Planning to Fail

Everyone has a plan until they get punched in the face — Mike Tyson.

I didn’t get punched in the face this week, but I failed to account for travel in my writing plans and thus derailed my delivery schedule...which felt like getting punched in the face. Obviously, this sort of thing happens all the time. But as it's top of mind, I decided to tack from my planned writing and briefly reflect on this situation.

I expected to get more done than I did while I was in San Francisco last week. Outside of the possibility that this was a time or scope problem, I figured I'd carve out time in the morning before meetings to get my most important work done or that I'd get to do it on my flight back. Ha! Compounding lack of sleep has a comic way of dissolving your ability to focus.

I even knew that this particular week I’d be spending my time in San Francisco — jumping around the city, engaging in conversations, and staying up late. However, I now sit here Sunday morning sitting at SFO realizing that I have a commitment to ship words and that the two pieces I’m simmering on need more time to stew. Or, at the very least, they need a set of sleep supported eyes to pull together. Now, I have to write something else (this piece) if I want to ship.

Off we go.

This got me thinking about routines. See, when you operate in isolation ("complete environmental control"), things are pretty easy. You get up, do the work, repeat. Introduce some complexity thought? Things quickly spiral out of control. Whether it's travel, people visiting, opting for spontaneity or dealing with emergencies, there are always things that come up that we should factor in.

Travel is perhaps the most prominent example because you're extracted from almost all of your scripts. The environment that supports your habits and routines is no longer there and you're left to operate on will power & discipline (which you don't really want rely on). That's where some simple planning can come into play. You can explore the various options for restaurants that support whatever constraints you have. You can check to see if there's a hotel gym. If not, better bring your running shoes. Busy days? Better plan your most important work in the morning before you start reacting.

Alternatively, you can choose not to do these things during this time. This is how I'm approaching my upcoming trip to Thailand. Instead of focusing on maintaining systems and order, I've intentionally blocked off the time to not do these things. Feels weird planning to not do, but having accounted for it in the plan I can go into it and be completely present. All I need to do is ensure that I'm communicating that this is what I'm doing to those who are expecting to hear from me.

Either way, as I'm reflecting on the past week (which was fantastic) I'm also recognizing the value of stress testing these systems in a more controlled manner. You may have a great exercise routine or fortitude to avoid drinking alcohol, but what happens when you get thrown into new environments or toss in some new variables outside of your control? Shit gets messy quickly.

I've found this exercise valuable because it's another feedback loop. By introducing some controlled complexity, you can poke holes in your routines and identify the areas you need to improve and come up with a plan to fix these things — without everything going to shit.

Of course, it won't feel good to do this. But putting yourself into these situations, recognizing where your systems fall apart, and then iterating is a massively important skill you have to develop.

So, dear friend, plan to fail and introduce some complexity into your life to see where you need support. Now for whatever reason, my sleep-deprived morning mind connected conceptually to the Mike Tyson quote, so I'm sticking with it.

Here's to getting punched in the face, testing your systems, and always improving.


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For further exploration of this idea, consume Ultraworking's Encounter Rate, Win-Loss Rate podcast episode.