The Real World Is Scary

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, Roosh,  Colin 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.