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In Episode 6, Kim is joined by relationship coach Mason O'Sullivan to answer listener questions about empathy, emotional support, grief, and long-standing self-sabotage patterns.
This episode focuses on one of the most common breakdowns in relationships: trying to fix emotions instead of understanding them. Kim and Mason unpack why empathy is not agreement, why problem-solving too fast makes partners feel alone, and how learning to sit with discomfort can change the entire tone of a relationship.
The conversation also explores how to show up for someone who is grieving when you feel awkward or unsure what to do, and how to begin untangling self-sabotaging behaviors that have been in place for years, especially when disability, shame, or past mistakes are involved.
–––––––––––––––––– Time Stamps & Topics
00:00 – Listener questions preview • Struggling to empathize instead of fixing • Supporting someone who is grieving or sad • Long-term self-sabotage and accountability
01:00 – Introduction to Mason O'Sullivan and his coaching background 02:30 – Why people seek coaching and therapy 03:35 – Creating safe spaces for vulnerability 04:30 – Finding your voice, identity, and boundaries 06:05 – What authenticity actually means 07:25 – People-pleasing and not knowing your needs
08:57 – Question 1: "I don't know how to empathize if I can't fix it" 10:23 – The urge to problem-solve and prove value 11:26 – Empathy vs sympathy explained 12:33 – Why solutions often miss the point 13:36 – Guessing needs vs asking directly 14:50 – Role play: what not to do 16:22 – Why reassurance can still feel invalidating 17:44 – Role play: responding with empathy 19:36 – Paraphrasing emotions and checking understanding 21:02 – Empathy is not agreement 22:30 – How validation opens the door to repair 24:09 – When and how to move into solutions
25:42 – Question 2: Supporting someone who is grieving or sad 26:35 – Awkwardness, nervous laughter, and discomfort 27:45 – Why grief is hard to sit with 28:21 – Letting someone lead with what they need 29:14 – Holding space instead of fixing 30:10 – Why silence can be supportive 31:10 – Grief, avoidance, and freezing time 32:42 – Talking through grief as healing 34:11 – Exploring your relationship with sadness
36:10 – Question 3: Breaking a decade of self-sabotage 37:41 – Disability vs avoidance as a coping strategy 39:13 – Realistic goals and self-assessment 40:08 – Self-fulfilling prophecies and sabotage 41:31 – Choice, agency, and accountability 42:22 – Core beliefs and self-worth 43:34 – Forgiveness, mistakes, and lovability 45:24 – Awareness as the first interruption 46:03 – Self-sabotage as predictability and protection 47:25 – Leaving before being left 48:37 – Encouragement and counting progress
––––––––––––––––––
This episode is especially helpful if you've been told you're "bad at empathy," feel helpless around grief, or recognize patterns of self-sabotage you're ready to change.
Kim's website: https://www.kimpolinder.com/
Kim's Instagram: https://www.instagram.com/kp_counseling/
Kim's YouTube: https://www.youtube.com/@engineeringlovepodcast
By Kim Polinder4.9
4949 ratings
In Episode 6, Kim is joined by relationship coach Mason O'Sullivan to answer listener questions about empathy, emotional support, grief, and long-standing self-sabotage patterns.
This episode focuses on one of the most common breakdowns in relationships: trying to fix emotions instead of understanding them. Kim and Mason unpack why empathy is not agreement, why problem-solving too fast makes partners feel alone, and how learning to sit with discomfort can change the entire tone of a relationship.
The conversation also explores how to show up for someone who is grieving when you feel awkward or unsure what to do, and how to begin untangling self-sabotaging behaviors that have been in place for years, especially when disability, shame, or past mistakes are involved.
–––––––––––––––––– Time Stamps & Topics
00:00 – Listener questions preview • Struggling to empathize instead of fixing • Supporting someone who is grieving or sad • Long-term self-sabotage and accountability
01:00 – Introduction to Mason O'Sullivan and his coaching background 02:30 – Why people seek coaching and therapy 03:35 – Creating safe spaces for vulnerability 04:30 – Finding your voice, identity, and boundaries 06:05 – What authenticity actually means 07:25 – People-pleasing and not knowing your needs
08:57 – Question 1: "I don't know how to empathize if I can't fix it" 10:23 – The urge to problem-solve and prove value 11:26 – Empathy vs sympathy explained 12:33 – Why solutions often miss the point 13:36 – Guessing needs vs asking directly 14:50 – Role play: what not to do 16:22 – Why reassurance can still feel invalidating 17:44 – Role play: responding with empathy 19:36 – Paraphrasing emotions and checking understanding 21:02 – Empathy is not agreement 22:30 – How validation opens the door to repair 24:09 – When and how to move into solutions
25:42 – Question 2: Supporting someone who is grieving or sad 26:35 – Awkwardness, nervous laughter, and discomfort 27:45 – Why grief is hard to sit with 28:21 – Letting someone lead with what they need 29:14 – Holding space instead of fixing 30:10 – Why silence can be supportive 31:10 – Grief, avoidance, and freezing time 32:42 – Talking through grief as healing 34:11 – Exploring your relationship with sadness
36:10 – Question 3: Breaking a decade of self-sabotage 37:41 – Disability vs avoidance as a coping strategy 39:13 – Realistic goals and self-assessment 40:08 – Self-fulfilling prophecies and sabotage 41:31 – Choice, agency, and accountability 42:22 – Core beliefs and self-worth 43:34 – Forgiveness, mistakes, and lovability 45:24 – Awareness as the first interruption 46:03 – Self-sabotage as predictability and protection 47:25 – Leaving before being left 48:37 – Encouragement and counting progress
––––––––––––––––––
This episode is especially helpful if you've been told you're "bad at empathy," feel helpless around grief, or recognize patterns of self-sabotage you're ready to change.
Kim's website: https://www.kimpolinder.com/
Kim's Instagram: https://www.instagram.com/kp_counseling/
Kim's YouTube: https://www.youtube.com/@engineeringlovepodcast