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An F in Retirement

Mike Drak

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 advisor.

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.

Here 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.

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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 that 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 advisor, to help clients design a fulfilling retirement. For more on Mike, head to BoomingEncore.com. Check out his earlier articles.

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colin haller
colin haller
1 month ago

I have my walking and about 5 bankers boxes full of books to get through. By the time I get through those maybe travel will be back on the table?

Roboticus Aquarius
Roboticus Aquarius
1 month ago

Thank you for a thoughtful exploration of some of the pitfalls of retirement.

The issue of meaning keeps coming back to me. Working itself has never been particularly meaningful for me, but raising a family and providing for them was. Now that I’m an empty-nester, though still in the workforce, I realize that I lack the intensity I once had. My skills and years of experience make it a minimal challenge to keep up with the demands of the role, but I’m not driving beyond that. I realize that I’ve lost meaning and need to find something new to keep me engaged.

It’s interesting because there is volunteer work I really want to do in retirement and am looking forward to it. Not to overlook the possibility that I won’t find that work as fulfilling as I anticipate, but I think the issue for me is filling the space in between now and then.

Kathleen M. Rehl, Ph.D., CFP®
Kathleen M. Rehl, Ph.D., CFP®
1 month ago

I actually have 5 Fs in “reFirement.” These include Family, Fun, Focused Purpose (as a nonprofit ambassador and legacy storyteller), Friends, and Fitness (body, mind, spirit & money). I love this life chapter, although I also enjoyed my prior career as a certified financial planner and then an encore career (speaking, doing & publishing research, and writing). Now in my 75th year, I’m excited about each new day!

Jerry Pinkard
Jerry Pinkard
1 month ago

I have been retired 11 years. I carefully my retirement with a mix of leisure and volunteer work. Neither panned out exactly like I planned them, but I adjusted and moved on.

I totally agree that life must have purpose. The purpose of playing golf or other sports everyday will quickly grow old for most. Doing meaningful volunteer work for your church or some non profit will likely be fulfilling and lasting.

I really loved this statement: “Retiring to nothing is equivalent to digging a premature grave.” Many people seem to think retirement should be all leisure activities and travel. They are great and we should do them, but they do not provide meaning that most humans crave in life.

Thanks for posting this great article.

Lynne
Lynne
1 month ago

I loved the job I was laid off from at 61. But for years I’d combined international business trips with exploring places I might retire to. So I wrapped up my NYC life, sold my apartment, and moved to Mexico almost three years ago.

Starting a new life, and in a tropical climate, isn’t for everyone. But it helped me avoid the mistakes Mike describes (of course, I made others!) Just about every moment has been interesting, and I learn so much every day. Perfecting my Spanish. Gut renovating an old house in the historic district. Making new friends, and visits from old friends. Volunteer work that makes a difference. Travel is more meaningful because I’m learning more about the country I live in.

And living in a very affordable country means not worrying about money, and enjoying experiences I mostly couldn’t afford in NYC. Like a personal trainer who charges $20/hour and devises great workouts for me in my new swimming pool.

Mike Drak
Mike Drak
1 month ago
Reply to  Lynne

I love the lifestyle you have created for yourself Lynne and I’m contemplating spending most of my winters in Mexico as well. The challenge I have with moving there permanently is losing regular contact with my friends and family. They are a big contributor to my overall happiness.

Lynne
Lynne
1 month ago
Reply to  Mike Drak

That’s a great plan. Many people snowbird here in Mexico very happily, even buying winter homes, and then spend spring/summer with family and friends back home (who will also visit you in Mexico!) Where in Mexico are you thinking of wintering? I’m in Merida, in the Yucatan Peninsula.

Gozo Rabat
Gozo Rabat
1 month ago

THE RELATIONSHIPS BETWEEN MONEY & RETIREMENT:*

This certainly was an engaging self-analysis of retirement’s wide-ranging concerns—including, yet ranging far beyond, the sole goal that most of us focus on: making our money last.

We mostly make a common mistake in America: we think of money—Financial Wealth—as if it were an actual commodity, like lead or oil or pork bellies.

Money truly represents Stored Time. In that sense, (A) one can only utilize so much extra “Time,” and (B) those who manage to use their existing Time to great advantage, need not focus on storing so much excess.

Here, it’s helpful to think of societies that we, in the Developed World, think of as “primitive” and “poor.” If you know what you’re doing with the “Time” of your life—as we so often see, or imagine, in the happy faces of peoples in developing societies, dancing their hearts out, eating among family and friends with great abandon.
____________________

As demonstrated in advertisements, we, through the graces of the financial-advisor industry, think of retirement as if its door is some fixed number:

“The Number,” or “How Much You Need to Retire.”

As Mike Drak’s essay points to, there’s a whole lot more to Retirement that a “Number.” If you do everything else fairly well, the “Number” part should naturally fall into place.

