7 Regrets Happy Retirees Will Never Have

March 15, 2019

Life can be full of regrets. When you are young you might regret not asking somebody out, or not trying out for the basketball team.

In middle age, you might regret not taking that overseas assignment that was offered to you, or buying that bigger house in the suburbs that might have pressured your finances but also provided a great place for your kids to grow up in.

Many regrets are forgotten with the passage of time. You move on to different things, your priorities change and you get busy. Your eye is always looking ahead.

Sure, once in a while you may become nostalgic and peak in the rearview mirror. You may think back about what might have happened if …. But as quickly as that thought pops in your head, life intervenes and you are on to the next thing.

Busy, busy, busy.

As long as you are in the flow of life and things keep moving you spend little time thinking about potential regrets. You are much more focused on what you need to do next and what it will take to climb that mountain.

But when things slow down or you experience a major life transition those old regrets parked deep in your memory have a way of showing up again in vivid color.

Transitions mark the ending of something significant in your life

Research has shown that one of the least talked about life transitions is that when you stop working fulltime and enter into what we typically characterize as retirement.

The transition into retirement is a difficult one for most people. Surveys show that after a brief honeymoon maybe lasting a year or two, many recent retirees enter a period of uncertainty and introspection.

Regret as to what could have been and should have been is common at this stage in life.

Some retirees manage to navigate through the fog while others linger behind in negativity. Regret is one of the strongest human emotions but it does not have to take up permanent residence in our lives.

Plenty of retirees have managed to overcome feelings of regret by proactively taking control of their lives and choosing positivity over brooding or ruminating over what could have been.

What are some of the roadblocks or behavior patterns that happy retirees have successfully overcome?


#1 Compulsively checking the rear-view mirror while driving on a deserted highway

Having great memories of your career and raising a family is fantastic but living in the past when you might have 30+ years in retirement is a bit too much.

People that live in the past tend to be very risk averse and reluctant to try new things or experiences. They are always implicitly comparing the present with the past. Our memories are not always accurate and people with this mindset may be glorifying their past and holding too high of a standard to beat.

People that live in the past tend to prefer doing the same things over and over. For example, they often socialize with the same core group of people that they have known forever.

In contrast, happily retired people tend to seek new challenges and enjoy pushing their physical and mental boundaries. They also seek new social connections whether they are long lost friends or new relationships.

#2 Going to the Bellagio in Vegas and leaving it all up to chance

Living in the moment and living for short-term pleasure and enjoyment is occasionally fine.

Happily retired people allow themselves to live in the moment but only after planning the financial as well as non-financial aspects of their retirement. If their plans allow for the occasional splurging on a big trip or expenditure, no problem.

Spending time on passive activities such as gambling is also a big red flag. Not when done in moderation but not as a sport or when betting disproportionate amounts relative to one’s means.

Planning your life in retirement does not have to involve not having any fun or tracking every little expense. It does, however, require an idea of what you can spend and on what types of activities or pursuits.

Recovering from an unplanned big bash can be stressful if not catastrophic to your financial health.

Photo by Anoir Chafik on Unsplash

#3 Treating friends and family like the reusable Whole Foods bags in your trunk

Nobody lives forever. Relationships become if anything more precious as time becomes more finite.

Research also shows that as people age their circle of friends shrinks. Taking care of your existing relationships with friends and family becomes very important.

Equally important is staying receptive to new friendships and re-acquainting yourself with long-lost friends from your distant past.

You want quality over quantity in terms of your social connections.

Holding grudges toward friends or family is a recipe for regret. The more time that goes by the more space those regrets will take up in your head.

Maintaining a tight group of relationships as you age has been shown by the Harvard Study of Adult Development to be the most critical factor in explaining longevity as well as overall happiness.

#4 Loading up on “pico de gallo” as your vegetable portion for the day

It is easy to gain weight in the early days of retirement. Many people look forward to relaxation and adopt a sedentary lifestyle. Big breakfast, a bit of TV, lunch, nap and Happy hour at 4. All calorie enhancing!

