Cherishing The Days Of Carefree Travel

Cherishing The Days Of Carefree Travel

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I’m not in a position to give anyone life advice, but I can’t help but share some thoughts I’ve been having lately, as it relates to travel, life, and getting older. In some ways I view this blog as a diary of sorts, and sometimes it feels good to just type things out.

For some context, I suppose I’m having a lot of these thoughts because I’m getting older. I’m 32 — I’m by no means “old,” but I’m also not young anymore. Growing up, I remember being told that the days are long but years are short. In the past couple of years I’ve definitely started to feel that way. That brings me to the travel angle, and how getting older impacts my perception of and desire to travel, and that’s both a good and bad thing.

Travel (and life) used to be so carefree

When I was younger, travel was so carefree for me. Admittedly I had a different youth than most — in college, I didn’t go to parties every weekend, but rather went on mileage runs. Even after graduating from college, I mainly only had myself to take care of, and I even lived in hotels full-time. It was me and my carry-on, and that was kind of liberating.

I think back fondly on those times, and I’m so happy I had those experiences. When I think back on that era, I think of US Airways Dividend Miles, British Midland Diamond Club, Lufthansa’s old first class product, the days when SWISS had tons of partner first class award availability, that brief period where Turkish Airlines leased Jet Airways 777s and had first class, etc. Fun times!

“The good old days” of Lufthansa’s old first class!

From an outsider’s perspective, some might think that sounds lonely or sad (I mean, I can’t count the number of people who told me exactly that at the time), but it’s something I genuinely enjoyed, and I have no regrets about it.

I’m not suggesting others should necessarily do the same thing. Rather my point is that pursuing whatever you’re passionate about at a young age — no matter how strange it might be — is great. Admittedly this assumes you’re able to do so. I know that I was extremely lucky, as I pursued my passion and was able to make a living with it.

Here in the miles & points world, when I see people a decade younger than me traveling a bunch, I think to myself “good for you, and I hope you always remember these good times.”

And that brings me to how my life has changed quite a bit, but not in a bad way…

The older I get it, the harder it is for me to travel

I just embarked on my current review trip, where I’ll be flying (almost) nonstop for the next several days. I love flying every bit as much as I did a decade ago, but the feeling of leaving home gets more difficult with each and every trip. Obviously I’ve come a long way here, because back in the day I didn’t even have a home. Even when I did finally get a home, I’d have an itch to go somewhere after a few days.

Leaving behind Ford, Miles, Winston, my mom, etc., simply gets harder with each trip:

  • Frankly leaving Ford (my husband) at home is the easiest part of all this; we both work from home and spend almost all of our time together, so a few days apart is good for our relationship
  • Leaving Winston (our dog) behind is the hardest part; he follows me every step, and I just can’t handle the look on his face when I pack my bag (which I only do about 15 minutes before heading out the door, on purpose)
  • Leaving Miles (our son) behind is hard, because I don’t want to miss anything in his development; but I know leaving him will only get harder in the future, when he’s actually old enough to process that I’m leaving and (hopefully!) misses me, etc.
  • And then of course my mom continues to battle cancer; while I’ve made it a huge priority to spend as much time with her as possible and have no regrets there, that doesn’t make it any easier to get on a plane and travel far away
These two are no fun to leave behind…

Back in the day I’d head to the airport without a worry in the world, while now going to the airport kind of eats me up inside. And I recognize at the end of the day that I’m incredibly blessed to have people (and creatures) to miss, because a lot of people don’t have that.

Let me be clear, I still totally love travel and am a huge avgeek. Within a day of leaving I try to forget what I’ve left behind. But as I head out the door, it makes my stomach turn a bit. I’m writing this post from a flight, and I’m reminded of just how much I love flying (and how Copa’s sauvignon blanc is sorta drinkable, but that’s for a different post). The cloud formations, the lightning in the distance, day turning into night… it’s simply magical.

Flying never gets old, but leaving home does

This evolution isn’t a bad thing

This post isn’t at all intended to be a “woe is me, life sucks, I’m mad I’m not young anymore” reflection. Quite to the contrary, it’s intended to be an acknowledgement of life having different phases. If I were in the same place I was a decade ago, I may very well be sad and lonely.

I wouldn’t trade my current situation for anything. I’m happier just being home and going about my daily life than I’ve ever been. But with that joy also comes sadness when there are things you miss.

