E62 : OUR REGRETS

In this episode of The Unquestioned Podcast, co-hosts Willem Himpe and Louis Debaere reflect on the personal, professional and financial decisions they would approach differently today.

They discuss living alone during COVID, moving back from the United States, missing financial opportunities, learning sales too late and choosing entrepreneurship without fully understanding how difficult it would be.

Rather than treating regret as something negative, Willem and Louis explore how it can become a source of self-awareness, courage and better decision-making.

This is an honest conversation about taking risks, trusting yourself, dealing with rejection and building a life around meaningful relationships rather than external expectations.

00:00 Why reflecting on regrets matters
02:47 Living alone during COVID and the importance of human connection
05:27 Moving back from the United States and trusting your own path
10:06 Spotify equity, investing and market timing
13:53 Learning sales, confidence and handling rejection
20:19 The reality of entrepreneurship and choosing an unconventional life
24:23 Support systems and living with fewer regrets

KEY TAKEAWAYS

• Regret becomes valuable when it changes how you make future decisions.
• Human connection often matters more than comfort, status or material success.
• Taking risks earlier creates more opportunities to learn and grow.
• Financial opportunities require both knowledge and timing.
• Sales strengthens confidence, communication and resilience.
• Entrepreneurship is often more difficult and uncertain than it appears.
• A strong support system makes it easier to take meaningful risks.

“Money is not the most important thing.”

“I should have been more selfish.”

“Market timing is crucial for investments.”