Why I Always Carry a Raincoat

The day seems safe enough; A clear blue sky.  An easy path.  So you decide to go fast and light.

But the weather changes quickly in the mountains. The wind comes up, clouds race over the peaks, and before you know it you are in a downpour, miles from camp, with the temperature dropping quickly.

Hopefully, you get through with nothing worse than a little discomfort. But you will have learned a lesson you will never forget.  

I’ve certainly learned it. Which is why – even on a two-hour day hike – I’m the guy humping a first aid kit, an extra layer, a space blanket, a flashlight, and yes . . . a raincoat

I over-pack in my business life as well, since being in a startup is not so different than an expedition. Sometimes the path seems clear and the climate is favorable. So it’s tempting to want to move a bit faster by adding a few people. Invest in things that may take a bit longer to pay off. Raise a bit less money to minimize dilution.

But I’ve seen the business climate change without warning.  Customers freeze their spending. The VCs’ interest cools. Your new product is a few quarters later than you expected.

It’s right about then you wished you had that raincoat.

Don’t get me wrong. I’m still heading to the mountains. I’ll still take risks and move fast. But rather than assume I know what will happen, I’m going to be prepared for what could happen.  

 A little extra weight may seem like overkill at the time but as my climbing buddies and I used to tell each other: “Getting to the top is optional. Getting back down is mandatory.”

Many ideas in this post were first discussed in the Neverland entrepreneurial community. Join us there!

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