When it comes to travel, one of the things I’m most looking forward to is being able to see travel (and the world) through Miles’ eyes. You can never recreate the first time you’ve had a particular travel experience, but you can see it through a child’s eyes, and I think that’s a beautiful thing.

The moral of the story is that if you’re younger, you’re traveling a lot, you’re a nomad, whatever… good for you. If you’re having fun and not hurting anyone, that’s what matters most. Some people may judge your life from the outside, but that doesn’t really matter. I think it’s worth enjoying each stage of life for what it has to offer, and joy can come in many forms.

And hopefully this won’t be the last stage of life I get to experience when it comes to travel, because things won’t always be the way they are now. Heck, maybe in 18+ years (when Miles is hopefully off doing his own thing, whatever it might be), Ford and I will be back to carefree travel, sipping dirty martinis in an airline lounge somewhere at 7AM before our engine-less Boom Overture flight to somewhere, without a care in the world… or not. Either is fine by me.

Life can be beautiful, even on the ground 😉

Bottom line

Life is an adventure, and I realize that more with every day that passes. Adventures can come in different forms, and in many cases don’t even have to involve leaving home. There’s a lot of joy in everyday life, even among the chaos.

As I reflect, I can’t help but realize how much my perspective has changed on life and travel in the past decade, and especially in the past five years. I used to not want to be anywhere for more than a few days, and couldn’t run out the door fast enough. Nowadays you basically have to drag me out the house (though not quite in a David Dao way). I’m just happy when I wake up healthy and fairly well rested, and those around me are okay.

Thanks for indulging me in this reflection… and if anyone has anything to add to the topic in the comments section, I’d love to hear it! I learn every day in life, and if I’m fortunate enough to be around in a decade, I’m curious to see how my perspective evolves. Time flies.

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  1. PM1 Guest

    Thanks for sharing Ben. A lot of your readers, myself included, were inspired by those days of travel. And now as we get older with family, it has become more and more difficult to travel. Even status, which used to be so easy to earn has become so difficult.

  2. Samo Guest

    I'm going sort of the opposite way and I travel more as I get older (almost 30 now). As more and more of my friends settle down and go for more "family-based" order (which I'm personally not interested in), I find it more and more pointless to stay at home. The days of spontaneous nights out with my friends are gone. Everything needs planning now, no one has time, and even when we manage to...

    I'm going sort of the opposite way and I travel more as I get older (almost 30 now). As more and more of my friends settle down and go for more "family-based" order (which I'm personally not interested in), I find it more and more pointless to stay at home. The days of spontaneous nights out with my friends are gone. Everything needs planning now, no one has time, and even when we manage to meet at last, everyone seems tired. Not to mention that friendships suffer when people go on completely different lifepaths (I can't really relate to topics they deal with).

    And so I increased my travelling. Basically anytime I have more than a weekend available, I go somewhere. Sometimes with my partner, sometimes alone (just like Ben said, it can help the relationship to give it a break for a few days every now and then). With a higher age, I lost the last remaining ties to my hometown and as I'm about to enter the fourth decade of my life, I don't see any reasons to not travel anymore.

  3. Amelia Guest

    Lucky, thank you for writing this. I can relate, a lot. I am an American in my mid-30s who spent the better part of their first 12 years after college living outside the US and traveling a ton for work (and some for pleasure). It was great. My career was going well and I was a points aficionado (many thanks to your blog). Now I'm back in the US, married to a loving partner and...

    Lucky, thank you for writing this. I can relate, a lot. I am an American in my mid-30s who spent the better part of their first 12 years after college living outside the US and traveling a ton for work (and some for pleasure). It was great. My career was going well and I was a points aficionado (many thanks to your blog). Now I'm back in the US, married to a loving partner and also helping care for my mother who is quite unwell. I am about to leave for a long international work trip and I just find myself not wanting to go. I wonder what's wrong with me, on one hand, but also you (and many of the people commenting here) are right: our priorities shift - and that's okay.

  4. Alex77W Guest

    Personally, I do not "Cherish the Days of Carefree Travel" more than traveling with my son when he was growing up. That was challenging because of my full time and rather demanding job and his time in school. With my wife working full time, we had no choice but to take him on the trips in the US and around the world. While in elementary school, I do remember him bringing back a drawing on...

