Being Unhappy in the Best City in the World

I'm sitting at my favorite coffee shop, in my favorite city, in the best country in the world, the USA.  So why do I feel so depressed?  First, there is a crazy homeless guy bothering the staff, it's freezing outside, and everyone around me seems gloomy and unhappy and unfulfilled.

Maybe the U.S. isn't the best county in the world afterall?  

If you asked me a year ago, my plan has always been to move back home after a few years of traveling. But this trip, I'm having second thoughts about ever moving back.  It was good seeing my family and friends again, but it seems like nothing ever changes and if anything things are slowly getting worse. Costs of living in the city are higher than ever, while jobs are getting harder to find.

One of my closest friends just bought a house an hour outside of San Francisco for $351,000 which I thought was insanely overpriced.  But he said, that's just the way it is now.  Everyone wants to live in SF but no one can afford it, as houses here are all over 1 million.  So people start moving outside of the city, driving those prices up as well.

Pros of Living in SF:
  • Ethnic diversity.  I didn't realize how much I missed Black people and Mexicans until I got back. It seems random, but I actually really like living in places with varied culture. 
  • Trader Joes.  Buying things like dark chocolate, grass fed beef, Kerrygold Butter, and natural toothpaste is super easy at my favorite grocery store.
  • Online Shopping. I love being able to order stuff online and unfortunately shipping to Thailand isn't all that easy yet.
Cons of Living in SF: 
  • Weather. People think it's warm in San Francisco.  It's not.  
  • Crazy People.  I didn't realize it until this trip as I was always just used to it.  But the U.S. has a huge mental health problem.
  • Expensive Everything.  Without doing anything different, I'm spending 3x as much everyday as I did in Chiang Mai, just having coffee, lunch and getting around.
  • Everyone's Busy.  People here have jobs and need to wake up early for work, and aren't free until 6:30pm to start hanging out.  

Maybe I'm Spoiled?

Am I being selfish for wanting a stress free life, warm weather, time with friends, and zero responsibilities? I feel like even though most people I know in the U.S. are unhappy at their jobs, stressed about money, and going through the grind that this is somehow what we are supposed to be doing?

Now I'm Scared.

A few years ago, I knew my life of travel was just a prolonged vacation.  I was happy that I figured out how to travel and live for cheap which I wrote about in my book 12 Weeks inThailand, but even then I knew my vacation would eventually end.  But now, that I've figured out E Commerce and have a legitimate online business I know that this vacation never has to end and it scares me.  

I used to dream about being comfortable, I strived to be content. Life seemed so easy, all I had to do was wake up, go to work, pay my bills, and partying on the weekends.  Now that life is uncharted and anything is possible, I realize that life is actually easier when you have less freedom.

I've actually forgot what it feels like to be scared, as it was so long ago, it's been hard to relate to people still living in the U.S., tied to a 9-5 job and the comforts and security of receiving a steady paycheck. I've been telling people that dream about moving to a place like Thailand and pursuing the life of a digital nomad to just do it.  

Quit your job, move to Thailand, and figure it out.

Those were my exact words I've repeated to countless people.  But now that I feel the same fear of the unknown, I'd like to formally apologize and tell everyone.  I understand.  

What now?

No idea.  I've started to realize that no one really knows what the heck is going on in this world.  I used to think the adults knew it all, that your boss knows best or wouldn't be in that position, or that authors of books somehow knew more than we did and were experts.

Now that I'm all three, I can tell you that no one knows shit and that you have to just follow your heart, and aim towards what you think might make you happy in life.  As long as you are a good person, don't screw anyone over or try to take short cuts, everything will work itself out, somehow, someway. Life is weird that way.  Keep following my blog, the Travel Like a Boss Podcast, and as soon as I figure out what the heck I'm going to do with my life, I'll let you guys know.

The only things I know for sure.
  • Somehow everything we've ever done, no matter how trivial it seems at the time, prepares us for who we are today and things we are going to do in the future.
  • I'm happier now with the random life I've built than I would be living in the biggest house in America, driving the more expensive car, working for the best corporation, and eating the most expensive food with the most famous runway model.  
  • Everything that I thought would make me happy, didn't.  The only things that really made me happy was finally being free of responsibilities, being my own boss, exploring the world and finding love.  

 I sincerely hope everyone reading this finds your own happiness.  My best advice is to trust in your gut and go for what you think will make you happy, regardless of what anyone else thinks or says. Somehow life always works itself out for the best.  Trust in yourself.  

