Beyond Optimism

On a mindset for doing hard things.

January 1, 2022 • 4 min read


We’re often called on to consider future events. While you may endeavour to be a realist – evaluating what may come based on the facts and odds – the future is inherently uncertain. Whether we like it or not, gut judgement drives a lot of how we anticipate and prepare for the future.

So faced with an uncertain future, how optimistic should we strive to be?

A balancing act

Much has been written about the benefits of optimism. Positive thinking is said to make us more resilient in the face of daily obstacles, and it takes a kind of audacious optimism to embark on and achieve anything truly difficult.

However, undue optimism – blind optimism – has caused many a shipwreck. Besides the literal shipwrecks, stubborn optimism has led countless leaders to ignore uncomfortable facts, minimize signals that things are off track, and bet everything on unwinnable gambits.

Read enough biographies and you’ll see a common pattern: flush with confidence from recent successes, our protagonist will ignore a massive problem until it’s too late. It could be a major industry shift, a big bet gone wrong, or the fact the product basically just doesn’t work and might not even be possible as described and has anybody noticed it’s feeling a bit fraudy in here?

So perhaps we don’t want to be too optimistic. Optimism gets things moving, but in high doses it can lead you off a cliff.

While a more pessimistic mindset can certainly protect you from the more spectacular types of failure, playing things too safely brings its own serious risks and pitfalls. Pessimists tend to operate conservatively, neglecting worthwhile opportunities. This can lead to problems festering that seem difficult but are in fact very solvable. A lack of optimism can put a damper on experimentation, and lead to a slower pace of learning overall.

Leading from pessimism is particularly challenging. “Follow me! There are probably terrible things in this cave. Mind flayers maybe, or god knows what else. Honestly, I’m skeptical of our odds. But we’re gonna prepare extensively. I shall make sure our defeat is, at least, slow.” It doesn’t really work. You gotta have a vision for how it’s all going to work out.

A paradox that isn’t

So you have this balancing act. Too optimistic, and you’re going to neglect important problems. Too pessimistic, and you’re going to stagnate where you are. When your focus is being drawn to some risk or problem, you may wonder: is this my pessimism getting me down, or is it realism saving me from going over a cliff?

A useful mindset for handling this is described in Jim Collins’ book Good To Great. The book has a few interesting mental models for leadership – I wrote a brief review of it on Goodreads – but I found its take on optimism and pessimism particularly useful. According to the book, great companies generally adopt the following mindset:

You must have the discipline to confront the most brutal facts of your current reality, whatever they might be. At the same time, you must maintain unwavering faith that you can and will prevail in the end, regardless of the difficulties.

Collins calls this a paradox, but I don’t see it as paradoxical. Challenging, yes, but still coherent. What better way to prevail in the end than to face the hard truths now?

There is no need to strike some universal balance of optimism vs. pessimism, or to attempt to reason through every unknown. Foster tenacious optimism about the long term; stay confident in your ability to overcome serious problems. Meanwhile, channel the pessimistic side of your brain into clearly acknowledging the reality in front of you.

Jason Crawford, in the MIT Technology Review, recently proposed the term “solutionism” for this way of thinking. In so many endeavours, we benefit from a mindset that both acknowledges the severity of problems and our potential for eventually overcoming them.

It’s this mindset that fuels one of the most productive activities out there: confident experimentation. Confidence in the long term direction, bolstered by a willingness to take a series of iterative bets on what path will lead us there.

Not blind optimism, and certainly not pessimism – just a thoughtful path forward.


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© Allen Pike. You can find me on Twitter, contact me, or check out Steamclock.