This is one of those questions around which a day (or even a life) could be organised.

Ask yourself – What if every day were structured such that when I win I win bigger than when I lose? That is the idea of an option in the financial markets. It is designed to allow you to benefit from market movements (up or down) with very limited exposure. Nevertheless, if you keep buying losing options you will eventually go bust. The trick, and hence the art, is investing in the right options. The same is true in life.

Applying this to real-life situations, upside optionality might mean pursuing endeavours that have limited risk or potential harm (i.e., downside) but offer a chance of significant positive outcomes or benefits (i.e., upside).

For example, let’s take my day and reflect on what I might do today that would offer me upside optionality. I have a number of calls and appointments in the diary and, whilst the relationships themselves clearly offer amazing potential for referrals and hence new opportunities, today’s calls actually offer limited fresh potential upside. Afterall, the focus is on what today might offer.

For me, the highest potential benefit over time is from strengthening existing relationships and creating new ones. Outside of my commitments today, that is what is most important and that is what I will do. You never know where any of these relationships might lead and the cumulative effect over time can be amazing.

The cost here is time or, in financial terms, opportunity cost. Therefore, what else might I do that might offer a higher benefit over time? And it is that “over time” piece that is really critical. I might do something today that may potentially pay a small benefit right away, but what if I were to do something that paid dividends for years? That is why it is essential to invest in the right options.

So, what might you do today that might pay dividends for years?

Questions in the Image:

  • Where is my upside optionality today?
  • What hidden opportunities might there be?
  • How might my day offer more possibility?

Want to Read More Around This Topic?

Antifragile: Things That Gain from Disorder by Nassim Nicholas Taleb (link to Nassim Taleb is one of the small band of authors I have read who offer truly original thinking. Antifragile is no different. He argues that certain things in life not only benefit from stress, disorder, volatility and turmoil but in fact need them and thrive under such conditions.

Nurturing Curiosity – Daily Practice: This is part of the Nurturing Curiosity series of tools, insights and questions designed to help nurture curiosity as part of our daily practice. In point of fact, every interaction we have is an opportunity to question what we are observing and how we and others are seeing the world. Also remember that questions come in many forms throughout our day. In fact, thinking about Taleb’s work and his contrarian nature made me ponder my own contrarian nature. Where might I benefit from being more contrarian? Where do I or others not benefit from being contrarian? I certainly find this a challenge in conversation at times where I question an underpinning assumption and it feels like the floor has fallen away.

About Tom O’Leary

My mission is to help others think differently – meaning more broadly and deeply – and thereby make better decisions. The key to thinking differently lies in our curiosity.

The more we question, the more possible answers we uncover, and the more we expand what we thought possible. Life has taught me that possibility lies not so much in seeking answers but in learning to ask better questions – the ones that help prioritise what is truly essential.

And yet, in a culture obsessed with efficiency and productivity, the paradox is that much energy and resources are wasted by a bias towards action over contemplation. If you are answering the wrong question, it doesn’t matter how ‘hard’ you work, you are still answering the wrong question.

That is why I am a big advocate of nurturing curiosity and innovative thinking at all ages, particularly amongst leaders because of the impact they have on us all. In my vision, leaders aren’t boxed in by traditional thinking or established playbooks. They are curious, open to fresh ideas and diverse perspectives, fostering a culture of exploration and learning.

How Might Tom Help?

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