Transitioning to Retirement

Key takeaways

  • Whether you’re in your 20s, 40s, or 70s, major life transitions can cause a lot of discomfort and unease.
  • Retirement is one of those big life transitions that often comes with fear and other worries attached to it, especially for those who haven’t come up with a plan for it in advance.
  • It’s important to start planning for the changes that will take place after retirement, reprioritizing the various aspects of daily life, and embracing your new and freer lifestyle.
  • Planning alleviates the fear of the unknown and creates order, making the time between the actual day of retirement and the day you feel settled and fully transitioned much shorter and easier.
  • You’ll know you’ve made it once your new schedule is full and you’re so busy doing the things you want to do, you don’t have time for anything else.

Back when I was 21, I was on the regimental staff at West Point. This “old” guy, a major—who  was about 36—said to us, “You are now them.” I answered, “Them?” He came back with, “You know, you’re now in charge. You’re now in a position of authority.” I didn’t like that. I liked being us. I didn’t like being them. Honestly, that was the first major life transition I remember where I thought, “This is not fun,” but, of course, I got through it and went on.

Another major transition I see a lot of people experience is retirement. You’re going along for a good 30, 40, or more years and, all of a sudden, life just switches gears on you. It’s a complete turnaround. You’re now retired. That scenario carries negative connotations with it for a lot of people. It doesn’t have to be that way. We’ve got to plan for it and get ready for it. We have to make sure we have the right mindset to successfully make the transition.

But here’s the interesting part: When I hear someone who’s been retired for a while—be it a client or someone else—say these words to me, “I never have enough time anymore,” I breathe a sigh of relief and think, “Great! They’ve made it. They made their transition.” The fact that they don’t have extra time means they’ve reprioritized, embraced changes, and filled up their life to match this new mode they’re in. But, the period in between the day of retirement and actually making the transition can be extremely challenging, filled with deep trepidation, et cetera.

If you’re a year or two out from the point where you’ll be making this big transition, it’s important to begin planning it out now. Start thinking about how you’re going to make the necessary changes. It doesn’t just magically happen. The way you do things and your priorities must change. It’s imperative you start setting that up.

Planning for transitioning to retirement always gets more difficult the older we get, but it’s worth it. It will get to a point where you can say to yourself and other people, “I just don’t have enough time anymore. I can’t believe I did what I used to do while I was also working.” When I hear that, I’ll know they’ve made it. Now, they are them. 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, Wealth of Everything 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.

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.
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All information is from sources deemed reliable, but no warranty is made to its accuracy or completeness.   This material is being provided for informational or educational purposes only, and does not take into account the investment objectives or financial situation of any client or prospective client.  The information is not intended as investment advice, and is not a recommendation to buy, sell, or invest in any particular investment or market segment.  Those seeking information regarding their particular investment needs should contact a financial professional.  Coyle, our employees, or our clients, may or may not be invested in any individual securities or market segments discussed in this material.  The opinions expressed were current as of the date of posting, but are subject to change without notice due to market, political, or economic conditions.


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