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Someday Is Here

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AUTHOR: Dennis Friedman on 12/24/2025

Rachel and I live comfortably now, but it didn’t happen by accident. For most of my adult life, I lived simply—sometimes inconveniently so—and saved steadily. At the time, it felt normal. Only looking back do I see how much those quiet choices shaped the life we have today.

We married in our 60s, in a house I had inherited and was still fixing up. I remember hugging her upstairs and whispering, “If you marry me, we can have a wonderful life together.” I believed it because we were already aligned. We’d lived very similar lives—frugal, practical, and well below our means.

Older cars. Smaller homes. Nothing fancy, but everything taken care of. I didn’t think of it as a sacrifice. It was just how I lived.

If I had to describe my pre-retirement life in a few words, I’d say it was small, inconvenient, and lacking. That pretty much sums up the condo I lived in for most of my adult life. One bedroom. No washer or dryer. Third floor. Underground garage. Forget something in the car and you really felt it. At the time, though, it just felt normal.

Keeping things simple made it easier to save, even though I never had a big salary. Looking back, that mattered far more than how much money I made.

Today, Rachel and I live much more comfortably. There’s no need to save for “someday” anymore. Someday is here. These days, we’re happy to spend money if it makes life easier. We fly business class because it’s kinder to aging bodies. We eat out more so cooking doesn’t feel like work. We hire a handyman so I don’t have to crawl under sinks or wrestle with plumbing.

When we travel—and we travel quite a bit now—we stay at four- and five-star hotels. Not because we need luxury, but because comfort matters more than it used to. Being well-rested makes the whole trip better.

Still, I sometimes feel guilty about the life we live. I have friends who are struggling, both financially and health-wise. One close friend spends most of his time caring for his wife. We talk often. When he called while Rachel and I were in Paris, I didn’t mention where we were. I remembered how hard it was when I was caring for my mother and saw others enjoying retirement.

That experience taught me to be more discreet. I don’t post travel photos on social media or bring up our trips in conversation. The only people who know when we’re away are the neighbor who keeps an eye on the house and my sister and brother-in-law.

From time to time, I think about how we ended up here. A few things stand out. Good health, for one. Years of exercising and trying to eat reasonably seem to have paid off. Owning our home mortgage-free kept our fixed costs low. And while we never earned big salaries, we also avoided money pits—no second homes, no boats, nothing that quietly drains cash.

Whatever extra money we had went into the stock market. We didn’t try to be clever. We just stayed consistent. Over time, that added up and gave us options.

I know a lot of people are worried right now. Prices are higher, jobs feel less secure, and businesses are cutting back. Seeing that only reinforces what I’ve come to believe: keeping life simple, expenses low, and savings steady doesn’t just make retirement possible—it makes life a little easier at every stage.

Rachel and I are not exchanging gifts this Christmas. We already have the best gift an older couple can have—that is each other.

Happy Holidays to everyone!

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Linda Grady
24 days ago

Thank you, Dennis. I’m always touched by your honesty and humility. I’m going to try to follow your lead in talking less about the trips I have taken recently and which I hope to take in the future. The feelings of our friends, neighbors and relatives are important.

Edmund Marsh
24 days ago

Dennis, you’re a kind soul for thinking of your friends’ feelings. But you have no reason to feel guilty. Folks who have money choose when to spend it–earlier in life or later. You chose later, as did many others here on HD. And I know you are thankful for the blessings have come your way, like your good health and a wonderful wife. Thank you for this article.

mytimetotravel
25 days ago

Congratulations on a successful life, and best wishes going forward.

Rick Connor
25 days ago

Dennis,
Thanks for this. Happy Holidays and Happy New Year to you and Rachel. Stay safe out there.

Andrew Forsythe
26 days ago

Great article, Dennis. And I share your belief that:

keeping life simple, expenses low, and savings steady doesn’t just make retirement possible—it makes life a little easier at every stage.

Happy Holidays to all my HD friends!

Andrew

DrLefty
26 days ago

Merry Christmas, Dennis & Rachel. Enjoy the life together that you worked and saved for.

I’ve also stopped sharing travel photos on social media for similar reasons. I liked having albums from trips on Facebook because I check FB Memories just about everyday, and it’s nice to remember what I was doing on a particular date. But I can look at my photos from French Polynesia (my retirement celebration trip this summer) anytime I want without causing others to feel bad.