    Personally, I do not "Cherish the Days of Carefree Travel" more than traveling with my son when he was growing up. That was challenging because of my full time and rather demanding job and his time in school. With my wife working full time, we had no choice but to take him on the trips in the US and around the world. While in elementary school, I do remember him bringing back a drawing on the family: him, dad, and mom next to a house with a small caption: next to mom (in Italy). Naturally, this raised some questions whether everything is OK with the family. On another occasion my wife and I "met" over the Atlantic ocean while flying in opposite directions while our son was at our friends' house. It was challenging but still is the most cherished time of my life. Now when he is out of the house and traveling by ourselves is just boring.

  5. Wilson Guest

    I’ve been reading your blog for a long while now but this is my first comment because I thought I should share my 2 cents.

    I’ve been traveling for a large part of the past close to two decades or so (I’m 37 now). I still do - weekend trip excite me (how fun to be somewhere different this weekend) but my ways of travel have also evolved (inevitably).

    From backpacker hostels and dorms I’ve...

    I’ve been reading your blog for a long while now but this is my first comment because I thought I should share my 2 cents.

    I’ve been traveling for a large part of the past close to two decades or so (I’m 37 now). I still do - weekend trip excite me (how fun to be somewhere different this weekend) but my ways of travel have also evolved (inevitably).

    From backpacker hostels and dorms I’ve “graduated” to private rooms and even hotels. From long-haul low cost flights (I still do but reluctantly) to full carrier (where possible business or premium economy). I’ve moved from backpacker to flashpacker and beyond.

    And having just got attached during the pandemic, I’ve now an added reluctance. I’m typing this as I am about to take off for the weekend but I am also equally torn to be away from my partner who is unable (or unwilling) to travel for just the weekend. I used to book flights and make trips on the whim, now I schedule to make sure we spend enough time together.

    Many of my friends and colleagues ask if I can still carry on these “weekend trips”. I’ll try to as much as I can but there’s no certainty if the body will always allow it. But I intend to do it while I still can. If anything, my own (twice) cancer episodes and recent pandemic has thought me is to always lead a fulfilling life (whether is that traveling or other objectives that make you feel fulfilled and with no regrets).

    Thanks for sharing and yes you aren’t alone in feeling the same way!

  6. JD Guest

    Welcome to caring about others. It’s a great enrichment in life. :) When I miss being carefree, i remind myself how much value I get from a husband, my family, my dogs, my friends. I really care about them.

    As far as getting over the desire for travel, it doesn’t have to happen. I look at friends taking their kids to Disneyworld, across the US, to Europe, to pretty much anywhere in the world,...

    Welcome to caring about others. It’s a great enrichment in life. :) When I miss being carefree, i remind myself how much value I get from a husband, my family, my dogs, my friends. I really care about them.

    As far as getting over the desire for travel, it doesn’t have to happen. I look at friends taking their kids to Disneyworld, across the US, to Europe, to pretty much anywhere in the world, I have heard so many of them say how much fun it is to see the world through their kids’ eyes- it’s all new again. Enjoy seeing someone you love discovering the world for the first time. It’s truly wonderful.

  7. Weymar Osborne Gold

    I think I'm probably where you were at about a decade ago. I'm 24, and sort of a "free agent", so to speak. I'm not tied down tightly to anything, and could be doing nearly anything right now if I had the desire to. I just redeemed miles for a Fiji Airways business class award to New Zealand with a stopover in Nadi next year because the space was available and I thought, "Why not"?...

    I think I'm probably where you were at about a decade ago. I'm 24, and sort of a "free agent", so to speak. I'm not tied down tightly to anything, and could be doing nearly anything right now if I had the desire to. I just redeemed miles for a Fiji Airways business class award to New Zealand with a stopover in Nadi next year because the space was available and I thought, "Why not"? I'm debating to myself whether I should fly to Munich on Sunday to spend two days at Oktoberfest (both of these things are possible because of your blog, btw!) That kind of spontaneity is just characteristic of being young, but tbh even now I couldn't imagine and don't even want to be doing that thing permanently. As time goes on I imagine I will value strong bonds with people and long-term accomplishments over the somewhat directionless, impulsive ad-libbing I do today. I'd like to settle down with a wife, I'd like to have a satisfying and meaningful career, and with that would almost certainly come traveling less. I don't think it's a bad thing, nor do I think that there is a certain time I need to make that transition. Someday, my heart will just tell me and I think that is what is happening to you.

    1. Randy Gold

      Go to Munich. I used to do lots of 2 day trips to Europe. Enjoy while you are young, it is easy to meet people. The old saying - I am going to retire and travel now. The best experience are traveling when you are young.

