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7 Biggest Regrets People Have About Retirement (And How to Avoid Them)

7 Biggest Regrets People Have About Retirement (And How to Avoid Them)

2/27/2025 6:52:17 AM   |   Comments: 0   |   Views: 85

What if you could retire earlier and actually enjoy your wealth while you’re still young and healthy? Most people plan to retire at 65, but when they get there, they often look back and wish they had done things differently. They regret not taking action sooner, prioritizing health, or investing wisely.

If you want to skip the reading and dive straight into these life-changing insights, watch my video:

The First and Most Common Regret: Not Retiring Early

Most doctors, dentists, and professionals start their careers thinking they’ll work until 65. But why? Who made that rule? Many people fear they’ll be bored or run out of money, so they keep delaying retirement.

A friend of mine, an oral surgeon, kept finding reasons to postpone his retirement—stock market dips, financial concerns, uncertainty. Finally, he took the leap. Now, he spends half his time at his vacation home in Mexico, hosting family and living stress-free. His only regret? Not retiring sooner.

Prioritizing Wealth Over Health

What’s the point of having all the money in the world if you’re not healthy enough to enjoy it?

Doctors and dentists spend their careers taking care of others but often ignore their own health. Many professionals in their 50s and 60s say, “I should have eaten better. I should have exercised more.” They worked long hours chasing wealth, thinking it would make them happy, only to realize they sacrificed their health in the process.

Making time for exercise, eating well, and reducing stress should be a priority—before it’s too late.

Fear of Taking Risks

Regret often comes from not doing something rather than failing at something.

So many people wish they had taken more risks—starting a business, investing in real estate, or jumping on an opportunity that came their way. Fear holds people back.

When I injured my wrist while skiing at 40, I had a wake-up call. What if I couldn’t work anymore? I had no backup plan. That’s when I started investing in real estate, and although I lost money at first, it changed my life. Now, I have passive income streams that don’t require me to treat patients.

Taking calculated risks earlier can lead to financial security much sooner than you think.

Neglecting Relationships

At the start of their careers, many professionals are laser-focused on building their business or practice. They assume they’ll always have time for their kids later.

Then, one day, they look up and realize their kids are grown. The little moments—the crawling, the bedtime stories, the soccer games—are gone.

Many retirees say they regret not spending more time with their family when they had the chance. Work will always be there, but your kids won’t always be young.

Fixing broken relationships is just as important. Holding grudges or avoiding difficult conversations can lead to regret later in life. Surround yourself with people who bring value to your life and let go of those who don’t.

Trying to Impress Others Instead of Living for Themselves

People waste years (and a lot of money) buying things they don’t actually want just to impress people they don’t even like.

The big house, the flashy car, the expensive watch—none of it matters if it doesn’t bring true happiness. Instead, focus on investing in things that create real freedom, like financial independence through real estate.

Not Saving or Investing Early Enough

The biggest financial regret? Not saving and investing sooner.

Time is the most powerful tool for building wealth. People in their 20s often either avoid investing altogether or invest too conservatively. Both are costly mistakes.

A 20-year-old has 40 years to grow their money before they need it. The earlier you start, the easier it is to build wealth. Waiting too long leads to lost opportunities and financial stress later in life.

Failing to Make a Retirement Plan

Many retirees wish they had created a financial plan earlier—both for saving and spending in retirement.

They spent years saving but never figured out how much they needed or how much they could safely spend once retired. As a result, some live in constant fear of running out of money, while others don’t enjoy their retirement because they don’t know what they can afford.

Having a solid retirement plan eliminates stress and allows you to actually enjoy the money you worked so hard to save.

Avoid These Regrets—Start Planning Today

Don’t wait until retirement to wish you had done things differently. Learn from those who have been there and take action now.

Want to see how I made my own transition from a traditional career to financial freedom? Watch my full video where I break down the steps to retiring early and living life on your terms.

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