Podcast Summary
Podcast: Aware and Aggravated
Host: Leo Skepi
Episode: 60. The Self Worth Reset After Trying To Earn Love
Date: February 14, 2026
Overview
In this deeply personal episode, Leo Skepi explores the struggles of self-worth when it is built upon trying to “earn” love and validation—both from others and from achievements. He unpacks his recent experiences with intense feelings of worthlessness despite continued external validation and success online. Through raw self-reflection, Leo discusses the trap of transactional self-worth, the painful emptiness that comes from not internalizing external praise, and his journey toward understanding and accepting unconditional love—especially self-love that isn't contingent on others' opinions or recognition.
Key Discussion Points & Insights
1. Feeling Worthless Despite Success
- (02:00-05:00) Leo confesses recent weeks of feeling “very worthless” despite ongoing success and a massive online following.
- (04:50) “It's like my life has been so much external validation and I've been so confused and I felt very defective about it. Like, what the—? I should not be feeling like this at this point.”
- Leo explains he doesn’t get lasting confidence from achievements; every milestone feels as if it resets to zero in his mind.
2. The Broken Cup Analogy
- (05:00-10:00) He describes himself as a “broken cup”—no matter how much validation or reassurance comes in, it just drains out.
- “It doesn't matter how much external validation comes in, it just falls through. And it's been sad for me.” (06:32)
- Even frequent positive interactions with fans do not reassure him about new ventures.
3. The Trap of Transactional Love
- (14:00-18:00) Deep dive into the idea of “transactional” relationships and how he’s always been comfortable earning love through actions or meeting expectations.
- “I've had to earn love my entire life...and I've tried it all.” (14:43)
- He examines how this approach has conditioned his brain to equate self-worth solely with what he can “exchange” for love.
4. Unconditional Love Dismantles the Old Self-Worth Scale
- (19:00-26:00) Leo discusses how contemplating unconditional love (especially in a spiritual sense) dismantled his lifelong system of measuring worth by “chips” or traits that attract love.
- “When you bring in the idea of unconditional love, it breaks that scale. It throws it out the window. The scale no longer exists. If you never had to earn love...there’s nothing to base your worth around. And that’s what I've been caught in.” (21:33)
- A period of darkness followed, as he realized he couldn’t find value in himself if it wasn’t about earning or exchanging for love.
5. The Poker Chip Analogy
- (26:05) All traits and accomplishments are likened to poker chips, used to “bet” for love or approval but rendered “invalid” by unconditional love.
- “You introduce the idea of unconditional love. The chips disappear, there’s no more chips, there’s no more traits...did I even like anything on those chips? Why did I have those chips?” (27:10)
6. The Challenge of Valuing Traits with No External Validation
- (29:00-32:00) Leo describes realizing he hasn’t valued any trait in himself unless it could be “exchanged” for approval.
- Questions the purpose of integrity, kindness, or being a “good friend” when these qualities aren’t always externally appreciated.
- “Why am I so hard and desperately holding on to my integrity? I see zero benefit of it. Besides, I get to sleep peaceful at night.” (32:25)
- Struggles with the idea of appreciating something about himself just for himself.
7. The Role of Money in Self-Worth
- (38:00-43:00) He delves into the connection between financial status and self-esteem, especially as a man.
- “I started to get like my self worth was so...tied up in it. And I'm like looking at all of the numbers that I have on social media, looking at all of the ways that I've worked and done so much...for me to be at this level and still worrying about money, I'm fucking pathetic.” (41:16)
- Dissects why he refuses to monetize every aspect of his platform, despite the financial pressure, and how that is now something he appreciates about himself.
8. Returning to Authenticity
- (46:00-49:00) Reminisces about his early podcast days, when he made content for himself, not numbers—a time he felt inner conviction.
- “Back then, before I got really big, I didn't give a fuck. Like, if I got cancelled, you couldn’t make me question myself at all.” (47:32)
- Vows to refocus on what he likes about himself and what he wants to do, for himself.
9. The Path Forward: Liking Traits for Themselves
- (52:00-55:00) Leo commits to discovering traits he likes regardless of whether they’re seen as valuable by others.
- “If you value it, it's valuable. It only takes one person to value something to make it valuable.” (55:10)
- He feels freed and “lifted out of this fog” by rewriting the foundation of his self-worth.
Notable Quotes & Memorable Moments
-
On transactional love:
“Everything's been a transaction for me...I like transactions. If you tell me, okay, you can behave this way and you do these things and then you get this outcome, I'll take it.” (14:15) -
On the emptiness of external validation:
“I felt trapped in this like personal hell of nothing I do can make me feel any kind of self esteem for long. It's like every single day I wake up, everything resets in my mind.” (07:25) -
On unconditional love breaking the rules:
“When you crack open your awareness to unconditional love, the scale goes away. It disappears...I could not think and figure out anything about myself that had value at all.” (21:38) -
On poker chip analogy:
“All the different traits and values that you have...are like all these little chips you’re collecting so it, like, helps your bargaining chances when you’re trying to gain people’s approval or gain their love.” (26:32) -
On personal realization:
“I started crying. I did. I boohooed. It felt like such a release and like an integration because I weirdly became aware that there’s so many things about myself that I haven't appreciated and haven't been able to appreciate because I can’t exchange them for anything.” (28:30) -
On living authentically:
“I gave up [a podcast deal] last year for the freedom...my soul didn’t want to be interrupted anymore. So I got rid of the podcast deal and then my podcast blew the fuck up again.” (44:34) -
On the meaning of self-value:
“If you value it, it’s valuable. It only takes one person to value something to make it valuable.” (55:10)
Important Segments & Timestamps
| Timestamp | Segment/Theme | |-----------|------------------------------------------------------------------------------| | 02:00 | Intense feelings of worthlessness despite ongoing online success | | 06:30 | The “broken cup” analogy for lack of internalized validation | | 14:15 | Admitting a lifelong pattern of transactional relationships | | 21:33 | Realizing unconditional love erases the “worth scale” | | 26:32 | The poker chip analogy and feeling invalidated | | 32:25 | Challenges appreciating integrity, kindness, friendship for their own sake | | 41:16 | Struggles with tying self-worth to money, refusing to monetize everything | | 47:32 | Remembering conviction pre-fame and returning to authentic content | | 55:10 | The liberating realization about self-value |
Tone & Style
Leo's tone throughout the episode is candid, vulnerable, introspective, sometimes humorous, and often self-deprecating. He uses colorful language, metaphors (broken cup, poker chips), and invites listeners into his inner thoughts and emotional process. The flair alternates between biting honesty, dark humor, and hopeful affirmation.
Takeaway
Leo’s journey in this episode is about shifting from a life of “earning” validation to one of discovering unconditional self-worth—valuing qualities and actions for their own sake, not just as chips to bargain for love and attention. He models radical vulnerability and the real work of self-love beyond achievement and public approval.