The Real World Is Scary

by Frost on October 12, 2011

Two weeks ago, I quit my job. Now I’m moving to Thailand to start a new life as an author/entrepreneur/vagabond. Details here.

At first, I was giddy as a pedophile on take-your-daughter to work day. A world of possibilities was opening up to me. I was giving myself the chance to create the kind of life I dreamed of. It had taken me a quarter of a century to do it, but I was finally ready to live on my own terms, and decide for myself what I really wanted to be doing.

That giddiness is still there. If it ever goes away, that will be my cue to end this experiment and try something new. But now that the novelty has passed and reality has set in, I’d be lying if I didn’t admit that I  occasionally wonder if I’ve just made the worst mistake of my life.

Turns out being a twenty-six year old retiree is not as relaxed and carefree as you (or I) might have thought. Here are some of the things that have been keeping me awake at night recently:

1) I’m leaving my family

This will be the first Christmas that I ever spend away from my father, my brother and sister. My dog is just starting to grow out of his habit of destroying anything left within five feet of ground level.  I’ll save money on presents and chewed-up shoes, but I’m going to miss them.

2) I’m leaving a girl I’m in love with

Quality girls are hard to find. For the second time in my life, I’m about to walk away from a good one. We’ve always been on different wavelengths regarding marriage, monogamy, settling down, and white picket fences, but we’ve shared a great two years together regardless. Part of me is excited to be fully and unambiguously single for the first time in a while. But I also know there will be some nights where I just don’t feel like putting on my game face to hunt fresh conquests, and would rather lounge around naked with someone I can be completely relaxed with.

3) I’m walking away from my career

By any reasonable standard, the job I left was a damn good one. Decent money, interesting work, and tons of security in an increasingly insecure world. I’m confident I’ll always be able to find a desk job to return to in a year or five, but quitting now is a black mark on my resume. If I ever decide I want to return to my old field and resume my climb up that ladder, it will be that much harder.

4) I might fail

I’m counting on my ability to build and operate online businesses as a means of paying for my life and travels. Do I have this ability? Can I turn enough of a profit to generate the income I need?

Will my book sell more than a dozen copies? Will this website continue to grow, or will it stagnate and decline? Will I continue to improve as a writer, or have I plateaued?

In my old life, true success was practically impossible. But so was failure. On the new path that I’ve chosen, the odds are much greater that I’ll wind up at one extreme or the other. Sure, I may become a millionaire and best-selling author. I also might wind up a broke, lonely, 35-year-old Walmart greeter.

5) I might be wrong about everything

What if I’ve just traded in one bullshit perspective on the world – the conventional wisdom – for another that’s equally flawed?

My Kindle and RSS feed are full of smart people who are living lives similar to the one I aspire to. But I found them, and I continue to be drawn to them, because they are the success stories.

What if, for every Tim Ferriss, Tucker Max, Charlie Hoehn, Ryan Holiday, Ramit Sethi, RooshColin Wright, and Chris Guillebeau, there are thousands and thousands who tried to do what they did, and failed miserably? And I’m not talking about the thousands who half-assedly tried to do what they did, and failed. (I guarantee that they exist.) I mean, what if the actual odds of duplicating the success of these and other successful lifestyle design artists is near-zero? If people like them are extraordinarily lucky, in addition to whichever aspects of their behaviours and attitudes I can learn and duplicate, I would have no way of knowing. Even they would have no way of knowing.


All of that said – I’ve had an incredible two weeks, grinding through the final editing stages of my book, working on designs and websites for my ecommerce sites, golfing, and partying. Even though I’m working harder and longer than when I had a real job, I feel calmer and more relaxed than I ever did before. I’ll always have my family, there will always be new girls, I’ll always be able to find a crappy job if I need it, and even though my life might be on the verge of self-destructing in epic, hilarious and very public fashion – fuck it. It’ll still be a fun year for me, and an entertaining one for you.

Tonight, I sleep like a baby.

{ 27 comments… read them below or add one }

Dirt Man October 18, 2011 at 10:14 am

I wish you all the best in your travels and endeavors Frost. Your post and life situation has me thinking a lot and I’ll have a post later today or tomorrow on all of this. Truly an exciting time for you. Learn and grow as much as you can, and have fun along the way.

John Lee Pettimore October 16, 2011 at 8:57 pm

Do it. Yes, you may fail, whatever that means. The experience certainly will not be what you expect — in some ways it will be better, and in other ways it will be worse. I am 49, and have no regrets about the chances I took and the losses I incurred, but just trust me that for a lot of reasons I don’t have 4,000 pages to explain, this is definitely the right thing to do. Go do it.

anonymous October 16, 2011 at 12:01 pm

there are not 1000s of failed rooshes, but there are millions of guys who never had the balls even to attempt

Dave October 14, 2011 at 4:16 pm

I envy ya, lad. 25 years ago, I had the opportunity to go off with a friend and work on a tramp merchant ship out of Argentina. We had our apprentice seaman cards, passports and everything. But I let myself get talked out of it. I am 45 now, and I regret not having done that every day. Put yourself out there, lad, and live life on your own terms. I am rooting for ya.

tim October 14, 2011 at 9:11 am

this is a stupid idea. don’t do it.

