11 Jobs That Led to My Early Retirement

MichaelCareer, Education, FIRE, How to, Misc22 Comments

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We all have to start somewhere, right?  In this post, I will share with you ALL 11 jobs that led to my early retirement at age 36.

Additionally, I will disclose how much I got paid along the way so you can get an idea of the progression.  I think it’s important to see this, especially for my millennial friends who admittedly concentrate a lot of their focus on “today”.

If you have the goal to FIRE, it’s critical to keep moving, growing, and by all means SAVING along the way.  Although I earned much more in my later years, some earlier jobs were more critical in my overall development… including my unpaid internship!


Job #1

Title: Concessions Assistant

Compensation: $4.25/hr, or $8160/year

Job Description: Serve soda and popcorn to patrons attending music events

I think it’s a great idea to take a job in your teens.  It’s a time when you potentially have a decent amount of free time on your hands… especially in the summer!

In addition to making a little extra money for yourself, you begin to understand the money and labor dynamic in a traditional sense.  This builds appreciation for “hard work”.

I only had one job in high school, but really wish I taken some others.  I also dabbled in some entrepreneurial endeavors as well, although I didn’t make much.  🙂


Job #2

Title: Dining Hall Assistant II

Compensation: $5.85/hr, or $11,232/year

Job Description: Prepare food for dining hall; Serve students entrees and sides; Kitchen clean up

If I’m being honest, I only took this job at the time to earn some extra cash for a paintball gun I wanted! No saving was ever intended with this income.

It was however, a great experience to really pull up my sleeves and trade time for dollars.  I can’t say that this model interested me for long!

Job #3

Title: Web Design Intern

Compensation: $0.00/hr, or $0/year

Job Description: Create local area band websites using HTML

Half way after declaring my major in economics, I realized I wanted to work in tech! So, I decided to pursue an internship in web design which ultimately led me to working in technology.

Although I didn’t earn a dime, this internship really gave a glimpse into the tech industry and helped me to learn real world skills that were tangible for many years to come.

Job #4

Title: Seminar Marketing Associate

Compensation: $7.00/hr, or $13,440/year

Job Description: Stamp and stuff envelopes with marketing materials for self-employed engineer

This part-time job was another low paying job, but super high in value. I ultimately became life-long friends with the owner of the business and she’s become more than just a mentor to me… she’s our children’s Godmother!

EARLY 20’s

Job #5

Title: Web Design Consultant

Compensation: $20.00/hr, or $38,400/year

Job Description: Create websites for realtors

Because I had tangible skills learned at my prior internship, I was able to work for a local web development company as a freelance web designer.

Job #6

Title: IT Support: Systems Administrator

Compensation: $21.88/hr, or $42,000/year

Job Description: Manage backups, Provide Tier I desktop and network support

Although I like web design, I couldn’t see myself sitting behind a computer screen all day long. I needed to get out and stretch my legs and see the world!

So, I began pursuing opportunities in I.T. specifically with networking and hardware. In fact, the company that I did web design for allowed me to build out their first network and server.

This led me to finding my first salaried job as a systems admin which would launch my career into outsourced IT.

Job #7

Title: IT Support: Systems & Network Administrator

Compensation: $30.21/hr, or $58,000/year

Job Description: Manage backups, Provide Tier I desktop and network support, Assist with internal system integrations, & manage internal web portal

I was like a sponge here. There were so many opportunities to learn. Being hands on at your first “real” job is critical to your success.

Pay attention to all the departments and how they work… not just your own!

After several months, I decided to ask for a raise. I did a ton of research and made my move.

I ended up with a generous increase. To read more about it this topic, check out my posts – Jumpstart Your Wealth with a Raise and 5 Simple Ways to Get the Raise You Deserve.

AGE 25 TO 30

Job #8

Title: Small Business Owner – IT Consultant, Systems Engineer

Compensation: $36.46/hr, or $70,000/year

Job Description: Provide IT support for small and medium businesses

A little less than two years into my first salaried job, the technology market took a huge crash!

Our company was hemorrhaging cash left and right and people began to get laid off.

After witnessing 6 rounds of layoffs, a couple of my friends and I decided that we had seen enough.  It was obvious if we stayed we would get laid off at some point, so we decided to resign and start-up a company of our own.

I was just 25 at the time, super naive, and unprepared to start a business.  Fortunately, I didn’t care.

I had built up enough confidence over the past few jobs to know I could be flexible and maneuver through challenges.

