5 Top Retirement Regrets

Key Takeaways

  • You want to be prepared for your retirement, not side-lined by it.
  • There are 5 top regrets people have when they enter retirement, and they are all things that can be avoided with some thoughtful planning and preparation.
  • A great pre-retirement resource to read is Younger Next Year by Chris Crowley and Henry Lodge.

I had a client who was a pilot that was forced to retire at age 60. At his retirement party, he had to go out to get some provisions at the store. He drove to the store, parked, turned the keys to shut the car off, and had a heart attack and died. It was shocking for everyone, and obviously a very severe reaction to retirement. However, we almost saw it coming based on the difficult time he had being forced in to retirement.

Hopefully something this extreme never happens to you, but you want to be prepared for retirement. Below are the 5 top regrets people who have retired sometimes have, so they are great things to keep in mind when planning during pre-retirement.

  1. Not taking advantage of retiring early. I’m not kidding here. A lot of people can retire earlier but didn’t know they could because they didn’t run the numbers or didn’t look at how they’re going to live their lifestyle.
  2. Not having a plan for your free time. It may sound nice to golf five or six times a week, but it gets old, fast. It may take a while to research and figure out what you want to do with your time, but if you do this, you’ll not only have things to look forward to once you retire, but you’ll also have a smoother transition.
  3. Making a rash moving decision. Retiring and getting out of the workforce is a big change. Adding a move on top of that right away can be disastrous. You go to someplace warm and south, do a quick visit, buy a house, then find out it’s not the neighborhood you want to be in, it’s the wrong this, the wrong that. You need to take your time on a big decision like relocating so soon after retiring.
  4. Making a bad decision for a surviving spouse. Not taking a good look at what happens when one of you dies versus the other, and the choices for social security, pensions, and a bunch of other things that are interrelated, taxwise and cash flow-wise. It’s very important to work these decisions out and have a plan so the surviving spouse is well taken care of.
  5. Not getting help from a professional advisor. You need someone who can help you walk through all the financial issues as well as the non-financial issues as they relate to the financial ones.

If you are two years out from retiring, and that really is when I would suggest you start looking at your retirement, I have a book suggestion for you. There are two versions, but it’s called Younger Next Year, written by Chris Crowley and Henry Lodge. Chris is a retiree, Henry is a doctor, and they both go back and forth from chapter to chapter. It’s a fun read and you’ll get a lot out of it, so I suggest you pick up a copy to help you think through pre-retirement.

Inertia, often caused by being overwhelmed, keeps smart people from planning. TransformingWealth™ , Coyle’s proprietary approach, is designed to get your arms around the big picture so you can make informed financial decisions. Take the first step to living the Good Life Managed Well™, and schedule a complimentary TransformingWealth Preview Meeting.

Until next time, enjoy.


Gary Klaben is in our Glenview, IL office and serves our clients who are now located all over the country. He has over 30 years of experience and is the author of Changing the Conversation, The Wealth Sanctuary and co-author of The Business BattlefieldWhether advising his clients, mentoring his team, or coaching entrepreneurs, he is always simplifying complexity and motivating others to take the next action that’s right for them.
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