Maximizing Your Opportunity Window


In my last post i talked about what NOW is the right time for. The implication, of course, is that there are certain periods of time where you can actually take advantage of opportunities that come your way. Let’s call that your Opportunity Window. In the Standard American Lifestyle, that window is narrow. Really narrow. It probably starts somewhere at the end of senior year in college and ends a few months afterwards.

There are small blips of opportunity afterwards, too. Getting fired creates a window. Some sort of windfall income might create a window.

That sucks. Someone with a Standard American Life probably has no more than a year of Opportunity Window in their lifetime. It’s only during those times that they can start a new business, leave their lives behind and try something new and exciting, or just make a drastic change.

Maybe you don’t want a large Opportunity Window. If you’re lucky/smart enough to make the right choice during your first window, you don’t need another one. I know people who picked something they’re happy to do for the rest of their lives during their first Opportunity window, and that’s all they need. This post isn’t for them; it’s for people who haven’t committed their life to a single goal and want to maintain their flexibility.

Let’s assume that you’re like me. You might like what you’re doing now, but you want to remain open to future possibilities that life might sling your way. If tomorrow brings some unforeseen opportunity, you want to be able to seize it.

If anything, my life has been an exercise in extending the opportunity window. In fact, my entire life has been lived in the opportunity window. I’ve never had an opportunity that I haven’t been able to take advantage of. Some examples:

  • In May of 1999 I didn’t know the first thing about gambling. I’d never played a single hand of any casino game, and certainly hadn’t made a dollar from it. A year later I started a gambling enterprise that funded my life for the next seven years.
  • In the summer of 2003 I was as clueless and shy as any other single guy. I had no idea it was possible to get better with women, and had no real prospects. One year later I was teaching pickup with Mystery, the world’s greatest pickup artist.
  • In 2007 I was sitting in a restaurant when the idea of becoming a nomad popped into my head. Six months later I was traveling around the world with just the possessions in my backpack.

Many people tell me I’m lucky, and they’re absolutely right. I’ve been incredibly lucky. The easiest way to be lucky is to enable yourself to take advantage of any opportunity that presents itself. I’ve been able to do this by living in my Opportunity Window.

I didn’t live in Project Hollywood with the rest of the Pick Up Artists because I was a good pickup artist or had amazing foresight. The invitation was extended to everyone on a forum called Mystery’s Lounge. I was probably the WORST pick up artist on the entire forum. But I was in a position where I could drop everything and move to Hollywood. So I did.

So how do you maximize your Opportunity Window? Well…

Don’t Do Things That Aren’t Awesome

Derek Sivers summed this up very well in a recent post. This sounds easy and obvious, but it’s actually pretty hard. It requires you to be able to make hard decisions like turning down a boring but high paying job, even with no other prospects in sight. Most people would tell you that’s a stupid decision. I disagree know how it feels, by the way. When I left my one real job ever, I was giving up a significant paycheck with no idea of what I’d do next. Technically I was fired, but I tried to quit a month before.

Want to meet the girl of your dreams? Don’t date a girl you’re halfway happy with. Mystery likes to say “The enemy of the best is the good.” So true.

Save Your Money

It would be nice to live in a fantasy world where money doesn’t matter, but the bottom line is that you need to be able to feed yourself.

Money is freedom, both having it and spending it wisely. The quality of your life can be measured more accurately by what you DO than by what you CONSUME. Buy the most precious commodity in the world with your money: time. Twenty thousand dollars is a new car OR most of a year of DOING what you want to do.

I was once trying to convince someone to save her money instead of wasting it on (more) clothes. She told me she wasn’t saving up for anything. I say that money saved is money invested in freedom.

Spend Your Money

If you have saved up $50k, be ready to invest it in yourself. Want to start a business? Live frugally off your savings while you build your business. At the same time, respect your money. If you’re living off your savings, you’d better be making it count. Buy necessities and work hard.

I know people who have saved money, but won’t leave their jobs to start the business they dream of. What’s the point of saving the money if you won’t invest it in yourself?

Stop Caring What Everyone Thinks

There is tremendous pressure put on us by family ,friends, society, etc. to “be responsible'”. Unfortunately, they define being responsible as getting a job and spending all the money you earn on useless crap. If you care what other people think, and try to satisfy them, your Opportunity Window will be tiny.

Build Something

When I quit gambling because my entire life savings was confiscated in one day, I learned a valuable lesson: build something. Build a business. Build a community. Build a reputation. When you work, let it be for something that will pay dividends, financial or social, after you quit.

When you quit a job, you have nothing. When I quit gambling I had nothing. My book doesn’t make me a ton of money, but it pays me every month. Some of the readers I write for will be a part of my life until I (or they) die.

Condition Yourself to Let Things Go

Some people ARE in an Opportunity Window, but they talk themselves out of it. Your desires should trump your abilities when you make decisions. Desire creates motivation, motivation creates hard work, and hard work creates success.

You live once. Use everything you have, mentally and financially, to create the life that you want. Just because something is scary, like dropping out of school, doesn’t mean that it’s a bad idea.

You don’t have to be who you were yesterday. Just because you were a lawyer doesn’t mean that you can’t be a rock singer in the future. Just because you were a stay at home wife yesterday doesn’t mean that you can’t be an artist tomorrow. When you can define yourself in a word, you’re in trouble.

I can’t tell you how many times I’ve caught myself imagining limitations on myself that don’t exist. Maybe you do it too.

Follow Your Curiosity

Keep an open mind. Listen to new ideas. Stare into space and imagine different paths that your life could take. There’s no point in being in your Opportunity Window if you aren’t looking for the opportunities.

Being curious about something is enough of a reason to check it out. I don’t know if life is supposed to be an adventure, but I know that it CAN be. I also know that it’s possible to limit yourself and have a boring life. I’ve seen both.

Trust Yourself

Trust yourself to figure things out. You’ve gotten yourself through life so far. You’ve made billions of decisions and none of them have been catastrophic. Don’t be scared to push yourself and live out of your comfort zone. Just like everyone else, you’re probably capable of a lot more than you think.

Make Sure that Your Attachments are Important

I would never get a dog. I like dogs, but the limits it would put on my life would be too extreme. I would have to be home frequently to feed it. I would have to live in a house or apartment that could accommodate the thing. If I wanted to travel I’d have to find someone to take care of the dog.

I’m not saying not to get a dog – I’m saying to consider what you give up by getting one. The same goes for girlfriends, children, houses, cars, jobs, or just about anything. If you’re going to have an attachment, make sure that you know what you’re giving up by taking it, and make sure that it’s worth it to you.

One overlooked attachment is the habit of collecting stuff. People make a whole lot of decisions based on how much stuff they have. TVs, DVD collections, computers, art, etc. You might be surprised how happy you’d be with very little stuff, and you’d certainly be amazed at the freedom getting rid of it gives you.

I don’t know a ton of people who have gotten rid of their possessions, but none of them have ever gone back.

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