Jordan October 13, 2011 at 6:25 pm

Stickman Bangkok is pretty much the spokesperson for the loser segment of the Thai ex-pat scene. Every entry is about how horrible Thais are and how pathetic and weak white people are and how white people have to kowtow to Thais in order to be accepted in Thailand.

I would stay well away from that site if you want to have a happy, successful visit to Thailand. The people on it have all failed to make a success of it and try and drag every newbie down to their level.

Thailand can be great fun! Enjoy!

Tschafer October 13, 2011 at 5:38 pm

Well, if you’re going to do something like this, now is certainly the time to do it. Good luck, enjoy Thailand, and I hope that you have some responsible looking after your dog (I’m sure you’ll have no problem finding someone to look after the girlfriend…)



Frost October 13, 2011 at 1:06 pm

Simon and DD,

Thanks. And yeah, even in my worst-case scenario, I’ll have no regrets. There will always be another desk job waiting for me if I choose to go back down that path. Worst case scenario, I live in a slightly smaller house and drive an old-model car when I go down the white-picket-fence route.

Best case scenario…..

Simon Rierdon October 13, 2011 at 11:31 am

Frost, I agree with DD, you’ll be fine. You’ll be doing and seeing things that 99% of people in this world never will. That in itself is worth any possible outcome.

Delusion Damage October 13, 2011 at 5:51 am

It’ll be fine. Success, failure, whatever.
On your deathbed, you’re not going to think “damn, I wish I’d put in an extra year in the cubicle instead of traveling the world”.

PUA Vault October 13, 2011 at 5:31 am

The nomadic/traveler lifestyle can be a bit empty no doubt. I moved around Europe for 9 months, staying around 2-3 months in 4 different places. I signed up for language classes in order to have some order to my day. Well, friendships, hookups in those situations is like Vegas, fickle and short, and eventually everyone goes back to their home countries. We take for granted how jobs help us ground to the places we live. I currently work from home, which gives me quite the freedom to go do shit during the day but there isn’t many people like me, and so in a way you’re bound by the normal 9-5 schedule of the normal workforce.

I’d like to think I could make friends if I moved to a new country, in a jiffy. I certainly can make insta-wing-friends at the club, where guys number close me, but I’m also realizing the value of real friendships, and common histories built together. If you’re constantly on the move, this might be something you miss out later in life.

Frost October 13, 2011 at 1:02 pm

That’s a concern of mine as well. I have some friends who are going to be coming with me for a few legs, and friends that I’ll be visiting, but I’ll also be on my own for most of the time. I don’t think I’ll mind, but I’ve never really been away from ALL of my close friends for a long period of time.

NomadicNeill October 12, 2011 at 6:29 pm

If there’s one piece of advice I can give you it’s not to become attached to any idea of how your free life should be.

The new ‘do whatever you want’ seems to be narrowed down to ‘earn money by showing other people how to be cool living a digital nomad lifestyle’. If it doesn’t suit you there’s no shame in trying something else (teaching English in China, becoming a diving instructor etc.)

For the moment I’m no longer ‘nomadic’ (though having lived in 10 different countries and having traveled to 40 more, including a trip that lasted 1.5 years I feel I deserve to keep the monicker) and I wanted to settle somewhere, make friends, build lasting relationships and make music with other people. To me that’s freedom, just a different kind.

Frost October 13, 2011 at 12:59 pm

Absolutely. Freedom means doing what you want, for yourself. You’ve gotten away from the mainstream culture’s suggestion that you work 9-5 and maybe go on a few two week vacations to Mexico or Bali in your life. But if you were to leave that, and then spend your life trying to live a lifestyle approved by the vagabonding/entrepreneurial counterculture, even though you’d rather put down some roots for now, how is that any different?

I’m looking at the next year as an experiment, in which I throw myself completely into the entrepreneur/vagabond/author lifestyle, and see how that works out.

Where are you settled now? London, IIRC?



Simon October 12, 2011 at 6:15 pm

The most important thing you’ll learn out of this, Frost, is that you’ll still be the same person. Moving overseas won’t change that. If you’re dissatisfied with your life, that’s your problem.

You create your own reality.

Frost October 13, 2011 at 12:52 pm

So you don’t think making changes in your life can affect your enjoyment of it?

