The curse of the arrogant optimist

What famous corporate failures have in common

Hey there —

Are you a glass half full or half empty kind of person? 🥃

This is often the question we use to conceptualize optimism — and it's one that can ultimately define how successful we are in life.

Because to be optimistic means to have hope and confidence in a future outcome. Without it, why would we ever try to do anything?

🤝 You wouldn’t apply for that job, if you didn’t believe there was a small chance you might get it.

💑 You wouldn’t ask that person out, if you knew for sure they’d reject you.

🏆 You wouldn’t start that business, if there wasn’t at least some potential for it to be successful.

Optimism is that glowing light at the end of the tunnel that edges us out of our comfort zone and keeps us going when things get tough.

But is it ever possible to be too confident that things will work out in your favor?

You only need to look at the failures of BlackBerry, Blockbuster, and Kodak to get your answer.

Each of these once-dominant companies barreled headfirst into obscurity, all because of their arrogant optimism.

Despite having developed the technology behind the digital camera in the 1970s, Kodak spent decades insisting that film was superior, wasting years of opportunities to pivot and ultimately filing for bankruptcy in 2012.

High on the success of their smartphone keyboard and certain their business customers would beat out the consumer market, BlackBerry missed the touchscreen wave and went from controlling 20% of the global smartphone market to 0.0481%. (But who’s counting?)

When handed the opportunity to purchase Netflix for $50 million back in 2000, Blockbuster’s CEO practically laughed Netflix’s leadership team out of the boardroom. By 2014, crushed under a mountain of debt, the video chain that once boasted 9,000 locations shuttered all of its corporate stores, leaving just 50 franchise owners to fend for themselves. (Today, only “The Last Blockbuster” in Bend, Oregon, remains to fan the flames of our nostalgia.)

The problem in each of these examples? Leaders who were so arrogantly optimistic about their companies’ success that it made them delusional about their products’ ability to survive a changing market without having to change their strategy. They continued to pour water into the glass until it was overflowing, only to realize too late that they were captaining a sinking ship.

So, how do you cultivate a sense of hope that propels you forward, without turning into an arrogant optimist?

💪 In the early days of a new venture, attack your goals with the blind ambition and steadfast determination of someone who believes they can’t fail.

👀 But once you’ve got things off the ground, be prepared to take off your blinders and collect data on what’s working and what’s not. And act on that data!

↪️ Don’t be afraid to change course. Instead of seeing new ideas as a threat, look for the opportunity. Never get so comfortable in your success that you fail to keep experimenting and innovating.

🙆 Above all, be humble. It’s much better to admit you got it wrong and pivot quickly than risk a worse fate by doubling down in an attempt to avoid even the appearance of failure.

Keep these things in mind, and you’ll be much more likely to experience success. And if, despite your best efforts, things don’t work out as you’d hoped, remember that failure has something to teach you, if you think critically about why what you tried didn’t work. Using that information, you can refine your ideas and steer your ship in a different direction, armed with more experience than you had before.

Balance your abundant optimism with a healthy dose of realism, and it’s hard to lose. 💫

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Obsidian

Created by Shida Li & Erica Xu
ToolOrganization

Feel like you’re constantly consuming interesting self-development content (like this newsletter!) but lack the headspace to do anything with it?

It may be time to build a second brain.

Obsidian is a digital knowledge base that uses a local folder of markdown files (that’s fancy tech talk for notes) to store and organize all your insights and learnings.

And because creativity is rarely linear, it even has a handy graph view to help you form unexpected connections between everything you’re learning.

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