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Seeking Reassurance

7 min

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"The obsessive planner, essentially, is demanding certain reassurances from the future—but the future isn’t the sort of thing that can ever provide the reassurance he craves, for the obvious reason that it’s still in the future."
Oliver Burkeman

I'm good at planning.

And I'm bad at planning.

I have goals, short and long term. Goals become objectives, which become key results, which become day to day tasks.

So I set a vision, and that vision informs my quarters, which inform my weeks, which inform my days.

So I'm good at knowing what I want, and creating a plan to get there.

But when it comes to moment to moment?

When it comes to setting a plan for how I will actually move throughout the day?

I don't bother to plan very much at all.

I come in to the office and maybe I get "right to work" on the "most important thing to do" that day.

Or maybe I futz around with the things on my desk a bit. Or answer some email. Or check Slack, or Facebook, or Twitter.

Maybe my actual behavior follows the meticulously-crafted plan...

And maybe it doesn't.

I often set out to do one thing and end up doing another, pulled in the direction of something more interesting, something more urgent.

Some days, I just flat out don't feel like doing anything at all. Some days, I'm too sad. Or too in-my-own-head. Or too lazy.

So, I'm good at planning: I set the vision, and I break that vision down into clear milestones.

But I'm also bad at planning: I don't always do what I set out to do. My day-to-day productivity varies quite a bit.

And that is Okay.

Not only is it Okay; I think it's ideal.


Here's a thing we often forget:

We're all animals.

Biological organisms. Squishy.

Biological systems seek to maintain a certain range within which they are successful. The body, for example, doesn't maintain a specific temperature throughout the day; instead, it stays within a range of temperatures it deems OK, typically anywhere between 97 to 99 degrees.

It does this through a process known as homeostasis. If your temperature rises too much, a variety of system kick in to lower it (you start to sweat, you move less, etc). If these processes cause your temperature to drop too low, other processes kick in to raise your temperature.

If you put your temperature variations on a graph, you'd see a whole bunch of up-and-down. If you average those smaller changes together, you get a wave.

A graph of core body temperature throughout the day. (Source)

You see this same kind of pattern in COVID-19 cases. This is why we refer to periods of increased infection rates as "waves" - they rise, often precipitously, before gradually falling back down again.

Why? For a variety of reasons. But - say a particularly contagious variant infects a whole lot of people very quickly (and case numbers go up). The more successful it is at infecting people,  the fewer new, uninfected people it has to choose from, causing case numbers to drop back down again.

Nearly every biological system on earth, when graphed over a period of time, will exhibit some form of this "wave" pattern - upward trends accompanied by downward trends.

This is, in a very real way, what life looks like.

Contrast this with the world of machines, computers, mechanization, spreadsheets, time-tables, schedules, and plans.

A timetable for the Tokyo subway system. (Source)

In machine-world, variation is a problem to be solved. A given input should always result in an identical output.

In machine-world, constant progress is expected. All graphs should point upwards and diagonal to the right. Any dips result in angry demands for explanations and plans to correct course. "If you can't fix this, we'll kick you out and find someone who can."

In machine world, the plan dictates the implementation. What was predicted should be what occurs. If I click a button online, that button should perform its expected function in the exact same way every. single. time. If not, it's a "bug."


We like machines because they do what they're supposed to do. They're reliable, most of the time. That's why we feel so betrayed when a machine doesn't act the way we expect.

Ever notice how frustrated we get when something doesn't work the first time? How irritated it makes us when the cash register takes more than a few seconds to work?

We feel personally attacked. We have enough variability and unpredictability with other people, damn it! Machines are supposed to be reliable! Not just like every other lousy, good-for-nothing animal we have to interact with. "I swear, sometimes it's like this thing has a mind of it's own!"

The real reason we love technology so much is that, well...

We're anxious.

The world's a scary place. It never does what you expect. One day, you're living your life, making birthday plans, and the next...Boom. World-wide pandemic, or typhoon, or earthquake, or the stock market tanks, or your wife's been seeing someone else, or your kid falls off his scooter and breaks his wrist.

You never know what's going to happen, but something always does. Something always wrecks your plans, throws a wrench in the works, messes everything up. It's exhausting.

There's so much uncertainty in our lives that we'll do just about anything to lower it.

And that brings us back around to planning.

Planning is just one more way of trying to seek reassurances from the future.

If we can make a plan, we feel prepared. We've thought through the possibilities, made sure we're ready, made sure we have what we need and we know what to expect.

There're three problems with this:

For one, nothing ever goes as planned. As Mike Tyson famously said: "Everyone's got a plan until they get punched in the face." This world of ours is really, really good at punching people in the face.

Secondly, plans give us a false sense of security. We believe that because we've thought through what we believe might happen, we're prepared for anything that might happen. But our plans are always limited by our imaginations, and quite frankly, we aren't very imaginative when it comes to envisioning the future.

Our projected futures are usually slight variations on the present: we plan for what we might do if the stock market goes up, for example, or goes down....but not for what we'll do if the stock market implodes altogether.

Finally, when we plan we forget our animal natures, or biological selves. We expect consistency, we expect up-and-to-the-right-graphs, we expect identical outputs for each input.

But this only sets ourselves up for failure. We can't perform in a mechanistic way; not consistently. Because our expectations don't align with our natures, when we plan we set ourselves up for failure. No matter how motivated we are to achieve a certain goal, to expect mechanical perfection from a biological system is a recipe for disappointment, frustration, and disappointment.

So what do we do instead? How can we plan in such a way that we still achieve our goals, but don't make ourselves miserable in the process?

All I can tell you is what's worked for me:

I get very clear on the TYPE of results I want to create.

I know what matters to me, what I can't live without, and what I'm willing to work for.

I get clear on the intermediate steps towards those results.

I know what I'm working on each quarter - what I'm experimenting with, what I'm looking to get from that experience, and how I can tell if I'm succeeding or not.

And then?

I let go.

I might set goals for the week, but I don't plan my days.

If I'm tired and depressed, I let myself be tired and depressed, even if it means missing whatever targets I might have set for myself.

If I'm feeling particularly pulled towards a project or topic, I let myself be excited and explore, even if it's not what I'm "supposed" to be working on.

I let myself underperform, because I know that all biological systems display variability.

Of course you have off-days.

Of course, somedays you are absolutely on fire, while others, you can barely get out of bed.

All biological systems display variability, and you are a biological system.

You can appreciate your biological nature, appreciate your body's wisdom, show compassion towards your self, while also making steady progress towards your goals.

Here's the process:

Get very clear on the type of results you want to create.

Get very clear on the intermediate steps towards those results.

And then, let go.

You'll be surprised what you're capable of.




Coronavirus: Game Over.

Is the pandemic...ending?

This article argues that it is.

I've found myself thinking a lot about when, exactly, I should start "going back to normal." If COVID-19 is here to stay - and I believe that it is - does that mean we stay in metaphorical "lockdown mode" forever?

I don't have a great answer for this; the article above does a good job of laying out an argument in favor of gradually getting back to life-as-we-knew it. Incorporate this into your own risk-management thinking and act accordingly. :-)

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