Podcast Summary: The Psychology of Your 20s

Episode 374: The Psychology of Regret
Host: Jemma Sbeg
Date: January 12, 2026
Podcast: iHeartPodcasts – The Psychology of Your 20s

Episode Overview

In this introspective episode, host Jemma Sbeg explores the complicated emotion of regret—specifically as it manifests in your 20s. She dives into the psychological mechanisms that create regret, the types of regret most commonly experienced at this life stage, and offers actionable insights on how to manage and even embrace regret as a motivator for growth. Jemma balances scientific research with personal anecdotes and audience insights, aiming to swap the paralyzing fear of regret for a more compassionate, empowered approach.

Key Discussion Points & Insights

1. The Landscape of Regret in Your 20s

[03:21]

• Jemma acknowledges the centrality of regret in the collective consciousness of her audience:

  "What if I regret the decisions I’m making right now? Or what if I regret the decisions I’m not making?"

• Highlights the irony that, while our 20s present the greatest number of opportunities, they often come with amplified pressure not to 'mess up'.
• Regret is described as a blend of sadness, disappointment, embarrassment—mostly rooted in grief over a path not taken.

2. The Anatomy of Regret: Counterfactual Thinking & Self-Blame

[04:37]

• Counterfactual Thinking:
  • Our brains construct alternative realities (“what ifs”).
  • Downward counterfactuals imagine how something could have been worse; upward counterfactuals imagine how it could have been better—these are more painful.
• Self-Blame:
  • Mere alternative imagining isn’t regret—regret requires self-blame.
  • Study cited: Higher regret intensity with self-blame links to worse mental health outcomes.

  "Regret is what happens when you look at that better imagined outcome… and you think, okay, that was on me, like, that was my fault." – Jemma ([06:56])

3. What Do People Actually Regret?

[08:00]

• Jemma’s own survey (5,000 respondents) of 20-somethings’ regrets:
  • Focusing too much on romantic relationships
  • Worrying about others' opinions
  • Not fighting for friendships
  • Not investing sooner
  • Decisions about college (both going and not going)
• Research Highlights:
  • Meta-analysis (University of Illinois): Top regrets across ages are education, career, romance, parenting, identity, and leisure.
  • Daniel Pink’s “Power of Regret” outlines four categories:
    1. Foundation regrets (e.g., not pursuing education)
    2. Boldness regrets (not taking chances)
    3. Moral regrets (not acting in line with values)
    4. Connection regrets (letting relationships fade)

  “Most people actually ended up regretting what they felt they had the greatest opportunity to change.” – Jemma ([11:52])

4. Pre-Regret: The Paralysis of Anticipated Regret

[16:54]

• Anticipatory regret (“pre-regret”) is pervasive among 20-somethings.
  • We overthink possible outcomes, making decision-making feel impossibly high-stakes.
• Availability Heuristic:
  • Vivid worst-case scenarios are easier to recall, so we overestimate their likelihood.
  • This often leads to decision paralysis.

  “A lot of us live in what we call pre-regret. You haven’t made the decision yet, but you’re already imagining that it’s the wrong one…” – Jemma ([17:38])

• The Paradox of the Perfect Decision:
  • The quest to avoid regret at all costs often results in inaction.

  “100% certainty only exists in hindsight. Every real choice comes with trade-offs, comes with losses, comes with gains as well.” – Jemma ([20:44])

5. Actions vs. Inactions: Where Regret Grows

[22:24]

• Research shows inaction leads to more regret than action:
  • 24% of regrets: “Things people did do”
  • 76%: “Things they didn’t do”

  “Overthinking is not going to do anything. Making a decision will—any decision at all.” – Jemma ([23:10])

• The unused life path is a mental construct—conveniently flawless and unrealistic.

6. The Protective Power of Regret

[25:56]

• Regret can serve as a teacher and a motivator for future decisions:
  • Regret over missed opportunities or poor actions can inspire more intentional choices next time.

  “Regret functions a bit like a bruise on your moral skin. You bump up against a lie you didn’t know was there and it hurts. And afterwards you remember that you move a little bit more carefully.” – Jemma ([27:05])

• Sometimes, regrets cannot be reframed positively. For these, acceptance becomes essential.

7. Acceptance and Radical Self-Compassion

[29:45]

• Acceptance means acknowledging the past can’t be changed and choosing to move forward.
• Cognitive Biases:
  • Hindsight bias makes past mistakes seem obvious in retrospect.
• Kristin Neff’s Model of Self-Compassion:
  • Self-kindness
  • Common humanity
  • Mindfulness (not overidentifying with regret)

  “Having radical self-compassion in that moment is not an attempt to excuse the behavior or to change it. It’s just the tone you take with yourself when you think back on it.” – Jemma ([32:49])

8. Final Takeaways: Regret as a Human Privilege

[34:00]

• Regret is an inevitable part of the human experience—proof that we have choices and agency.

  “If I didn’t regret, I wouldn’t have choices and I wouldn’t have the freedom to choose. And that in itself is a blessing.” – Jemma ([34:20])

• The episode closes with an invitation for reflection:

  “What’s something you actually thought you would regret but didn’t?” – Jemma ([34:40])

Notable Quotes & Memorable Moments

• On the pain of regret:

  “Regret is sadness. It’s disappointment, embarrassment. It’s a sad mix of all those things, but I think it’s mostly rooted in grief, to be honest. Grief over a life path we could have lived and the stories we could have made…”
  – Jemma ([03:44])

• On decision paralysis:

  “The more you chase a perfect decision—one that guarantees permanent emotional comfort—the harder it becomes to choose anything at all.”
  – Jemma ([19:33])

• On the limits of preempting regret:

  “Trying to outthink regret doesn’t work. Making a decision will.”
  – Jemma ([23:10])

• On regret’s value:

  “Would life be better without regret? Honestly, I think the world would be way worse. People would be terrible to each other because they wouldn’t have regrets about it.”
  – Jemma ([34:13])

Timestamps for Key Segments

• Defining Regret, Counterfactuals & Self-Blame – [04:37]
• Biggest Regrets in the 20s (Survey + Research) – [08:00]
• Pre-Regret & The Paradox of Decisions – [16:54]
• Action vs. Inaction Regrets – [22:24]
• Regret as Motivation & Teacher – [25:56]
• Acceptance and Self-Compassion – [29:45]
• Final Thoughts & Audience Prompt – [34:00]

Overall Tone & Style

Jemma’s approach is conversational, warm, and deeply compassionate. She pairs scientific insight with relatable analogies and candid admissions of her own experiences. Throughout, she emphasizes empathy and self-forgiveness, inviting listeners to see regret not as something to be feared or avoided, but as a sign of a meaningful, conscious life.

Useful Links

• Previous episode: The 20 Biggest Regrets People Have in Their 20s
• Daniel Pink's Book: The Power of Regret
• Host’s Book: psychologyofyour20s.com/general-clean

This summary captures the heart and insights of the episode, making it a valuable reference for anyone who wants to understand the psychology—and potential utility—of regret in shaping a meaningful life in your 20s and beyond.