How to climb a mountain
I spent a lot of my childhood scrambling up and down mountains. When I discovered this metaphor at 13 years old it resonated for me – and still does today. The idea is that you need to get to the top of a mountain, and there are two different ways to do so.
Two different approaches
You can plot, and plan, and spend months studying a challenge. You can walk the circumference of your mountain. Study it from every angle, consider potential routes, and plan your ascent. And then you take a single trip up the mountain – and hopefully succeed.
Or you can do the opposite, and study your mountain while attempting to climb it.
You’ll almost certainly fail. You might even fall down. But every day, you get back up and throw your full capacity against the challenge until you might eventually succeed.
Both of these approaches are valid. There isn’t one correct approach to tackling a challenge.
My real estate “mountain”
I’ve just completed eight weeks of intensive study of real estate. I’ve never learned so much in such a short period of time in my life before!
Last week, my girlfriend and I backed out of escrow. While I’m still waiting to get my deposit back, we’ve emerged largely unscathed.
This article isn’t an argument for throwing yourself at a problem, and learning on the way. It is an articulation of these two choices, and why I tend to operate the way I do.
The dangers of overthinking
I’m very susceptible to analysis paralysis. I’ll come up with two opposing perspectives and get stuck between them. To avoid this indecision, I’ve learned to take action by default. I throw myself at a problem and trust my ability to learn on the fly.
In real estate, this meant finding a property we were interested in, learning enough to put an offer on the house, and then sprinting to learn everything I needed to know to make an informed decision.
The downsides of haste
When you’re climbing a mountain that’s too difficult for you, you’re more likely to get injured.
When I throw myself at a problem, I’m more likely to make mistakes or offend people than if I’d spent months or years studying the subject. I can be less prepared than I might like, even when preparation is a winning advantage!
At the end of our real estate sprint, my girlfriend and I are both exhausted. The only arguments we’ve ever had have been about real estate.
The benefits of speed
But the advantage of quick, decisive action is also significant.
We attempted something that neither of us would have otherwise considered. We didn’t get stuck in indecision; we took decisive action.
And, fortunately, backed out before we found ourselves in a difficult situation.
Finding your way up the mountain
The two different ways to navigate a challenge are a choice between preparation and speed.
There isn’t one correct balance of preparation versus speed—only the balance that best suits you.
I’m more likely to charge headlong into a challenge. Here’s how to assess what’s best for yourself:
Assess your default
Reflect on whether you gravitate toward preparation or more immediate action. If you usually plan carefully, try taking small risks. If you tend toward immediate action, try pausing occasionally to strategize.
Reflect and Iterate
After completing a big project, reflect on what worked and what didn’t. Which approach did you use, and how effective was it?
Through every challenge, we have a choice for how to tackle something difficult. Ultimately, it’s nobody’s responsibility but your own to decide how you’d like to tackle your next big mountain.
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3 things I’ve loved this week
Quote I’m considering:
“There are mountains beyond mountains.” – Haitian proverb
I first read this through the writings of Paul Farmer, a medical doctor who devoted his life to help the Haitian poor. The quote is intended to remind us that there are challenges beyond those we can see.
Standing desk I love:
Quik Lok laptop stand
I’m often working on the go – taking Zoom calls or answering emails while in transit. Years ago, I cobbled together a standing laptop deck, composed of a music stand and a camera tripod. It still works, but ten years later it is a bit unstable.
During our real estate journey, I saw a home inspector with this sturdy Quik Lok laptop stand. You can even lock your laptop in place.
Quik Lok started by making DJ equipment, and several of their products work well as sturdy laptop stands.
Manifesto I’m revisiting:
Responsive.org Manifesto
As I’m gearing up for Responsive Conference 2025, I re-read the Responsive.org Manifesto. Written in 2015, it feels even more relevant ten years later.
If you spend any time working – and we all do – it is worth reading.
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Until next week,
Robin
