie. He was stingy and came across as a grumpy miser. I think he was just squeezing any cash out of the place he could before he retired. I would see him for about 10-20 minutes a day and he was rude and surly with paying customers. It was the most stressful part of the job, dealing with my boss. I never understood how he owned a business, or why.

I learned about working for a tough boss. I also learned about how to look at a business and seeing where it could be improved for the better. I kept running through my head the ways that I would invest in the place in order to make it better.

I only worked there for one summer (that was enough with this boss) and earned minimum wage, which was probably about $4 per hour back then. The bigger takeaway for me was the business sense that I developed.

3. Soccer Referee
I loved this job. I played soccer for years…started at about 5 years old and played up to the JV team in high school. I played for one coach who was also the referee coordinator for our league. When I was old enough, I went and started refereeing games for him.

I made $10 per game during the season and $5 per game during tournaments, where I would ref 4 or 5 games in a row. This wasn’t about the money, it was too much fun to think about money.

I enjoyed playing soccer and being a ref was cool at my age (early teens). I learned how to take charge in situations but also to blend in. A soccer referee is best when they are invisible. Make the calls as needed but quickly blend into the background, let the players be the highlight.

I learned to deal with tough players and parents, heated situations, fair play, following rules, and most importantly, showing confidence on a big stage. This was a stepping stone for me, giving me greater confidence during my awkward teenage years.

4. Busboy
This one was similar to being a paperboy, in a way. I worked at a busy restaurant in town, and worked my butt off for crappy pay. I hustled and worked hard, because that’s what I knew.

I was paid about $2 an hour plus tips. Really that means I was paid in tips, which came from a share of the waiters and waitresses I worked with on that night. They paid me at the end of each night. There were many nights where I felt I got stiffed by waitresses. But I learned from that…no pay meant slower hustle from me. There was one waiter who always paid me well, and his tables were cleared in seconds, ready for the next paying customers. There was one waitress who paid me crap, and her tables took much longer to clear off.

In the end, I only worked there for about 4 months because I was leaving for the Navy. I learned to work extra hard for those who tipped the best, just like being a paperboy.

5. Contractor Helper
I was delayed when I went to join the Navy, waiting out a simple medical issue. I had quit the busboy job and my parents suggested I find some work for the next 3 months. It was a good idea and lead me to my job as a contractor helper over the summer, working for my uncle and his contracting business.

Every day I put on a t-shirt, cutoff jean shorts, and a tool belt for this job. I would grab some coffee and breakfast and meet the guys before we split up the day’s jobs and jumped in a van headed to the job site (someone’s house). For some reason, this felt like freedom to me, like I was let out of school early with no other responsibilities for the day.

My uncle was a demanding boss, always pushing his crew for speed and quality. I humped lumber and tools, put up siding, helped frame rooms, cut and installed molding…any odd job they could quickly teach me to do, but it had to be done fast.

This is where I learned that time is money. I also learned the feeling of freedom in a job, something I had never experienced before (probably because I was too young). I was paid very well, in cash…probably a few hundred bucks a week for 12+ hour days.

6. Navy – From Enlisted Sailor to Naval Officer
There is a saying in the Marine Corps that every Marine is a rifleman, which means that Marines are trained to fight first and do everything else second. In the Navy we could probably say that every Sailor is a fire fighter, but I like to say that every Sailor is a janitor.

I have never cleaned things so much in my life, and I’m not talking about basic training where you scrub the floor with your toothbrush like in the movies. I’m talking about everywhere, all the time. As I got older, I understood the reason for all the cleaning. Fly in a Navy aircraft once and you will understand why you put so much faith and trust in your maintenance crew, trusting that they cleaned and maintained your equipment to the highest standards. Take a cruise on a ship full of old, antiquated equipment that still works somehow in the harsh elements of salt water and salt air that is constantly trying to degrade your equipment. You will be surrounded by amazing Sailors who keep this equipment working despite the tough conditions.

