EP 0095 – Grieving Regrets and Woke is Shameful (Subscription)

EP 0095 – Grieving Regrets and Woke is Shameful (Subscription)

It’s Not You – It’s Your Unlived Vulnerability

You think grief hits hardest from loss alone? Wrong. The real killer is the mountain of regrets you carry into it—regrets born from walls you built, vulnerability you refused, and truths you never spoke. Stop pretending therapy-speak or positivity will bypass the ache. Healing demands you face the delayed mourning for who you never let yourself be.

The Brutal Link Between Regret and Grief
Grief isn’t just about losing someone. It’s amplified by the regrets that surface when time runs out. You sat by your best friend’s hospice bed, desperate to soak up every remaining second, realizing too late how much deeper the connection could have been if vulnerability had shown up sooner. The macho armor, the guarded bullshit—it all crumbled in those final months, revealing truths hidden for years. The same pattern repeats with childhood grief. You look back and hate yourself for not fighting back, not protecting that small version of you from the screaming, shaming giant. But back then you had no model, no capacity, no safety. The regret isn’t that you failed; it’s that survival demanded you disconnect, bury the pain, and pretend decades later that it never happened.

Why You Keep Avoiding the Real Work
You avoid vulnerability because it feels like danger. Opening up means risking the same rejection, shame, or abandonment you tasted as a kid. It’s easier to hide behind walls, isolate when triggered, or chase external fixes—relationships, success, approval—that promise safety but deliver more emptiness. Shame convinces you that owning your flaws makes you defective. So you chase an impossible perfect image, then spiral into self-hate when you inevitably fall short. Add in a culture obsessed with woke rules and political correctness, and the fear doubles: one wrong word and you’re canceled, judged, shamed all over again. You learned early that being yourself was wrong. Now the world polices you for it. No wonder you stay guarded.

The Crushing Price of Staying Guarded
Avoidance costs you everything authentic. Relationships stay surface-level. You lose people without ever truly knowing them or letting them know you. Self-hate festers because you refuse to accept your limits, your damage, your humanity. You numb with addictions, people-pleasing, or outrage at the world’s insanity, but the inner emptiness grows. You become a dinosaur in your own life—disconnected, reactive, offended by everything yet terrified of being seen. The longer you delay grieving those regrets, the tighter the shame binds you, the smaller your world becomes.

Three Important Takeaways

• Regrets amplify grief because they stem from unlived vulnerability—face them now or pay later when time runs out on the people who matter.
• Vulnerability isn’t weakness; owning your shame, flaws, and damage strips them of power and turns them into strength.
• Evolving means building integrity from the inside, not conforming to external rules—true growth comes from self-acceptance, not perfection or woke checklists.

Conclusion
Stop waiting for a shortcut or for the world to stop judging. You will never be the flawless version in your head, and that’s not the point. The point is owning who you actually are—damaged, imperfect, human—and grieving the regrets so you can finally live without the constant weight of shame. Start small: sit with one uncomfortable feeling today, notice when you escape into thought, and gently return to your body. No one is coming to save you from this work. But every step toward acceptance frees up space inside, quiets the self-hate, and lets you show up real in whatever time you have left. Freedom waits on the other side of the pain you’ve been avoiding. Go get it.