How to Be an Optimist in Difficult Times

Neil Lewis
4 min readFeb 18, 2021

Startup leaders and founders are called to set up a vision for a better future — but how do you do that when times are tough?

Quote from Admiral Stockdale — after whom the Stockdale Paradox was named

Startup leaders need to be optimistic, forward looking and full of hope. That much goes without saying.

But how do you do optimism when times are tough, people are hurting out of loneliness and isolation or suffering from loss of income or the loss(es) of loved ones?

To answer this question I often quote the Stockdale Paradox; ‘the biggest optimists die first’!

But I also subscribe to a previous Israeli premier’s view that ‘Optimists and pessimists die the same. It’s how they live that is different’.

So how do these two — apparently contradictory — thoughts fit together and how can you use this insight to be an optimist in tough times? Read on…

Firstly, the context of Admiral Stockdale’s statement ‘the biggest optimists die first’ came from his experience of eight years in a Vietnamese prisoner of war camp during the Vietnam war of the 1970s.

Stockdale observed that his fellow POWs who believed ‘it would all be over by Christmas’ were crushed when they saw Christmas come and Christmas go and then next year, saw Christmas come and Christmas go again.

At this point, they gave up hope and ‘died of a broken heart’.

So who survived in Stockdale’s view? The pessimists? Well, not quite…

Those who made it out of the camp alive, where the ones who firstly faced the brutal facts of their capture, their treatment and that no immediate end was in sight — and *then* choose to be optimistic about how they would deal with that.

Stockdale says “I never doubted not only that I would get out, but also that I would prevail in the end.

The point is, they firstly faced (honestly) the brutal facts of their situation and then chose to be optimistic, to believe that they would prevail.

Those who were optimistic without first facing the hard realities were ultimately crushed by their optimism.

So how this affect us, today?

As we move into the second year of Covid-19 pandemic in the Western world, it is a good time to remember this advice, as we’ve been told many times that it will be over soon.

Of course, for many startups, digital business and virtual workers, the last year has seen a boom. This boom too has reached the garden, DIY and home improvement industry too.

Nevertheless, we live in communities that are suffering huge pain and damage. We are seeing friends and sometimes family lose in the fight against Covid and even if our businesses are secure, the damage around us is extensive and deep.

To be optimistic in these times demands that we firstly fact the brutal facts — and don’t gloss over the realities, as over confident political leaders have done, and then chose to be optimistic that we will, as individuals and as communities, prevail.

And that is the key to understanding Simon Peres’s statement that the difference between an optimist and a pessimist is how they choose to live.

But is it not blind optimism. It is not boosterism. It is not wrapping ourselves in a flag and ignoring the realities around us.

You might call it hard-nosed optimism rather than blind optimism.

It is the kind of optimism that will see us navigate the rapids and dangers ahead. It is the kind of optimism that gets us to where we are headed.

How do you put this insight into action in your startup?

Ask yourself / your team:

What are the Brutal Facts that we/ you have been ignoring?

…and of course, the follow up question,

…having faced those facts, how do we create hope and optimism?

For instance, one thing I learnt a decade ago is that entrepreneurs and founders don’t fail — businesses (or business models) fail — but leaders never fail if they learn from what happened/ happens and decide to ‘go again’.

Oddly, knowing this fact often means that our project or business doesn’t fail — because, as I wrote here, if we decide to do whatever it takes — even whilst accepting the circumstances — this mindset and depth of conviction is what helps lead us to success.

— — —

ps. here’s the Stockdale quote in full:

“You must never confuse faith that you will prevail in the end — which you can never afford to lose — with the discipline to confront the most brutal facts of your current reality, whatever they might be.”

And, that quote from Shimon Peres:

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I’m Neil Lewis, non-exec founder. You can find more good stuff at my website https://mediamodo.co.uk/

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