I got paid crap (seriously, the demands placed on our military volunteers is astounding but they are paid the equivalent of a high school dropout data-entry office drone), but I was too consumed to notice most of the time. I got to do some of the coolest stuff I could ever imagine…flew airplanes and helos, sailed in ships twice as old as me to far flung places, risked life and limb in countless scenarios, and worked with amazing people. I was like a kid in a candy store. And I only did it for 8 years.

It’s hard to call the Navy just one “job” because it meant so much to my life. I enlisted at 18, made it to an officer program, and finished serving as an officer where it was my privilege to lead some fine people. The Navy transformed me during my transformative years. The lessons are deeply ingrained and will never leave me. I am grateful for all that I learned and all that I gained from the Navy.

7. Bartender – Winery
This job was an eye opener to a whole new world for me. I stumbled into one of the most fun jobs I’ve ever had. In fact, I have to say this is my favorite job ever.

I worked at a small winery in Temecula, California…a tiny wine region but an awesome area. I worked as a bartender on the weekends, serving wine to big crowds from 9 to 5 for $12 per hour. Then I started doing event bartending at the winery, mostly weddings, for $15 per hour and late nights. We made tips as well, mostly on the wedding side. I enjoyed every minute and never really considered it “work.”

When I grew up, wine came in boxes and came out at parties. Anything in bottles was usually the beer in the cooler. In my 20s I drank beer, plain domestic yellow fizz. I don’t recall drinking wine, except maybe for special dinners at my in-laws house.

With that as my background, I still don’t know what drove me to apply and interview for a bartender job at a local winery, except that I was bored to tears with my regular job. I was interviewed by an older guy with a huge beard and a great laugh. Turns out he was a former Navy guy too and something about the way I smiled and laughed made him hire me. I never let him down.

I hustled hard at this job. I loved the people mostly, but also the work and the free wine education. I learned so much about wine, things I had no idea about. I got to talk with and entertain customers, most of whom were on vacation or taking a day excursion to wine country. These were the best people to talk to, it was so easy and laid back. Every so often you would get a few pompous, “I know more about wine than you” type of people, but I learned how to disarm them with my sarcastic humor.

One of the best things I learned about wine was that more expensive does NOT mean better wine. We tasted wine all the time. Sure we drank a lot of wine, but we mostly tasted it. I actually developed a wine preference…who knew? Every year the owners had a Christmas party at their house in the La Jolla hills for the winery staff. Mr. Owner was the wine guy and he would break out some of the most expensive bottles of wine I had ever seen, some over $100 per bottle. Then we would do these blind taste tests for 5 or 6 bottles of the same varietal (eg. Cabernet Sauvignon, Merlot, etc). There would be 10-15 of us tasting the wines and we would do a consensus ranking for which we thought were best. The funny thing is that we could always nail which ones were our wines, but we also rated the mid-price wines the highest. The high-price wines were almost always rated low. This taught me that there is great wine at $10-40 per bottle and $110 per bottle might be crappy wine. It’s all subjective, so follow your taste and not the price.

One last thing I learned is that it takes great beer to make great wine. Among the winemakers and other wine people that I worked with, I found that many enjoyed good craft beer. They opened up another world to me with great beers, too.

8. Blogger
Several years ago, I was interested in the idea of making money online, found Pat Flynn, and I was hooked. I started up a cycling blog because that was my passion at the time (still is in many ways). I called the blog I Wear Spandex and poked fun at myself.

I thought I would make money. I didn’t…well, not in any significant way. Enough to pay for web hosting and other expenses, but that was about it. But after a while, the money didn’t matter. I found a whole new outlet with writing and connecting with other like-minded people, many of whom live in other countries. I had more online friends who live in the United Kingdom than I had real friends at home.

I ran that cycling blog for about two and a half years and eventually got tired of trying to maintain it. I found that I was trying to keep up with the Joneses with my cycling, like the guys who ride 40 miles every day or the bike commuters who are hardcore, and I started losing my passion and desire for riding.

But I liked the idea of blogging. That’s where this blog came from…I had another burning desire to write about something and wanted to connect with a whole new segment of people. People who understand what I mean when I say that I obsess over spreadsheets or that I’m excited to pay down debt because it’s giving me more monthly cash flow or that I’m collecting dividend income every month and it’s growing.

