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The Heretic is a free dispatch delivering insights into what it takes to lead into & in the unknown. For entrepreneurs, corporate irritants and change makers. Raw, unfiltered and opinionated.

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Jan 13th, 2022 Share: Share on Twitter Share on Facebook Share on LinkedIn

Leading Into and in the Unknown

I am writing this dispatch in the middle of the great COVID-19 Omicron Charlie Foxtrot. The WHO just shared the sobering news that they expect half of Europe to be infected within weeks, and the rest of the world doesn’t look much better off either. Meanwhile, the US is enjoying a whopping 7% inflation rate, the planet is getting hotter and hotter, the Marshall fire destroyed more than 1,000 homes a mere 5 miles south of where we reside, and we live through something Mays Business School professor Anthony Koltz dubbed “the great resignation”.

Times of high uncertainty and complexity. Times highlighting one of the most important leadership skills of this era: Your ability to lead into and in the unknown.

In a world which is constantly shifting, where everything is connected to everything, and where your ability to find solid footing and a clear path forward has vanished, you have to become comfortable with not-knowing. With leading into a world of unknowns, a world where you don’t have the answer — and the best you can do is to ask better questions, as well as help those around you to do the same. Where you iterate your way forward, taking one step at a time, constantly iterating over your options, and changing on a dime.

The problem with this world is that it is diametrically opposed to the way many of us have found success in life. In school, you got your good grades for having the right answer. In business, we got promoted for knowing the way forward. As leaders, we got celebrated for showing the way.

All this is over. The best we can do is to find our North Star — articulating the goal and then embark onto a journey of many iterative steps; not afraid to take a step (or a couple) back when we find out that we were heading into the wrong direction.

The process resembles something my friend Corey Ford likes to call “the Drunken Walk of the Entrepreneur”.

What are the questions you are going to ask of the future?

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