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When you were in your 20s and 30s, what did you dream of doing—and why weren’t those dreams realized? Here are four of the daydreams I had, but which remained just that:
Buy a sports car and drive across the country. This one got nixed by a host of factors—not enough vacation time, lack of money, the arrival of my first child at age 25. But truth be told, what seemed like a fun adventure slowly lost its allure, as I imagined long hours on the road.
Purchase and edit a small town newspaper. I got my start in journalism at age 19, working for a tiny newspaper in the Maryland suburbs of Washington, D.C. In the years that followed, even as I worked for major publications, I mused about the possibility of running my own paper. If it had become a real possibility, I suspect I’d have quickly realized I couldn’t afford my dream, given the need to save for retirement and to put two kids through college. Still, this daydream sort of came true. I may not be running a small town newspaper, but I have had the chance to run my own publication, thanks to HumbleDollar.
Explore the U.S. in an RV. This dream never got very far. Yes, I spent time scouring the internet for different types of RV. But I was always put off by the idea of driving the darn thing. Even small RVs seemed uncomfortably large. And burned into my memory is a scene from Fort Worth, where I was attending a conference. I watched as a couple tried to navigate the city’s streets in their RV. I don’t know whether they were stressed, but I sure was, and I was just a bystander.
Buy a beach house. This particular dream came a little later, in my early 40s. My favorite town on the New Jersey shore is Ocean Grove. I’d often stop there for lunch and a walk, and every so often I’d bicycle the 42 miles from my home in central New Jersey to Ocean Grove. In 2007, as property prices tumbled, I toyed with purchasing a small home or an apartment, and even checked out a handful of properties. But all of them seemed either overpriced or too rundown. In this case, my dilly-dallying proved fortuitous. Ocean Grove got badly roughed up by 2012’s Hurricane Sandy.
So, what dreams did you let slip away?
I too, wanted to drive across country. I wanted to have a beachfront condo in Florida or South Carolina…but alas, not on a high school math teacher’s salary.
I was going to be a ROCK STAR….that worked out really well, LOL. I have been fortunate enough to become a semi pro musician, regularly getting paid gigs. BUT never enough to quit my day job. I went to Nashville early on to try to get some studio work, but quickly realized how good those guys were and hung my head and came back to Georgia.
But, I am playing this month 6/20 at a beautiful setting called West Milford Farms in Cumming, GA. Paid gig with PA and sound guys provided. Ahhhh just have to take my own gear. They do the rest. Love those lazy gigs! LOL
Thanks for starting this conversation, Jonathan. I’m grateful many of my dreams have come true.
I’m Living the American Dream
As an immigrant, living the American dream meant owning my home.
I was 32 when I became a homeowner of a tiny duplex, while most of my other single female friends still rented. Over the years I traded up to a single-family home. I can’t imagine any 20 or 30-year-olds buying homes these days.
I was lucky enough to cover Wall Street as a financial journalist in the 1980s, and then for nearly two decades as a Washington reporter covering the intersection of politics and policy until the Great Recession, when my fairy godmother plucked me out of journalism just as many publications cut back and laid off reporters.
I wanted to travel the globe but I didn’t have much money back then, and I squirreled away my savings to visit my aging and sick parents in India every year. My mother just turned 97 a few months ago, and I’m grateful I was there to celebrate her birthday.
When I turned 60, Me and Bobby McGee’s “Freedom’s just another word for nothing left to lose” became my anthem. I stopped saying “some day I will do this or that..” and started crossing items off my list.
I visited Santa Fe, Vienna, Prague and Salzburg, the French Alps. I returned to my favorite cities–Paris, London and Oxford. In a few months I’m heading Down Under.
So what dreams did I let slip away? I wanted to be marry and have children, but that didn’t happen. When I moved to Washington in my early 30s, friends warned me that there were six times as many women in the DMV area than men, and dating was tough. Much tougher than I imagined.
My dreams have also evolved over time.
Now, as I look ahead to retiring in a couple of years at that magical birthday of 70 when I hope to collect the maximum Social Security benefit, I’m ready to finish that collection of short stories I put aside a couple of decades ago, improve my birding skills, and welcome my siblings’ grandchildren.
