Outside the Box: I failed at retirement. How to avoid my mistakes.

It’s embarrassing to admit in a public forum that I failed at retirement. But I’m doing so — because I think people can learn from me, and thereby avoid making the same mistakes.

I spent my entire 38-year career in the banking industry. Naturally, I learned a lot about money and investing. I helped thousands of clients save for their own retirement. On top of that, my wife is an investment adviser.

But despite all that knowledge and expertise — and having enough money to retire comfortably — I still managed to find my way into retirement hell. And believe me: If it can happen to me, there’s no reason it couldn’t happen to you.

Following are the five biggest mistakes I made. Please learn from them, so you can avoid the stress and anxiety I experienced figuring this out for myself.

Mistake No. 1: Focusing only on the money, and believing that the quality of my retirement depended on how much I had.

Looking back, I now realize that many of my beliefs about retirement were wrong — because they were all linked to the money aspect of retirement. I’ve learned you don’t just fall into a happy retirement because you have a lot of money. You need financial security, of course, but designing a satisfying life takes thought, time and planning. You need to know your needs and values, and what makes you happy, and then you have to find ways to satisfy these aspirations on a regular basis.

Mistake No. 2: Thinking retiring would be easy. It’s not.

Quitting the workforce is considered one of the 10 most stressful events a person will ever experience. That stress is caused by all the change and the feelings of loss. It was stressful to slam on the brakes and suddenly stop what I’d been doing for 38 years — even though I didn’t like my job. How crazy is that?

Mistake No. 3: Believing the retirement commercials of the financial-services companies.

I blindly accepted the advertisers’ narrative — that, when I retired, I could slow down and just take it easy for the next 20 to 30 years. Just like the people in those retirement commercials. I learned that playing golf, frolicking on a beach, taking care of the grandkids and volunteering one day a week wasn’t enough to fulfill a goal-driven retiree like me.

Mistake No. 4: Believing that retiring would make all my problems magically go away.

I imagined that, by retiring, my life would turn around, and I would be happy and less stressed. But I was wrong again.

Retirement will not change you. You will still be the same person you were the day before you retired, so you will have the same problems, too.

Most near-retirees mistakenly believe that once they get their freedom back, once they feel less stressed, all their bad habits will vanish. They will magically transform into that happy person they always wanted to be. They will hit the gym daily, eat healthier, travel to exotic places, write a book, learn to play the guitar, start a business, and spend more time with family and friends.

It’s a great dream. But it can’t happen without a deliberate plan that you execute on. Falling into retirement, with only vague ideas about what your life is going to be like, will cost you. When your dream turns into a nightmare, you’ll start questioning your decision to retire in the first place.

Mistake No. 5: Now, we get to my biggest mistake: not having something to retire to.

When we retire, our sense of purpose takes a major hit. Suddenly, I was waking up to days with no meetings and deadlines. My identity was slipping away. I needed to fill the big hole created when I was forced to retire. Until I filled it, I felt that something was missing in my life.

How did I fill that void? I went back to work, but I did it my way this time, not for the money but more for the pleasure of working. I became an author, a retirement coach and public speaker. I love running my own business. My new work gives me the autonomy and flexibility I’ve always craved.

Will these things fill your retirement void? Probably not. You’ll need to figure this one out for yourself — which may involve a lot of soul searching and careful thought.

We’re all wired to want purpose and meaning. We all need something to live for. When you retire, you’ll need to find these things again. Without them, you risk your health, happiness and longevity. Retiring to nothing is equivalent to digging a premature grave.

Having a sense of purpose is something we all need until our last breath. Having a lot of money will never change that.

It’s easy to see that my retirement mistakes had nothing to do with money. Yet most retirement planning is focused on the financial. I’ve learned the hard way that preparing for the emotional challenges is just as vital. Bear that in mind when preparing for your own retirement.

Mike Drak is a 38-year veteran of the financial-services industry. He’s the author of “Retirement Heaven or Hell,” published in 2021, as well as an earlier book, “Victory Lap Retirement.” Mike works with his wife, an investment adviser, to help clients design a fulfilling retirement. For more on Mike, head to BoomingEncore.com. Check out his earlier articles.

This column originally appeared on Humble Dollar. It was republished with permission.

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