Editor’s Note: This post was originally published on Seattle 2.0, and imported to GeekWire as part of our acquisition of Seattle 2.0 and its archival content. For more background, see this post.

By David Aronchick

Business is all about making mistakes. We all do our best to predict what’s coming next. But the fact is, you’re never going to get it right the first time around; if you actually catch an error when you can still course correct and save your business, consider yourself lucky. If you did nothing else every day, spending a few minutes figuring out what’s going wrong with your business, you’d be ahead of 90% of the other folks out there.

In fact, it’s so unlikely to avoid making the mistake before you make it, you should really optimize for the after effects. Your server crashes because you’re getting to much traffic? Ok, buy some more machines and apologize. You screwed up a sale because the contracts were focused on the wrong deliverable? Tough break, get a case study out of it and move on. The business gets a black eye because the best reviewer in the field had a terrible experience? Tough one, write them a letter and tell them how you’ll address their concerns, and beg them to review it again when you do. In each case, your best bet is just to take an honest look at the situation, evaluate what’s happened, and do your best to see it coming next time and (for real experts only) don’t make it again.

It is ironic then that the second time around people will make some of the biggest mistakes themselves. In fact, when you take on your next project, whatever it might be, the WORST thing you can do is spend a ridiculous amount of time and energy trying not to make the mistakes you made the first time around. I’ve heard so many stories about people doing this to themselves, it’s almost impossible to choose the best example. Engineering, marketing, sales, finance – no discipline is immune.

Second System Syndrome (SSS) – as defined by Fred Brooks in the wonderful and seminal Mythical Man Month – is the failure of a team to over engineer to avoid the mistakes you made the first time around. While Wikipedia and others focus on the second version of a product (see Rewriting Considered Harmful for an extensive and interesting analysis of this problem), the problem is not just restricted to the technical world; SSS is absolutely something that happens at a company-wide level, where enormous effort is made to solve problems that have yet to happen, and said effort is usually a perfect fit to solving some catastrophic error in the planner’s past work experience.

It’s like Yoga Berra said – “Predictions are hard, especially about the future.” What happens is that people get so burned the first time around, they never want to have something horrible happen to them again. But the fact is you never know – I don’t care how irritating and painful it was the first time around, you really can’t be sure it’s going to happen again. Yes, you may avoid the mistake you ran into last time, but you have every likelihood of wasting so much time on a problem that will never happen that you end up in a deeper hole than if you had just waited for the mistake to happen in the first place.

And, for those that think this is an engineering only issue, look hard and fast at your own priorities and tasks, and make sure you’re focusing on what’s next. Here are some examples:

  • Hiring – Yes, you were understaffed in your last job – EVERYONE is understaffed, overhiring helps no one.
  • Sales – Sales ALWAYS takes too long, especially with large organizations – that doesn’t mean you should be starting conversations before you have something to bring to the table.
  • Marketing – Getting traction in the press takes forever, but overselling the promise of your product or company will be a mess.
  • Finances – Doing daily tracking on expenses is a pain but don’t jump to that point where you stop tracking the sub $100 – every penny counts.
  • Technology – Building too big, too robust, for too many users – you don’t have them, don’t build for them.

The experience someone gets from building a business is worth its weight in gold, and absolutely makes someone a better leader/employee. However, the history must be tempered – the most experienced folks can also be the most vulnerable to spending countless cycles working on something you are absolutely never going to need.

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