My dream, was to marry my best friend 1968, one year before graduation 1969, then started work within one month. My wife would work as I finished my last year of school. This dream came true then graduation and birth of our first child, also 1969, it was very close timing, but it all worked out. My other dreams have developed as life advanced. I am totally content, travelled worldwide, and all over the US, especially my favorite places, the National Parks. One trip to the West Coast included several Parks, and was 8410 miles, now that is a 28 day car trip! Also enjoyed boating on Table Rock Lake in MO, with a dock and Condo. Now retired at 78, and living in a CCRC, Continuing Care Retirement Community, and it is like a cruise on land with all kinds of activities with especially friendly people. Don’t worry, I am still dreaming.
I’ve fulfilled most of my dreams: From the time I was four years old I wanted to fly and have spent 57 years( and still counting) at the controls. I wanted to live and work overseas and spent 20 years living in southern Africa —regrets? small ones. I’ve been blessed with good health and good luck. It’s been a good run.
Finished graduate B school in ’72 and wanted to run something big and make a lot of money. The money thing worked out OK, but mostly because I was lucky enough to marry someone who is thrifty and a saver. I also got my chance to manage something big, but quickly figured out that I didn’t like it and that it would ruin my life and my marriage if I kept at it. A corporate merger ended what I thought was my dream job, but in retrospect, it was the best thing that ever happened to me.
The message to this? As much as we might plan for our future, life has a way of affecting us more than we affect it. Sometimes you just have to go with the flow and see where it takes you. Be happy with what you have and try to manage your expectations and regrets about what you don’t.
I crewed on a sailboat from St Pete FL to Isla Mujeres MX and back at 21. Told myself I’d circumnavigate the earth after that – it was life changing. So was meeting the love of my life, Ellen. I forgot about the ocean. Five children, five self start businesses, 9 grandchildren. So far.
And then I woke up one day at age 58 and thought “why the heck am I still working?” Answer: it had become easy, predictable, respectable, enriching, boring.
I “sold” my last endeavor to a great young man with a lovely wife and new baby. Full list of happy clients and he’s expanding and killing it.
Bought two sailboats, a little one to see if it was still in my blood. Turned out to be a gateway drug. I now have a gorgeous blue water boat and pretty much all the training offered by the big three (ASA, US Sailing, USCG).
I’m 65 and keep Soliloquy in the Chesapeake where I found her. I’ve explored much of New England. Next year I’m beginning a year long circumnavigation of the Atlantic. If that doesn’t do it, I’ll be heading west until I get back to where I started. Planning 5 years so I can stop and get to know people.
It’s not too late. Just do it.
that is very inspiring ! so happy for you and that is not sarcasm :)…
I expected I would marry and raise a family while over my working career I would rise to at least a mid-level executive position. Neither happened. In my early twenties I did have girlfriends but around age thirty it’s like someone turned the switch off. This was in the pre-internet days and even now I wonder what I should have done differently. I joined rec leagues, took cooking classes, no luck. Demographics may have played a role; I lived in Silicon Valley and to this day if you go to coffee shops or bars you see groups of guys but never groups of 3 or 4 women at a table. So chance meetings seldom if ever happen. As for career I started as and engineer and when I retired that’s still what I was. I got raises along the way and was making a more-than-decent salary my last years but few people got promoted to even first-level manager. I wonder what I should have done or what qualities those who did end up rising in management had, but still don’t have any answers. Not the life I assumed I was going to have, that’s for sure.
Mark, I’m hoping that your dreams have evolved and you are busy creating a life that is different than you first envisioned but fulfilling for you nonetheless.
In college we half jokingly talked about riding bicycles to Brazil, because, hey, it‘s downhill all the way 🥰.
My dream job was to be a small town lawyer. Think To Kill a Mockingbird. Atticus and Perry Mason were my role models. After law school my job in a father and son firm (not my father) disappeared in a flash after the father had to stop working and the son lawyer ran for a judge position. My father strongly advised me to work for a large firm to “learn how to be a lawyer”.
Long story short, I did learn how, but never loved being a lawyer for corporations as clients. But it paid the bills and small towns that you could build a good practice are hard to come by.
35 years later, I try not to fantasize about the “what ifs”….and enjoy the here and now.
