What one boomer did to stop ‘awfulizing’ retirement

Here’s some advice we endorse: If you fear things will go wrong in retirement, get over it! That comes from retiree Jonathan Look, Jr, and when we tell you that he now lives on the banks of the Mekong River in Vientiane, Laos, you’ll know he takes his own advice seriously! We saw this piece on the website of our friends at NextAvenue.org, and thought you should too.

I had been planning my retirement for years. I read all the literature about my pension and ran all the calculations. I reduced my spending. I got completely out of debt and even added a little padding to my savings. So why did I fear what is supposed to be the best time of life? Why did I awfulize retirement — thinking so much about the things that could go wrong that I was afraid to retire?

The truth is, I was far from alone.

Jon with partner Sarah in Tibet.

Now that I’m retired and traveling around the world, I have met many retirees— tourists, expats, and nomads— who’ve expressed frustration with themselves about how they had awfulized what has turned out to be the best time of their lives.

Why I Was Awfulizing Retirement

In my case, even I was surprised that I had awfulized retirement. After all, from the time I began working as a teenager, I fantasized about living what I now call “Life Part 2” (which is also the name of my blog about my experiences as a retiree globetrotter). And although I enjoyed my 25 years working as an air traffic controller, near the end of my career I longed for the days when I could set my own course, travel the world, and do my photography. I wanted to leave the comfortable cage I had built for myself, live life “closer to the bone,” challenge my boundaries, and explore the world. I was ready.

Or so I thought. But what, I wondered, if my assumptions and estimates were wrong? What if I hadn’t saved enough? What if the cost of health care soared out of reach? What if inflation shot up? What if my investments took a dive? What if I outlived my plan?

How Fear Distorts the Picture

When pondering retirement, many people fantasize about, say, life on the beach or having time to write the next great American novel or finally being able to spend more time with the grandchildren. But when action and decision-making are required, fear distorts the picture. Opportunity starts to look like a nightmare. The human brain is an amazing thing, but it doesn’t deal with uncertainty very well.

Retirement is a bet on the future, and no one can anticipate all the unknowns. The data is necessarily incomplete. When confronted with incomplete data, our brains look at the information gaps and fill with fear. To the brain, anything is better than ambiguity.

In our minds, the worst-case scenarios suddenly become the most likely of circumstances. We begin to doubt our calculations. We begin to doubt the experts. At the very time we need to trust our judgment the most, fear gets into our heads, distorts our outlook, and overwhelms our assumptions.

Hence the term psychologists use to define this phenomenon: awfulizing.

Dreams Deferred or Crushed

Many dreams of an enjoyable retirement have been deferred, or even crushed, under the weight of awfulizing. It is easy to find excuses for waiting to retire. Doubts begin to creep in and fear overwhelms the confidence we have in our preparations.

Because we are awfulizing the future, the present (no matter how much we want to break free) starts to feel “comfortable enough.” Fear tricks us into inaction and we put off our dreams a little longer. When we should be taking control, awfulizing keeps us paralyzed and wanting.

How I Stopped Awfulizing Retirement

So, how did I overcome my fears, move forward, and stop awfulizing retirement?

I envisioned my dreams of traveling the world, of enhancing my photography skills, and of learning about different cultures. I gave up on my need to know with certainty that my plans were the right ones. Instead, I wholeheartedly embraced the adventure.

I gave notice at work, sold all my belongings including my house, and created a scenario where I left myself with no choice other than to move forward.

I decided to live by the words of Dwight D. Eisenhower: “Plans are worthless, but planning is everything.” In other words, I told myself, any plan or forecast that I made would be wrong moments after I wrote it down. I made a personal pact that I would periodically adjust my plans, based not only on changing conditions but also on my changing desires and expectations.


Retirement Planning vs. Reality

Planning can teach us a lot, but what you plan and what you get can be two different things.

In the five years since I’ve retired, I’ve become comfortable with uncertainty. In fact, I have even learned to embrace it!

I have found that many of the excuses, limitations, and doubts I had put on myself were merely fictions created out of fear.

Time is our most valuable asset and how much time remains is one of the biggest variables in retirement. What we do know is, with every minute that passes, we have less time available. In the end, we all reach the same destination.

The Opportunity of Retirement

Deferring your dreams, after you have wrung all the joy out of parts of your life because you are afraid to move forward, is surrendering to your fears. Retirement is an opportunity to unapologetically try new things, reinvent yourself, expand your horizons, help others, or even just bask in the glow of what you have accomplished. But it is no more predictable than life before retirement.

Yes, retirement is a big step. Of course, you’ll have concerns. Just don’t let awfulizing crush your dreams, whatever they are.

I have yet to meet a retired traveler who wishes he or she had delayed quitting work a few more years before embarking on adventures or beginning to fulfill dreams. To the contrary, in most cases, once they started retirement, any fears of running out of financial resources have transformed into fears of running out of time.

© Twin Cities Public Television – 2017. All rights reserved.


  1. Great article!.. Boy, that’s me. 43 years as a Realtor.. Business is good. money is good, life is great… I’ll be 68 this week,,, Most men in my Family cash it in at 75 or so… My wife says for me to ‘forget 6 days a week, throw in the towel and enjoy.

    This article is a step for me.

  2. I found your optimistic, go-for-it attitude just what my wife and I need to read and reread. We are anticipating the start of our retirement soon. Just as you suggest, we are finding ourselves becoming ambivalent because of all the potential “black swan” events that may escort us from financial independence to poverty. It’s understandable why, for some pre-retirees, moving from years of asset accumulation to an uncertain future of deaccumulation can be a daunting emotional hurdle. Thanks for your pep talk. I hope to run into you on the road — Iceland would be nice.

  3. “The human brain is an amazing thing, but it doesn’t deal with uncertainty very well.” Magnificent! This is a special piece of a literary commentary. Cheers to you, Jonathan. I hope it doesn’t inspire others like yourself to take that leap of faith. We can never forget John Lennon’s words: “Life is what happens while youarr busy making other plans.”

  4. 10 years later at 72 I am frightened shirtless. It seems like I did it all, and remember almost all but the mind only thinks the bad or worst as learning processes . Been there, done that and negative is all my mind seems to say. So many aspirations, all fulfilled. Where, what, who[me]is left or next. What goals are to be thought of? To many deaths and disappointments at one time recently put me into a shaking anxiety fueled depression. I can’t pinpoint my fears, but they are real. I don’t fit the mold as some other people/men do. I did as I wanted, I traveled, ran businesses, horses, cars galore, boats, airplanes, gold, gambled, politics, family, everything worked out one way or another. I lost my sense of appreciation. Still, Why do I exist is my question. Or is it all a lie/fabricated cruel memory test? Yet still inside I feel the heart race and head dizzy, scared and confused. A lifetime of selling myself and defining a workaholic. Others must be in my situation so I can’t be alone. Is there an answer? Or is it like defining ones consciousness or existence?

    1. Hola Clifford: I appreciate your honesty. From my POV, I believe many people experience the same feelings in some degree.

      It’s hard for me to imagine that someone who has done so much, feels so adrift. But, one sentence caught my attention, “I lost my sense of appreciation.” Hmmm, for me, so many things happened I did not plan, I learned the meaning of “living in the moment.” It is a unique feeling. This lead me to practicing gratitude. While at first, I recited “I am so grateful for x”, but gradually the recitals moved into a sense of wonder and joy. Every unplanned event has had a silver lining.

      Do you think you are an “adrenaline” addict? Afraid to slow down?

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