Warm Regards,


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  1. Dude, you actually bring up good points that I have been considering over the past few months. I came overseas to teach English in Indonesia for a year, and now in Thailand (even though I'm going to teach Social Studies since I have a History degree haha) . My eventual long term plan isn't to stay with teaching, as much as I love it, it's not my long term goal.

    One of my main plans is to create an online Real Estate Investing business that I could just as easily do here in Bangkok as I could back in the states since that's where the business will take place. Also grow my youtube channel and even have a bloggity blog encouraging people to get out of the rat race and go places to teach, or by promoting stuff that actually works like Anton's course. The other was to lose all the weight I grained from stress which was a hell of a lot. I left for Indonesia over 300lbs.

    I told them I refused to come back permanently until I get back to my normal weight of 200lbs and have something generating income when I am back there because I refuse to go back into temp jobs. That was hell.

    I'd always envisioned going back to live permanently in some kick ass shape and making my online business work perfectly. It'd be a personal victory to prove all the people wrong who tore my spirit down. I wouldn't run up to them physically or anything like that because that's just being a dick. Just knowing that I proved them wrong would be enough.

    I've been here in Thailand since Feb 7th and even though it'd been only four months, I've been asking myself the question, "Do I really want to move back permanently?" Even though I wouldn't be working for someone who thinks I'm just a piece of fodder that can be replaced with a snap of a finger and living life on my own terms, is it worth going back?

    Bangkok has been pretty cool to me. I feel at ease here. It's something I haven't felt in years and something I'm truly grateful for. Of course I'll go back to visit family and stuff like that, but I really don't know if I want to go back permanently anymore.

    I'm glad to see you have the same thoughts man. :)

    1. Hey Matthew, congrats on having the courage to move out to Indonesia and now Thailand even with people doubting you and trying to hold you back. I'm glad you are enjoying life in Bangkok and that you are feeling at ease, it really is a great feeling to be stress free and happy. Good luck with the weight loss and online business goals, keep working towards it and it'll happen. It took me 4 years to figure out what worked best for me and now that it does, I'm happy with it as a personal victory and I know you will as well. Keep in touch and let me know how it goes! Best wishes in your success.

  2. Great post! Keep writing.

  3. Johnny.....Bravo! Reading this was deep! I am really happy for you and thankful that you do what you do! Looking forward to your next podcast bro!

  4. Johnny, just wanted to say that this is your best, most inspirational post yet. Thank you for the motivation.

    1. Dexter, Alexis, Eddie, I'm really glad you all enjoyed this post. At first I felt like it was a bit of a rant and didn't even want to post it, but then I realized how important it is to share the way I feel, not just the fun adventures and business tips, but also the downsides of being a digital nomad as well. Glad you guys are enjoying the blog and the podcast!

  5. Hey Johnny..

    It's easy to crap on the US.. really easy. I've been living in SEA 2 out of the last 4 years and the one thing I came to realize is how ungrateful I was starting to become of what the US has given me.

    I've come across too many people who would give their left nut just to have the freedom of that blue passport that you hold, who would want those 9-5 jobs that you despise.. you're coming from a position of power. Just keep that in perspective.

    1. Hey Anonymous, I'm 100% happy that I had the opportunity to grow up in the U.S., and have the creative freedom and opportunities thus far. But as far as wanting one of those 9-5 jobs back in the U.S., I really think people from other countries are chasing the "American dream" thinking it'll be amazing, when they have the opportunity to create an amazing life in their home country with the same or less effort. It's really hard for a local thai or filipino to think they have good opportunities, since living in the U.S. sounds incredible. But in reality, they live in incredible, beautiful countries and they have SO MUCH opportunity for entrepreneurship and business.

    2. Hey Anonymous and Johnny,
      First, thanks Johnny that was a great read, and it made me want to read all the comments. Good conversation kick off. I've been in Chiang Mai for a year and a half. I count my life today as an incredible blessing. I'm 54 and I did non-profit work for most of my life. It was a fulfilling career. But, (you knew there was a but coming didn't you?)

