Should You Let Your Kid Fail? A Parent Q&A on Pressure, Resilience, and Emotions
In this Q&A episode of Thriving Kids Podcast, Dave Anderson answers listener questions following last week’s conversation with Jennifer Wallace on achievement culture and helping kids feel like they matter.
Parents asked practical, hard questions about failure, pressure, motivation, and emotional regulation. This episode focuses on finding balance—between support and independence, structure and flexibility, validation and limits.
Questions covered:
Natural consequences vs. stepping in
- Did you rob your child of a lesson by rescuing a forgotten school project?
- How to decide based on context and stakes.
Kids who cheat because they hate losing
- What’s developmentally normal at younger ages.
- When rule-following matters for peer relationships.
- How to address cheating without turning games into power struggles.
Paying kids for good grades
- Does it increase pressure?
- The role of external reinforcement.
- How to use rewards thoughtfully and fade them over time.
When your child says, “I suck at this”
- How to respond to negative self-talk.
- Helping kids move from global self-blame to problem-solving.
The brutal car ride home after a loss
- Why “I loved watching you play” can backfire.
- How to ask what support your teen actually wants.
- Coaching emotional regulation without forcing a conversation.
When schools make failure feel high-stakes
- What to say when mistakes lead to remedial groups or lost electives.
- Supporting your child when systems increase pressure.
- How parents can act as “counterprogramming” to achievement culture.
Key takeaways
- There is rarely one “right” parenting move.
- Kids need both scaffolding and space to struggle.
- Pressure affects children differently.
- Validation doesn’t mean fixing feelings.
- Effort matters more than perfection.
This episode is especially helpful if you’re parenting a child who is sensitive to failure, perfectionistic, or feeling overwhelmed by expectations at school or in sports.
Creators and Guests
Host
Dave Anderson
Dave Anderson, PhD, is the Vice-President of Public Engagement and Education and a senior psychologist in the ADHD and Behavior Disorders Center at the Child Mind Institute. Dr. Anderson focuses on the expansion of our awareness-building and prevention programs while also leading initiatives that build the Child Mind Institute brand, foster strategic partnerships, and forge new relationships with policy makers and youth mental health leaders.
Producer
Andrew Dearling
Andrew Dearling is the Digital Director at the Child Mind Institute, where he leads strategy and execution across web, email, social media, and digital campaigns. He focuses on using digital tools to connect more families with mental health resources, expand the organization’s reach, and drive measurable impact. Andrew combines deep expertise in content, platforms, and performance marketing with a clear understanding of how to reach people where they are, and move them to take action.
Producer
Chad Garber
Chad Garber, a seasoned Creative Producer with over 15 years of experience, shapes branded video, digital, and experiential content for Fortune 100 companies, agencies, and in-house teams to Child Mind Institute. Known for building high-performing creative operations, he led pro-bono productions to multimillion-dollar campaigns for brands like Verizon, Microsoft, New Balance, Budweiser, and FedEx. His sharp storytelling, deep production expertise, and collaborative leadership move ideas from concept to screen with impact.