P.S. My only other dream was to be a Navy Aviator and fly off a carrier. Got close to joining but was accepted to a good law school and everyone pushed me in that direction. I still want to catapult off the deck in a jet!
I had few dreams or big goals. I just read Randy Pausch’s _The Last Lecture_ and I felt he probably negatively judged those of us who didn’t have big dreams or a bucket list. I zigged and zagged, pursuing whatever interesting crossed my path. Big dreams typically didn’t govern what I did next, and when I did pursue a dream, such as living in Manhattan, it turned out that it wasn’t necessarily the best choice. Maybe Queens or Amstedam would have been just as good or better.
I did have a few dreams. I dreamt of being a well know, perhaps famous, artist. As a student in art school, I stood out. But school is not the real world; it is a sandbox. Whereas I have the art skills, making them pay out in the real world requires additional skill sets, such as self promotion, social skills, and schoozing. Not me.
The good news is I fell into a related field which was fascinating and paid a salary. So in that respect, making money doing something truly engaging, I did fulfil my dreams. And I knew I wanted kids. I have a wonderful partner of 30+ years and two adult children, so I got that.
I think the art dream was misguided. I continue to be an artist, and while recognition by others is great, it’s not nearly as important as making the art.
Pursuing dreams makes us feel like we have control and choice. Look out for and embrace the good unplanned things that come along.
I remember writing a list of things I wanted to do before I died when I was in high school; sadly, I lost that list in one of the many moves I’ve made since then. I remember a few of the things, like live in a foreign country, which I did – I lived in Japan for 2.5 years after I graduated from college. And hike the Pacific Crest Trail, which I did not. I do a fair amount of backpacking, but they tend to be shorter trips – 1-2 weeks rather than 5 months! One of the other goals was to travel the world. I’ve been working on this one since I graduated from college – the only thing that’s changed is that as I’ve gotten older I’ve realized how little I need. My luggage consists of one 22L day pack (the Flash 22 from REI) – it makes travel a breeze!
Thanks for posing the question, Jonathan! It’s been fun to think about and to read other people’s stories!
That 22L is impressive, Cecilia!
When I was 7, I wanted to be a blonde named Judy and drive a red convertible.
I had curly red hair and everyone misspelled or mispronounced my name. While the first two never happened I owned enjoyed my fair share of sports cars over the years—mostly stick shifts. A 1970 yellow MG Midget, 1985 Datsun B-210 and a 1998 VW EOS,
After college I wanted to be a high school history teacher because I had godawful history teachers in hs.
I applied to every county in Virginia to pay back my teachers’ scholarship without a single job offer despite a 3.8 GPA. Why? I forgot to learn how to coach football (though I DID have the credits to coach drama). Every single social studies teacher then was a boys’ sports coach. Which says to much about the state of civics today.
Then, I decided to learn about the stock market and when the stupidest young jocks at the Bethesda Merrill Lynch office were getting jobs at $25% while I was making $6K as a sales assistant, I studied and took my Series Vii exam.
I passed the math portion with a nearly perfect score and failed the Personality test. I was told I wasn’t aggressive enough to be a stock broker. Two years later, I got a check for $300 in the mail, the result of a class action suit brought on behalf of every woman who had ever failed. The test was judged to be gender biased.
Then, I decided to fall back on my acting and moved to New York to trip the lights fantastic.
Only to find out that every girl at every audition had had leads in all her high school and college plays. And had better teeth and no sibilant S. I was bursting with pride to get a callback (a 2nd audition) only to discover that every single girl had long, red hair. Then I became an exotic dancer during the pipeline in Alaska, then New York and other places, earned a shit-town of money, moved in with my bf, got a CETA job for a historical society that turned into 7 professional jobs, including four CEO positions, over 43 years helping artists, scholars, humanities and culturals organizations.
Then, my dream, was to marry a happy person (as opposed to an alcoholic, Marxist critical theorist, may he RIP) and sell everything I own and travel the world slowly.
Which I have now done for 5 years (well, the relationship and subsequent happiness is 18 years old now).
Now, like many of my septuagenarian+ peers, I dream of a relatively pain-free aging and death where all my scores are settled and I dream in peace.
“To sleep, perchance to dream: I, there’s the rub. For in that sleep of death, what dreams may come when we have shuffled off this mortal coil, must give us pause.”
