What Does Your Retirement *Look* Like?

Fantasy or real?

“The only thing worse than being blind is having sight but no vision.”
–Helen Keller

When I got out of college, I figured I’d be in the Army for 20 years, do my time, get the Army retirement pension, and then…


I really didn’t think that far ahead. I just set the marker in the sand at 20 years and then being done.

Beyond defining done as “not being in the Army,” I’d done no further planning.

While I’ve previously covered the importance of not retiring from work in the article “Retire TO Something!”, I haven’t filled in the blank on one other important piece of the puzzle in helping motivate you towards reaching your retirement goals.

But first, a little personal story.

When I was 22 and fresh out of college and a wet-behind-the-ears second lieutenant, I had no idea what it was that I really wanted out of life. About the only think I knew I wanted it to be was NOT like West Point. Anything else, at that point, seemed to be pretty fair game to me. It took me quite a bit of living to really get a handle on what was meaningful and important to me and what could potentially give me eudaimonia.

Therefore, it wasn’t until more than a decade later that I started to really come up with a vision for what I wanted to do when I no longer worked.

What’s my retirement vision?

Aside from doing a few scouting trips (including one that I detailed in the article “Practicing What I Preach: The Chile Trip Report,”) I haven’t done a lot of the physical legwork to see if this is the life I’d like to live, although I have done a lot of research online. At some point, though, Internet research will be no substitute for actually doing it.

I’d love to live as a quasi-permanent vagabond. Not in the sense of going all hippie and living on the beaches of Thailand as a surfer (which would probably be my friend Doug Nordman’s ultimate dream were he not already living in Hawaii), but, rather, going somewhere neat for three to six months, coming back to a home base in the U.S. for a little while, going somewhere else for another three to six months, coming back, and repeating the cycle until I got tired of it.

I’m pretty sure that while I’d lived in Germany and read Tim Ferriss’s The 4-Hour Workweek (#aff), it was this article that really started stoking the fires, along with a trip to Botswana where I stayed with a friend who lived on a FANTASTIC palatial estate that came with a full-time live-in maid (who was in another building somewhere on the 15 acres) and a half-time gardener for $1,500 a month. Talking to Amanda, who had worked most of her professional life in Africa, stoked the fire and the New York Times article poured gasoline on it.

Pretty quickly, my vision had crystallized in my mind. Of course, convincing my wife that she had the same vision has taken a lot more work (and is still, admittedly, a work in progress).

By no means is this vision completely clear. I can’t tell you all of the places that I’d like to go, although I certainly have a list of places I want to scout out before we quit working. I have no idea what we’ll do when we get there. I haven’t planned it out to the nth degree.

But I do have a picture in my mind of what this lifestyle will be like and a reasonable idea of how much it will cost.

It’s that picture that has been important in providing me motivation over the years, although as NYU’s Gabrielle Oettingen points out, while the images were key, they weren’t enough to help me solidify my desires to make those mental pictures a reality.

According to Oettingen, there is a fine line between fantasy and converting those mental images of fantasy into reality. We previously discussed how simply imagining something doesn’t make it come true in “Visualization Does Not Equal Execution”, and Oettingen’s research supports the notion that if you simply fantasize about something, then Monkey Brain, your limbic system, is going to act as if it’s already been done and won’t encourage you to actually act on those images. The fantasy will remain fantasy forever, and, when you’re confronted with a reality that is not the beautiful picture you had in mind – often much harsher than your mental la-la land – you wind up doing worse in achieving your goals than if you never fantasized in the first place.

The missing ingredient is positive motivation. You have to believe that you’re going to be able to reach a goal in the first place. If you think that you can reach a goal and then you create mental images of what the goal will look like when you achieve it, then and only then do you get Monkey Brain to come along for the ride.

You: “You know, if we diet and go to the gym, we can probably have six pack abs in 4 months.”


You: “Yes, we can do it. Look! See what we’ll look like with a real six pack?”

Monkey Brain: “OOH. SHINY!”

If you are setting a goal that is unrealistic and you don’t think you can achieve it (“I’m going to be a quadrillionaire by next week!!!!”), then if you start fantasizing about that life, you’re setting yourself up for disappointment. Once you realize that you can’t actually reach the goal you’ve started fantasizing about, you’ll lose motivation, and then you will slide.

How Can You Envision a Retirement Goal You Can Achieve?

The first key aspect of this process is figuring out what’s realistic. No point in fantasizing about your fleet of 400 yachts if you’ll never be able to get there. There’s also no point in fantasizing about your fleet of 400 yachts if having 400 yachts isn’t important to you. You have to make this vision of your destination one that you want to reach and one that can be reached. It doesn’t have to be a gimme (“I want to be able to afford Ramen noodles next week”), so there can be some aspirational aspect to it, but it does have to be a) attainable, and b) one that you will believe you can hit.

Then, the next key is to solidify a picture in your mind about what that retirement goal will look like. You can daydream about it. You can look up pictures on the Internet. You can take pictures. You can draw pictures. The key is to create something visual, ideally one that then gets cemented in your mind’s eye and one that Monkey Brain will hang up in his cage and look at every day for motivation.

Once you’ve set that picture in your mind, revisit it each time you’re budgeting, deciding how much you want to save for retirement, and when you want to make a big purchase. Your goal is to create a memory palace of pictures of what that retirement looks like when you’re facing decisions in your life which could either reinforce that goal or cause you to go astray (note: to learn more about memory palaces, you can either read Joseph Campbell’s The Power of Myth or Tim Ferriss’s The 4-Hour Chef (#aff)).

Published by

Jason Hull was the co-founder of Broadtree Partners, a firm that acquires $1-5MM EBITDA companies. He also was the co-founder of open source search consultancy OpenSource Connections, a premier Solr and ElasticSearch firm. He and his wife FIREd (financial independence retire early) at 46 and 45, respectively. He has a BS from the United States Military Academy at West Point and a MBA from the University of Virginia Darden Graduate School of Business. He held a CFP certification from 2015 - 2021. You can read more about him in the About Page. If you live in Johnson County, Texas or the surrounding areas, he and his wife are cash buyers of Johnson County, Texas houses.

4 thoughts on “What Does Your Retirement *Look* Like?

  1. Great post, Jason! Coincidentally we’re planning to spend a few weeks in Bangkok soon, so I’ll file a full surf, er, trip report afterward.

    When I retired from the military over 11 years ago, I just wanted more control over my time. I had the usual vague plans and a “To Do” list, but I felt that I was gaining all of the time in the world.

    Today I’m in my 50s, and an alarming number of my peers are experiencing health crises– or even worse. “Just one more year” is not a plan. “Now” is the time for readers in their 30s and 40s to create those mental retirement pictures so that the real planning can get underway.

    Six-pack abs? Well, those do not get easier with age, either– but surfing helps…

    1. I promise I was unaware of that trip when I wrote the article!

      Your website is very clear about your philanthropic goals; having found that sense of purpose has prevented you from doing nothing all day and given you a stock answer to the question “What will I do all day when I’m retired?”

      “Now” is the time for readers in their 30s and 40s to create those mental retirement pictures so that the real planning can get underway.

      Pure gold. I have a forthcoming article about an American Century Investments survey regarding regrets fifty and sixtysomethings have when it comes to retirement planning. The stereotypical fiftysomething has just realized that retirement is around the corner and the retirement accounts are horrendously paltry. Getting a 20-30 year head start on arriving at that point will reduce future fifty and sixtysomething angst.

  2. Your posts on the monkey brain crack me up! I’d heard a lot about the benefits of visualization but hadn’t heard of the need to pair it with positive motivation for it to be effective. Interesting stuff.

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