J is for Jobs

Inspiration for this post came from J. Money’s list of jobs on his blog at Budgets Are Sexy. You can read all about it here. With his permission, we’ve done the same. Simply listing the jobs we have had during our not so illustrious careers. I will say, I think OG1 is selling his experience a bit short. His stint in the Merchant Marines sent him all over the world, setting foot in every continent except South America and Antarctica. He has some crazy stories that always captivate in whatever social scene he’s part of.

OG2: Here’s my list of jobs

  1. Paper route (12-13 yo, no idea what I made. It was a unique route through a series of 3 story apartment complexes. I would simply through the paper up to the 2nd or 3rd floors)
  2. Little Caesars Pizza (14yo, $3.35/hr – child labor laws restricted when I could work and what I could touch. The manager paid no attention to that. Best perk? Free pizza every shift with piles of toppings)
  3. Hardee’s (cook)
  4. Harris Teeter (cashier)
  5. Winn Dixie (bagger)
  6. Movie Theater (usher)
  7. Kroger (3rd shift shelf stocker – allowed me to see my girlfriend all day, have her home before my 11pm shift started)
  8. Intramural referee in college
  9. Blockbuster (what are VHS tapes?)
  10. 3 jobs at the same time – Construction ($5/hr built wood fences mainly, framed a few houses)/ Doorman, bouncer at a couple of nightclubs while in college / Bookie – for 1 football/basketball season
  11. Side Hustle – wrote papers for other students
  12. Dishwasher – short stint b/c I didn’t have a car and it was hard to get to. It was good because I could eat well… yes, food from unfinished dinners.
  13. 2 jobs at the same time – Day shift worked landscaping at a wastewater treatment facility/night shift worked a stand up forklift in a warehouse)
  14. Bartender at Westin in Hilton Head SC
  15. Dry Cleaners – People actually brought in pants with poop in them
  16. Call center catalog order taker for art supply company
  17. Landscaping
  18. Waiter at Fondue restaurant (both in Raleigh NC, then Boca Raton FL)
  19. Salesman at Brooks Brothers on Worth Ave Palm Beach FL (it’s Rodeo Drive with an ocean)
  20. 2 jobs (moved to Northern VA to get serious about careers)- Data Entry during the week for a shady mortgage company charging 25% interest, desk check-in person at health club (pay sucked, but it was a free gym)
  21. Data Entry for startup telecom company, Teligent (no longer exists)
  22. Programming  (turned previous role into IT job at same company – started at $30k in data entry, up to $40k in 2 years)
  23. Programming (contractor for Nextel – I literally walked across the street from one company to the next, doubling my salary to $80k)
  24. Programming Consultant (traveled by train every week to Philly, NY, Boston)
  25. Programming to Management at current company since 2001 (six figure salary)

**I’m sure I’m forgetting some short stint jobs and I didn’t include any one off/single day jobs.


Interestingly enough, job #14 is the one I’m most fond of. Up until that point, I never had excess cash. I was clearing about $1k/week and actually had money after bills. I bought my first tv and vcr. The hours were 9-5pm at a pool/beach bar. The scenery was fantastic 😉 and the vibe was nothing but fun. I had my nights free to go out and party, eat, you name it. It was a great time of my life, all the while doing it with my girlfriend (future wife). During this time we got engaged, took road trips to Disney World, Charleston, Savannah, Atlanta, to name a few. Since the bills were paid, it was the first time in my life I wasn’t concerned about what the next day was going to bring. Honestly, it was the start of a blessed life. Largely in part because of my wife being in my life. Job #19 wasn’t as lucrative, but my fiance and I drove A1A along the ocean 5 days a week and ate lunch together on the beach. Fun times… but we were broker than broke. The ‘real’ jobs started shortly after.


Thus, starting with job #2, I’ve been working for 33 years. I’m glad I can call it quits in 2026.

OG 1 here…and today the conversation seems to be on how we got to where we are today.  Work is where we trade our time for money and FI is where we get our money to help us buy our time back!

It was fun to reflect on all the different jobs I have had.  I think my work life followed a path that many would find familiar and perhaps younger people can take heart in the understanding of what is presented below.  You are on a path and your first experiences do not define the totality of your life. The shitty jobs can prepare and inspire your future.


In somewhat chronological order, these are the jobs I have had.  I started with the paper route and mowing lawns when I was eleven or twelve.  Only two of the jobs paid ‘well’ at $12 per hour while the bulk of them all paid between $5 and $7 dollars per hour.  I saved, but never seemed to amass more than a couple thousand dollars. Life until age 29 was a constant swing between having something and having nothing.

It was obvious early on that I had little ability to move into a good paying job without a degree.  Locally, the power plants were considered great jobs and one way to get in was through a program at the local technical college with a 2-yr program in Nuclear Engineering Technology.  Typically, the program was filled by graduating high school students that qualified for a full scholarship and graduating led directly to a job. Only two students, myself and another guy looking for a better future, were admitted outside of the scholarship program…I don’t recall ever meeting another graduate that came from outside the formal program. Real disappointment came when, even after graduating with honors, we were unable to move into jobs…openings were reserved for the scholarship students.

It took nearly a decade of miserable jobs to enable enough schooling for a bachelor’s degree and, funny enough, I was able to land a job at the power plant almost on accident.  I left school in my last semester to get to work and I was able to complete my degree while employed. I am still at that job and looking forward to retirement several years from now.  Looking back, I am glad for the experience of many of the shitty jobs. In some, I gained real skills, in others I simply gained a solid conviction that I needed to do something else for a living.  My favorite experiences came from my time in the Merchant Marines. I will be telling those stories for the rest of my life. That said, the ordinariness of my career has allowed a great quality of life for my family and I’m grateful.  

These are the jobs that built my life.  How did you build yours?

Newspaper route

Mowing lawns

Farm hand

Lawn care


Retail (knife store)

Housing construction

Ice Cream man



Laundry maintenance worker

Odd Jobs (daywork, whatever came along)

Merchant Marines

Retail security

Private security

River tour crew

Casino security

Gas station attendant

Plant Operator (Industrial waste treatment)

Lab Technician (Processing titanium scrap)

Janitor – again

Work Planner

IT Developer

IT Systems Analyst


There you have the job history of the old guys. The similar thread is that we’ve both worked hard, had a lot of jobs that sucked,  learned a lot on the job and took advantage of opportunities when presented. We bristle at the idea that ‘there are no jobs out there’. There are plenty of jobs available. It just may not be what you think is ideal. Willingness to endure and a solid work ethic will never be looked poorly upon.

What’s your list look like?

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