This is why I’ve been called back to your podcast and writing, over and over, for years. Your focus on meaning and connection resonates so strongly with me.
I’ve been moving from job to job for my entire adult life, prioritizing time with my family in whatever stage of life we happen to be in. I’ve criticized myself for not having created a career or made a decent income as a result, and at 47, the world is telling me that I’m far from ready for a comfortable financial retirement. Yet, my relationship with my kids, husband and family feels strong. I’ve also given much energy to my passion project, sharing about hikes and outdoor spaces, which has yet to bring in a decent income, but has been an energetic lifeline for over ten years! Thank you for reminding me that my path, an intentional one, is not a failure. Thank you for all of the wisdom you share, Jonathan!
So glad to know we've been traveling together for so long, Jill. And, thanks so much for the kind words. We all know money matters, but it's not a replacement for meaning and connection. And both have similar returns when we're conscious about them, and invest in them.
Tough one because I've seen people take it too far the other way and be irresponsible with money, get too far down the path to do anything about it and then get hit with unexpected medical problems that they can't afford. This happened to my father in law who is medically complex with early dementia. The financial burden has been shifted onto his family members who are unable to afford the care he needs. Very sad situation. I guess I'm not arguing on the side of hoarding money but just that there are two sides to this. Prudence and planning ahead financially can ease the burden on one's children. We can't know our future and things don't always turn out the way we wanted. That's life. (Sorry to be the downer commenter.)
Absolutely, Elizabeth. Not a downer at all. It's why I mentioned it's not an either/or thing, but more of a yes/and. It's not about throwing caution to the wind and just letting the money side of things "take care of itself." It's about honoring the fact that money matter and compounds when you invest in it over time, but so does being present in the lives of those we love. And, there's also a bit of a magic window to create that foundation for compounding over time as well, which I think we sometimes forget.
As a financial planner (specifically for women midlife and better) I really appreciate this post! Of course there are plenty of people, and clients of mine, who have worked their tails off and arrive in their 50’s without piles of cash, without that optionality that we all want. Yes, sometimes it can be addressed by reducing one’s cost of living, but many folks still need to continue to work. And ageism often gets in the way of their continuing the in the career or profession they’ve worked in for decades. That said, plenty of us reach our 50’s and start to reevaluate what’s important, and would like to reimagine and reinvent their relationships with work, and “wealth,” and their people. Sometimes my biggest challenge is trying to convince my clients that they can afford (money-wise) to take that family vacation, leave that job with the a**hole boss, take that bucket-list trip while their knees will still let them do all the walking it requires. Thanks for addressing this!
Love the word, "optionality," Stephanie. That's what we're really after, in the end. Both when it comes to wealth and freedom, and also in the context of having deep, sustaining relationships remain on the menu of options, too.
Perfect post! Thank you! -- "No one offers this contrast to the classic narrative that says put your head down, surrender your life to work for the first two to three decades, compound your wealth, then circle back and assume your life will be there for you, your relationships will survive, your kids will know, love and trust you, and you them."
I’ve spent the last 23 years on what some might call a “non-conventional” career path.
Ten years traveling the world as a media exec. Lived in over a dozen countries. Burned out. Settled in South America. Built a remote business from scratch that let me spend the last decade raising my daughter, staying close to my wife (across two countries), and staying grounded physically and emotionally.
I’m 50 now. Not very wealthy by traditional standards, but profoundly rich in time, presence, and connection.
And yet… yeah, part of me wonders: Could I have made more if I’d worked harder? Probably.
But at what cost?
Now I’m stepping into a new season, guiding others through the inner work it takes to build this kind of life. And I can honestly say I’ve never felt more fulfilled.
I also hear the concern that some have shared regarding unexpected expenses, especially those related to healthcare. I’ve lived mostly in Europe and other countries with stronger safety nets, but also slower economies. However, after all is said and done, I’m betting on a global trend that I do believe in: the freedom to live and work from anywhere, with anyone, in increasingly fluid and aligned ways.
