As I’ve absorbed information related to various strategies for escaping the mundanity of the corporate world over the past few months, I’ve recognized a few patterns and tendencies. One of the most disturbing is advice relating to obtaining sufficiency. It strikes me that the conventional wisdom is to steadily build a business until the income equals the income you need to pay our bills, then quit your job and you’re off to the races. This seems to be especially popular among writers. That advice sounds reasonable. It’s not sexy, but it’s reasonable. I don’t like it. I hate it. I don’t want sufficiency. I don’t want freedom from an office just so I can work from inside my boat all day. I don’t want location independence, I want the absolute independence to do whatever I want whenever I want. Period. Forgetting average advice, ignoring the goal of mediocrity, and thinking on a grander scale is the only way to get there unless you’re playing the lottery or waiting for Uncle Moneybags to kick-off.

It reminds me of the conventional wisdom in baseball that home runs are too much show… that home runs aren’t important because it’s ultimately the higher percentage base hits that win games. When I played baseball as a kid, I hated when coaches launched into that spiel. I probably amassed five zillion base hits from tee-ball to high school ball. Here’s the thing… I remember only a few base hits. I only remember the ones I remember because they hit the wall and I was mad that I didn’t hit them a little better. Still, I don’t even remember each of the hits that glanced off the wall. I don’t remember the runs that scored because of them. What I do remember clearly is every home run I ever hit. I remember the one inside-the-park home run and I remember the whopping three home runs that cleared the fence. I’m relatively certain I could point out the dents in the ground to this day.

Indians - 22 Yankees - 4

Some years after my baseball career came to a lackluster finish, I began trading online. Curiously, the home run analogy pops up in financial trading. Like everyone else, I went into trading with one assumption, “buy low, sell high”. If you are trading or investing, erase that phrase from your mind now. Never bring it up again. It turns out that this is a great strategy to lose large sums of money in financial markets. More accurately, it’s a great strategy to give your money away to the other people who know it’s total bullshit.

The real axiom for being successful in financial markets is coming up in a second. I’d grab a Post-It note or something and a fat Sharpie pen and write it down. It’s not really so hard to remember, but it’s powerful. The key to making money trading is, “Cut your losses short. Let your profits run”. The problem with “buy low, sell high” is that it doesn’t account for the inevitability that certain positions are losers now and they’ll still be losers the day you die. “Buy low, sell high” is the ride Enron to the ground and ruin your financial future strategy. It relies on the “what goes up must come down” assumption. Guess what? Lead doesn’t bounce, neither did Enron… or countless others. Cut your losses short by determining a risk threshold and liquidate when your position hits it.

Where I get excited is the upside of the equation. What does the ‘high’ in “sell high” mean? It sounds nice, but it’s not specific enough to be useful. Letting your profits run is a different story. When you get a hit, ride it as far as possible. Selling at a point just high enough to make a profit isn’t good enough. That would be the base hit strategy. The advantage is that home runs in trading aren’t limited to four runs. A home run yields exponential profits rather than incremental profits. A base hit might cover your trading for a day, a home run could cover your grandchildrens’ tuition.

Grandiose analogies and comparisons are nice, but what’s the point if we’re talking about writing or freelancing as a designer or developer? If you’re a writer, is your goal to write articles on a per word basis, per page basis, per article basis? Is your goal to write a $49 eBook? All of these things are geared toward mediocrity. Yes, there are exceptional examples of success, but these are still base hit strategies. In the year that you spent writing 200 blog posts equaling about 300 pages of work and a 50 page eBook to make $60,000, could you have instead written a 120 page screen play and sold it for $1,300,000? I don’t doubt that you could have written it, but selling it isn’t easy. It isn’t easy, but if you put as much time into honing the craft and contacting industry people as you do on Google Reader and Twitter promoting your blog, your chances would be better than you think. How about selling the idea for a TV show for $400,000? People have gotten away with that in TV without even writing the damned thing.

If you’re a designer or a developer, are you accepting every job that comes across your plate that pencils out at $20 or $50 or $100 an hour? In the time it took you to build/design 20 websites at $3000 a pop, or 2 websites for $30,000 each, could you have been analyzing the web for needed services and building a website/service you could flip for $170,000,000?

I realize that reality sometimes prevents taking a year off to focus all time on a single piece of work. That’s no excuse to delay working on your home run idea. If you’re working on a bunch of small stuff without working on the big idea, you’re on the road to mediocrity. I’m onto you.

Base hit strategies feel safe. I don’t know why that is. Thinking about being required to hit a base hit every day for the rest of my life terrifies me.