Self-sabotage can look like procrastination, perfectionism, negative self-talk, unhealthy coping, or pushing people away when things start going well.
In this episode, the hosts unpack how fear (of failure/rejection and of success), low self-worth, and learned patterns can quietly derail progress—then share practical ways to interrupt the cycle with awareness, small steps, support, and self-compassion.
Key points
Self-sabotage is often unconscious: “We don’t wake up… and think… today I’m gonna undermine my own happiness…” — Greg
Common signs include procrastination, perfectionism, harsh self-criticism, relationship conflict or avoidance, unrealistic goals, and self-medicating.
Fear of failure can create “failure on our terms” (a false sense of control); fear of success can trigger imposter feelings and discomfort with change.
The first step is awareness: notice patterns, triggers, and themes (journaling helps).
Challenge unhelpful thoughts (“Is this true? Is this helpful?”).
Practice self-compassion: treat yourself as you would a good friend.
Break big goals into small, actionable steps; add accountability (a friend, coach, or therapist).
Build healthier coping options (movement, meditation, talking with someone supportive).
Host highlights
Greg: “Self-sabotage is a psychological and behavioral pattern that we can overcome.”
Takeaway:
Progress > perfection—celebrate tiny course corrections as real wins.
Rich (procrastination): “Breaking larger tasks down into small, manageable tasks…” reduces overwhelm.
Takeaway:
Start with the first micro-step (e.g., “write that first email”).
Jay (perfectionism/stuckness): “Stepping away from the task… and coming back to it” can help.
Takeaway:
If you don’t know the next step, ask someone for help to regain traction.
Derek (relationships): “Setting alarms on my phone” and using Post-its or visual cues helps him reconnect.
Takeaway:
Design reminders ahead of time so future-you follows through. Bonus: “Let’s flip the record over… put a new album on.”
Sarah (self-compassion): “Nobody is crueler to me than me ever… we should be the kindest to ourselves.”
Takeaway:
If you wouldn’t say it to a loved one, don’t say it to yourself—rewrite it more kindly.
Memorable moments
Derek shares a painful reflection (a letter from his father) and names the need for external help.
Jay connects addiction recovery and self-sabotage, expressing gratitude for a healthier chapter.
Lightning round: community care and “look out for your neighbors” (Rich, Sarah).
Resources & links mentioned
Contact: info@kindnessrx.org
Companion site mentioned: KindnessRX — kindnessrx.org
Listener action steps
Do one tiny starter step in the next five minutes.
Set a 15-minute “good enough” timer, then stop.
Tell one trusted person your goal (accountability).
Replace one inner-critic line with a kinder rewrite.
Set a weekly reminder to reach out to someone important.