It’s OK to be pragmatic (with a little help from the “crazy ones”)


Being pragmatic is engrained in me. I’m at my best being practical and boring.

Here’s the problem — experience has taught me that you’ll never do your best work through sheer pragmatism alone.

While I’m good at weighing options and making decisions, I’m not that visionary who can conceptualize grand ideas.

While planning comes very naturally to me, I find it difficult to inspire others.

And though I’m good at shipping, I often do so using following established conventions.

So while the incremental, risk-averse nature of being pragmatic can be good for many aspects day to day of work, it’s not everything.

What you’re good at and what’s good for you aren’t always the same thing.

To make long-term, deep progress in your professional growth, you need to think big sometimes.

You need to try things that don’t have predictable outcomes. You need ideas and ways of thinking that inspire innovation. You need to stretch way beyond your comfort zone.

But as a pragmatist, how can you do all this when it’s so foreign to you?


Surround yourself with the “crazy ones”

The idea of the “crazy ones” may be Apple’s, but that kind of creativity, inspiration and genius is all around you.

Look for opportunities to work with people who are the opposite of you — the dreamers, big thinkers, and contrarians.

These will be the people who will push you toward bigger and better things.

Yes, it’s going to be very hard and uncomfortable for you. You’re going to feel like you’re on a bizarro planet where everything is backwards and nobody thinks like you.

This is a good thing.

Having people challenge your baby-steps thinking with big-leaps thinking is a good thing.

Not understanding what the hell one of your colleagues is thinking (at first) is a good thing.

Having healthy discourse around big ideas is a good thing.

And shaking hands and finding compromise is a great thing.

Their thinking will seem crazy and executing their ideas will seem impossible. But in end you’ll pull it off — not in spite of you, but because of you.

You’ll be better in every way because you stretched well outside your comfort zone. And really, what’s more rewarding for a pragmatist than shipping something you didn’t think was possible? 🤘


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I was lucky enough to work with some of the crazy ones on Basecamp 3— especially Jamie Dihiansan, the designer of the Basecamp 3 Android app. Check out what happens when you get a happy mix of pragmatism and crazy!


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