Creative Wayfinding For Ambitious Optimists.

All the Downside, None of the Upside

September, 24, 2022

🧭 This blog post is adapted from my Creative Wayfinding Newsletter.

It’s been warm and humid here lately.

And without air conditioning in the apartment, we’ve come to map our daily routine to the arc of the sun.

We start our days with windows open and the fans on.

Around 10 am, we shut the windows and draw the thick curtains in our East-facing living room.

At 3:30 pm or so, my office, facing west shifts into range of the sun and I close both the window and wooden shutters to keep the room from quickly warming 10 degrees and becoming unbearable to work in.

This daily dance works, for the most part.

Apart from the hottest of days, the apartment remains entirely comfortable even without the aid of an AC unit.

At least until bedtime.

Despite opening all the windows and positioning the fans for maximal air flow through the apartment, it simply doesn’t cool off enough outside by 10 or 11 pm for the bedroom to reach a comfortable sleeping temperature (for me, ~18C).

If we left the windows open over night, the room would cool down fairly quickly, I suspect.

There are a couple of problems standing in the way of doing so, however.

For one, our bedroom windows open onto a fairly busy street, with a good amount of noise from both traffic and the bar across the street, Café Imperio.

Second, the bedroom windows are fitted with wooden shutters, which, while they do an exquisite job of blocking out the light from the street lamps immediately outside our second floor window… also do an admirable job of blocking any air flow, even if the windows are cracked.

The challenge was a formidable one: How to allow the air flow in while minimizing the light and street noise?

After a string of fitful, sweaty nights with the windows and shutters closed, I decided I needed to take it on.

And so, before getting into bed, I did my best to close the shutters far enough to block out the majority of light, while at the same time leaving the windows behind them open far enough to allow in a steady stream of cool air throughout the night.

And the noise? Well, that I’d just have to do my best to tune out.

The result of my effort was the worst night of sleep yet.

The reason became apparent when I groggily opened the shutters in the morning.

It turns out that in pushing the shutters closed far enough to even somewhat darken the room, the windows behind them had been closed to the point where there was no longer a gap through to the cool night air.

They were, however, open far enough to allow the street noise in. Plenty of it.

The result was a room that was significantly brighter and noisier, without any noticeable decrease in temperature.

Said differently, I’d managed to amplify both of the nuisances I was trying to mitigate while leaving my desired positive outcome unchanged.

It made me think of how we often do this to ourselves with our creative work and businesses.

We all have aspects of our work that we’d rather avoid.

Social media, email newsletters, prospecting, pitching and follow ups all come to mind immediately.

We know these tasks have potential positive benefits associated with them. But achieving them requires us to put up with some level of discomfort.

And so we do our best to mitigate the discomforts of the task at hand while still nominally completing it.

Maybe it’s a social strategy that’s entirely based on repurposed and reposted content, without any genuine interaction or originality.

Or maybe it’s a weekly newsletter that gets hastily written at 5 pm on Friday using the dregs of our creative energy.

Whatever the situation, the result is the same.

While we may manage to partially mitigate the discomfort and nuisance we were seeking to avoid, in the process, we completely suppress any chance of the positive outcome we were hoping to achieve.

As in my situation, leaving the window cracked has a way of leaving us with all of the downside and none of the up.

In some cases, the negative effects may extend beyond just our personal experience with the task.

We’re better off not writing a newsletter at all (and avoid the flood of unsubscribes), for example, than write an uninspired, uninteresting one, written and sent only because we know we’re supposed to email our list every week.

What we need to realize is that every upside comes inextricably entangled with one or more accompanying downsides.

Which means we have a choice to make.

Do we accept that in many cases, to get the thing we desire, we’ll have to put up with some things we don’t?

Or do we decide that maybe, the thing we wanted isn’t worth everything that comes along with it?

Either option is perfectly fine. But we should make the choice intentionally.

Open the window and accept the cool night breeze along with the street noise and light.

Or close it, and block it all out.

Just don’t leave it cracked.


Explore how to navigate a creative life that matters

This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”

It’s something I’m proud to create and I’d be honoured to share it with you.


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    Hi, I'm Jeremy, I'm glad you're here.

    No matter what you create, I'm guessing you spend a good amount of time feeling lost, hopeless, and unsure about how to get from where you are to where you want to be.

    So do I. And so does everyone doing creative work.

    This is the Creative Wilderness.

    Every week, I publish a new article in my Creative Wayfinding newsletter about how we as creators and marketers can navigate it with more clarity and confidence.

    If you're building something that matters, but aren't quite sure how to take the next step forward, I'd be honoured to have you join us.