Episode 60: I Know Exactly How You Feel?

Creative Work Hour Podcast

Air Date: July 19, 2025

Crew: Greg, Alessandra, Devin, Dr. Melanie, Ellie, Gretchen, Hillary, Shadows Pub, Wai Ling

In this episode, the Creative Work Hour crew dives into the complexities of empathy and listening—what really helps when you share a struggle with a friend? The team explores why the classic “I know exactly how you feel” can miss the mark, offering personal stories and practical advice for responding with real presence and care. The conversation also touches on emotional intelligence, active listening, and the skills needed to support others (and ourselves).

“Sometimes people mean very well when they say, ‘I know exactly how you feel,’… but it can be very dismissive; it shifts the focus away from you and your struggle and onto them.”

Greg opens up about the pitfalls of assumed understanding and stresses the importance of genuine empathy.

“Do we have the kindness skills to be with someone who may be hurting or struggling?”

Highlights how creative people pride themselves on emotional sensitivity but still struggle to listen well under stress.

“A good movie line often just captures a whole concept or sentiment.”

Shares how humor and pop culture references can lighten tough conversations—but warns against one-upping or minimizing another’s pain.

“My first tendency is to fix it. And that’s not always the best first step.”

Reflects on the urge to offer solutions and the greater value of simply being heard.

“The second that somebody’s following advice about how to respond, it means that they’re not actually tuned in and it falls flat.”

Points out that real listening is about presence, not technique—stock phrases rarely land well.

“It came to a point where I would say, ‘I don’t want a solution. I need you to listen.’”

Shares a hard-won, practical approach: ask what the other person needs (support, ideas, or just to vent).

“Active listening is a skill. Not waiting to reply but to marinate in what they said… that’s when somebody feels heard.”

Emphasizes clarifying questions and the value of Toastmasters for practicing these skills.

“I’d want to see some indication that I’m not only being listened to but that I’m being understood.”

Notes the power of feeling truly understood, not just heard.

“Listening is really a gift that you can give… people should be comfortable with silence.”

Advocates for active listening, emotional intelligence, and holding space without rushing to fill every pause.

Closeness doesn’t guarantee understanding: We’re often less accurate with those closest to us due to “closeness-communication bias.”
Avoid empathy pitfalls: These include projection (“I know exactly how you feel”), comparison, “one-upping,” jumping to solutions, and assuming you understand.
Better habits for supporting others:


Listen actively and without distraction.
Ask open-ended or clarifying questions.
Validate feelings instead of immediately reframing or fixing.
Respect silence; don’t rush the conversation.
Offer support tailored to what’s needed—sometimes it’s advice, sometimes just space.



Communication is a two-way street: The person sharing can help clarify what they need; listeners can ask directly.

Greg’s Blog Post: “I Know Exactly How You Feel?”
Toastmasters International: toastmasters.org
Center for Nonviolent Communication: cnvc.org
Find A Helpline (Global): findahelpline.com
988 Lifeline: 988lifeline.org

Share Your Thoughts: What response do you find most helpful when you’re struggling? Leave us a comment or send us an email!
Try Active Listening: Next time a friend shares something tough, ask what they need—advice or just an ear—and notice how it changes the conversation.
Explore Toastmasters/NVC: Want to improve your listening and speaking skills? Check out Toastmasters International or Nonviolent Communication resources linked above.
Read Greg’s Blog Post: Dive deeper into today’s topic with Greg’s article on empathy and communication mistakes.
Join Us Next Week: Subscribe and return for our next episode—reach out with your own questions or suggested topics!

Visit us at creativeworkhour.com for more episodes and resources.

This post challenges the common phrase, “I know exactly how you feel,” revealing that true understanding is often more complicated, especially with those closest to us. It highlights research on the “closeness-communication bias,” showing we’re actually more likely to misunderstand loved ones than strangers. The post emphasizes that real empathy isn’t about assuming or mind-reading but about listening and being present. Key takeaways and tips include:

Closeness can make us overconfident and less accurate in understanding others.
Common empathy mistakes: projection, comparison, “one-upping,” jumping to solutions, and assuming understanding.
Better communication habits: listen actively, ask open-ended questions, check understanding, validate feelings, and avoid unsolicited advice.
Genuine listening builds trust, emotional safety, and stronger relationships.

Read the full post

Toastmasters International is a nonprofit educational organization that helps people improve their public speaking and leadership skills through a worldwide network of clubs. The Toastmasters website offers resources for personal and professional development, including information about joining local or online clubs, public speaking tips, and access to Toastmaster Magazine and webinars.

Whether you’re looking to boost your confidence, advance your career, or become a better communicator, Toastmasters provides supportive environments and proven programs to help you reach your goals. Learn more or find a club.

Nonviolent Communication (NVC) is an organization dedicated to fostering compassionate, empathetic communication in personal, professional, and community settings. Founded on principles developed by Dr. Marshall B. Rosenberg, NVC provides resources, training, and workshops worldwide to help individuals resolve conflicts peacefully and connect more deeply with themselves and others.

The official website offers information about the NVC approach, upcoming events, certified trainers, and practical tools to support nonviolent, effective communication in daily life.

Learn more about NVC

If you or someone you care about is struggling or in a crisis and needs help, here are a couple of resources that may be helpful:

Find a Helpline – Global Support 24/7
988 Lifeline

All spelling and grammar have been corrected. Formatting is organized for clarity and accessibility; all original content has been preserved.