Because it is a complex system, most of life is a choice between differing errors.

Because it is a complex system, most of life is a choice between differing errors. So rather than trying to be on time and ending up accidentally early or late, it is better to make leading or lagging a specific choice.

I love surfing. It is relaxing to be in the water and when you catch a good wave, you’re actually flying. But like boxing (my other favorite sport), surfing is about timing. If you go too early, the wave crests on top of you; if you’re too late, you miss the momentum and bob over the top. To surf, you have to be close enough to the right time to balance the two forces.

Fortunately, you can intervene. If you’re slightly too early, you can cut along the wave to bleed off momentum and prevent crashing out; if you’re slightly too late, you can pump a little to generate speed. In reality, you’re always doing one of these, because you’ll never be perfectly on time.

So good surfers make an explicit choice of errors. Rather than trying to be perfect, they acknowledge the reality of imperfect timing and make a strategic decision to either cut or pump based on the reality of the situation. And the earlier they recognize early versus late and make an adjustment, the better they surf.

While recording Jez Groom’s episode of An N of 1, he mentioned that his weakness in the workplace was giving people responsibility too early on. I remember because it resonated: I’ve often been guilty of the same thing, reasoning that it was better to frustrate someone by forcing the pace of their growth than by holding them back.

But by choosing in advance a specific early/late strategy, Jez and I can put in place safeguards to adjust for the limitation. Consciously giving people too much responsibility means also building a safety net for when it doesn’t work out; giving them not enough responsibility means also creating innovation forums for them to channel their additional energy into.

Microsoft is a great example of doing this well (and really, really badly). As was pointed out to me when I joined, MSFT has never been first to anything. It wasn’t the first mainstream GUI (Apple), first-party premium laptop (MacBook), productivity suite (WordPerfect), search (Google), cloud (AWS), modern console (PlayStation)…the list goes on. And yet it has achieved significant ($billion+) market share in each of those verticals by getting great at being late. Ride the tail of the wave, pump your way to the mid, call it a day.

But, of course, even the best surfers have bad rides, especially when they try to switch strategies. Microsoft tried to be early to AI and while the day isn’t done, that is likely to have been a waste in retrospect. There are other failed attempts to be early (Zune Music Pass? Microsoft Band?), which feels inevitable when a company with a fantastic playbook for one thing tries to do something completely different.

Don’t make the same mistake. Be deliberate, choose your error, and then hedge your way to the right place on the wave.