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Will You Have Retirement Regrets?

Updated: Mar 22



















I can still remember the first time I heard a “Retirement Regrets” conversation. It was almost 4 years ago, and my wife and I were visiting her relatives in the mountains for the Christmas holidays. On this particular day, we were out in the town browsing the local shops for any post- Christmas deals. I was strolling through the men’s clothing section of one store when I overheard two gentlemen chatting:


“How are things going?” one asked the other.


“Well, it’s going ok. You know, keeping busy and all that,” his friend replied. “It’s been a difficult adjustment for my wife and I because we aren’t

used to living so carefully. Fixed income is not much fun.”


The first guy responded, “Oh, I know what you mean. I’ve been retired for about 5 years now, and let me tell you something…if I had to do it all over again, I would have started preparing much, much earlier.”


It was like thunder in my ears. I fought off every urge I had to interject myself into this exchange that was happening about 3 feet away…mostly because I didn’t want to appear rude, or worse—opportunistic. These guys were having a genuine discussion about how difficult the retirement transition was for each of them, and they had not been prepared (financially at least) for the drastic difference.


Naturally, I continued on my way without speaking to either of them; however, that conversation has stayed with me ever since. Since then, I have heard similar conversations many times over, and each one makes an impression. The sad thing is—-it seems to be a common occurrence that people are not preparing adequately for retirement.


In this article from USA today, one of the major regrets highlighted is the fact that people are not saving enough for retirement, or they are not preparing to adjust their lifestyles for the transition from work to retirement. The sentiments reflected in this article are much more real to me as a planner when I hear them in real life—-with real people.


Ever since that day, I have wondered— If people know that one day they will no longer be working, why is there such a failure in our retirement readiness? Wells Fargo recently did a study where 22% of people admitted that they would rather die early than run out of money in retirement. That’s almost 1 out of 4 people who would rather die than run out of funds!!

Again, if running out of money is that scary, why aren’t people doing more to avoid that outcome?


I may be off base here, but in my experience, here are some thoughts about some potential obstacles for those who need to save and plan for retirement:



1) Some people are experiencing their desired lifestyle right now, and they don’t believe it will ever change. More and more people are buying the bigger homes, nicer cars and boats, and luxury items they desire today versus putting money into their savings. Our culture has become very materialistic, and one that wants what it wants—-right now. This drive to have the best of everything today is robbing us of having something for tomorrow.


2) We procrastinate. Having financial discipline can be difficult and challenging, and some people simply aren’t ready to adjust. We know it’s important—— I cannot tell you how many times I have told someone about what I do for a living or worse, given a workshop, and someone will say “Man, I really need to talk to you”…..but they’ll find every reason to not even set the first appointment. Have we really become so disconnected from our own financial wellness that even taking a small step is a huge task?


3) We think we have time. Guess what—-tomorrow you’re 55 or 60 or 65….time flies and it waits for no one. My wife and I had our first child last year, and I cannot believe how quickly the time has gone by. The greatest asset you have is time because you cannot get it back….if you let it dwindle away, one day you’ll wonder where all that time went.


4) We are drowning in debt. We live in the wealthiest nation on earth, and yet we find ways to borrow for everything. There are two main types of debt that is crushing us and preventing people from being able to save—-the necessary and unnecessary debt.


Necessary debts—- Mortgages and Student Loans. I call these debts “necessary” because for some people there just isn’t any way to own a home or attend college without borrowing the funds. Trust me, I get it. My challenge to you is——are you buying too much house?

Student Loans, on the other hand, are the 6-headed hydra of debt….some people simply cannot kill them; and it’s destroying their household economy. My word of caution—if you are going to use student loans, be very clear about the terms of the loan, and I would encourage you to choose your schools wisely. Perhaps you can even encourage your child to take the basic courses at a local community college before transferring to a bigger school.


Unnecessary debts—all other consumer debt goes here. I am even going to be so bold to include auto loans here. Why? Well, I understand that we need cars to travel, commute, do our job, etc…. but do you really need that 7-series BMW? or the 50k-plus SUV? If we are really honest with ourselves, some of us would be admitting that they own (owe) too much car.


5) We don’t know what we don’t know. The American College recently did a survey to poll Americans about retirement literacy, and guess what? America failed. That’s right—-America got a big “F” with only 20% of people scoring a “passing” grade of 60% or better. I don’t know about you, but when I was in school 60% was a “D”…and nothing I would be excited to tell mom and dad about.


One of the key concerns that this survey discovered was that there is a large disconnect between confidence and literacy. The results of the survey showed that people are generally confident about retirement, yet they lack basic knowledge in the areas of retirement income, social security, annuities, retirement investments, longevity, and long-term care. Forbes did a write-up of the survey results, and you can read that article here.





What’s the key takeaway from this post?


STOP. If any of the talking points describe you or your behavior, just stop. Next to healthcare, I can’t think of another topic like financial matters where people have a more vested interest in their personal well-being. We simply need to STOP the destructive behaviors that are preventing us from taking positive, meaningful steps.


When I played basketball, I went to one of the elite basketball camps every summer to hone my skills. I had an opportunity to compete against many players who eventually went on to play in the NBA. One day, during a “pep talk” session, one of the speakers told the camp that our preparation in the off-season would determine our success during the season.


Specifically, he said:


“There will come a time when winter will ask you what you did all summer. What will be your response?”


The same holds true for each of us. Whether we like it or not, there will be a season like retirement where we no longer desire to work or are no longer able to work. When that time comes, what will be your story?


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