This kind of says it all, Alexis - "And I can honestly say I’ve never felt more fulfilled." Such an interesting point, also, about living in a country with a stronger safety net. And love that concept of freedom and fluidity as yet another form of compound interest.
Sadly, what I've seen is people hit their 50s with even MORE $$$$ accumulated than they planned for (or in some cases even dreamed about) and have been told they will die at 100 with $250 MILLION leftover and they get trapped Can't step off the accumulating wheel despite deeeeeep unhappiness with life. It truly boggles my mind and shows me it is (almost) never about the actual money, once you hit that "enough" level (which I think used to be $75k/year?).
It's a delicate balance, for sure, Angie. I'm not anti-money in any way, just pro other things that matter and have similar compounding effect when we center and invest in them.
You can do both if you're willing to be very "weird". I prioritized money but NOT status, access, and prestige. I used the time freed up by that to travel, to be there for my wife and kids every day and crucially when they needed me most (hospitalizations), be there for my dad when he passed, currently to be there for my mother in law as she has her fight with cancer, and show my kids that I am not some far away money earner but with them every day.
By weird, I mean I was the guy working at the Singapore regional office of Visa wearing jeans from Costco that I got on trips back to visit my parents while my co-workers were the type who wore Rolex and Gucci and I don't even know what else. I got to that position based on expertise and a reputation for hard work and an ownership mindset.
I'm "retiring" now at 41 (in reality I have more projects to do, but now wholly on my own terms) because I got lucky with money in some respect but also because I've always prioritized only important spending and never fancy cars, clothes, or houses.
It's not without costs, we have a really hard time "fitting in" because we don't fit molds, but I wouldn't do it any other way if I had to do it again.
This is why I’ve been called back to your podcast and writing, over and over, for years. Your focus on meaning and connection resonates so strongly with me.
I’ve been moving from job to job for my entire adult life, prioritizing time with my family in whatever stage of life we happen to be in. I’ve criticized myself for not having created a career or made a decent income as a result, and at 47, the world is telling me that I’m far from ready for a comfortable financial retirement. Yet, my relationship with my kids, husband and family feels strong. I’ve also given much energy to my passion project, sharing about hikes and outdoor spaces, which has yet to bring in a decent income, but has been an energetic lifeline for over ten years! Thank you for reminding me that my path, an intentional one, is not a failure. Thank you for all of the wisdom you share, Jonathan!
So glad to know we've been traveling together for so long, Jill. And, thanks so much for the kind words. We all know money matters, but it's not a replacement for meaning and connection. And both have similar returns when we're conscious about them, and invest in them.
Yes! Well said.
May we all find fulfilling, well-paying work that supports the quality of life and time with our loved ones most of us crave.
Tough one because I've seen people take it too far the other way and be irresponsible with money, get too far down the path to do anything about it and then get hit with unexpected medical problems that they can't afford. This happened to my father in law who is medically complex with early dementia. The financial burden has been shifted onto his family members who are unable to afford the care he needs. Very sad situation. I guess I'm not arguing on the side of hoarding money but just that there are two sides to this. Prudence and planning ahead financially can ease the burden on one's children. We can't know our future and things don't always turn out the way we wanted. That's life. (Sorry to be the downer commenter.)
Absolutely, Elizabeth. Not a downer at all. It's why I mentioned it's not an either/or thing, but more of a yes/and. It's not about throwing caution to the wind and just letting the money side of things "take care of itself." It's about honoring the fact that money matter and compounds when you invest in it over time, but so does being present in the lives of those we love. And, there's also a bit of a magic window to create that foundation for compounding over time as well, which I think we sometimes forget.
