#247 4 Steps to Help Your Kid Take Smarter Risks with Matthew Confer

Flourish Coaching

Oct 6, 2026

Taking a risk does not have to mean jumping in blindly, especially when the stakes feel high for a young person.

In this episode, Lisa Marker-Robbins and Matthew Confer explore how young people can think through uncertainty, prepare for setbacks, and take action before they feel fully confident.

Lisa and Matthew discuss:

Why capable young people freeze when it’s time to take action on their career, even when they know what to do
What a pre-mortem is and how imagining failure before it happens actually builds the courage to act
How to apply the RISK framework to a real internship or job search so young people stop putting all their eggs in one basket
Why thinking in adjacent industries and cross-functional skills matters more than targeting one perfect opportunity
How parents can use this process with their young person without stepping in and taking over

Key Takeaways:

A pre-mortem asks you to assume failure before you start, name what could go wrong, and build a plan while you can still change course
The RISK framework walks through four steps: Recognize the threats, Imagine the disaster, Solve for vulnerability, and Kickstart the solution
When young people say their worst-case scenario out loud, it almost always turns out to be less scary than keeping it hidden inside
Putting all your internship or job search effort into one industry or company type is one of the most common and avoidable mistakes
Parents can run this framework alongside their young person by brainwriting threats separately first, then comparing, so no one voice dominates the conversation

“The vast majority of times you will find that colossal failure is not as scary.” – Matthew Confer

About Matthew Confer:

Matthew Confer is the Chief Strategy Officer at Abilitie, an Austin-based leadership development company. He is the author of The Upside of Downside Thinking: A Premortem Approach to Better Decision Making, published by ATD Press. His TEDx talk on decision-making, “Before You Decide,” has been viewed more than one million times. He also hosts the Learn To Lead Podcast, where he explores leadership, decision-making, and the ideas that help people grow personally and professionally.

Episode References:

Free LinkedIn Profile Builder: https://flourishcoachingco.com/linkedin
Matthew’s book: The Upside of Downside Thinking: https://www.theupsideofdownsidethinking.com/
Matthew’s TEDx talk: Before You Decide: https://www.youtube.com/watch?v=d7Jnmi2BkS8
Learn more about Launch Career Clarity at https://flourishcoachingco.com/course

Get Lisa’s Free on-demand video: THE CAREER IDENTIFICATION COMPASS: How To Be Certain Your 15 To 25 Year Old is On The Right Path to Launch With Confidence–Not Confusion: flourishcoachingco.com/video