Here's an issue that keeps coming up both at work and a few side projects I've been working on (including this blog).  When making any kind of decisions, you have to do everything you can to make sure that decision will still make sense a month or a year from now.

The Old Way

Unfortunately, I think the most intuitive way to try to make decisions that stand the test of time is often the worst way.  At first glance, it seems like the way to future-proof decisions is to figure out exactly how you expect things to play out.  If you can predict the future, it's easy to make sure you're doing your best to prepare for it.

The problem is that no one can predict the future so people end up coming up with plans based on false assumptions.  That's a pretty easy way to ensure that your decisions will look incredibly stupid when you look back on them.

I can't count the number of times I've sat in a meeting discussing exactly how the plan will work.  I've spent hours figuring out the exact order we'll build new features, exactly how we'll get new features to market and how we can expect our user base to be affected.  Months later you're sitting around trying to figure out the source of problems.  Most problems can be traced back to a bad decision that was made months ago.

The thing is, I'm not an idiot, and I don't work with idiots.  The decisions are good.  It's the assumptions that drove the decisions that are to blame.

The New Way

For the past couple of months, I've tried taking a new approach.  I don't ever try to figure out what will happen.  Instead I try to figure out everything that might happen and I make sure that I can handle any senario I can dream up.  The key to this is constantly re-evaluating everything I do.

This is harder than it sounds.  When you just spent a week developing something, it's really difficult to look at it and realize that everything you did was misguided.  It's natural to defend past decisions if at all possible both because it really sucks admitting that you just wasted a week of your time, but also because it means you were wrong at some point.

Here's an example.  I don't think that it really makes sense to have a blog with no real name or URL or anything like that.  There's a branding problem with this blog.  The reason I haven't fixed this problem yet is that I have no idea how this site will play out.  Maybe tylerking.net should only be a blog.  Maybe I'll develop a love of gardening and decide to write exclusively about that.  If I made a decision now, it would end up being based on some kind of assumption.  That's why I'm just writing content and assuming that the role of this blog will slowly take shape.

Prepare, Don't Plan

To summarize, I'm not advocating acting without any regard for the future.  I'm just saying that it's arrogant to think you know what will happen.  The best you can do is make sure that whatever you do today doesn't close off any possibilities for tomorrow.  Do that every day, and you'll never back yourself into a corner.