Entrepreneurs, Options & Opportunities

Last updated: August 18, 2026

I was playing chess with my son and he had me cornered, it looked like I had no options. I stayed with the problem, I zoomed out my perspective and considered every angle, and then I saw it, an opportunity to not only get unstuck but to change the game.

Options

An option is the power or liberty to choose. Often, we don't see our choices because of our framing or conditioning. Certainly, circumstances can restrict our liberty to choose, and yet we always have a choice.

Viktor Frankl, the author of the book, Man's Search for Meaning, a Jewish prisoner of the Nazi death camps destined for the gas chamber, realized…

"Everything can be taken from a man but one thing: the last of the human freedoms – to choose one's attitude in any given set of circumstances, to choose one's own way."

This power to choose one's own intentions and actions is at the core of self-leadership. It is summed up in the poem Invictus that inspired another prisoner, Nelson Mandela.

"It matters not how straight the gate,

how charged with punishments the scroll,

I am the master of my fate:

I am the captain of my soul."

Entrepreneurs

The French word, 'entreprendre' means to undertake and it used to mean to undertake the risk of a journey. The French economist Jean Baptiste Say coined the term Entrepreneur to mean, undertaking the risk of business.

Recently, I was speaking to a cohort of entrepreneurs being developed by a global early-stage venture capital company. I shared learnings from my interviews with entrepreneurs from Singapore, Silicon Valley, and Sweden. I shared how entrepreneurs, like good chess players, keep their options open. The CV of a successful entrepreneur usually shows several businesses started before the right opportunity is found. If you want the fuller practice behind this, not just the mindset but the specific daily habits, see Self-Leadership for Entrepreneurs: Lead Yourself First, Then Your Business.

Opportunity

Do you know the meaning of the word opportunity?

It means a favorable wind. It comes from the Latin phrase 'ob portum veniens' - coming toward a port.

During the height of the pandemic, I was coaching a CEO who was struggling with limited options to grow his company. We explored the metaphor of a sailing ship's captain when stuck in the doldrums (an area of little or no wind around the equator).

A good captain will set his crew to clean the boat and fix the sails, so that when the wind returns everyone, and everything is ready to maximize the opportunity.

My CEO client took this metaphor and ensured his company was 'ship shape' so that he could 'hoist the sails' when opportunities returned. The result was two record-breaking quarters!

SELF→LEADERSHIP & The Future of Work

"Self-leadership is the practice of intentionally influencing your thinking, feeling, and actions towards your objectives" – Bryant and Kazan 2012

Self-leadership is owning your options and maximizing opportunities, which is why self-leadership is an essential practice for entrepreneurs, and for anyone who wants to remain relevant.

Research by the McKinsey Global Institute has looked at the kind of jobs that will be lost, as well as those that will be created, as automation, AI, and robotics take hold. And it has inferred the type of high-level skills that will become increasingly important as a result.

Digital fluency is not a surprise, but did you realize how important self-leadership is to the future of work?

So, are you constantly considering your options, and are you ready to hoist your sails and take the opportunities when they arise?

And finally, here's a Haiku I wrote to sum up this post.

Frequently Asked Questions

What does the word "opportunity" actually mean?
It comes from the Latin phrase 'ob portum veniens', meaning coming toward a port, and originally referred to a favorable wind for sailing. An opportunity was, literally, the right conditions arriving to move you forward, not something you had to force.

What are entrepreneurial options, and why do they matter?
An option is the power or liberty to choose, and entrepreneurs who keep multiple paths open, rather than committing rigidly to one idea, tend to find the right opportunity faster. Most successful founders' CVs show several ventures tried before the one that worked, not one perfect first guess.

What is the origin of the word "entrepreneur"?
It comes from the French 'entreprendre', to undertake, originally used for undertaking the risk of a journey. French economist Jean-Baptiste Say later coined "entrepreneur" specifically to mean undertaking the risk of business.

How do you find opportunity when you feel like you have no options?
Zoom out before you decide you're stuck. Viktor Frankl, writing from a Nazi death camp, observed that circumstances can restrict our choices but never eliminate the freedom to choose our attitude and response. Most "no options" situations are actually a framing problem: you can't see the move yet, not that the move doesn't exist.