I’m a Self-Made Millionaire: Here’s the Hardest Part About Retiring Early

Mature african woman looking outside window with uncertainty.
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Retiring early seems to be the new American Dream.

Instead of working for 40 to 45 years at the same company to retire in their late 60s, many Americans are choosing to exit the workforce in their 50s, 40s or even their 30s.

It takes a decent income and discipline to save up to 50% of your income (or more), but early retirement is possible if you start saving and investing while you’re young.

But early retirement is not without its challenges. And having millions of dollars in the bank only solves money problems but can’t fix every problem in your life.

We interviewed several self-made millionaires who shared with us the most difficult part of retiring early. While this might sound like a “good problem to have,” these difficulties are real-life problems that you might wrestle with if you choose to retire early too

The Hardest Part About Retiring Early

Retiring early can feel like a dream, but there are some tough parts about the process you’ll want to know about before choosing to retire early yourself. Here’s what several millionaires have to say about the difficulties of retiring early:

How Do I Spend My Time?

Gino Sesto, founder of Dash Two, is 53 years old and has a net worth of $5 million. He said that he has “zero reason to work other than it keeps me busy.”

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But he has had trouble actually putting in his notice.

“I’m sure you are going to get this from others,” Sesto said. “But for me unequivocally the hardest part about retiring early is what do I do when I retire? Work unfortunately gives us meaning and for the last three years I have wanted to retire but I keep at it.”

Work keeps you occupied for at least 40 hours per week. Finding activities to fill that time can be a challenge.

Understanding Why I Wanted To Retire Early

Retiring early without asking yourself “why” can set you up for failure. Simply amassing wealth to quit a job doesn’t prepare you for the realities of early retirement.

Rodric Lenhart, early retiree and founder of Million Dollar Flip Flops, didn’t have a strong “why” when he retired. “I retired at 42 after the sale of my last company,” Lenhart said. “I lasted six months before embarking on the biggest mission of my life (sending 1,000,000 kids abroad through our foundation – in partnership with EF Tours). My advice, as it is for people at any stage of life, is to deeply understand their WHY. WHY do you want to retire early? With enough reflection, most will discover they aren’t actually driven by the ‘normal’ answers.”

Filling the Emotional and Psychological Void

Sometimes you can’t put a number on how you are going to feel when you retire early. Work holds a place in our lives until it doesn’t. It’s important to retire TO something instead of just retiring. Otherwise, you might struggle to figure out what you are working toward.

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Bryan Clayton, CEO of GreenPal, essentially had an identity crisis after retiring early. “After selling my first landscaping business, I did attempt to retire early, and let me tell you, it wasn’t all it’s cracked up to be,” Clayton said. “The hardest part for me was the emotional and psychological void. Sure, I had the time and money to do whatever I wanted, but after a lifetime of equating my self-worth with my work, stopping so abruptly led to an identity crisis. I needed a new avenue to pour my energy into, something that would bring a sense of accomplishment and contribution.”

Lifestyle Adjustment

Getting up, going to work and earning a paycheck become integral parts of your lifestyle. Once you stop going to work, it can be a shock.

Anshul Sharma, self-made millionaire and early retiree, struggled with adjusting to the daily lifestyle of retirement. “I’m a millionaire who retired early at the age of 45,” Sharma said. “I’ve been retired for five years now, and I’ve learned a lot about the challenges and rewards of early retirement. The hardest part of early retirement for me was adjusting to a new lifestyle. I went from working 50+ hours a week to having all the time in the world. It was a lot of adjusting to do, and I had to learn how to fill my time in a meaningful way.”

Jamie River, early retiree and founder of Passive Book, had a similar shock when retiring early. 

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“As a self-made millionaire who retired early, I can certainly shed some light on the hardest part of this journey,” River said. “Retiring early may seem like a dream come true, but it does come with its challenges. The hardest part of early retirement, in my experience, was adjusting to a new lifestyle. When you retire early, you suddenly find yourself with an abundance of free time. This may sound exciting at first, but it can also be overwhelming. Without the structure of a regular job, it’s easy to feel lost or purposeless.”

How To Avoid the Pitfalls of Early Retirement

Early retirement isn’t all sunshine and rainbows, and you have to prepare for the mental and emotional challenges just as much as the financial challenges. Here are a few tips to help you avoid the pitfalls of early retirement:

“One practical tip I have for those considering early retirement is to create a schedule or routine for yourself,” River said. “Having a daily plan can give you a sense of purpose and direction. It doesn’t have to be as rigid as a work schedule, but having some structure in your day can be incredibly helpful. Lastly, I would advise anyone considering early retirement to think beyond just the financial aspect. While financial independence is crucial, it’s equally important to cultivate a fulfilling and meaningful life outside of work. Explore your passions, engage in hobbies, and build strong relationships with loved ones. These non-financial aspects will contribute greatly to your overall happiness and well-being in retirement.”

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“If you’re considering early retirement, here are a few pieces of advice,” Sharma said:

  • “Make sure you have a good financial plan in place
  • Be prepared to adjust to a new lifestyle
  • Stay busy and stay active
  • Stay connected with your friends and family”

“Plan meticulously, and not just financially,” Clayton said. “Know what will give your life meaning post-retirement. Understand that it’s not a one-way door. You can always go back to work, and there’s no shame in that. Stay mentally and physically active. This is crucial for long-term well-being. Most importantly, know your ‘why.’ If you don’t have a mission or a purpose, you might find yourself in the same boat I was — financially comfortable but emotionally and psychologically unfulfilled.”

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