Am I living a Philippines midlife crisis retirement

In this report, I ask the question, “Am I living a Philippines midlife crisis retirement?”

When I was around 8 years old, I remember pulling up to a traffic light and seeing a shiny little red corvette in the lane next to us. My mother was driving me to a baseball game in the family station wagon. I looked up and saw one of our neighbors driving the red corvette.

My mom looked over at our neighbor and said under her breath, “He must be starting his midlife crisis.” I didn’t know what that meant at the time, but it was 1968. A few years later, he was divorced and driving that red corvette around town with a younger woman.

Am I living the Philippines midlife crisis retirement?

When I walk around in the Philippines, I see older men with younger women. When I see that, sometimes my mother’s words playback in my head. “Is he living his midlife crisis?” If so, then having a midlife crisis seems to be a rampant contagious phenomenon in the Philippines.

This is not a man-hate thing I am talking about. My sister is living with a man 15 years younger than her. So I am talking about human behavior more generally. The two people you are watching in this video are Qiang Hui of and myself. My name is Dan.

When I make these videos of Qiang and I traveling around the world and enjoying white sand beaches, I sometimes wonder if I have been in my midlife crisis. I have only known Qiang for 5 of the last 14 years, but she is 25 years younger than me. I just turned 61, she is 35.

So if it turns out that I am living a midlife crisis, then travel is my corvette and Qiang is the younger woman.

So, I left the USA in 2007 at the age of 47. I was not enjoying my work anymore and I got the opportunity to take a job overseas. My friends told me not to take the job. One said it was too risky, drastic, and impulsive … I must be going through a midlife crisis. I wondered if I was now the guy in the red corvette.

But I took that job because my dream was to travel the world. It didn’t feel like a midlife crisis to me at the time. It seemed like an easy way out of a life I just wasn’t that into anymore. And although it was a risky career move at the time, the pay was almost double.

So I left the USA 14+ years ago and have lived in our visited 67 countries so far.

But looking back now, I think I was in a midlife crisis when I left the USA. I will give the formal definition and symptoms of a midlife crisis in a moment, and explain what I was feeling about my life at the time. I will diagnose myself for your pleasure, but first I want to finish my backstory.

I have really loved seeing the world even more than I expected. So, after living and working overseas for the first few years, I wanted even more freedom. There must be a way I could become a perpetual world traveler–all year long.

At about that same time I was desiring more freedom, I read “The 4 Hour Work Week,” by Tim Ferris. That book blew my mind. It talked about how the Internet had changed everything. How we could be anywhere in the world and still do our job. The book redefined work and early retirement.

Tim Ferris put a burning desire in me to live the life of freedom all year long. I wanted a chance to create that life. So 3 years after leaving the USA, I asked my boss, “Can I work half-time remotely for half-pay?”

You see, I needed less money because I was living in cheap places. And I needed more time to start and build my online business. My boss agreed to let me work remotely. My life changed that day. But it has changed even more drastically since my business took off.

So, here I am 14+ years later. Traveling the world all year long. My online business was slow growing but eventually made it. Now I just work for myself. I teach people like you, how I was able to retire early for cheap and slow travel the world. So I have a question for you?

Has my life become just one continuous midlife crisis?

I am going to answer that question now. But if you are interested in learning how I was able to fire my boss, make money online, and travel the world for 14+ years, make sure to grab my FREE eBook at the link in the notes below this Youtube video.

Okay, back to my midlife crisis.

Back when I was deciding whether or not to leave the USA, one friend said, “You will fail and be back at your desk within 6 months.” He was mostly joking, we love to tease each other. Another friend said, “You would be quitting a dream job, you must be having a midlife crisis.”

So was quitting my job and moving to the third world a midlife crisis? Today I want to examine that question a little closer. So what is the formal definition of a midlife crisis?

“A midlife crisis is a transition of identity and self-confidence that can occur in middle-aged individuals, typically 45 to 65 years old. The phenomenon is described as a psychological crisis brought about by events that highlight a person’s growing age, inevitable mortality, and possibly lack of accomplishments in life.” Wikipedia. They may even have extraordinary accomplishments but they may not have lived up to their own goals and dreams.

Dr. William Nathan Upshaw shares the common symptoms of a midlife crisis for men and women: feeling unfulfilled, nostalgic, boredom, emptiness, meaninglessness, impulsiveness, rash actions, constant thoughts of infidelity, and regrets. Dr. W. Nate Uptown, MD.

Now I am not a doctor so I am not qualified to help anyone else. So I will just talk about what I was going through at the time I left the USA. So, if you have any sense that your life may be at risk, please call the National Suicide Prevention Lifeline for free and confidential support. In the USA, that number is 1-800-273-8255.

So what symptoms was I experiencing before I left the USA? When I decided to quit my job and leave the USA, I was bored of my job. I often found myself dreaming about a better life. I wanted a life that felt more challenging to me. I was just going through the motions. My old job paid well, but I wasn’t really making anybody’s life better. I was just helping a large faceless billion-dollar company make even more money.

In that sense, the job felt meaningless to me. But I still had some remaining hope. I felt that there was still time left for me to live a life of meaning. What I was doing at work felt empty. I felt unfulfilled. I even felt nostalgic for years gone past when I ran my own business when I was younger.

I wanted to be proud of myself again. I remembered how I felt when I worked for myself as a young man, but I couldn’t get myself to start working on a plan to start my own business. I felt stuck. Though I was bored and my work felt meaningless, the pay was good, the job title was significant, and the career course was much more socially respectable.

When I worked for myself as a young man, I felt proud of myself. Like I was in charge of my life. I wasn’t just a cog in someone else’s wheel. So although I was nostalgic about a better past, I just sat at my desk unwilling to quit and take another chance while knowing a better life was possible.