Ahhh, my Shakespeare quote was Freudian, triggering the memory I have forgotten when I learned to be happy. That of being not to be.
In the immersive Camus/Sartre teen years, I attempted suicide 4 times. Sheer will and intentional meaning-creation via existentialist writer Colin Wilson kept the instincts at bay until my undiagnosed bi-polar disorder was revealed 20 years later, followed by successful therapy and meds. The stitches in my wrist are all that remind me now.
I thought about this and then the memories began tumbling out. As a child and pre-teen I was a dreamer with a vivid imagination. My parents had a small personal library and I was fascinated by the world and inventions described in those books, the Compton’s 1918 Encyclopedia and the years of National Graphic magazines on the shelves. I read everything including Gone With the Wind, which my mother confiscated because she thought it was inappropriate for my age. One book was by a young man who travelled the world in the 1930s who wrote of his adventures. As I recall the title was “The Royal Road to Romance.” As a small child I found these things inspiring and was transfixed. I dreamt of being limitless, of escape and adventure. I wanted a purpose, to be skillful and accomplish something with my life. I was raised in a conversation about contributing to others and to society. And, I wanted to invent and to build. Eventually it coalesced as a life of purpose. I dreamt that I would accomplish all of my dreams and that my life would end at a time when I was complete. That time is coming close.
Helping others, in whatever way we are able, is the greatest purpose in life, in my opinion, Norman. And you have done that.
This was such a thought-provoking question that I’ve been thinking about it since reading it yesterday. While working at Travel & Leisure magazine as a fact-checker, I dreamt for a short while about a beach house in the Hamptons. My family were weekend guests there once and also once at the Rhode Island beach community of Little Compton. But I came to the realization that our family really wouldn’t have fit in and relaxing on the beach …well, not really my thing. Driving across the country sounded like fun, but when we married at 22, husband had already done that. Once was enough. We shared the dream of visiting Morocco for four decades and finally realized it in 2015, departing the day after I retired. The dreams I couldn’t have imagined have come true: three children grown and thriving. Our small tribe is reuniting soon for the high school graduation of the oldest grandchild. I’m indeed blessed.
Oh my, a life lived without a bucket list. I am in the minority or from another planet. Early on it was just get to the next day. Now, in retirement, about the same. Things have just happened. The next shiny object that looks good was selected. If the door on the right did not open, take the next one that did open. Lots of things were liked, but none burned in the brain.
Lots of successes along the way, but still no “box” I have to check.
Hats off to you who have that list. I envy you and wish for your passion. My main wish now is for the Padres to go on a long winning streak. Not bored, just satisfied.
I love the posts on this site. Sorry I did not find it sooner. Please don’t throw me off the train for the lack of a proper imagination.;-)
James, I also identify strongly with your words. At any point in life I have just pursued what looked the most interesting or suited my skills the best.
And I can’t think of a single regret through it all.
That said, I think that retirement, when it eventually comes, will likely be more challenging than for those with a healthy list of things to tick off.
James, I identify with your post. Much of my life just happened. The only list I deal with is my Chrissy’s honey-do list.
I remember a conversation had between 2 friends of mine, brothers Ken and Guy. Ken was adventurous, retiring in his 50’s, moving to Vegas, always trying new hobbies and ventures. Guy still resides in the tiny town where he grew up, living in the house he bought as a newlywed some 60 years ago. Ken told Guy he was in a rut, to which Guy replied, “well it’s a comfortable rut”.
Early in my career I dreamt of buying more precious (read: expensive) antiquarian medical and science books. Think Vesalius, and hundreds of thousands of dollars. Have accepted that that would not make me happy.
More recently, a second home back in the Pac NW, where I did my residency. We loved the climate and geography, and don’t love our central TX heat. Now we have the money for that, but are tethered to TX by choice because of aging in-laws (who we are happy to help).
I am retiring in October of this year, about 4 mos. Going to get the fancy home espresso machine I have always dreamed of. Have postponed because I anticipated that while working I would not have the time to play with it.
One thing I did splurge on years ago, and am so happy about: For any of you surfers, I had a board made by the then very-much-aging Dale Velzy. About 6 months later, after many handwritten notes from he or his wife, and a few phone calls, my stunning board arrived. Its a 9’6″ triple stringer, shaped and finished by Dale. His signature on the board belies his age. It may be one of the last boards he build start to finish before he died. Best $1500 I ever spent.