  8. Alisson Guest

    It’s so heartwarming to read your words. I’m at my mid-20s/ early career phase and traveling is always my top priority for fun, whenever I have the time. Believe me when I say I get loads of funny looks when I tell people I’m setting off on another solo trip with dozens of willingly taken flights. And I do enjoy family trips and trips with friends, but there’s something so liberating about being able to...

    It’s so heartwarming to read your words. I’m at my mid-20s/ early career phase and traveling is always my top priority for fun, whenever I have the time. Believe me when I say I get loads of funny looks when I tell people I’m setting off on another solo trip with dozens of willingly taken flights. And I do enjoy family trips and trips with friends, but there’s something so liberating about being able to just do my own thing, set my own pace, choose my favorite destinations and do whatever I like on a trip. However it can get lonely sometimes and it makes me wonder if I might me missing something in terms of making and maintaining relationships. So reading your article really warms the heart of another young avgeek. Hopefully in some years I’l be missing home as much. Promise to report it back!

  9. glenn t Diamond

    I can assure you at the age of 32 yo still have years of comfortable flying and travel ahead or you.
    Wait until your body tells you that Economy is no longer an option for more than one hour, that having booze and (especially)coffee on-board in unwise unless you have a convenient lavatory close by for frequent visits, and that jetlag become increasingly difficult to shake off.
    Just a few of the non-delightful...

    I can assure you at the age of 32 yo still have years of comfortable flying and travel ahead or you.
    Wait until your body tells you that Economy is no longer an option for more than one hour, that having booze and (especially)coffee on-board in unwise unless you have a convenient lavatory close by for frequent visits, and that jetlag become increasingly difficult to shake off.
    Just a few of the non-delightful things you have to look forward to!
    As I constantly tell my much younger friends, "do it now, while you can!"

  10. Randy Gold

    32 is still very young. When I was your age, FF programs did not exist, So my 4 MM flown miles was earned after 40 and non-business travel. Lots of mileage runs, bicoastal social life, and weekend international flights to Europe.

    You are still starting. Of course the baby changes everything, You should likely be thinking of a sibling. Every gay couple I know with children have 2. All the noted celebrity gay couples do as well.

    1. glenn t Diamond

      Steady on Randy, it's One Miles At A Time!

  11. iamhere Guest

    I think most people do not realize that living out of a hotel for a long time is kind of boring in some way. The idea seems cool at first but then after many weeks it is not quite the same.

  12. iamhere Guest

    Disagree with your comment about the older you get the harder it is. This is because of what you have to do when you travel because of your work. You need to take so many photos and you need to review the to the detail of all aspects of your journey. That's tiring no matter at what age.

  13. Alison Guest

    I love the picture of Miles and Winston! I appreciate your reflections. As I just got back from our first post-pandemic trip, I was also thinking about travel. But I am twice your age and am enjoying empty-nester travel which is a throwback to the carefree days in our 20s, but with better hotels, business class flights and a lot more aches and pains. Still, one thing you learn as you get older is to...

    I love the picture of Miles and Winston! I appreciate your reflections. As I just got back from our first post-pandemic trip, I was also thinking about travel. But I am twice your age and am enjoying empty-nester travel which is a throwback to the carefree days in our 20s, but with better hotels, business class flights and a lot more aches and pains. Still, one thing you learn as you get older is to travel while you can and while you are still mobile. We have definitely slowed down, but we appreciate every moment. I only wish I could duplicate the 17,000 steps a day I do in Europe at home! Enjoy your travels, enjoy Miles and thanks for your blog.

  14. lasdiner Guest

    If it is tough on you you should quit
    Or find someone who travels for you when you don’t want and you write the reports.
    You have a lot of talent and youll be successful in pretty much everything you’ll embark on -although not necessarily as famous as you got with the blog.
    I’m just baffled your son is named MILES-i obviously missed a few posts- congrats

  15. Miz Fiz Guest

    I am 81 1/2 with a trip planned in a month to Europe again and I am so excited. Don’t think the travel bug will ever leave you! I never even flew on an airplane until I was 22 because my mother was freaked out at the idea and I was an only child. Other friends my age were backpacking to Europe alone so I studied French and had a big Paris poster in my...