As a financial planner (specifically for women midlife and better) I really appreciate this post! Of course there are plenty of people, and clients of mine, who have worked their tails off and arrive in their 50’s without piles of cash, without that optionality that we all want. Yes, sometimes it can be addressed by reducing one’s cost of living, but many folks still need to continue to work. And ageism often gets in the way of their continuing the in the career or profession they’ve worked in for decades. That said, plenty of us reach our 50’s and start to reevaluate what’s important, and would like to reimagine and reinvent their relationships with work, and “wealth,” and their people. Sometimes my biggest challenge is trying to convince my clients that they can afford (money-wise) to take that family vacation, leave that job with the a**hole boss, take that bucket-list trip while their knees will still let them do all the walking it requires. Thanks for addressing this!
Love the word, "optionality," Stephanie. That's what we're really after, in the end. Both when it comes to wealth and freedom, and also in the context of having deep, sustaining relationships remain on the menu of options, too.
Perfect post! Thank you! -- "No one offers this contrast to the classic narrative that says put your head down, surrender your life to work for the first two to three decades, compound your wealth, then circle back and assume your life will be there for you, your relationships will survive, your kids will know, love and trust you, and you them."
So glad it resonated!
This hits like a tuning fork.
I’ve spent the last 23 years on what some might call a “non-conventional” career path.
Ten years traveling the world as a media exec. Lived in over a dozen countries. Burned out. Settled in South America. Built a remote business from scratch that let me spend the last decade raising my daughter, staying close to my wife (across two countries), and staying grounded physically and emotionally.
I’m 50 now. Not very wealthy by traditional standards, but profoundly rich in time, presence, and connection.
And yet… yeah, part of me wonders: Could I have made more if I’d worked harder? Probably.
But at what cost?
Now I’m stepping into a new season, guiding others through the inner work it takes to build this kind of life. And I can honestly say I’ve never felt more fulfilled.
I also hear the concern that some have shared regarding unexpected expenses, especially those related to healthcare. I’ve lived mostly in Europe and other countries with stronger safety nets, but also slower economies. However, after all is said and done, I’m betting on a global trend that I do believe in: the freedom to live and work from anywhere, with anyone, in increasingly fluid and aligned ways.
That’s a form of compound interest, too.
This kind of says it all, Alexis - "And I can honestly say I’ve never felt more fulfilled." Such an interesting point, also, about living in a country with a stronger safety net. And love that concept of freedom and fluidity as yet another form of compound interest.
Sadly, what I've seen is people hit their 50s with even MORE $$$$ accumulated than they planned for (or in some cases even dreamed about) and have been told they will die at 100 with $250 MILLION leftover and they get trapped Can't step off the accumulating wheel despite deeeeeep unhappiness with life. It truly boggles my mind and shows me it is (almost) never about the actual money, once you hit that "enough" level (which I think used to be $75k/year?).
It's a delicate balance, for sure, Angie. I'm not anti-money in any way, just pro other things that matter and have similar compounding effect when we center and invest in them.
Beautiful perspective thank you 🙏🏻
Thanks, Amy.
Lovely
You can do both if you're willing to be very "weird". I prioritized money but NOT status, access, and prestige. I used the time freed up by that to travel, to be there for my wife and kids every day and crucially when they needed me most (hospitalizations), be there for my dad when he passed, currently to be there for my mother in law as she has her fight with cancer, and show my kids that I am not some far away money earner but with them every day.
By weird, I mean I was the guy working at the Singapore regional office of Visa wearing jeans from Costco that I got on trips back to visit my parents while my co-workers were the type who wore Rolex and Gucci and I don't even know what else. I got to that position based on expertise and a reputation for hard work and an ownership mindset.
I'm "retiring" now at 41 (in reality I have more projects to do, but now wholly on my own terms) because I got lucky with money in some respect but also because I've always prioritized only important spending and never fancy cars, clothes, or houses.
It's not without costs, we have a really hard time "fitting in" because we don't fit molds, but I wouldn't do it any other way if I had to do it again.