PS – Curious if any other surfers on this board?
In retirement sell the house and all belongings and buy an RV to be a domestic nomad. North in the summer, and south in the winter, until it grows old, then settle in the are we liked the most. This was even before the internet and cell phones were a thing. It would be so much “easier” today. Wife nixed idea.
A cruise of the Nile to see the pyramids, the newly opened Grand Egyptian Museum, and other ancient civilizations along the Nile. Even though the thought of being crammed on a ship with thousands of my closest friends nauseates me, I think it would be the safest and best way to accomplish this dream. Along with this trip would be an African safari. I figure if you’re going to fly all the way to Africa might as well combine both dreams. Still working on my wife on this one.
Some things are absolutely better done while young and resilient. I was in college when we grabbed flights to Israel and just backpacked around there and Egypt on a pretty established backpacker circuit. Wandering the closed up parts of old Jerusalem, pondering on the fundamental commonality that 3 divisive religions had exactly the same holy site , snorkelling at Dahab, wacthing sunrise from the top of Mt Sinai. Eating rice and beans in a variety of street shacks. Sailing the Nile in a felucca, enjoying the pyramids, Luxor, Valley of the Kings and Abu Simbel. Getting explosive gastro issues on a long bumpy dusty bus ride. Partying in a Eilat nightclub.
The packaged cruise experience would certainly detach from all those memories. & Norovirus/food poisoning is the same no matter how plushy the bed.
I got my worst food poisoning in Eilat. This was right after the Israel-Jordan peace treaty, so I came in from Jordan using the new crossing at Aqaba. The first thing I did was get a street snack that violated several safe eating rules I knew well and usually followed. It didn’t take long to know that was a very big mistake.
The cultural change in that few minutes from Aqaba to Eilat was like going through a wormhole to a different world. I forgot all about the usual cautions. Of course the germs were the same.
“Norovirus/food poisoning is the same no matter how plushy the bed.” One of my many concerns. Also I do not like the idea of having paid for meals each day, and eating (I believe) two of the three meals each day on the ship. I would rather eat all meals when docked at a local restaurant, but believe having prepaid for meals would make that “difficult to swallow” financially.
Pun intended 😂
When we did river cruises in Europe, part of the experience was small groups of us going to local homes for a meal. That was the best part of the trip. Great fun and food- most of the time. A challenge when the host didn’t speak English. Nobody ever got sick though.
“When we did river cruises in Europe, part of the experience was small groups of us going to local homes for a meal.”
Had no idea that was a possibility. That would really be an exciting experience to explore.
My parents switched from land based tour groups to river cruises when my mother started having more issues due to dementia. This was advantageous for two reasons: One they could unpack once the entire trip.
Two if my mother was having a bad day the could just stay on the boat.
We did do a windjammer sail on a small schooner out of Maine. Much different experience than a cruise ship. Capacity was 28.
On our trip to Greece we had a private meal at a gorgeous home on top of a hill in Olympia. The food was outstanding.
The beach house resonates with me. We talked about it for quite a while, and started to think seriously about it after our kids finished college. It was like to be a modest condo, but 2 things helped make it a bit better. First, the global financial crisis hit the inflated housing prices about the same time we started looking. Second, my wife received a modest inheritance from her Aunt in 2011. This allowed us to make a bigger down payment and look at nicer homes in a nicer area. We purchased the home in March, 2012. We later found out we paid about $200K less than the previous owner had paid in 2005. As Jonathan mentioned, Sandy hit 8 months later. Although the town suffered damage in spots, our area was safe. I’ve also had dreams of cross-country trips, possibly in a conversion van or small RV. Still haven’t driven across country, but you never know.
Rick, you gotta drive across this great country. Take that bride of yours and put New Jersey in the rear view mirror. Because of my 30 years of military service, I’ve driven across the country many times, mostly from the south (FL, AL) to the Pacific Northwest, California, and one move to Kodiak, AK. In fact, last June, as a roundabout way of delivering a car to my son in Oakland, I drove from Mobile to Cody, WY to connect with him then we visited Yellowstone, Grand Teton, and Great Basin NPs on the way down to Oakland. Fantastic. The things you see, the people, the changes in culture, and oh my gosh, the National Parks. One thing that will move you is driving through a portion of the Navajo lands in NE Arizona and New Mexico. That helped me understand, viscerally, the horrible situation Native Americans find themselves in.