Regards,
(($; -)}™
Gozo

*Note of Apology: I am not [yet] any sort of competent writer on money and related issues. But many Humble Dollar posts trigger my thoughts, and encourage me to make an effort. The above “comment,” here, is such an effort. Shot from the hip as I sit at my computer, it constitutes an early effort to manage to put my own thoughts in words. I’m regularly grateful to Jonathan Clements and Humble Dollar, and here, to Mike Drak, for providing the stimulus and the response space, willingly or otherwise.

Last edited 1 month ago by Gozo Rabat
Mike Drak
Mike Drak
1 month ago
Reply to  Gozo Rabat

Gozo my number for retirement is based on a combination of passive income from my retirement assets and government pensions plus the money I earn doing something I love. Converted to an equation it looks like this
Freedom = passive income + active income from work I love to do > my living expenses

Mike Drak
Mike Drak
1 month ago

I agree with you Piper starting up a new business isn’t easy but the payoff can be significant in terms of personal satisfaction. I’m a fan of small simple businesses where I can have a little fun plus make a little beer money.

Piper
Piper
1 month ago

I thought I would retire next year and sell my business since I’m financially ready to do so. I’m 52 now and I’ve grown to hate business ownership after 20 years. A mentor taught me that, for retirement, I should make sure I’m running to something and not away from something else. But I’ve been unable to find something to run to and so I may just keep running the business as a default option until I find something else to do with my life.

With that said, I honestly think that SOME people miscalculate the time, effort, and stress that go into running a good business that is truly focused on helping people (aka “customer service”). I wouldn’t be inclined to tell someone that starting a business is a good option in retirement unless they are prepared for the possibility of creating a monster. That is how my wife and I describe our business. And it is largely the same feeling for most of the members in the small business owners guild of which I am a part. Business ownership isn’t what it used to be thanks to regulation, insurance, Amazon, scarcity of certain goods, and just plain awful treatment by suppliers. And service-based businesses come with a host of other stressors. My wife and I never dreamed that our business would moderately successful. Thankfully, it is. But we never knew we’d have the nightmares of website security, PCI compliance, sales tax calculations and payments for 16,000 US tax jurisdictions, website coding updates, and a mass of irrational customers (who I still love) that click and order stuff before they even know what they are buying.

Sometimes, it’s seems like a good problem to have since it keeps us sharp. We’re blessed and we know it, but it also can bring us to our knees and I wouldn’t recommend it as something to do in retirement. Be careful what you wish for, I guess.

I’d rather have an unsuccessful business that makes me happy than a successful business that makes me regret it.

Last edited 1 month ago by Piper
SanLouisKid
SanLouisKid
1 month ago

In the famous words of Roseanne Roseannadanna, “It’s always something.” She might go on about retirement saying, “If it’s not the money, it’s the lack of activity, and if it’s not that it’s your health (and so on).”

I had a health scare a few years ago and was in a wheelchair for a while. On the retirement days when I’m not that busy I like to stop and think how great it is to walk again and basically be able to do a lot of the things I want to do. It doesn’t even have to be that much. 

Even on the days I should probably be bored I’m not. Everyone is different and requires a different level of activity but the bedrock of my retirement was the financial planning I did along the way. Without that I wouldn’t even have the opportunity to be bored. I’d be desperate and miserable.  

Mike Drak
Mike Drak
1 month ago
Reply to  SanLouisKid

My financial independence is the bedrock of my retirement. Because of it I have the freedom to do what I want, with who I want, when I want. Life doesn’t get much better than that.

John Yeigh
John Yeigh
1 month ago

Mike,
Great article. I agree that many of us just don’t do “retirement” well, including myself and many friends. Indeed, I even followed your script and wrote the book (Win The Youth Sports Game) which comes out next month, but discovered that isn’t enough. For our next chapter, my wife and I are starting a business which I’m sure to chronicle in future Humble Dollar posts.

Mike Drak
Mike Drak
1 month ago
Reply to  John Yeigh

Can’t wait to see what you are up to John.

kristinehayes2014
kristinehayes2014
1 month ago

I have often wondered how much the ‘difficulty’ of transitioning from working to retirement is influenced by personality and job type. I’ve been working full-time for 30 years now. I’ve never been particularly passionate about any of the jobs I’ve had. They’ve simply been a means to provide me with enough income to allow me to partake in the hobbies and activities I do enjoy.

On top of that, I’m an extreme introvert and don’t particularly enjoy the social interactions I have with co-workers. I prefer working on my own and getting the job done.

I’m looking forward to leaving full-time work behind. I doubt I’ll have any problem saying ‘good-bye’ to my job one day and ‘hello’ to a new life the next.

I can imagine for folks who love what they do and who enjoy spending time socializing at work, it could be a much more difficult transition.

