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.