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becoming strategic

I've played chess off-and-on since I can remember, but I've never been very good, and a lot of my life reflects that problem -- but to achieve something real and meaningful, I've got to change that trend.

It's tough. When you haven't been a long-view thinker for most of your life, there are some seriously entrenched habits that must be changed. Luckily, it's like Oliver Wendell Holmes said, "Man's mind, once stretched by a new idea, never regains its original dimension."

That's absolutely true: Once  you start to think strategically about things, it's addictive. The difference in results is so profound that you find you almost don't want to think any other way.

Demolishing a Game

A great illustration of this is the very first night I read seriously on strategy and strategic thinking. I've forgotten the specific website -- something about life lessons from chess -- but that's less important, because there are many sites with this kind of information. What was rare and valuable about the learning is my immediate results.

I routinely play a simple game on my phone for brain-clearing. Like most games, there are increasingly-difficult levels, and usually a level takes several days or weeks to master, when played occasionally. Immediately after gaining an understanding of strategy, though, I flipped over to my game and quickly shot through three levels, including one that had already consumed two days.

The difference had to do mostly with thinking through scenarios in advance. It wasn't something I was trying to do; it just made good sense based on what I'd been reading. My game play was slightly slower, but my overall win rate was much higher. It seems obvious when I say it, but you really have to experience it.

Developing a Plan

 For about six months, I've vacillated between my three primary skills: writing, coding, and sewing. Which one should I highlight? Why don't I just divide up my time and do them all? Can I do each one for a little while and then switch?

Once I started thinking strategically, though, it quickly became obvious I couldn't do them all. As I drilled down into them, I observed a few useful things:

  • Coding brings in more money as a day job, but far less money as a craft, and if you're getting great sales, you have huge support and maintenance headaches. You'd better develop a really great app to begin with, because as a solo inventor, you're going to be pretty much tied to that one app for a long time. And there are lots of would-be killer apps, and the programmers behind them, competing for space in a non-linear selling format called an "app store."
  • Writing is something I'm good at, in the sense of stringing words together, but I'm much better with non-fiction than fiction. Yes, I have some killer ideas, and I might pursue them, but I don't have a lot of experience, and writing is a very crowded profession. 
  • Sewing is place where you can excel, but volume is where you can fall short quickly. How many items can you produce in a week? A month? A year? How much can you reasonably charge for those items each? Can you get the volume up enough to make money?
Eventually, I figured out that sewing -- or rather, crafting -- is a less-crowded marketplace, especially if you're doing custom, specialty pieces. Your income is influenced more by your own throughput than in writing or coding.

Strategic Constraints and Goals


Keeping my exact plans private, my biggest problem achieving my goals is earning significantly more money. This particular issue is where I always got hung up before. How can I bootstrap a business and earn money? How should I set my goals? What kind of growth possibilities should I consider? Things all fell into place when I acknowledged that multiple outcomes were possible.

Suddenly, I'm quickly staging four or five options over a longer time span; I'm researching product life cycles and typical revenue curves, experience data, and historical results from similar situations. In less than four hours, I have a plan with five possible paths, associated revenue projections, and a deep realization that I might be able to keep up with demand for 6 or 7 months if my marketing is any good at all.

What should I do when demand exceeds my ability to deliver? Hire someone? Change products? Raise prices? Work faster, or quit my day job? The old me (the tactical me) would have felt compelled to answer all of these questions now, with one, perfect answer. The strategic me answered some of them with a series of possible outcomes, and left others until I have more experience data.

What's the most strategic thing I can do right now?


What really changed my thinking, though, is this one question: What is the most strategic thing I can do right now? Asking this question over just two days has pushed me to do all kinds of things I just wasn't motivated to do before:

  • Apply for a different job that isn't a perfect fit, because I realized that there were more useful outcomes than just getting the job (like getting back in the market, and updating my resume, and possibly even having some more interview experience).
  • Clean up and de-clutter my studio, so that working is more of a pleasure and less like being trapped in the corner of a warehouse.
  • Evaluate a new sewing method I'd been considering. I quickly determined it wouldn't work, but I know why it won't work, and what to do about it, including buying a new pattern and adding some contrast material to a major project.
  • Have better conversations with my spouse, including a much easier dinner-out decision.
  • Talk myself down from the snack machine more than once, and starting to eat more healthy.
  • Make a clear decision on paper versus electronic; this was hard for my tactical mind, but simple strategically: My only connection to the Internet comes through my phone, which is also my most-used and carried device. I can back up my electronic files all I want, but if the phone goes out, they're hard to get to -- so they really aren't backups. Paper it is.
  • About a half-dozen other decisions, but I don't want to list them here.
There's no magic to it. There's no universal principle that can be stated in 10 words or less, just a personal determination to think more strategically.

And I'm instantly better at chess, too.

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