So if some folks click on an affiliate link or an advertisement here or there, then great, but it’s not my driving force. I would rather that folks click on a link because it can help them like it helped me.

If you want to support the blog, click on the Amazon link when you are going there to buy stuff and I’ll collect that little “thanks for referring customers” from Amazon.

9. Real Estate Investor
My latest job is more of a vision of where I want to go…real estate investor. My research on investing, and specifically real estate investing, tells me that buy and hold investing in rental properties is the place to be. The advantages include monthly cash flow, price appreciation, tax benefits, and more. If done correctly with smart purchases, these investments can supplement and eventually replace my current income.

As I said, this is the vision. I jumped into real estate as a side gig when I started this blog and it was the reason that I was absent from the blog for so long. I was actively working to startup my real estate business with a specific kind of business called wholesaling.

I’ve learned that wholesaling is tough and takes a lot of active work. It’s enticing to many new real estate investors, like me, because the capital required to start is rather low. It’s not zero, as you may hear from many gurus, but it’s not too high.

I mothballed my wholesaling business for now because I could not keep up with the capital needs of the business with no revenue coming in. I have too much debt on the books to support it and decided to stop. I may come back to it, or I may just take the experience I learned and put that to use with buy and hold investing (buying rental properties).

I intend to invest in real estate as a supplement to my current stock market investing and peer-to-peer (P2P) investing. That way my investing is diversified into various vehicles.


Each job I have worked in my life has taught me lessons. Everything from customer service to efficiency to quality. The nine jobs I listed above were the most important in my life because they taught me the most lessons.

Ironically, those jobs did not pay well but they included the most fun I’ve had in the working world. In fact, those jobs were most of the lowest paying jobs I ever worked in my life. And that’s a big lesson right there…a higher salary doesn’t mean you will learn more or enjoy your job more.

I enjoyed this trip down memory lane and hope you have as well. Thanks for reading to this point and taking the time to learn more about me. For more background, you can visit my About Page where I ramble even more about who I am.

I wish you could have seen the smile on my face as I wrote this post. I truly enjoyed the jobs I wrote about and the time periods they represent in my life. I really want to continue seeking out that joy I found from these jobs and apply them to my present and future endeavors.

Now, leave a comment and tell me about your favorite job and some lessons you learned. Or write a blog post about your jobs and link to it in the comments so I can learn more about you.

As always, you can follow me on Twitter for more financial ramblings.

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  • Nice post! Right on about the busboy gig – I’ve been there. It’s amazing how much slower those low-tippers’ tables got bussed…!

    Favorite job? Well, they’re all good and bad. I ran my own consulting firm for a while before retiring, and if you’re interested, I recently wrote a post about a couple money-making lessons I learned doing it: http://www.financialibre.com/a-quiet-secret-for-getting-what-you-want/

    Thanks for the good read, and best of luck with the RE investing!

    • That consulting gig sounded fun, well from the perspective that you really seemed to enjoy it. The lessons learned were great, especially the whisper. I have to try that one.

      Thanks for the comments and for sharing the link.

  • That is a lot of jobs!! 🙂

    It’s funny how the lower-paying jobs are usually the ones you enjoy the most. I did one summer landscaping and thought it was fantastic. Although it paid well for a kid my age, it still wasn’t a ton of money. In the meantime, I was outdoors getting sun and exercise. And at the end of each long day, I would be too tired to spend any of the money I made.

    I used to think that I would be like Forrest Gump and just mow lawns when I retired.

    — Jim

    • I love the Forrest Gump reference. Can’t go wrong with that kind of thinking…work hard when you are younger, try everything until it works, live off the passive income when you are older, and mow lawns for free.

      I had a lot of fun running through the memory banks for this post, which is not something I do often. I’m present and future oriented. But I was surprised at how many fun jobs I’ve had over the years.

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About Brian Stephens

Brian is on a journey from massive debt to real estate mogul. Join him as he stumbles and fails on his way towards long term success. Debt isn't pretty and turning it around won't be either. His primary goal here is to tell the story and network with like minded people who want financial independence through real estate investing.

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