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DEEP DIVE: The Optionality Guide to Pivots

DEEP DIVE: The Optionality Guide to Pivots

We asked Expert Pivoters for their Advice on Changing it Up without Blowing Things Up. Here’s what they said.

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Jory Des Jardins
Feb 28, 2025
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DEEP DIVE: The Optionality Guide to Pivots
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When we first started thinking about our thematic focus for the month, I originally demurred from writing about pivots. After all, isn’t Optionality’s raison d’etre to facilitate transitions for experienced professionals seeking new ways of working? (Hint: Yes it is.)

But then I thought about it a bit more. The definition of a pivot in a business context is to “completely change the way in which one does something.” Much of the transition work we’ve done has been around addressing changes that happened to us, be it a divorce, illness, layoff, or corporate exit. Pivots are actions we initiate, even if by forced circumstances.

In that respect pivots are harder than transitions because we must choose them and accept the associated consequences of making them. But they come from a position of agency, which is a more empowered approach to change.

Pivots are strategic decisions.

This whole month we’ve met with successful pivoters who actively chose to pivot their businesses, their focuses, their skills, and were more fulfilled for it. In this guide we bring you their insights to successful pivots.

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