Mike Drak
Mike Drak
1 month ago

It is and it was hard to be kicked out of a tribe that I had been in for 36 years. My father suffered from retirement shock and I had a good friend die because of it. Some people will suffer and others will be relieved that it’s finally over.

kristinehayes2014
kristinehayes2014
1 month ago
Reply to  Mike Drak

I definitely fall into the “relieved that it’s finally over” camp!

Susan Frederick
Susan Frederick
1 month ago

Kristine Hayes – you expressed my feelings exactly. Like you I’m an introvert and rarely, in 37 years of professional work, felt passionate about work. There was never enough time to do all the things I wanted to do. As soon as an early retirement package was offered, I was gone (at 57).
7 years later and there’s still not time to do EVERYTHING, but these years have allowed me to travel the world, spend time with family, and explore my creative, spiritual and athletic sides.

kristinehayes2014
kristinehayes2014
1 month ago

Susan–It sounds like we are kindred spirits! I spend most of my days at work thinking about all the other activities I could be checking off my ‘to do’ list if I wasn’t working. I also suspect, like you, that even when I don’t have to work, I still won’t have time to do everything I want to. My mind rarely stops thinking about new ways for me to spend my time. It sounds like you’re thoroughly enjoying your retirement and I can’t wait to experience mine!

polamalu2009
polamalu2009
1 month ago

Excellent article. Food for thought. I’m a 70 year old physician and I love taking care of patients, many of whom I have known for over thirty years. Half my workday is procedural and half is cognitive. But it is the physical part that is wearing me down. Standing for nearly five hours each and every day is wearying. The small joints of the hands are bone on bone. The neck and back ache. I am of that generation where medicine was our entire identity and filled every waking (and often sleeping) hour. It will be a great challenge to find something, anything, so rewarding mentally and spiritually.

Mike Drak
Mike Drak
1 month ago
Reply to  polamalu2009

I agree with you polamalu – how do you replace a calling? I hate to say it but it’s not going to be easy for you if you can’t find a new adequate source of purpose.

Piper
Piper
1 month ago
Reply to  polamalu2009

I’m not one of your patients but thank you for what you do and have done.

Neil Gartner
Neil Gartner
1 month ago

Excellent article, thanks for sharing! I “retired” to an encore career as a “solopreneur” financial planner/advisor and will selectively share this with “retirement red zone” clients without a plan for the non-financial aspects of retirement (the vast majority in my experience).

Building a new career from scratch has been a roller coaster ride, very challenging initially, but it was the right move for me. I tell my clients that it has taken them decades to build their current life, so don’t expect to serendipitously land in a perfect, care-free retirement life right out of the gate. Be intentional – the sooner you begin to plan, the sooner you’ll discover what works for you.

Mike Drak
Mike Drak
1 month ago
Reply to  Neil Gartner

Well said Neil. It took me 6 years of hard work to get it right, creating new work for myself but I can honestly say life has never been better. I now have work that I don’t have to retire from.

Mike Drak
Mike Drak
1 month ago

Not all retirees are the same and this article was written as a warning for people like me. A lot of people will experience retirement shock like I did but it’s avoidable through proper preparation.

R Quinn
R Quinn
1 month ago
Reply to  Mike Drak

Mike, I reread your article and the second time I saw the words “forced to retire.” Did you mean forced to leave your job or forced to accept you retired? If the former maybe that shock added to your stress.

Mike Drak
Mike Drak
1 month ago
Reply to  R Quinn

I was packaged off by the bank but I was preparing to leave anyway because the stress was starting to get to me. Getting severance at age 59 was like winning the lottery but I still ended up suffering from retirement shock.

R Quinn
R Quinn
1 month ago

All you observe can be true and for many it is, but that experience is highly personal and based one individual personalities. I agree one needs to find a different life to live in retirement, but I’m not sure it is a dramatic as “Retiring to nothing is equivalent to digging a premature grave.”

Sometimes that new life needs to be a dramatic change but other times not so much. I found mine in travel, in being more involved in family, especially grandkids, dabbling in drawing, starting a blog for fun and spending time with my wife. It’s only been the last year that I have a new group of golfing buddies.

I worked for the same company from my 18th birthday in November 1961 to January 2010. All that time I was in employee benefits working with thousands of people and their retirement benefits and planning. I can’t recall ever thinking about my own retirement planning or life after work – perhaps I should have. I doubt many people were more involved in their job than I was – just ask my wife and she will tell you I worked 24×7 just checking e-mail and preparing communications.

Then something changed. I had reached the top as VP, the Chairman of the Board who I had a very good working relationship retired and gradually a new corporate attitude toward employees and retirees began. It was time to go.

I fully agree retirement planning should be more than about money although not having the stress around money is a major factor, but I’m not sure it is all as scary as you see it. It just takes time to adjust.

For some people that can be quite a transition period, but for many it’s a matter of days. Giving up the freedom of retirement for a work schedule of any kind is not something I want to think about.

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