Traveling, writing, and starting online businesses is an experiment. How will it work out? I don’t know. But I do know that my old path wasn’t the one for me.

If your point is that running off to some third-world beach to party and fuck won’t necessarily cure my malaise, then I agree. I’m looking for something, and it’s not mindless entertainment.



davver October 12, 2011 at 3:34 pm

Roosh is pretty upfront about being poor as shit, but prefers is anyway as he can still afford to eat and he’s healthy and doesn’t need medicine.

Frost October 13, 2011 at 12:47 pm

I don’t think Roosh is that poor!

He has a popular site with thousands of subscribers, a huge forum community of followers, and several books out. Also, I believe he teaches workshops occasionally.

Your point stands though, because he spent many years grinding his way up to where he is now.

davver October 13, 2011 at 12:50 pm

His recent posts still talk about money. And he’s sold a whopping 600 books or so?

Anyway, why don’t you ask him, or meet him.

AC October 12, 2011 at 2:11 pm

I take it as a given that people who blog about their cool-ass lives are the lucky few that not only personally enjoy their lifestyles, but attained a level of success that can make even conventional people envious. I think emulating their style is worth doing only if you’d be happy even if you “failed.” Would you be happy if you only got some degree of their freedom and success? If you put in the same amount of work but only got 20% of their wealth and success with women? If the lifestyle is what makes you happy, go for it. If you’re expecting to get outcomes like theirs, you’ll likely be disappointed. (Also to some extent every one of them covers up their awkward dead ends, their failures, and the non-cool sounding effort they put in behind the scenes.)

For myself, I’m having dastardly fun incorporating game, paleo, and so on into my rooted life, and enjoying the leg up that gives me, without moving to Thailand. And I enjoy your blog as an example of focused self-improvement in specific areas. Would love to hear more about your specific things you changed in your own life, your successes, your setbacks, and the final effect it had on your life. Following up your grand plan is definitely cool, but for me and I suspect a good part of your readership, the real money is a worked example of how these reactionary changes can work in one person’s life.

Frost October 13, 2011 at 12:41 pm

AC, agree that moving/living abroad is definitely not for everyone, right at this moment in their lives. I’ve corresponded with a few people like you, who are happy in their lives and just want that edge. Maybe that’ll be me as well in a year or two or ten.

For me, traveling is something I’ve never done and always wanted to do, so it’s getting thrown into the pile of new habits and experiences I’m throwing into my life. Maybe I’ll find that I love life on the road, and never look back. Maybe I’ll realize I can’t bear to be away from my dog for more than a week at a time.

Most likely, I think I’ll realize that i love being on the road, but I also want roots and stability. Say, 6 months on, 6 months off. We’ll see!



Ryu October 12, 2011 at 1:42 pm

All that glitters is not gold, Frosty.

I’m surprised you didn’t mention Stickman Bangkok. I’ve always considered him the premier expert on Thailand on the web. He talks alot about this; young men going to Thailand for easy pussy and the slow life. Boom and ten years goes by.

What the PU + travel folks are selling is a different form of snake oil, a new old ponzi scheme. The dream is to ESCAPE! Man, those suckers in their damn cubicles. Come! Live the easy life with me! Fast cars, easy women, the good life.

Okay. But what about when the camera’s off. That guy gets old. Loses connection to his family. Resume sucks. Health deteriourates. With this manner of lifestyle, the profit comes up front, the costs come later. Nothing, nothing in this world is free. You will make gains, you will take losses. Guaranteed.

Frost October 13, 2011 at 12:37 pm

Ryu, thanks for pointing me towards Stickman Bangkok. First I’d heard of him.

Regarding escapism, purpose, and the long game… I’ll just say that I think you’re going to like my book.



Jeff October 12, 2011 at 12:01 pm

You’ll be fine. Maybe your first business will fail or your first couple ideas will suck, but you’ll make it eventually. Even if you have to pick up a few “real” jobs along the way to steady yourself.

It’s actually not that hard to make money without a job, and for someone with your intelligence I doubt it’ll be a big deal.

Email me if you have any questions about freelancing, which in my opinion is 10x easier than selling products (though I’ve done both).

Frost October 13, 2011 at 12:32 pm

Email sent. If you’d like to write a guest post on freelancing, please do!

Carmo October 12, 2011 at 9:11 am

Seems like there is an endless supply of “life style design/location independent” guru’s hawking more or less the same type of product. Not sure what your ecommerce plans are but it sounds like it would be quite challenging to stand out and carve out enough of a niche to support your future endeavors while abroad. I went down this road briefly but changed gears and built a business that provides tangible high demand products instead of services. Anyway good look man, you have at least 1 of your 12 book sales in que with me.

Frost October 13, 2011 at 12:30 pm


What kind of businesses, if you don’t mind me asking?

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