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What I Did to Stop 'Awfulizing' Retirement

If you fear things will go wrong, this retiree says, get over it

By Jonathan Look

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?

Jonathan Look  |  Credit:

The truth is, I was far from alone.

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 our 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 fills them with fear. To the brain, anything is better than ambiguity.

In our mind, 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 head, distorts our outlook and overwhelms all 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 will 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, that 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.

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Jonathan Look At age 50, Jonathan Look Jr., sold everything he owned, took early retirement and began exploring the world. He believed the best of life comes from being true to yourself and pushing against the edges of your comfort zone. Unfortunately, Jonathan passed away in March of 2021. He shared his unique philosophy and stories of his adventures on his website, Read More
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