Wins and Losses Series: Charles from That Charles Life – “Family time is valuable and sacrifices should be made to accommodate it”

Wins and Losses Series: Charles from That Charles Life - "Family time is valuable and sacrifices should be made to accommodate it"

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Hi, Team!


Welcome to another edition of MikedUp Blog’s Wins and Losses Series, where we interview a generous participant about 4 of the best and worst moments of their life. The point? To learn from the past so that we can improve in the future!


If you’re interested in participating in the Wins and Losses Series, please send me a note here (you don’t have to be a blogger to participate!)



Check out the complete Wins and Losses Series Here


(Photo courtesy of Justin Montemarano)


This week we have: Charles from That Charles Life!




First off, I am very excited to be a part of this project series.  We all go through different experiences in our life, and when they’ve happened so long ago we can tend to forget just how much they impacted us; how wonderful they were, or how awful and what we learned.  So I am happy to be taking a walk down memory lane for this purpose.


A bit about myself, I currently live in Shenzhen, China.  I teach ESL to Chinese children and it is allowing me to aggressively pursue Financial Independence/Freedom.  All while traveling and experiencing new cultures. You can read more about myself and my journey to retire at 40 at


Best moment No. 1: I don’t really want to travel to Africa.


The first ‘best moment of my life’ that I can recall is traveling to South Africa with my family to celebrate my father’s retirement.  This moment lasts for about 2 weeks. There are many reasons why this experience was so important and special to me.  Among them, my family had become busy with each of our own pursuits and hadn’t spent lots of time together just the 4 of us.  So this allowed us some true family time. It was also a big life accomplishment for my father He retired at 55, and definitely what I would consider financially free and independent.  And finally, because I almost skipped the trip.  


The purpose of the trip was to experience a Safari hunt.  My father and sister are big hunters, my sister had done a lot of travel previously and gotten some connections for hunting in Africa.  I know this might rub some people the wrong way, but the company we went through was very responsible with their hunting programs. We only harvested plains game like deer and antelope and all the meat was eaten by either the hunters and workers, or nearby villages.  All the skins and bones were also donated to local villages for making crafts that stimulates their little economies. I digress.


Originally, I wasn’t planning on attending the trip because it was not going to be a cheap one, and I had been saving up to visit Thailand; a country I’d had my eyes on for years.  But being the only member of my immediate family not attending, didn’t feel quite right to skip.  I also really considered;


“If I don’t go to Africa now, I’ll probably never go”.


So I decided to grab the once in a lifetime opportunity.  It turned out to be an amazing trip, and I completely fell in love with the beauty of Africa.  I cannot wait to go back.


What I learned from this moment and trip


I learned that family time is valuable and sacrifices should be made to accommodate it. I also developed a new mantra for traveling which is ‘If you have the opportunity to go someplace you never thought you wanted to go.. Always seize the opportunity!’  This mantra actually leads well into my next best moment.


My best moment No. 2: I guess I’m a teacher now?


A few years later after my South African trip, and one of the worst moments / decisions I’ve potentially ever made, which you will read about shortly – that cost me potentially hundreds of thousands of dollars – was the day I decided to flip my life upside down, move to South Korea and teach ESL.


I wrote an article on my website on how there was a period of my life where I was in a job that was a dead end for my personal self, and about to buy a house that would have kept me chained to my hometown forever. Right around the time I was offered the chance to move to South Korea and teach English abroad.  Ultimately the decision to quit the job that wasn’t working for me, abstain from homeownership, pursue FIRE and financial freedom came down to discovering a blog called Greater Fool.


This blog talked about the benefits of investing and not getting in over your head with real estate. Then it showcased some 30-year-old millionaire retirees. This and discovering just how much money I could make teaching ESL pushed me to pull the trigger.


What I’ve gained from this experience


2 years later I am much richer, have traveled to 10 more countries, and am much more motivated to succeed in life.  I am on the way to retire financially independent in less than 12 years, by the time I’m 40. Saying yes to teaching ESL completely changed my life in so many ways.  I am also fortunate enough now to help others come to teach English abroad. So if any readers might be interested in teaching ESL..  Let’s talk!


