How These People Retired by Age 50

Young pensive businessman holding hand on chin and looking at desktop PC in the office.
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When Greg Wilson was barely out of high school and at an age when most don’t have the future figured out, he knew one thing. He wanted financial security down the road.

His next step? Investing in rental properties. That decision, combined with smart money management made during his career at a major financial services firm, allowed him to retire early last November. Very early. 

“I was able to retire at age 42 because of decisions I made in my late teens that I stuck with,” said Wilson, who lives in St. Louis. “I bought several rental houses in my early 20s with the goal of having enough in taxable accounts to last me from age 40-something to 60. Concurrently, I put as much in my 401(k) as I could to last me from age 60 until death.”

Wilson offers evidence that you don’t need to work until age 62 or 65 or 67 if you make good decisions along the way. Retiring by age 50 without wondering how to fund the second half of your life? Not an impossible dream, but it takes dedication and a plan, financial experts said. 

Are You Retirement Ready?

“The key to achieving a goal like retiring at 50 is a combination of a high savings rate and a smart investment strategy,” said Eric Roberge, a certified financial planner and founder of Beyond Your Hammock in the Boston area. “A high savings rate refers to the percentage of your gross income that you save each year. For our clients who pursue aggressive early retirement goals, we recommend contributing at least 30% of gross income to long-term investments – like retirement plans and brokerages.”

The Aggressive Approach

Pursuing a high-savings strategy is just what Michelle Schroeder-Gardner did. She graduated from college with two undergraduate degrees, plus an MBA, and became a financial analyst. She paid off nearly $40,000 in student loan debt in seven months, she said, then quit her job to take up a writing career and run her own business.

I was able to grow my income a significant amount while keeping my expenses quite low in comparison,” she said. “This allowed me to save anywhere from 75% to 90% each month as my monthly expenses have stayed low over the years.”

Are You Retirement Ready?

Now, she said, she has saved enough money to fully fund her retirement. As the operator of the website Making Sense of Cents, she earns semi-passive income that allows her to live on a sailboat and travel full-time.

“I decided to reach for early retirement after learning about it and realizing that it was attainable for me,” she said. “When I first learned about early retirement, I had debt, I was living paycheck to paycheck and I thought that it was only for the rich.

“However, I quickly learned that I could make it a possibility for myself as well. Then, I decided to pay off my student loans as quickly as possible and become a digital nomad and turn my side business into my full-time business. I didn’t want to worry about money every day for the rest of my life, so I knew that I wanted to make the change and retire early. I also want to have freedom, travel whenever I want, work when and if I want and be in more control.”

Are You Retirement Ready?

Wilson also generates income from a website he and his wife, Erin, bought,, which teaches readers about living a happy and healthy life on a budget.

Wilson said that while he has “made sacrifices,” he and his wife live a more stress-free life – even with three preschool-aged children – than when he was working full-time.

“I only retired two months ago, but I have been planning this for 22 years,” he said. “My quality of life is great. My wife and I live a comfortable life, in a nice house, in a nice area and we spend on what makes us happy. But I don’t complain about all of the nonsense I did when I was working. I wanted to buy my time back, and I did.”

Tips To Achieve Early Retirement

If you didn’t have the foresight to buy an investment property or have the ability to bank much of your income, it isn’t too late to start catching up if you’re in your 20s or 30s. Some tips from the experts:

Manage your debt: “As part of your retirement planning process, take stock of all debt and to see where you can be more aggressive about paying down loans,” said Katherine Fox, a certified financial planner in Portland, Oregon. After paying down any higher-interest credit card or personal debt, focus on auto loans and then consider dedicating a portion of your monthly income to paying down your mortgage principal balance.

Are You Retirement Ready?

Increase your income: “When it comes down to it, the number you can save is determined by your income. Early retirees are well aware of the need of raising their income if they wish to retire before the age of 50,” said Jeff Mains, the CEO of Champion Leadership Group. “Possessing a modest interest or company on the side might be beneficial in terms of generating additional money, both before and after retirement.*

Diversify your income: Putting your money into a variety of income streams is vital, said Kyle Kroeger, founder of The Impact Investor. Real estate investment, e-commerce, stocks and cryptocurrency are among the avenues to explore, he said.

Max out your 401(k) and other retirement plan options: “If your company offers a 401(k) plan, you should contribute the maximum amount authorized,” said Adam Wood, co-founder of Revenue Geeks. “This might amount to up to $18,000 each year. It’s even better if your employer matches your donation. You should also consider contributing to a traditional IRA, even if you won’t be able to deduct your payments owing to income restrictions. The account’s investment returns will continue to accumulate tax-deferred, which is exactly what you want.”

Are You Retirement Ready?

Invest and be patient: That’s key, said Oliver Cohen, marketing and communications consultant for LPL Financial, a wealth management firm. “Invest intelligently and don’t get in your own way. Set an allocation that will provide adequate returns to meet your growth goals. … Let compounding interest work for you, and that means time in the market with a proper allocation. Don’t react to volatility and behave emotionally. Stick to the plan and follow it diligently.”

Plan what retirement will look like: “Some people may want to be done working entirely, while others may want to invest in themselves to start a new business, or take a year or two off work before jumping into a new, part-time career,” Fox said. “Take time to visualize how you want your ‘first retirement’ to look and consider the financial implications of your goals. Saving money to fund a year or two of expenses before starting a more flexible, part-time job may require a lower level of savings than if you hope to never work again a day in your life.”

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