Fortunately, we landed our first few clients quickly and I was already making more money than I was prior to a few months earlier.

Job #9

Title: Small Business Owner – IT Consultant, Systems Engineer, CFO

Compensation: $44.27/hr, or $85,000/year

Job Description: Provide IT support for small and medium businesses, Manage company financial processes (AP, AR, invoicing, etc.)

I like working with clients at times, but I was also super interested in business.  So, I took it upon myself to really grow it with systems and processes.

As CFO, I managed our cash flow wisely and we were able to make a couple acquisitions along the way which really fed our client base nicely.

Remember, if you ever start your own business, cash flow is KING!  Because I controlled the company cash flow, I made sure to pay ourselves fairly, but also not pay out everything.

AGE 30 TO 36

Job #10

Title: Business Owner – IT Consultant, Chairman, President

Compensation: $52.08/hr, or $100,000/year

Job Description: Provide IT support for small and medium businesses, Manage company financial processes (AP, AR, invoicing, etc.), Manage department heads

Over the next few years, I took a more active role in leading the company growth.  I knew that someday when we sold the company, our recurring revenue contracts would be the assets that had actual tangible value.

I spent a lot of time growing our business from a place trading time for money, into an actual scalable business complete with a management team and processes to run the day-to-day operations.

This focus would ultimately lead to a larger pay off later on, outside of my regular salary.

Job #11

Title: VP of Outsourced IT Solutions (On-Premise)

Compensation: $67.71/hr, or $130,000/year

Job Description: Manage multi-state outsourced IT operations; Help land new clients and lead integration team; Assist with new acquisitions

My last job was a position I had for a little over a year.  After we sold the company, we merged our teams, and I was responsible for the outsourced IT team that did onsite calls and projects.

I enjoyed a nice salary during this time, but the leadership of the new entity left more to be desired and we ended up parting ways.

I was able to negotiate a generous severance package which I used to transition into early retirement.

AGE 36 – ???

Today I am super blessed to be a Stay-At-Home Dad first and foremost.  I meet so many people who had regrets about not spending enough time with their kids when they were younger.  So, I’m soaking it up as much as I can, while I can!

To keep my mind active and grow our asset base, I pursue other projects.  Other hats I get to wear are: investor, financial coach, e-retailer, etc.

To me, early retirement is not about STOPPING work.  Rather it’s an inflection point where I can simply work on exactly what I want to, when I want to.

There is definitely more work to be done, but I will always stop and smell the roses along the way.


hourly wage over time

Climbing a ladder is much easier than scaling a high wall all at once.  It can be done, but I’d rather increase my odds of success over time to guarantee my outcome.

Make sure that each job you have is serving you and your goal of early retirement.

And remember, it’s not the amount of earnings that will take you to early retirement, rather it’s your mindset and your subsequent habits.


Readers, what kind of  jobs did you take along your career path that really impacted you in a positive way?  Were there jobs that were super challenging, but really made a difference?  Where will you “jump to” next?

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Hi, I have been blessed to take an early retirement in my mid-30's so I can focus on becoming a better father, blogger, and investor.

My goal is to help you find your personal path to financial freedom, and to enjoy the entire journey.

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22 Comments on “11 Jobs That Led to My Early Retirement”

  1. I like the detailed overview, Michael, and the progression you made job by job! I thought it was interesting that you went from an IT focus to also taking on the CFO role for the small business. You’re definitely good with numbers and finance so I’m not surprised. Thanks for sharing.

    1. Yeah, it helped that my Dad was a CPA and I could pick his brain whenever we had company finance questions. But, I did do a lot of studying on my own and really wanted to understand every aspect of a business.

  2. “To me, early retirement is not about STOPPING work. Rather it’s an inflection point where I can simply work on exactly what I want to, when I want to.” Beautifully said, my friend.

    Love that you shared your job history and what you were paid. Often, we hear what someone is making with no respect to how they got there. Seeing what others make in one point in time can be discouraging to say the least if we’re nowhere near those numbers. So thanks again for sharing.

    1. I’m glad this resonated well with you OB. My hope is that my younger readers can see that there were crucial points along the way that were super important to transitioning to the more “fruitful” years.

  3. Thanks for sharing Michael. Your path seemed like a rather linear move upward. This is very different from my experience, which included leaving a higher paying job because it was awful and finding a more fulfilling lower paying job (then moving up again), a failed business, and so much more before I getting to what I consider to be a very successful place. I think it is important for your readers to realize that the road to success is often not as smooth as yours sounded.

