How do you know the voice in your head is lying to you?

In this episode, Kier Gaines sits down with comedian, media personality, Jess Hilarious, for an honest conversation about imposter syndrome, self-doubt, and what it really means to earn your place in the room.

What starts as a conversation about confidence quickly becomes something much deeper. Kier explores the idea that imposter syndrome isn't really about ability it's about belonging. Even after reaching milestones, building successful careers, and proving ourselves over and over again, many of us still carry the fear that someone will eventually discover we don't deserve to be where we are.

Jess opens up about her journey from creating viral content to co-hosting The Breakfast Club, writing her first book, and navigating public growth while staying true to herself. Together, she and Kier unpack the pressure of evolving in front of millions, balancing authenticity with responsibility, and learning to trust yourself even when the doubt never completely disappears.

The conversation also explores resilience, social media, mental health, parenthood, public criticism, and why success doesn't eliminate fear it simply gives you a new opportunity to face it.

Because sometimes the feeling that you don't belong isn't evidence that you're in the wrong room...

It's proof that you've grown into one you've never been in before.

In This Episode

• What imposter syndrome actually is and why so many high achievers experience it

• Why belonging feels harder than succeeding

• Jess Hilarious on building confidence through consistency instead of validation

• Transitioning from social media to The Breakfast Club

• Why your next level requires a different version of you

• Balancing comedy, criticism, family, and mental health

• Learning to evolve without abandoning yourself

• Why doubt is a feeling not a fact

Connect With Us

🌐 Website:
Learned The Hard Way Podcast

🎙️ Leave a Voice Note: Drop Kier a message directly on the site

📧 Email: learnedthehardwaypod@gmail.com

📱 Follow the Show:
Instagram – Learned The Hard Way Pod

👤 Follow Kier:
Instagram – Kier Gaines

Tap in: Share your thoughts, leave a review, or send this episode to someone trying to figure out who they are beyond survival mode.

Produced & Edited by Idea to Launch Productions

See omnystudio.com/listener for privacy information.

Are leaders born... or do they become one decision at a time?

In this solo episode of Learned The Hard Way, Kier Gaines challenges one of the most common beliefs about leadership: that it's something you're entitled to instead of something you earn.

From relationships and parenthood to business and community, Kier explores what leadership actually looks like when you remove ego, dominance, and performance from the equation. Because being the loudest person in the room isn't leadership. Neither is making every decision alone.

Instead, real leadership is about creating environments where the people around you can thrive even when you're not the smartest, strongest, or most visible person in the room.

Through personal stories, therapy insights, and examples from his own family, Kier unpacks why leadership is less about control and more about responsibility, humility, and service.

If you've ever been told you're supposed to lead or you've questioned whether you're doing it well...this conversation will challenge the way you think about influence, authority, and the legacy you're building every day.

In This Episode

• Why leadership is earned not inherited

• The difference between leadership and dominance

• Why control isn't the same as influence

• The hidden pressure many men feel to "have all the answers"

• How servant leadership creates stronger families and teams

• Why giving others a voice makes you a better leader

• What leadership looks like in marriage and parenting

• The role humility plays in becoming someone people actually want to follow

• Questions every leader should ask themselves

Key Takeaway

Leadership isn't about being in charge.

It's about making the people around you stronger because you were there.

Sometimes the greatest leaders aren't the ones standing in front of everyone—they're the ones creating space for everyone else to rise.

Connect With Us

🌐 Website:
Learned The Hard Way Podcast

🎙️ Leave a Voice Note: Drop Kier a message directly on the site

📧 Email: learnedthehardwaypod@gmail.com

📱 Follow the Show:
Instagram – Learned The Hard Way Pod

👤 Follow Kier:
Instagram – Kier Gaines

Tap in: Share your thoughts, leave a review, or send this episode to someone trying to figure out who they are beyond survival mode.

Produced & Edited by Idea to Launch Productions

See omnystudio.com/listener for privacy information.

What happens when being the person everyone depends on becomes the thing that's breaking you?

In this episode, Kier Gaines sits down with media personality, cultural critic, and podcast host Crissle for a conversation about empathy, emotional labor, boundaries, and the hidden weight of being the person everyone turns to when life falls apart.

What starts as a discussion about therapy training quickly becomes something much bigger.

Kier and Crissle explore what happens when caring isn't just something you do it's something you're wired for. Both have spent years studying people, understanding behavior, navigating relationships, and helping others make sense of their lives. But somewhere along the way comes a difficult question:

How much responsibility are you supposed to carry for other people's healing?

Together, they unpack the complicated line between support and enabling.Because sometimes caring looks like showing up.And sometimes caring looks like stepping back.

In This Episode

• Why people with therapy training often see relationships differently
• What happens when your identity becomes tied to helping others
• Compassion fatigue and emotional burnout
• The difference between support and enabling
• Being the person everyone calls during a crisis
• How to know when someone's problem isn't yours to solve
• Boundaries that don't feel like abandonment
• Caring for yourself without feeling selfish
• The emotional labor expected of Black men and Black women
• What Crissle's Couch offers that traditional therapy cannot
• Who you are when you're no longer taking care of everyone else

At its core, this episode asks a question many people never stop to consider:

If being needed disappeared tomorrow...

Who would you be?

Connect With Us

🌐 Website:
Learned The Hard Way Podcast

🎙️ Leave a Voice Note: Drop Kier a message directly on the site

📧 Email: learnedthehardwaypod@gmail.com

📱 Follow the Show:
Instagram – Learned The Hard Way Pod

👤 Follow Kier:
Instagram – Kier Gaines

👤 Follow Crissle:
Instagram – Crissle

Tap in: Share your thoughts, leave a review, or send this episode to someone trying to figure out who they are beyond survival mode.

Produced & Edited by Idea to Launch Productions

See omnystudio.com/listener for privacy information.