How middle management jobs helped me retire early

  • Alvaro Munevar Jr. credits middle management jobs for his early retirement.
  • The jobs gave him enough free time to run a side business to cover his retirement expenses.
  • Meanwhile, senior management positions would require longer hours.

The career model you usually hear about in the US is to work for a company until you’re 65 and then retire and enjoy your last years to the fullest.

I’ve worked in technology since the 1990s, and I’ve always known that I wanted to retire early to enjoy my most active years.

I realized that I can accelerate my retirement date by working smarter. By working my way up through middle management positions, I made sure I had enough time to build a side business in real estate rentals.

With this income, plus my savings from my IT salary, I retired in September 2024 at age 59.

Middle management positions always involved reasonable hours compared to colleagues above and below me

After four years clerking for corporate law firms, I turned to an IT career in 1994, working as a software support engineer in Seattle. I enjoyed working on a new operating system as part of the job. It felt more like a fun hobby than actual work.

I was promoted to middle management after performing well in identifying and resolving system bugs. My core responsibilities were to help and train new support engineers and track their ability to solve problems for customers.

I left that job after almost two years and went on to develop several other middle management roles, including as a project manager and application engineer at startups and larger companies.

Middle management positions always came with reasonable hours compared to my IT colleagues above and below me.

Software developers usually had to come in overtime to complete coding tasks. As far as I could tell, the management teams above me worked 50 to 65 hours a week to supervise team members and carry out executive duties and responsibilities, while I only worked 40 hours a week.

Planning, policy and budgeting discussions mostly took place in senior management roles, so I didn’t have to spend hours attending these meetings.

In the management teams above me, people worked harder and got paid more. In the dev teams below me, people worked harder for a little less pay. The sweet spot was middle management.

Out of interest and boredom, I applied for several senior management roles at various points in my career, but was never offered the job.

Ultimately, I felt that I would be more successful being the CEO of my own money and outside businesses than being a senior manager.

The extra time allowed me to start my own businesses while keeping my day job

Colleagues occasionally asked me how I planned to retire one day. Did I have too much in my bitcoin wallet, apple shares, or was I going to receive a large inheritance? The answer was no.

What I did was a work strategy that focused on staying in middle management while building my business outside of work. I had always seen doing Side Hustles as a fun way to learn new skills and build my savings faster than just having a paycheck with a company.

My 40-hour work schedule gave me enough time to create several side businesses, including building websites for other businesses and developing a portfolio of rental properties that now pays me my current retirement salary.

I would have bought a house with my salary savings in 2001. In 2014, I started renting out my residence after buying a second house, which then became my primary residence. Once he started renting regularly, I added another rental property to my portfolio which also provided passive income.

Having a solid W-2 software position made this side business possible. Lenders are always looking for borrowers with high credit scores and predictable income. I was able to show the bankers that I could repay my loans, making the home loan process relatively smooth.

My wife, who is a neuroscientist, retired at the same time as me. We planned for this by mapping out our household’s expected expenses each year from now until 99.

We used the 4% rule, a retirement planning method that involves withdrawing less than 4% of your savings each year. We worked backwards using the rule to calculate the one, two, three and four percent annual withdrawal scenarios.

After factoring in the income from the rental property, we realized that we had enough income from our savings and rental to retire. It was on this day in August 2024 that I gave my retirement notice.

Having a job and owning your own business is my key to retirement success

Real estate income helped me build my savings, but my early retirement wouldn’t have been entirely possible without my IT salary.

Throughout my tech career, I made a six-figure salary. Over the years, my wife and I both put savings from our paychecks into our after-tax investments and our pre-tax retirement savings accounts. We were even able to save the maximum US 401(k) contribution amounts over the last 10 years.

I strongly believe that in order to succeed financially and retire early, you must build your business while remaining employed.

I don’t regret the way I played my career. Salaries do get higher if you work your way up to C-suite positions, but I enjoyed working in middle management while also owning my own business, where I made all the decisions and got all the benefits.

Now that I’m fully retired, I’m living the life I dreamed of when I sat in on the daily team meetings. I exercise almost every day and can consume books and podcasts that I didn’t have time for during my working years.

Some retirees have told me I’m just experiencing the “honeymoon” euphoria of retirement, which they say will wear off, but I’m glad I can enjoy my life while I’m still relatively young.

Do you have an early retirement story you’d like to share with Business Insider? Email ccheong@businessinsider.com