John Katz
26 days ago

I don’t think there is a need to feel guilty about the life you lead. Continue to have empathy and compassion for the less fortunate in your orbit. And help out when you can. People don’t benefit if you skip a trip to London, or fly economy rather than business class.

DAN SMITH
26 days ago

Dennis, it’s always great to read your posts, especially this one. Your post, along with all of the comments below, remind me how special the people who contribute to HumbleDollar are.
Merry Christmas,
Dan

Last edited 26 days ago by DAN SMITH
Kristine Hayes
26 days ago

Dennis–love this! I too lived quite frugally all of my adult life. I never came close to a six-figure salary despite working full-time for thirty years. It hasn’t been easy to transition from saving to spending, although earning a bit of income through our dog-training business has helped ease my concerns.

Thanks for your uplifting article on Christmas Eve!

baldscreen
26 days ago

Thank you so much for this, Dennis. I am in the middle of feeling like you did when you were taking care of your mom, it helped to know I am not alone. I feel sad retirement is not going like I thought it would. The papers for guardianship of Spouse’s mom were filed yesterday. I hope we will get to a place where we can have adventures like you and Rachel. Merry Christmas to you both. Chris

baldscreen
25 days ago

Thanks, Dennis, I appreciate your kind words. Chris

R Quinn
26 days ago

Enjoy every day, do all you plan and desire, take every trip possible. Trust me, when you get to the 80s things start changing.

We packed in travel from the day I retired in 2010, I bought the car of my dreams at 70 because that’s when I could afford to do so.

These days in our 80s life if filled with doctors visits, but our greatest pleasure is being able to use our life’s investments to help family in any way we can and to give to charities more than another other time in our lives.

It took us 60+ years to get here from zero, but it was worth every part of the journey.

Mark Crothers
26 days ago

Dennis, life offers us countless paths, each with its own rhythm and rewards. Perhaps the truest measure of a life well-lived isn’t found in any single choice we make, but in two rare gifts: the ability to be content in the present moment, and the peace that comes from looking back without regret. You seem to have found both, and that’s something genuinely meaningful.

My own journey took a different shape—I didn’t save my travels and experiences for later. Instead, I chose to live more in the moment as it came, even if that meant some trade-offs for my future self. And yet, I’ve arrived at that same place of contentment you’ve found. The irony is that now, having wandered so extensively over the years, the restless urge to travel has quieted in me. Perhaps we’re only given so much wanderlust in a lifetime, and I spent mine freely along the way.

Happy Christmas and enjoy the wanderlust.

Last edited 26 days ago by Mark Crothers
mytimetotravel
26 days ago
Reply to  Mark Crothers

I relate to your comment about wanderlust. I spent fifteen years traveling extensively, and now I’m having trouble working up enthusiasm for a trip to England in the spring. I did buy the plane ticket, but I’ve yet to book anything else. I’m very comfortable where I am….

Mark Crothers
26 days ago
Reply to  mytimetotravel

My problem is inertia—I’m genuinely happy and content with my daily life as it is. The whole process of travel feels like a hassle, but I push myself to overcome that resistance because I know once I actually get to my destination, I’ll enjoy the vacation.

Greg Tomamichel
26 days ago

Thanks Dennis for your heartfelt post. I’ve just finished work on Christmas Eve, so a nice time to reflect.

We have charted a similar path through life, but haven’t moved into retirement yet. We have also lived a simple life, happy to have a smaller house, older cars, simple clothes that we wear until they fall apart.

I also wholeheartedly agree with being discreet. We live in a low socio-economic rural town. We make a point of keeping everything about our life low key. Feeling comfortable around our friends in town feels a lot more important than buying a new car or talking about an international trip.

Merry Christmas to you, and I hope you continue to enjoy your retirement.

Bill C
26 days ago

And Merry Christmas to you and Rachel, Dennis. Always enjoy your posts, as they reinforce much of how my wife and I have lived until retirement 8 years ago. Lived well below our means, but maybe not quite as frugally as what you describe. The decumulation years have been very enjoyable, and like you have adjusted to the comforts of added spending.

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