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5 Ways to Prepare for the Terrifying and Exciting Transition to Retirement

By Howard Fishman January 17, 2022 Lifestyle

There’s no advance warning system to predict one’s response to retirement.

You can chat yourself up before the actual day arrives. You can bathe in some fuzzy ‘before-glow’ about the leisurely life you’re about to experience. However, nothing can prepare you for the moment your world shifts from deadlines and demands to dead time and sweat pants.

Assuredly, you can’t return to the office. That special ‘it’s all about me’ place of refuge where everybody knows your name is off limits. Your month-long career celebration left work buddies too exhausted to watch you circle the cubicles in yet another victory lap.

The world you knew has gone silent.

No emails. No voice mails. No texts. You’re a freshman member in the state of ‘carefree,’ perfectly depicted by the lyrics to Kenny Chesneys, No Shoes, No Shirt, No Problems

But that is the problem. You’re conditioned to dead-heats… not dead-stops.

The Unremitting Series of Sprints Leading to Retirement

You’ve been traveling at the speed of light since the age of five. First, you were unceremoniously nudged into Kindergarten. It was a year-long Nirvana experience where unsuspecting children are tantalized – Pied Piper style – by the soft indulgences of finger painting, peaceful naps and sing-a-longs.

Then, unfortunately, you get kidnapped into a Twilight Zone of commitment that will become the rest of your life.

Caught on an education carousel, your life becomes a series of cycles. You go through grade school, high school, college, career, the start of family, real estate purchases, recessions, depressions, regressions and hard-won victories on an unbalanced ladder of achievement.

You have to stay alert to all this, while also keeping vigil over the ultimate exit strategy – a 401K savings plan frighteningly sensitive to the whims of every volatile global situation, from Brexit to Kim Jong Un to a global pandemic.

It’s a marathon race lasting 60 years, at the end of which you’ve run so far over the cliff’s edge, there’s no solid ground beneath you. Emotional gravity takes over for the quick plunge toward earth. Without a strong internal sense of purpose, you’ll soon find that retirement – just like ageing – isn’t for the weak.

The Cold Turkey Dive into the Retirement Pool

Three weeks into the deep end, and I’m sorting through some emotional jitters of my own.

During evenings of wine-induced glibness preceding the big day, promises were made to myself and others that I’d shine with an intense new light in my post-career career.

Those regrettably delivered commitments have created a pressure cooker of demand for great ideas that are not readily forthcoming. Synapses were apparently damaged in the fall.

I should get a simple job. Make myself useful. A greeter at Walmart. Or grocery packer at the nearest supermarket. Nothing strenuous or challenging.

I reach out to my financial adviser for emotional support:

  • Have I retired too early? No
  • Do I have enough money to live comfortably? Yes
  • What if I live to be 100? No worries.
  • What’s your prognosis for the market this year? We’ve discussed this a million times. You can’t time the market.
  • Couldn’t we earmark even a small amount of cash for me to execute some day trading? Under no circumstances.

With God-like patience, he listened. Then he defined the difference between his services and the services of a good psychiatrist.

Perhaps a new life mission statement was in order. Something resonant enough to return me to those halcyon Chicken Soup for the Soul days.

To move faster toward that goal, I thought actively about enrolling in Tony Robbin’s highly-touted Firewalk, that speedy trip over burning hot coals, guaranteed to overcome unconscious fears and master personal development.

Then again, maybe not.

So I went old school and began a slow drive onto that worn highway of existential pain commonly known as the To-Do list. But while pondering weak and weary over next steps, it became clear I was currently more suited to work on my honey’s honey-do list until mental clarity was restored.

And then it happened, while hanging family photos in the den of our new home, re-energized by simple engagement with what’s truly important, I developed this:

A Simple Global Positioning Guide for Retirement’s First Phase

  • Give yourself time to parachute to a soft landing. Start retirement with a long vacation.
  • It’s not about how you fill your days, it’s about the self-fulfilling waiting to be found in those days.
  • Reinvest in relationships with important significant others in your life and find sustenance.
  • Listen to the wisdom of your inner voice and commit only to those things you might not regret in six months or one year.
  • Take out that old box of Crayolas. Start to draw like that crazy Kindergarten kid who wasn’t afraid to go outside of the lines.

Article completed! Intellectual juices now coursing through my veins!

How did you manage your own transition into retirement? Or what are your intentions as you get closer to that day? Are you sharing experiences with others moving through the same life stage? Are we being good enough to ourselves during this life-altering moment or should we just keep a stiff upper lip? Please share your valuable insights below.

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The Author

Howard Fishman is a writer. An expat from California, now residing in Spain, Howard is focused on a journalistic second career, sharing insights on the expat experience, the culture of aging, meaningful friendships, generational workplace issues, and the arts that best express who we are at fifty plus. His writings can be found at

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