    I am 81 1/2 with a trip planned in a month to Europe again and I am so excited. Don’t think the travel bug will ever leave you! I never even flew on an airplane until I was 22 because my mother was freaked out at the idea and I was an only child. Other friends my age were backpacking to Europe alone so I studied French and had a big Paris poster in my college dorm room, but actually never made it to Paris till I was 59 years old and my three sons were out on their own. I have traveled alone and also with many mix of friends and now, all these years later, I am taking four people to Portugal who have never seen it and I’m throwing in a trip to the Guggenheim in Bilboa which is new to me on the way.
    My back is a problem so I do short flights and my longest flight in the three weeks will be across the Atlantic on Aer Lingus which is fabulous. I don’t travel for business so I don’t have the rewards that you do, but that’s OK because I know how to hunt for bargains. Every time a plane takes off I feel uplifted! I also do the train a lot because I can get up and walk around with plenty of stretch room. I like short air flights because if somebody near me is bothersome I don’t have to put up with them for long nor they with me. I read your blog every day and enjoy it! But like you have dogs at home and now grand children that I’m trying to take on trips with me when I can afford it. Cheers! Let me know if you need a blog for seniors (smile)

  16. David Diamond

    This is why I visit this blog. It’s not written by a travel robot who only cares about pushing credit cards and a big exit event.

    Thanks for sharing about how travel is changing (not strictly better or worse, but into a different phase), and love the bit about flying in an engine-less Boom. ;)

  17. NFSF Gold

    Very poignant post and that photo captioned “Flying never gets old, but leaving home does” is incredible.

  18. Eskimo Guest

    Time to consider you are about to outgrow your full-time hobby now.
    I hope you have considered how you plan to evolve the site and your career having a family and your hobby is no longer fun. Your time for transition is running out. You need to shift and build some traction before the end of the road.

  19. Desperado Guest

    Amazing…truly happy to see you & your growing family.

    Enjoy your changing perspective as well.

    Great post.

  20. grichard Guest

    Nice post, thanks.

    Since your travel is tied to your livelihood, you sort of have a tiger by the tail. Serious question: why not change jobs, and travel for pleasure?

    An obvious alternative would be to run a boutique travel agency specializing in mileage bookings. You clearly have the expertise; you're used to running your own small business; you could do the work remotely from anywhere. Become a miles-only version of Cranky Flier/Concierge.

    Anyhow,...

    Nice post, thanks.

    Since your travel is tied to your livelihood, you sort of have a tiger by the tail. Serious question: why not change jobs, and travel for pleasure?

    An obvious alternative would be to run a boutique travel agency specializing in mileage bookings. You clearly have the expertise; you're used to running your own small business; you could do the work remotely from anywhere. Become a miles-only version of Cranky Flier/Concierge.

    Anyhow, good luck with wherever your work and travel take you.

  21. Greg Guest

    Same here - not sure if it's age or living in a less hectic place and calling it home, or having better meals and company at home

    The inflight experience isn't what it was either so less of a lure

  22. Tammy Lau Guest

    What an AMAZING post. This is genuinely one of the best post in the industry not involving miles and travel. I used to travel NON stop but the older I get, the same way I feel like you.

    ALL THE BEST BEN. I am so happy for you having a SON . GOD bless you

  23. Jonathan Member

    Ben,
    This is probably one of the best, most relatable life reflection posts I’ve ever read.
    As someone who’s been reading your blog for over a decade (since I was 14), it’s been a pleasure to live vicariously through you, be inspired by you, and most importantly grow with you.
    Hope all goes well in this next stage of your life. The stories from your journey gives me a glimpse of what’s to come :)

  24. Judith Walter Guest

    What a beautiful well written story. I am 67 years old and it applies to life in general. As you get older you need to move on and accept the new interests and changes in your life. You will be more at peace and happier if you do.

  25. Lee Guest

    To piggyback on Tim Dunn's comment, it hits you at about 50 years old. That is, hits your body. Things that never used to hurt start to hurt. By 75, you'll think about moving closer to your kids because you simply don't want to travel.

  26. West Coast Flyer Guest

    "32 and not young anymore"..... thanks for the morning laugh!

    Best wishes in your travels.

  27. Donna Diamond

    I was with you in the old days when you were living out of hotels and I believe one of the things that keeps me here now is that the blog is always evolving, like our lives. I’ve been a road warrior longer than you’ve been alive and air travel has changed drastically during my run and as much as I’d like to bring back Dividend Miles and easy upgrades, I feel air travel is...

