Do You Have an Exit Strategy Built Into Your Retirement Plan?

Exit strategy from your retirement?

No, I’m not talking about prepaid funeral expenses/burial plots or DNR/power-of-attorney stuff.

I’m talking about a retirement strategy that includes a contingency plan should (when) the euphoria of a leap from labor-to-leisure fades and one finds themselves wading into the hidden perils of a self-indulgent, leisure-based retirement.

OK, I understand the raised eyebrows. I don’t imagine this was ever a part of the conversations that took place with your financial planner – that is if you were one of the 25% of retirees who have chosen to work with a planner.

Can you imagine the customer retention rate of a financial planner that says: “OK, now that we have your plan laid out, let’s talk about what you would like to do when you discover that this traditional off-the-cliff retirement thing is for the birds.”

Why would I need to have an exit plan from something that is supposedly the apex of a life-well-lived?

Relaxation. Fun. Sleep. Rinse. Repeat.

Feels so, so good – easy to get used to and to become habitual.

Hard to exit.


A couple of weeks ago I wrote about the dangers of “the dip”, that early phase of retirement, how easy it is to get stuck there, and how retirement can be like a cul-de-sac – circular, safe, comfortable, dead end.

An exit strategy is a good thing to have for “the dip.”

In 2018, I did an article about the stages of retirement (see it here) where I referenced the research done by Ken Dychtwald, the founder of AgeWave and the foremost thought leader on issues related to aging.  His organization has done extensive research on retirement, using a database of over 50,000 retirees.  They concluded that retirement has five stages:

  1. Imagination – 5-15 years before retirement

  2. Anticipation – 5 years before retirement

  3. Liberation – retirement day, anticipation realized. Average duration: one year

  4. Re-orientation – 1-15 years after retirement. Critical life questions surface; post-partem depression is common; growing concerns about health and finances; boredom; unstimulated

  5. Reconciliation – late 70-80s; trying to come to terms with who they really are; friends and family dying; money concerns intensify; concerns about legacy

Number 3 is the entrance to “the dip.” If you knew the downsides of staying in #3, wouldn’t an exit plan of some sort be sensible to avoid #4 and #5?


Mikey likes it!!

Mike Drak is a budding new author that exercised an exit strategy from a retirement gone sour. Mike got his walking papers unexpectedly after 36 years in the banking industry, with much of it in upper management roles. After working hard throughout his career, saving for and anticipating his retirement, his experience was nothing like he expected it to be when it came around.

In his words, “- I felt lost, aimless, well on the way to spiraling down into Retirement Hell.”

Mike’s exit strategy was to write and to help others avoid what he experienced. His first book, “Victory Lap Retirement: Work While You Play. Play While You Work” has been a big success.

Mike treated me to an advance copy of his second book entitled Retirement Heaven or Hell: Which Will You Choose? 9 Principles for Designing Your Ideal Post-Career Lifestyle.”  It’s a solid guide for retirees who are experiencing the disenchantment of traditional retirement.  Better yet, it’s a guide for those anticipating retirement to avoid what can become “retirement hell.”

Mike’s story of entering “retirement hell” will resonate for some who have entered retirement without a carefully thought-out non-financial plan  – which is the case for 2 out of 3 retirees – with no plan for exiting “the dip.”

I’ll wrap with a paragraph from Mike’s book:

“This book contains everything I’ve learned about retirement and how we can live longer, healthier, happier lives. It’s a  book about possibility, finding purpose, and having fun in retirement. I felt the need to write it because the conventional retirement story they like to tell us no longer works today. It’s a big mistake to live a retirement devoid of accomplishment, success, and failures. We were not born to merely survive and then retire, full stop. Once we’ve left our primary career behind, we need to continue to matter, to make a difference, to contribute, to help the world be a better place. And believe me, the world needs a lot of help right now.” 


Did you have a retirement exit plan that you’d be willing to share? We’d love your thoughts or comments on this. Scroll down and leave us a note. Also, tell your friends about this weekly publication and suggest they join the growing tribe at www.makeagingwork.com.  There’s a free 25-page ebook on how to live longer and healthier in it for them.