I knew a more meaningful life was possible but I wasn’t moving towards it. I felt listless because I knew if I quit and started a new business, it would take years of hard work and I had bills to pay now.

Somehow I knew there was a better life out there but I was not trying to find it. How could I get myself to break free of my present trajectory when my income was going up rapidly each year? If I could just keep my nose on the grindstone for a decade more I would be set up for life. But I felt like I was selling myself short, taking the easy route. Failing to take action felt like a surrender.

So, I was judging myself for not having the courage to leave that old job or start something new on the side.

But everything changed one day when a job recruiter called and said, “Would you be willing to leave the USA and take another job if we paid you enough money?” I heard my mind silently answer “yes” without hesitation before I knew any details. But I played it cool and answered, “Tell me more.”

A short time later I was living overseas.

So without hesitation, I would say that my decision to leave the USA, was indeed a rash and impulsive decision. And that impulsive decision was fueled by a deep sense of boredom, emptiness, meaninglessness, and nostalgia. So, it seems I was suffering through a textbook midlife crisis.

Now I am not a doctor, and I was never diagnosed by a doctor, but quitting my job and leaving the USA was probably a midlife crisis. At age 47 I made a rash life-changing decision to leave a life I had spent decades building. I was in crisis. So that brings another question to my mind.

Am I still living through a midlife crisis 14+ years later?

I would say no. My midlife crisis seemed to have ended about 6 months into the new job. It felt like a load had been lifted off my shoulders. First, I had the courage to change the trajectory of my life which took me out of a victim state and put me into an action state. Second, I was authentically enjoying the new job. I was working face to face, helping real people in a foreign country.

I was no longer just making a billion-dollar company even more money. Instead, I was helping young people standing right in front of me, increase their skill sets, make more money, and give their families a brighter future. My life suddenly had tangible meaning I could read on people’s faces every day. Their faces said they were proud of their life’s trajectory and it made me proud of mine. My life was full of meaning again.

So I estimate that my midlife crisis was over about 6 months after I made that risky rash decision to leave the USA, and I have never looked back, not even once. But it could have gone the other way.

If my boss was a dick or if the people I was teaching didn’t see a positive trajectory in their life, or if I just didn’t like living outside the USA, things could have gone the other way. So I feel lucky that all of the stars lined up and my crisis ended.

Now, I know what some of you are thinking as you watch all these images of us traveling. What about the younger woman in the photos, Qiang, is she a midlife crisis?

Is the Younger Woman a Midlife Crisis?

Okay, let’s talk about that. The definition of a midlife crisis includes a crisis onset by “a person’s growing age, and inevitable mortality.” So, it would seem that some midlife crises are brought on by aging and feelings of lost youth. So, some people seek refuge in rash actions brought on by constant thoughts of infidelity.

But I was not in a relationship when I met Qiang, so if I was still in a midlife crisis, at least there was no infidelity involved. But I would admit, that since I was divorced in 2001, at the age of 41 years old, I have dated mainly women in their 30s. So for 20 years, from age 41 to age 61, I have been dating women in their 30s.

I have also dated women in their 40s and 50s and one in their mid-twenties, but mostly I have been in relationships with women in their 30s. And I must admit, when I am with a younger woman, I just feel younger. Maybe that is proof of a midlife crisis.

So being attracted to the same age as I grow older might be reinforcing some tendency I have to deny my growing age and inevitable mortality. But I have also noticed that younger women seem to be less settled in their life and are generally more open to living a nest-free world travel existence.

In fact, when I was single traveling the world and I put my profile up in each city I visited, very few women over 35 ever responded to my profile at all. Maybe it is because I was always upfront about the fact that I am slow traveling the world and I do not maintain a residence anywhere in the world. I was looking for someone that could travel the world with me.

I am not saying there are no women in their 40s and 50s that would be interested in my lifestyle because I know there are. But they rarely responded to my online profile that I posted when I was in traveling through each part of the world. So I dated mostly women in their 30s before I met Qiang.  Qiang was 30 when I met her  

So I guess I don’t really know if Qiang is evidence of a midlife crisis. And frankly, I don’t care. If it is a crisis, I hope my crisis continues. I am having fun. Qiang and I seem to fit nicely together for many reasons which I won’t go into here.

But if you are dating a younger person, do think about how that fits into their life in the long run.

Are you being fair to the younger person?

If you are in the autumn years of your life and you are going to have a long-term relationship with a younger person, do spend some time thinking about how your time with them affects their life as an older person.

Try to pick a person that has similar life goals. Does she want children? Do you want children? If you differ on any number of subjects as fundamental as family plans or major life plans, consider finding someone that matches your plans more closely.

If you spend 10 years with a woman in her late twenties that wants a traditional life with a nest and children, and you don’t want that life, you may be aging her out of her childbearing years. So make sure you think and talk about these things before too long.

Also, if you ask a woman to quit her job and stay home with you, or travel the world with you, think about how that might affect her working years trajectory, income, and retirement savings. Do you have some assets you can leave her so she is not regretting the time she spent with you when she is older?

Or if you have a tight budget likely to expire with you, she needs to plan for her own retirement. The same issues apply to an older woman dating a younger man. Make sure young people are thinking through how this goes when you pass away.

Make sure to think these things through and help them think them through also. Younger people are often more romantic and less practical until they are more mature. I suppose most people will think about these things on their own, but I thought I would give you a gentle reminder.

Thanks for listening to me answer my own question, “Am I living a Philippines midlife crisis retirement?”

Make sure to grab a free copy of my eBook: How I Fired My Boss and Traveled the World for 14 Years!

Please subscribe to or our Youtube Channel to watch us move around the world, 14 years and 67 countries so far.

Thank you for stopping by. The world is your home. What time will you be home for dinner?

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