Retirement Cold Feet

After years of planning, a 65-year-old has retirement cold feet, despite being financially prepared. How can he get past his fears and learn to relax? Advice columnist Eric Thomas weighs in – plus added suggestions from a retirement educator.


Dear Eric:

I will turn 65 in a few months and have announced my plans to retire. I have a long list of things I want to do, and after 50 years of employment and saving, I am well situated for these next years. At least, that is what my financial adviser and balance sheets tell me.

I really yearn for more discretionary time and my physical health tells me I need to get out from under a desk. My problem is that I am getting cold feet about leaving a paycheck behind.

I know this is a good problem to have on the surface, but it really is torturing me. I need some words of wisdom to help me get to the other side. Can you help me?

– Undecided Plans

Dear Plans:

There’s a version of yourself in the past who started on this journey of saving and planning with the hope that he would one day be in your shoes. And every time you/he struggled to get through a work week, perhaps you thought of this moment. So, congratulations, to you in the past and in the present. You did something incredible.

Feet up on a table relaxing after getting over retirement cold feet.

You know how sometimes you go on vacation but you’re not in the mood to vacation for a day or two? Unfortunately, we don’t have a relaxation switch. So, don’t try to force yourself to suddenly be in retirement mode if you’re not. Make a plan for your days and your goals that’s realistic. You have time to get used to this new phase and get past your retirement cold feet.

You’ve trusted your financial adviser thus far; when you start to feel anxious about leaving a check behind, reach out. “Remind me that I’m fine.” People do this with financial advisers all the time. It’s perfectly normal to need reassurance.

This is a transition, a big one. While it might seem like a phase of life that one would leap into happily, it’s right to acknowledge the complicated feelings around it, too. You’re shifting the way that you live and breaking routines that you’ve had for decades. This is going to take some adjustment. Give yourself space and time to feel that and the freedom to change course whenever you want.

Tips on retirement cold feet from an experienced educator

Dear Eric:

I read the question and your answer to “Undecided Plans”, who was having cold feet about retiring. I’ve been teaching an all-day workshop on retiring a few times a year for quite a few years now (even though I retired a few years ago at 71). I have several things to add to your suggestions.

  1. Many people are ready financially for retirement significantly before they are emotionally ready.
  2. After 50 years of saving for retirement it is challenging for most to start spending down what they have saved.
  3. Most of us know what we are retiring from but aren’t always sure what we are retiring to.
  4. Research indicates that transitioning into retirement is more successful for those who’ve planned for it.

– Retire Well

Dear Retire Well:

Thank you for sharing your knowledge. I love that you teach a class; these are life skills that can be learned and honed.


Updated March 28 with tips from an experienced educator

R. Eric Thomas (he/him) is a national bestselling author, playwright, and screenwriter. His accomplishments include “Eric Reads the News,” a daily humor column covering pop culture and politics, serving as the interim Prudie for the advice column “Dear Prudence,” and author of “Congratulations, The Best Is Over!” Send questions to R. Eric Thomas at eric@askingeric.com or P.O. Box 22474, Philadelphia, PA 19110. Follow him on Instagram and sign up for his weekly newsletter at rericthomas.com.

For more like the advice on overcoming retirement cold feet, check out the Boomer Advice for Life department and more wisdom in Seniors Guide like expectations of grieving friends, connecting with shy grandkids, and parental rejection.

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