How to Plan for Uncertainty

Hi everyone!

It’s finally December in a year that has brought us some major surprises. With 2020 wrapping up, it’s hard to predict what 2021 will look like. Will it feel a lot like 2020? Or will everyone commit to wearing masks — as those on the frontlines plead for — to start getting a handle on COVID-19? As always, the future offers more questions than answers.

Here’s the latest.

Today’s dispatch comes to us from Betsy Rowbottom, Director of Business Development.

I read an article recently about ‘how to plan for uncertainty’. The writer talked about how Kodak was shoring their bets by investing in digital photography. Did I mention the article was about 25 years old? Spoiler alert: it didn’t work out great for Kodak. For the technology they invented in 1975, they misjudged the opportunity. Wildly. Kodak is now a cautionary tale that big CEOs tell little CEOs as ghost stories (because Kodak is dead).

As we plan for 2021, we again face tremendous uncertainty. Leaders are being tasked with deciding whether to bet big, hedge, or wait and see. Earlier in 2020, some business leaders hedged their bets with what worked in the past with only slight tweaks. Other leaders used the world’s pandemic “Pause” button to bet big. They used 2020 to recraft and retool, with the intention of launching their new inventions when the world presses “Play” again. It’s only in retrospect that we know if our bets paid off. Is there ever a good time to take a risk?

Last week, we lost one of the world’s biggest risk-takers, Tony Hsieh. I met Hsieh in 2014 while I was pitching my business to Zappos. I flew to Las Vegas to meet their team and from the moment I entered their HQ, I felt all the feels of “Delivering Happiness”, the book that Hsieh wrote 10+ years ago and the company motto that he worked tirelessly to create. After I arrived straight from the airport with my carry-on in tow, the warm and bubbly receptionist sprang from behind a large desk to assist me and offered to check my bag in a storage room. It was clear to me within 20 seconds of entering the Zappos office that ‘Delivering Happiness’ didn’t begin in a shoebox. The company’s motto lived everywhere. And their brand promise was demonstrated in places that most companies don’t measure or evaluate. The entire Zappos team was welcoming and transparent. Nothing felt secret or off-limits. Even the “F” word wasn’t off-limits (fun) in the workplace. In an endless row of cubicles, each decorated to reflect the individual who spent 8+ hours inhabiting it. Each Zappos team member was empowered to solve their customer’s problem; the place felt truly revolutionary.

All leaders face instability. There’s never a perfect moment to take a big risk. It’s true, 2021 feels especially uncertain but we’ve navigated this rocky climate for the past 10 months. For many, 2020 will be remembered as a pivot year when innovative products and services were born.

Hsieh will be remembered for his contribution to inspire future leaders to intentionally shape their company cultures. I will remember him as a man who embraced uncertainty and won big. Not because he sold an online shoe company to Amazon for $1.2 billion, a big payday that any American would be proud of. I will always remember him as a man who charted his own course. Tony Hsieh built Zappos by embracing uncertainty. And he had fun, too.