Podcast Summary: Aware and Aggravated

Episode 50 – Things Secretly Making You Insecure

Host: Leo Skeppy
Date: October 19, 2025

Episode Overview

In this deeply candid and energetic episode, Leo Skeppy opens up about the subtle and surprising factors that undermine our self-esteem and sense of self-worth. The episode is focused on recognizing "invisible" contributors to insecurity—ranging from trying to like what everyone else likes, to how the people closest to us treat us, to the effects of social media arguments and even our diets. Leo uses their signature blend of honesty, humor, and spirited storytelling to help listeners identify, understand, and move past these insidious sources of insecurity in pursuit of their "leveled up" selves.

Key Discussion Points & Insights

1. Channeling Excitement into Productivity

• [00:02] Leo kicks off by sharing the pre-festival excitement and how they're channeling that energy into something productive (recording early), instead of letting it create restlessness.
• The message: Use emotional energy intentionally so you end the day with a sense of accomplishment.

2. Trying to Like What You Don’t Like

• Watches & Fitting In ([03:30] onward):
  • Leo describes feeling pressure to like luxury watches because of social expectations, especially in Miami—where most people sport either real or fake luxury watches.
  • "For so long I've been trying to get myself to like watches, and I finally was just like, fuck it. If I don't like it, I don't like it." [06:30]
  • Realization: It's okay to dislike what others like—embracing it builds real confidence.
  • “Your desires are not your fault. Desires come and flow through you. They're not something that you have to fight and fuck yourself up over and change.” [13:10]
• Jewelry as Comfort:
  • Leo shares the personal story behind wearing bracelets—it started as a way to manage insecurity about hand movement, and evolved into genuine self-expression.

3. Resentment of Your Uniqueness & Life Path

• Not Being Able to Disconnect ([16:40]):
  • Leo talks about the spiritual path and how it sometimes feels burdensome—not being able to "party" or disconnect without severe emotional costs.
  • “I have to stay in tune with myself to do what I do, to have my happiness, to have my spark, to have my connection with myself and also have my success.” [20:45]
• Comparison to Others:
  • Frustration at seeing others succeed by “playing the game” or sacrificing their own voice for money—in contrast, Leo’s intuition won't allow it.
  • “My soul will uppercut me and drop kick me right off this balcony if I try and do that, like, my life will crumble.” [28:20]
• Flipping the Script:
  • What once felt like a curse—inability to fit into molds—is now a source of unique strength and success. Embrace your “exceptionality” rather than resent it.

4. Emotional Pendulum Swings

• Feeling Mentally Unstable? ([33:20]):
  • Leo describes cycles of up-and-down mental states and the resulting self-judgment.
  • Realization: Emotional swings are normal, especially for soul-led, intuitive individuals. Stability isn’t the point; embracing it brings clarity, not chaos.
  • "There's a difference between being emotionally reactive or just being emotional...feeling the emotions is fine." [36:00]
• Stop Justifying Your Feelings:
  • “You're allowed to feel however the fuck you feel at any time, okay? You don't have to act on it.” [37:27]

5. How the Closest People Treat You

• Direct Impact on Self-Esteem ([40:00]):
  • The people nearest to us can sap or boost our confidence—especially through small acts (or absence) of validation, laughter, or care.
  • "If people closest to you act like you're not funny...you're gonna start thinking you're not funny." [41:16]
• The Danger of Neglect:
  • Neutral reactions, neglect, lack of compliments, or priority lower self-worth.
  • Advice: Take space from those who make you feel invisible. “Neglect is a form of abuse.” [45:13]
  • Exception: Leo is clear this doesn’t apply to children—kids come first.

6. Food Hangovers: The Secret Mood Killer

• [51:00]: What we eat influences our mental state far more than commonly realized. Fast food, processed snacks, and overindulgence can leave a person not just physically sluggish but mentally and emotionally insecure.
  • “When you eat junk and eat bad food, it will ruin your mood and your mental state and you will wake up the next day feeling like shit.” [51:20]
  • Balance, not restriction, is the answer.

7. Assuming People Only Want Something From You

• [55:00]: Surrounded by people who seemed indifferent or transactional, Leo internalized a belief that every relationship was about extraction—clout, money, association.
  • This lens distorts reality and leads to isolation.
  • “You are funny, you are lovable, you are nice to spend time with...people do find what you have to say interesting.” [58:20]
  • Solution: Challenge the belief, reconnect, and remember that genuine connection exists.

8. Fighting with Bots and Rage-Bait on Social Media

• [01:01:13]: Arguing on social media—often with bots or people looking for attention—is a waste of energy and does real damage to self-esteem.
  • The proliferation of sophisticated AI bots makes online engagement suspect—and the “world” on social media isn’t real.
  • “Social media is being run by something bigger than all of us that wants us distracted and emotionally uncontrolled.” [01:03:40]
  • Advice: Post, then log off. Don’t engage with “ragebait” or obvious nonsense—it’s designed to emotionally hijack you.

Notable Quotes & Memorable Moments

• On Authenticity:
  “The less you try to fit in, the more you’ll feel a sense of belonging with yourself.” [approx. 12:40]

• On Self-Compassion:
  “I can't abandon myself and feel good. I can't abandon myself and, like, see success—all of my success will stop as soon as I start abandoning myself.” [19:20]

• On People’s Reactions:
  “If someone doesn't laugh at your jokes, you're gonna start thinking you're not funny. Neglect is a form of abuse.” [41:16, 45:13]

• Food & Mood:
  “It's not cheaper to eat fast food. Okay. I've been sitting here like a lazy dick for the past couple of weeks and I've been Uber Eating... Drastic [difference]” [52:15]

• On Social Media Fights:
  “As soon as you notice you see a comment or see something and you have like that ping of an emotional reaction, do not engage.” [01:06:35]

• On Emotional Validation:
  “Stop justifying your feelings. You're allowed to feel however the fuck you feel at any time." [37:27]

Timestamps for Important Segments

• 00:02 – Channeling excited energy productively
• 03:30 – Watches, taste, and fitting in
• 13:10 – Authentic desires and self-permission
• 16:40 – Resentment of one's spiritual path/uniqueness
• 20:45 – Staying in tune vs. “success at all costs”
• 28:20 – On not selling your voice or soul for money/opportunities
• 33:20 – Emotional pendulum swings and self-compassion
• 41:16 – Impact of close peoples’ reactions on self-esteem
• 51:00 – Food hangovers and mental state
• 55:00 – The assumption people want only what they can get
• 58:20 – Remembering you're lovable and interesting
• 01:01:13 – The dangers of social media arguments and bots
• 01:06:35 – “Don’t engage” mantra for online drama

Episode Tone & Style

Leo’s delivery is energetic, conversational, irreverent, and emotionally raw, peppered with humor and profanity. The approach is part friend, part tough-love coach: honest, supportive, and occasionally blunt.

Quick Tips & Takeaways

• Give yourself permission to dislike things others like—it’s a superpower, not a failing.
• Pay close attention to how your closest relationships make you feel. Take space if someone constantly brings you down.
• Don’t fall for the trap of online “rage-bait.” Not everyone (or everything) arguing with you is real—or worth your energy.
• Notice the quiet factors affecting your self-esteem—food, social environment, and your inner narrative about others’ motives.
• Emotional swings are normal; stop pathologizing them.

(To join the emoji check-in, leave a firework emoji in Leo's comments—see [01:12:15] for details!)

For more candid self-development talks, check out next Sunday’s episode or browse previous ones linked in the podcast notes.