My worst moment No. 1: I am not invincible


I always try to remind myself during the low parts of life; if we never experienced pain or unhappiness, we’d never be able to really enjoy wins and happiness.  One of the most awful points in my life was when I broke my ankle while teaching in South Korea. Money, success, and social standing all fall away real quick when your health is in question.


I broke my ankle about 7 or 8 months into the year I spent in South Korea.  Even more unfortunate, was I broke it about a week into my best friends month-long trip to visit me.  We had many trips and excursions planned that were now essentially canceled. Breaking a body part sucks, anyone who’s gone through that experience can attest.  What made it worse was needing to have surgery. Surgery in a foreign country was even more daunting.


The surgery was quick and painless.  It cost a little more than I liked – being Canadian – but probably a heck of a lot less than it would have in America.  South Korea has an amazing and modern medical system and I was treated well.  I healed quickly, I was off crutches after a month. But that first month and a few weeks after was absolutely awful.  I had no one to really care for me or drive me around. So I had to crutch to and from school, and while taking public transit.  I had to get my groceries and do the rest of life’s necessities pretty much alone. My school did help with a few things; especially getting the surgery and various doctors visits.  But the rest I was on my own.


How this experience humbled me


Firstly, I was reminded of my mortality.  I now am a little more cautious with the risks I take, knowing what the potential consequences can be.  I am more aware of my physical limitations.


I was also humbled mentally by this experience.  I was gaining quite an ego leading up to this experience for a number of reasons.  But breaking my ankle really set me back and made me reevaluate myself; it allowed for some introspection.  


I was also able to realize how hard life can be for those who aren’t blessed with a healthy family environment or a strong friend circle.  Again, I realized how important it is to nurture friendships and family relations.


My worst moment No. 2: One of the worst decisions I’ve ever made


While I took my trip to Africa, I had been working for a startup tech company for nearly a year.  I had some really ambitious, motivated and intelligent management. I worked with some great employees.  But the work was getting very tedious – my position was inside sales.  Leads were becoming saturated and fewer new ones were coming up, and I was focused on other side endeavors.  At this point, I was still buzzing from reading ‘The 4 Hour Work Week’ by Tim Ferriss. I’ll give it to him, the guy knows how to sell books.



I was caught up in trying to find ways to work way less.  And live the 4 hour work week life before I had really earned it.  


Shortly after my African trip, I left the company.  I felt free to pursue some other entrepreneurial pursuits and enjoyed lots more time off.  Eventually, I would go on to sell cars then move to South Korea.


Well about half way through my Korean experience, I woke up one day to find on social media that this old tech company had sold for 9 figures.  And some longtime employees who I had started with got paid out.. In the 6 figure range.


What I learned from this decision


The realization that I could have an extra digit in my net worth right now is a bit unnerving, but that’s life.  If anything, this experience taught me to live peacefully with all the decisions I make.


Since I’ve started teaching ESL I have developed a much better work ethic and drive to succeed.  I currently work 70 hours a week between 2 jobs and side work. It kind of pains me that I wasn’t able to develop this mentally of hustle back then at that job, but life works out as it should.


I guess I’ve also learned that there’s no right or wrong way to live, had I not left that job I probably would never have started teaching ESL, and maybe still never left my hometown.  It’s hard to put a price on the experience of travel and the perspective of learning from foreign cultures.


To sum up


I hope this was an enjoyable read, and my personal wins and losses throughout my life are able to add some perspective to all the readers out there.  I’ll try to answer any questions and respond to comments below! And again, if any readers are interested in learning more about Teaching English abroad, please contact me over at



Thanks for reading!


If you’re interested in discovering a better version of yourself – whether with fitness, finance, or family – then subscribe below to MikedUp Blog’s FREE newsletter and let’s improve together!


I’m glad you’re here. Thanks again and talk soon!


– Mike
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