      But, I was blinded by a system that intentionally disconnects us. I was. The incredible wealth disparity in the US has killed the American Dream. No more social services, cutbacks in education, skyrocketing student debt, flat wages for more than 10 years, and the recent economic recovery going directly into the pockets of the 1% (which as it turns out is more like .01%). I'm a Skype conversation coach, and I talk with people all over the world. From Saudi Arabia to Sweden, they still believe the stereotype of the 50's, when more people had access to the American "Economic" Dream (certainly not a social dream). Today we are wage slaves to our debts - to the oligarchy. Seriously, Princeton University just released a study, this week, saying we've lost our democracy, we are now effectively an oligarchy ruled by a small group of the super rich. I agree it's extremely important to recognize our privileges, I'm a feminist and privileges are like one of my 'things' <> but it's even more important I think, to recognize that capitalism is killing us, literally and figuratively.

      I have more freedom as a digital nomad than I have ever had in my life. Isn't that what the American dream was supposed to be? I found freedom when I left the U.S.

    3. Hey Dani, thanks for taking the time to write such an insightful comment. I had no idea this would kick of a conversation at all and didn't even realize it would be a topic of interest for so many people. It seems like I accidently stumbled onto a pain point/nerve.

      I definitely agree that I too have much more freedom now as a location independent digital nomad than I ever did living in the U.S. but I doubt I would have saw that if I grew up in a 3rd world country, as I would have been blinded to the opportunities. That can be changing for the new generation however, as they are growing up with the internet and a lot more exposure to the world, instead of just what they assume the world to be from stereotypes from the 50's.

      I'd love to grab a coffee with you when I'm back in Chiang Mai by the way if you're up for it, I have a feeling we'd have a great conversation!

    4. I've seen you via Marion's posts on FB (you can find me on her list.) Let's meet up. (Malee is my Thai nickname.)

    5. So sick of people saying you should just be glad to be an American. I'm sorry but living in a debt culture run by oligarchs is not healthy or fun. Having a USA passport is great! In fact it has become one of the ONLY great things about being American. And guess what? Johnny FD is using his passport quite often! Very American of him isn't it?

  6. Awesome post, Johnny! I understand everything you said - however, NYC is the best city in the world :P

    But seriously, the unnatural paths we carve for ourselves as location-independent entrepreneurs is just that, unnatural. But that doesn't make it any less valid. Everyone has to decide what is best for them, and there are plenty of people very happy leading the "normal" lives we can't relate to anymore.

    I often ask myself questions about the future, my business and feels uneasy knowing that the normalcy of American life will never satisfy me again. It IS scary, but we can use that fear to push us beyond what we initially thought was possible.

    Also, I love that you realized we know nothing. I spent my younger years searching for answers, and regained my childlike surprise when I realized I didn't know anything and didn't need to. Then I fell in love with life all over again.

    Glad you didn't delete this post, and even more that you had the courage to write it.

    See you in Thailand!

    1. Hey hey Anha the Global Social Media queen! When are you coming to Thailand? I'm on Twitter now by the way, in part thanks to you =)

      New York is definitely one of the best cities in the world and I would say the pros and cons of NYC are multiplied when comparing it against SF.

      NY is 3x Colder in the winter, cost of living, rent and food is 3x more expensive, and since there are so many people, you somehow feel even lonelier when you are there and ignore all the crazy people even more as you are used to it. However there are 3x even more amazing restaurants, culture and things to do. But I'm starting to think, at least right at this moment in my life, Chiang Mai might be the best city in the world for having all of the above but at 1/10th of the cost, great weather, an incredible community of people and virtually zero stress. Come to CM Rebekah!

  7. Awesome post bro... definitely one of your best.

    When I started traveling just over a year ago I thought it would be for a few months max and now I can't even picture myself going back for any extended amount of time.

    Like you pointed out, it goes well beyond the financial benefits of living in a place like SE Asia. Life is just so easy to optimize here and it's insanely simple to surround yourself with likeminded people who are truly happy. Even between the hours of 8am - 6pm on Monday - Friday :)

    1. Hey buddy I'm glad you ended up staying as well and not going back to New York. What you've taught me about dropshipping is one of the major reasons why I'm even able to have the choice to stay out in SE Asia for so long. I'm sitting in a starbucks right now in Los Angeles surrounded by nursing students and it's a very different feeling than being in Chiang Mai surrounded by other digital nomads all working on their own businesses. But as you said, more than just the money and the costs of living, people we meet while traveling are genuinely happy, even the ones that are still broke, no one is really in the grind or in the rat race. While it seems that everyone here, no matter how much money they have is stressed out and coping through spending more and more money on things they don't need.

  8. Definitely a different perspective to look at. I enjoyed the post.

  9. I like how lost you seemed in this post, it was very captivating


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