    I was with you in the old days when you were living out of hotels and I believe one of the things that keeps me here now is that the blog is always evolving, like our lives. I’ve been a road warrior longer than you’ve been alive and air travel has changed drastically during my run and as much as I’d like to bring back Dividend Miles and easy upgrades, I feel air travel is moving in a good direction. Like @Tim says, travel gets physically harder and flying east on long hauls, in spite of quick turnarounds, takes a toll and jet lag is real but I’m sure you’ll figure out strategies and let us all know. I must say I’m a bit nostalgic about your nomad days, perhaps you could occasionally repost an old post with a Flashback Friday theme from time to time. Those were so much fun and remind us all of lost youth and how much everything changes or even, in many cases, stays the same. Hang in there!

    1. Clem Diamond

      What a great idea! Would be a lot of fun to read some of these really old reviews from way back when indeed :) .

  28. Andy Diamond

    Thanks, Ben, for sharing your sentiments. I’m single and my parents are fortunately still well, so the situation is different. Yes, I sometimes miss them, as well as my very good friends, but on my travels I usually meet some other friends, which is nice. So I don’t feel such a change, as you do.

    Contrary to what some respondents say, I’m very happy to be back in the air after the pandemic. The lockdowns...

    Thanks, Ben, for sharing your sentiments. I’m single and my parents are fortunately still well, so the situation is different. Yes, I sometimes miss them, as well as my very good friends, but on my travels I usually meet some other friends, which is nice. So I don’t feel such a change, as you do.

    Contrary to what some respondents say, I’m very happy to be back in the air after the pandemic. The lockdowns meant that my work went to videoconferencing 24/7. When I travel and attend presential meetings, I’m simply not available for anyone else. Fortunately, nobody expects me to attend videocalls a 3am (what appeared to be the “new normal” during lockdowns).

    1. Donna Diamond

      @Andy - I, too, am VERY happy to be back on the road again without restrictions. Hoping 2023 will bring a return to 2019 “normal” to air travel, both business and leisure.

  29. Jimmy’s Travel Report Gold

    Ben, I imagine this first “business trip” away from the family will be the most poignant. It will get easier with time, and you’ll find a work and family life balance that can work for you. Remember you’re providing for your child’s present and future and setting an (again future) example of what a loving parent does for his family. After raising two independent girls who love to travel, we have no regrets on the...

    Ben, I imagine this first “business trip” away from the family will be the most poignant. It will get easier with time, and you’ll find a work and family life balance that can work for you. Remember you’re providing for your child’s present and future and setting an (again future) example of what a loving parent does for his family. After raising two independent girls who love to travel, we have no regrets on the sacrifices we made to give them the childhood they enjoyed.

  30. Tim Dunn Diamond

    First, thank you for being honest. You are to be commended for living your life transparently.

    Second, welcome to the sandwich generation. We as humans are supposed to receive the torch of life from our parents, guard it well, and then pass it along to our children (or others in whom we choose to invest). It isn't easy caring for those above and below us in age; by God's grace, you will get a full...

    First, thank you for being honest. You are to be commended for living your life transparently.

    Second, welcome to the sandwich generation. We as humans are supposed to receive the torch of life from our parents, guard it well, and then pass it along to our children (or others in whom we choose to invest). It isn't easy caring for those above and below us in age; by God's grace, you will get a full generation in this phase of life but you will be torn the entire time between caring for others and caring for yourself.

    Third, by the time your kid(s) are out of the house, your body won't be as kind to you as it once was - and even is now. Hotel beds and pillows and other people's food doesn't set just like it did; airplane seats get less and less comfortable - without the airline changing a thing. Every road warrior moves from travel being easy to becoming a chore - the degree of which depends on the person.

    As Solomon said, enjoy your days and what you have now. It isn't necessarily better later.

    1. Desperado New Member

      Excellent post and the comments exceptional as well. I appreciate the wisdom of those older and more experienced than me - comments making me emotional thinking about how much my parents sacrificed for me.

    2. Vancouver - Char Gold

      Yes, As Tim Dunn accurately notes. I appreciate and enjoy following your transparent life; you will find an open door in Vancouver. And, as Solomon notes, as we live within our means and not hurt others, enjoy our days as best as possible

  31. Santos Guest

    The the fun part of getting older is you hear the voice of your heart much clearer. The hard part of getting older is making sure to listen to it.

  32. Daniel B. Guest

    Lovely post Lucky.
    Hopefully Miles will love travel too, but be prepared that there is a chance that he will not be interested in that at all. We parents often hope that our children will have the same interest as us. We collect things like baseball cards, Matchbox cars, etc., hoping that one day our children will appreciate those when we give it to them. Then you realize those mean nothing to them.
    ...