Try it in a car Rick, we did it twice since 2014.
Back in 1962 I drive cross country in my VW bug.
When I was perhaps age 17 I recall telling a girlfriend that I would retire at age 25, though I don’t recall having a clue how that would be accomplished.
I did dream of being self-employed, thinking ownership of a retail store was my best option. An adult toy store seemed appealing…. No, not that kind of adult toy store! Things like electronics, pool tables, arcade games, and all the other things you may desire for such a place.
But life interfered and 30 years slipped away while I sold and delivered Budweiser. I will say that job was a bit like being self-employed. I had near total autonomy in the manner in which I serviced my customers. So long as I did a good job I was never interfered with, never had anyone looking over my shoulder. My numbers were always good, as were comments from customers, so feedback from my employer was always positive.
That wasn’t the case when I left the beer business behind for a job in financial services (Your Results May Vary). It was horrible, but it lit a fire inside me, and I finally realized the dream of owning a business, (Beer to Taxes).
I realize that all my life’s decisions were not optimal, still I have no regrets. I’m right where I want to be; with the love of my life and living in my vinyl resting place (see Our Spending Spree).
https://humbledollar.com/2024/06/your-results-may-vary/
https://humbledollar.com/2023/09/beer-to-taxes/
https://humbledollar.com/2024/03/our-spending-spree/
It’s amazing how many of your dreams were on my list too. I can’t help but wonder if there’s a common thread—something about our age and the influences of the times we grew up in. “See the USA in your Chevrolet” wasn’t just a jingle—it was a promise.
If there’s a common thread, perhaps it’s a desire to escape our current life. It’s easy to imagine the fun of traveling the world or owning a second home, while the hassles involved don’t immediately come to mind.
I started physical therapy school with the idea of owning a clinic, but after graduation my new wife hated the idea. It’s worked out well.
In1998 or 99, we had dreams of hiking the world, starting with Machu Picchu. We started the planning, bought dinner for my wife’s former professor and her husband —he had made the trip—but life swerved and we stumbled before we started.
Where would your newspaper have been located, Jonathan? I’m picturing Kipling’s newspaperman in “The Man Who Would be King”.
I never had a particular place in mind. But whenever I traveled, I’d always grab a copy of the local newspaper and ponder what I’d do to improve it.
Makes me think of a woman who told me she would mail edited copies of articles run by our local paper to the editor. This was after an HD contributor worked as editor at the paper.
I hesitate to comment only because I have been so fortunate to achieve all my dreams from those days.
meet someone and have a family 👍
buy a Mercedes 👍
travel the world 👍
buy a beach house on Cape Cod 👍
send our children to college 👍
kiss the Blarney Stone and walk on Hadrians Wall, visit the Alamo and Little Big Horn 👍
visit every state 👍
become a vice president 👍
write a book 😢 but Jonathan gave me the chance to participate at least-with My Money Journey.
You have been very fortunate to achieve all that life has given you, and from reading your other writings, I know this is a short list. There is still time to write a book.
In reference to Jonathan’s last sentence, what dreams did you let slip away?
I have been thinking about that, but have yet to come up with anything significant.
I also flew in the MetLife blimp and a hot air balloon and crashed in the desert.
Wanted to overland motorbike from Alaska to Tierra del Fuego. Thought it would be a grand travel adventure (and a bike easier to get on a boat round the Darien Gap). My motorbiking travels never got far beyond riding a 200cc Honda round Bali for a week and breaking a moped on Martha’s Vineyard as I realised the odds of becoming an old bold biker were not great.
Check out “Long Way Up” on Apple TV. Ewan McGregor and friends travel from Tierra Del Fuego to Los Angeles on experimental E- Harley Davidsons. Great adventure, great scenery. I’ve done more than my share of long distance motorcycle rides, but this one I will have to experience vicariously.
I was staying at a hotel out west once a a couple of quite senior bikers pulled up. I ask how far they had traveled today. They said 600 miles. And we’re on their was across country. Quite an accomplishment.