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  • Written By
    Christian Simmons

    Christian Simmons

    Financial Writer and Certified Educator in Personal Finance

    Christian Simmons is a financial writer who has worked professionally as a journalist since 2016. As an active member of the Association for Financial Counseling & Planning (AFCPE), Christian prides himself on his ability to break down complex financial topics in ways that Annuity.org readers can easily understand.

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    Lamia Chowdhury
    Lamia Chowdhury

    Lamia Chowdhury

    Financial Editor

    Lamia Chowdhury is a financial editor at Annuity.org. Lamia carries an extensive skillset in the content marketing field, and her work as a copywriter spans industries as diverse as finance, health care, travel and restaurants.

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  • Updated: August 14, 2023
  • 5 min read time
  • This page features 1 Cited Research Article
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How to Cite Annuity.org's Article

APA Simmons, C. (2023, August 14). Retired at 42: How a Plan Devised as a Teenager Resulted in a Successful Early Retirement. Annuity.org. Retrieved May 28, 2024, from https://dev.annuity.org/personal-takes/retired-at-42-how-a-plan-devised-as-a-teenager-resulted-in-a-successful-early-retirement/

MLA Simmons, Christian. "Retired at 42: How a Plan Devised as a Teenager Resulted in a Successful Early Retirement." Annuity.org, 14 Aug 2023, https://dev.annuity.org/personal-takes/retired-at-42-how-a-plan-devised-as-a-teenager-resulted-in-a-successful-early-retirement/.

Chicago Simmons, Christian. "Retired at 42: How a Plan Devised as a Teenager Resulted in a Successful Early Retirement." Annuity.org. Last modified August 14, 2023. https://dev.annuity.org/personal-takes/retired-at-42-how-a-plan-devised-as-a-teenager-resulted-in-a-successful-early-retirement/.


Planning at a Young Age for a Young Retirement

Retiring early is a dream scenario for many Americans, especially those who have spent time in the workforce and are looking for more freedom in their life. But for Greg Wilson, that dream formed at a much younger age.

By the time he was 18, the St. Louis resident knew that achieving financial independence early was his goal.

The Interviewee

Greg Wilson Greg Wilson
Retired Decades Early

“When I was a teenager, I decided that I didn’t want to work my entire life. I didn’t think that people should be identified by their job and just work until they’re old,” Wilson told Annuity.org. “And I also was very intentional about wanting to be present for my family and be engaged with my kids, which I didn’t have then. I had very young parents and I kind of wanted to do things the opposite. I wanted to get money out of the way so I could be present for my kids.”

Thanks to an effective strategy (that didn’t change much from when he started) and some smart investing in rental properties, Wilson achieved his goal of early retirement at 42.

“When I was 20, 21, I started buying rental houses and concurrently was putting as much into my 401(k) as I could,” he said. “I didn’t even make $60,000 in my career until I was 30 or 31.”

Retiring early is far from easy and it took a lot of work on Wilson’s part. He started out by setting a simple goal of establishing two retirement buckets. In the first bucket he established taxable assets to last him from his early retirement until the standard retirement age of his mid-60s. In the second bucket, he put tax-deferred assets that could care for him and his family past the normal retirement age.

“It was kind of like a two-retirement approach,” he said.

Wilson worked mainly in finance, spending time as a technical writer and mortgage broker before getting into financial services. But early retirement is not always easy on just a standard salary. That was where the rental properties came in.

In part thanks to bank loans, Wilson was able to begin acquiring properties in his early 20s despite only starting out with $800 of his own money. Before long, he was achieving tremendous success.

“I worked my mortgages intentionally to where I could absorb two and a half vacancies,” he said. “As the houses would become more profitable, I would shorten my mortgages so I could more aggressively pay them off. So they’d be paid off in my 40s instead of my 50s and 60s.”

Even though he was beginning to make money and work toward his goal of early retirement, there were still challenges. Small things, like using the phone book to find an electrician who could work on his properties, were not issues many people encounter in their mid-20s.

“When you’re 25 walking 50-year-old people through rental houses or you’re the landlord to people in their 40s, 50s and 60s, it’s an entirely different dynamic,” Wilson said. “They thought I was privileged and they thought I was rich.”

Achieving an Early Retirement

After years of hard work, Wilson is happily living out his dream of an early retirement, where he has plenty of time to spend with his three young children.

Working to retire at such a young age was a grind, but the results have been what he hoped for.

“I absolutely love the flexibility of it. I love not needing to deal with a lot of the stresses that everyone complains about with their day job,” he said. “All the little stresses like ‘I don’t want to go to this meeting,’ I don’t have that. That to me is heaven.”

One area that many people struggle with in retirement is determining what to do with all their time. People are wired to have goals and stick to routines and schedules. With some of his free time, Wilson has stayed busy by getting into website building and management – such as Cha Ching Queen, where he posts advice and information on how to spend, save and make money.

“That’s something that gives me a puzzle to work on,” he said. “I can work on that to help fill the time void.”

While staying busy has been important, being unattached to a job or company hasn’t been an issue for Wilson. Unlike most Americans, this had been his dream since he was a teenager. And he’s finally living it.

“Most people are wired to identify as their job. And when you no longer have that job, you lose your identity,” he said. “That was not an issue for me; I decided when I was a kid that that wouldn’t be an issue.”

The FIRE Movement

Wilson is far from being the only American who has worked towards an unexpectedly early retirement.

The concept of retiring early has picked up in recent years, in part due to the arrival of the Financial Independence, Retire Early (FIRE) Movement. For decades, the conventional mindset for most Americans was to follow the standard path of entering the workforce in their early 20s, and holding a job until they hit their mid-60s and could afford to retire.

But for some people, their goal is all about wealth accumulation and living frugally to save enough money necessary to achieve financial independence at a young age.

Leaving the workforce early is far from easy, however. It can take a significant amount of money to retire early, especially due to rising health care costs and life expectancies.

According to AARP, many factors that impact early retirement aren’t always carefully considered, such as rising housing expenses and the importance of being able to generate some form of income.

Despite the challenges (and often the need to live a frugal life), Wilson is one example showing that early retirement can be accomplished. But it often requires hard work, multiple forms of income and the execution of a sound plan from a young age.

Thoughts and opinions expressed in these stories are strictly anecdotal and should not be taken as financial advice. Views of the interviewee do not necessarily reflect those of the author, editor or Annuity.org.
Last Modified: August 14, 2023

1 Cited Research Article

  1. Waggoner, J. (2023, April 13). 10 Things No One Tells You About Early Retirement. Retrieved from https://www.aarp.org/retirement/planning-for-retirement/info-2021/pre-early-retirement-reality-check.html