    Lovely post Lucky.
    Hopefully Miles will love travel too, but be prepared that there is a chance that he will not be interested in that at all. We parents often hope that our children will have the same interest as us. We collect things like baseball cards, Matchbox cars, etc., hoping that one day our children will appreciate those when we give it to them. Then you realize those mean nothing to them.
    As for you introducing him to travel early on - again impossible to tell how it will influence his approach to travel. My parents travelled a lot with me and my brother. Now I love travelling, but my brother hates it and says that the fact that he was dragged along every trip made him hate travel.

    1. Jlee Guest

      Your dog is fortunate that you’re considerate enough of his feelings to pack your bags only 15 minutes prior to leaving home. It says a lot about who you are and how loving you must be to your dog and family. Your family is very lucky.

  33. John T Guest

    Now might be an appropriate time to take on some more staff so they can do some of the tasks you no longer want to.

    1. Ryan Guest

      She runs point.me now. Her LinkedIn says she's still affiliated with OMAAT, though.

  34. Frances Price Member

    Thanks for this Lucky - this is why your blog is my favorite, your put your thoughtful personality into it. I'm with you that leaving my cat is the hardest thing, and I also gather what I want to pack and throw it into the suitcase at the last possible minute so she doesn't get upset :)
    Since my bout with ovarian cancer nearly 10 years ago at age 45 (still ok!), I've realized...

    Thanks for this Lucky - this is why your blog is my favorite, your put your thoughtful personality into it. I'm with you that leaving my cat is the hardest thing, and I also gather what I want to pack and throw it into the suitcase at the last possible minute so she doesn't get upset :)
    Since my bout with ovarian cancer nearly 10 years ago at age 45 (still ok!), I've realized you never know what life will throw at you, so enjoy what you like while you can. I travel more now than I did when I was young, though when I'm home I'm very much a homebody.
    I think of your mom often, hope she's doing ok.

  35. Ryan Guest

    So is life and I definitely can understand what you're saying. I'm 38 and never had an uber-successful blog to fund my travels, but don't worry, travel is still fun and as long as they keep opening new hotels, there will be new pursuits. I feel ya about leaving the dog. I found some great sitters using Facebook groups in my little city and don't feel as bad leaving him any more.

    Finally, travel...

    So is life and I definitely can understand what you're saying. I'm 38 and never had an uber-successful blog to fund my travels, but don't worry, travel is still fun and as long as they keep opening new hotels, there will be new pursuits. I feel ya about leaving the dog. I found some great sitters using Facebook groups in my little city and don't feel as bad leaving him any more.

    Finally, travel with children only gets better. I just got back from Andaz Mayakoba with my 3.5 year old and 2 weeks before that a road trip vacation at Hyatt Regency Lost Pines. It's so fun when she's actually having fun. Like yeah, it's cool to travel when they're a baby, but it's great making memories when they start remembering.

    1. Never In Doubt Guest

      Don’t kid yourself. Your 3.5 year old won’t “remember” anything.

      Bring them places that are fun now. Save the “memorable” places for much later.

  36. Joseph Guest

    I've come to another realization now that I'm in my mid-30s and realizing that I just don't want to travel as much as I did before. Even just 5 years ago it was common for us to have a free Saturday and fly spontaneously to Seattle or Phoenix for the day, or catch a red-eye to Florida and come back the next day, thanks largely to the tools I learned from this blog.

    Now...

    I've come to another realization now that I'm in my mid-30s and realizing that I just don't want to travel as much as I did before. Even just 5 years ago it was common for us to have a free Saturday and fly spontaneously to Seattle or Phoenix for the day, or catch a red-eye to Florida and come back the next day, thanks largely to the tools I learned from this blog.

    Now I find myself happier with fewer longer trips. I used to love hopping around to as many places as possible, and taking a trip at least every other weekend. Now we take 4 trips or so a year that work around school schedules. This summer we went to Hawaii and the West Coast for 2 months, we'll go to New Zealand for a month in December, and who knows what Spring Break will bring.

    It feels weird to recognize the transition as its happening, and to realize that 5 years ago I would have thought I was getting soft for slowing down, but the truth is, now I enjoy being at home more than I ever did before. I'm looking forward to hearing some of those trip reports with Miles. Traveling with kids is a whole new ballgame, but it sure is rewarding.