    And I agree that taking a job as a teenager is really valuable. It is definitely a good primer for business and expected responsibilities.

    1. Jef, I like that you share your perspective here. I never really realized how linear my path was until I saw it on the chart! There are probably many other readers with you experiences that include dynamic ups and downs. I think the main message is to keep moving forward no matter what. Know your outcome and the path to get there ultimately doesn’t matter once you get there.

    1. Haha, I think I remember the numbers because they seemed so low at the time! 🙂

      Yeah, I started and ran a business for a little over a decade. In fact, I’ll be sharing some more of this story soon with a guest post over at Financial Samurai!

  4. I love hearing other people’s journey into FI. Took a long road to get there, Michael! I also wish that I had taken more jobs in high school. I get a lot of enjoyment out of working (my parents look at me weirdly when I tell them that) and wish I had earned some extra dollars during HS. Summers were spent doing nothing!

    1. FS, summers were both great and terrible at the same time! Too much free time and so much energy, right? I did try a few hair brained home assembly businesses, but they were pretty much all scams. 🙂

      1. Yes! If only I could go back in time and tell myself that the energy I had was a blessing. I probably would have stopped playing a lot of video games. I can bet that no one was after you because we could have always played the “kid” card 😉

  5. Thanks for sharing your job history Michael. As Jeff mentioned previously, it’s definitely interesting to see how linear your job history and earnings were. But I do caution people not to assume that their earnings will always go up. This is why it’s so important to live on less in order to avoid getting dependent on the higher income.

    As an attorney, our wage progression often fluctuates a ton! A lot of attorneys take pretty massive pay cuts to move into in house work or government work or just to get a job with a better quality of life (Think of any big time government attorney or judge you’ve ever heard of – These folks basically took millions of dollars worth of paycuts). Just something I thought would be worth sharing.

    1. FP, excellent point and thank you for sharing.

      I agree that it’s important to always live on less than you are earning regardless of where your earnings are at currently. It’s always easier to do this when you have a sizable increase, which for me was entering into my first salaried job (systems admin). So, create the discipline early before you get used to the increased cash flow. Never take anything for granted!

  6. Man, really appreciate you breaking it down there. Great to see how you progressed along the way 🙂
    I’d have to say reflecting upon my career being able to see what parts of a role I enjoy and what I don’t have been great learning experiences

    I’m still getting there and starting to focus on what investments will look like to get me to FIRE although I’d love to find out more about you roles/mindset in your last 4 roles as a business owner..

    Also noticed another Jeff commenting, although he’s a 2 f jeff haha 😉

    1. Jef, I think my mindset has always been “jump” when it gets uncomfortable. That’s the only way you’ll ever find out what’s on the other side!

      The truth is that I could have landed terribly with the business, but I was too determined and naive to believe it wouldn’t work out… in other words, I made it a MUST. People get what they MUST have and usually don’t get what they just WANT. I’ll be sure to talk more in depth about this mindset in other upcoming posts. 🙂

      BTW, Jeff with 2 f’s is my good buddy and a CPC marketing guru!

  7. Very engaging post Michael. I followed a similar trajectory in my career. My first job was as a Starbucks barista, then in an optical lab, then an assistant to an optometrist and finally an optometrist. You’re exactly right it can look daunting in the beginning so people should not get too worked up if they’re not making a boatload of money right out of the gate. Learn lots of skills and make yourself indispensable!

    1. Nice, Syed! Starbucks seems like it’d be a pretty cool first job. I’m a fan of Howard Schultz. 🙂

      I love how you mentioned, “Make yourself indispensable!” This is a key distinction for making upward moves within an organization, or even moving on to another one. I would go so far as to say become and intrapreneur within your organization (if possible).

  8. Super cool post as always. I started working on a horse farm for $3.50 an hour and then worked in Asphalt Construction for $5.25 an hour. From there I sold kitchen cutlery, was a bank teller, a stock brokerage intern, landscaper, youth program assistant, gym teacher, accounting intern, equity analyst, financial analyst, accounting manager. I recently hit a major annual income milestone due to some special circumstances with some corporate takeovers and some investments maturing. It was pretty exciting! It has been a crazy ride and I am ready to do something different in a few years. But I want to just move to that next exiting challenge and not stop working. I had to take a little hiatus from blogging since I got promoted in May and things have been a little crazy. Keep offering your insights – loving it.

    1. Thanks PWB. I love that you started working on a farm! It looks like you have a great work history that likely provided you with fantastic experience over the years.

      Congrats on the milestone!!!

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