Two Approaches to Risk in Times of Change and Uncertainty

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Today’s edition of The Executiv was written by Ariela Freed, Executiv Member, Founder & Principal at Funnel Digital Inc.

Change has been a constant presence lately, and not just in news headlines. Change and uncertainty are being discussed regularly in everyday conversations.

There are discussions about how AI is reshaping work and which skills will matter most. Layoffs are impacting even senior leaders who once had stable, upward careers. And for many women “of a certain age,” change is surfacing as a quieter contemplation: Is this what I want to keep doing for the next 15 or 20 years?

Comfort with change varies widely. Some people have moved cities, shifted industries, and reinvented themselves more than once. The more experience someone has with disruption, the less foreign it tends to feel. For others, stability has defined their careers. In those cases, change can feel unsafe, unsupported, or outside their control. It can feel like something happening to them rather than something chosen.

Wherever someone falls on that spectrum, I’ve found two ways of framing risk that can help when deciding what to do next.

The first way is captured in this quote often attributed to Lucille Ball:
“I’d rather regret the things I’ve done than regret the things I haven’t done.”

This mindset focuses on future regret rather than present fear. It invites someone to imagine herself five or ten years from now - would future me wish she had tried? For people motivated by growth, curiosity, or autonomy, this framing is powerful. It shifts the internal dialogue from “What if it fails?” to “What if I never give myself the chance?” Risk becomes a missed opportunity rather than a potential loss.

I’ve often relied on that mindset when I’ve come to a fork in the road on my own journey.

But when I was contemplating leaving full-time employment to start my own consulting business, that wasn’t enough. While I knew I might regret not trying to take more control of my career, the fear from the uncertainty felt overwhelming.

What moved me forward was framing my concerns with this question:
What’s really the worst that can happen?

This question aligns with Richard Branson’s approach to risk. He often evaluates decisions based on whether the worst-case scenario is survivable. This isn’t about ignoring possibilities we don’t like. It’s about bringing them to light. When the downside is defined, be it financial, professional, or emotional, it becomes possible to assess whether the outcome is temporary, reversible, or manageable, and then plan for it.

For people who are more risk-aware, or facing major disruption after years of stability, this approach reduces anxiety. It turns an undefined fear into something concrete. And once it’s concrete, it is usually far less catastrophic than it first seemed.

When I answered that question honestly for myself, I was able to give myself a timeline, and plan for ways to mitigate or adapt to potential challenges ahead. In short, I could start to figure out an approach.

Neither mindset is inherently better. One pulls a person toward possibility. The other steadies her by containing risk. Both are useful.

What they share is simple: neither works without action.

Action does not have to be a dramatic leap. It can mean exploring, testing, gathering information, or taking one step that keeps options open. Full certainty is not required. The entire path does not need to be mapped out.

In the end, it’s less about which mindset is right, and more about finding the one that gives you permission to move forward in uncertain times.

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“And the trouble is, if you don’t risk anything, you risk more.”

Erica Jong