    1. DLPTATL Diamond

      Ditto...part of it is that we've done most of the quick trips at least once, you just don't get the same buzz taking the same trips over and over (at least we don't). Now the buzz comes from travel that is further away, requires more planning, and more $s and points. This results in fewer, longer, and more exotic trips.

  37. Jay Jacobsmuhlen Guest

    Thank you so much for this post. It really hit a chord with me.

  38. DenB Diamond

    32 and not young anymore... you'll laugh at that statement in your 60s.

    When you're reunited with your man, your kid and (last but not least) your dog, pause for a moment and notice how you feel. Deposit those feelings in your memory. You can withdraw them at moments like today. Deposit, withdraw. You'll maintain a healthy balance in that account.

  39. Ann Guest

    To be fair, you never really travelled like most 20 somethings do.

    I m sure all the chain hotels were cool but you missed out on the fun parts of travel in ones early 20s

    1. Ben Schlappig OMAAT

      @ Ann -- While I don't for a second doubt that others had a great time traveling very differently in their early 20s, I still had a pretty fun time. :-)

  40. willmo Guest

    How does Winston feel about Miles?
    What is the relationship like at this early stage?

    1. Ben Schlappig OMAAT

      @ willmo -- Winston is getting along with him much better than we were expecting. Winston was a shelter dog, so he has been VERY possessive and jealous, as he has abandonment issues. However, he adores Miles, and is endlessly interested by him. He also knows he needs to be gentle with him, so that's good.

      I think Winston is just a little annoyed he's not getting any reaction from Miles yet, no matter what tricks he "performs." I'm sure that'll change soon enough!

  41. Jason Guest

    Where are you flying on Copa? And returning from on LATAM? you simply say South America. That's a big place. Looking forward to the review!

    1. Jason Guest

      Oh and I appreciated this post. I hear what you're saying. And do fondly recall all your old shenanigans. Enjoy!

    2. Ben Schlappig OMAAT

      @ Jason -- For what it's worth, I was intentionally vague before traveling, given the history of some people trying to screw with my reservations. But since I've taken the flights, I was flying Miami to Panama City to Lima to Miami -- just a pretty simple routing.

    3. Jason Guest

      ah!! i wasnt sure if it was Lima or Santiago. have fun!
      (people screw with your reservations??? weird, and sorry to hear).

    4. DenB Diamond

      Given the title of the post, I guess pre-celebrity was the "Carefree Days". Imagine knowing, as most of us do, that nobody will approach you in an airport full of enthusiastic chatter. Tradeoffs abound in a full life.

    5. Daniel B. Guest

      @Lucky: "some people trying to screw with your reservations"? Really??? Did something like that happen? It sounds unbelievable.

Featured Comments Most helpful comments ( as chosen by the OMAAT community ).

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Tim Dunn Diamond

First, thank you for being honest. You are to be commended for living your life transparently. Second, welcome to the sandwich generation. We as humans are supposed to receive the torch of life from our parents, guard it well, and then pass it along to our children (or others in whom we choose to invest). It isn't easy caring for those above and below us in age; by God's grace, you will get a full generation in this phase of life but you will be torn the entire time between caring for others and caring for yourself. Third, by the time your kid(s) are out of the house, your body won't be as kind to you as it once was - and even is now. Hotel beds and pillows and other people's food doesn't set just like it did; airplane seats get less and less comfortable - without the airline changing a thing. Every road warrior moves from travel being easy to becoming a chore - the degree of which depends on the person. As Solomon said, enjoy your days and what you have now. It isn't necessarily better later.

7
Ben Schlappig OMAAT

@ Ann -- While I don't for a second doubt that others had a great time traveling very differently in their early 20s, I still had a pretty fun time. :-)

5
Donna Diamond

I was with you in the old days when you were living out of hotels and I believe one of the things that keeps me here now is that the blog is always evolving, like our lives. I’ve been a road warrior longer than you’ve been alive and air travel has changed drastically during my run and as much as I’d like to bring back Dividend Miles and easy upgrades, I feel air travel is moving in a good direction. Like @Tim says, travel gets physically harder and flying east on long hauls, in spite of quick turnarounds, takes a toll and jet lag is real but I’m sure you’ll figure out strategies and let us all know. I must say I’m a bit nostalgic about your nomad days, perhaps you could occasionally repost an old post with a Flashback Friday theme from time to time. Those were so much fun and remind us all of lost youth and how much everything changes or even, in many cases, stays the same. Hang in there!

4
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4,788,713 Miles Traveled

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