If anything it is more important to take care of yourself as you age. Weight gain is associated with all kinds of health problems not to mention expending more energy to simply move around.

Happily retired people take great care of their physical and mental health by eating nutritious food, sleeping well, remaining physically active and pursuing challenging mental tasks such as learning new things.

The mind and body connection is well established by scientists. A healthy mindset coupled with healthy daily behaviors is important for optimizing your physical and mental health. Keeping a healthy weight is one of the keys to your health and happiness.

Photo by Rex Pickar on Unsplash

#5 Thinking like a lizard

Our primitive portion of our brain known is known as the reptilian brain. This part of the brain protects us from perceived threats. It assesses danger and reacts quickly through our reflexes, balance, breathing, and heartbeat.

The sole role of the reptilian brain is survival. Planning and rational thinking are not in its repertoire.

The problem is that many times our first instinctual response driven by the reptilian brain leads us astray in our modern world. We jump to conclusions without thinking rationally about the consequences or alternative courses of action.

Most of our daily behavior is unconscious, but many of our major decisions in life need to be thought over in a rational manner.

Finding space between emotion and action is a skill that high functioning people have mastered by identifying triggers, developing greater awareness, and deliberately choosing an appropriate behavior.

#6 Getting overly attached to your Lazy Boy recliner

Nothing against a good recliner. They are wonderful when watching a movie or a sporting event. They even look good these days and come in more colors than that old brown one in your basement growing up.

Occasional use is advised. Over-use is not. One of the main ways of managing the aging process is through exercise.

As Dr. Mark Williams illustrates in his book “The Art and Science of Aging Well” there need not be any major loss in overall body functioning as we age assuming that the individual pursues a reasonable program of cardio, strength and flexibility exercises.

Getting out of the Lazy Boy and exercising has great benefits for your physical health. The added bonus is the often forgotten benefits to your mental health. Exercise, for example, is one of the best ways to deal with stress.

#7 Using your TV as your alarm clock and mood meter in your house

Newly minted retirees often look forward to just relaxing and not having any demands on their time.

They want to do whatever comes to mind at the moment. The problem is that often times very little comes to mind and it becomes easy to just turn on the TV and wait for inspiration.

In surveys by the Bureau of Labor Statistics, the typical retire in the US spends 48 hours a week in front of their TV. Then you have internet browsing. Suddenly those 8 to 10 hours a day previously spent at work are now taken up by TV and the internet.

It’s not only the amount of time spent passively watching TV or on the internet but also the type of content being consumed. As they say in the computer world, “Garbage in, garbage out”.

But it is even worse as often times what you consume digitally has an effect on your mood. If you are watching a lot of news or financial shows you will probably start seeing problems all around you and your anxiety level will rise.

Happily retired people lead active lives. Replacing passive activities such as TV watching with getting out and experiencing life are great ways to get more juice out of your retirement years.

“When one door closes, another opens; but we often look so long and so regretfully upon the closed door that we do not see the one which has opened for us”

Alexander Graham Bell

Become your own Retirement Super Hero

Regrets are one of the most common emotions felt by people especially as they contemplate their own mortality.

We all have regrets living deep in our memories but not everybody lets regrets linger on and bring them down.

Happy retirees have successfully slain these self-made dragons. They have made peace with their past. They have taken action to resolve any lingering conflicts. Their daily behavior is consistent with their values.

Life is about taking action. You have the ability to influence the path you are on in your life regardless of how old you are or feel.

Learn from the behavior of people who have mastered the art of slaying past regrets.

Find your own retirement super-heroes. Maybe your superhero is somebody like Warren Buffet or Ruth Bader Ginsburg. Maybe it is somebody in your family. For me, it is my 90-year-old uncle that still travels the world on his own.


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About the author

Eric Weigel

My goal is sharing my experience as an investment manager, certified retirement coach, and fellow Baby Boomer to enable people to design the life they want and that matters to them in their next phase in life. We all want to live longer, but we also want to lead a life of meaning, joy, and fulfillment.