Help Wanted — "Should I Tell My Coworker She Hurt My Feelings? Help!"
Podcast: Help Wanted (Money News Network)
Hosts: Jason Feifer & Nicole Lapin
Date: February 3, 2026
Episode Overview
This episode explores the complex territory of emotional honesty in the workplace, specifically: Should you tell a coworker or business partner when they've hurt your feelings? Entrepreneur magazine editor-in-chief Jason Feifer and money expert Nicole Lapin tackle a real-life scenario from Nicole's professional past, grappling with when and how to communicate hurt, disappointment, and loss in business partnerships. The episode combines lived experience, practical advice, and candid reflection, aiming to help listeners navigate work relationships without tanking reputations or losing money.
Key Discussion Points & Insights
1. The Drafted (But Unsents) “Feelings Email”
[02:27 – 09:38]
- Nicole introduces a situation where she drafted but didn’t send an emotional email to a former friend and business partner after a deal fell through.
- The context: After nearly a year of good-faith collaboration and significant upfront investment, her partner abruptly pulled out.
- Nicole reads her unsent message:
- Focuses on her disappointment, her investment ($10,000), and the importance of trust and relationships.
- Expresses feeling personally “screwed” while trying to maintain professionalism and hope for future friendship.
Memorable Quote:
“I am personally pretty bummed it has gotten here...While business is not a sorority, I believe there should be a level of trust and respect for relationships like this.”
– Nicole Lapin, [06:35]
Jason’s Reaction:
Jason is surprised by how thoughtful the draft is, having expected a “fuck-you” email, but instead finds it generous and constructive.
“This is an email that tries to build things. So before we get to...when do you introduce how you’re feeling...I really do feel like you were trying to respect every part of what was happening here.”
– Jason Feifer, [12:34]
2. Should You Ever Send the “Feelings Email”?
[09:38 – 18:32]
- Nicole and Jason discuss whether and how emotion has a place in work correspondence.
- The "forward-test": Jason suggests a litmus test—would you be comfortable if the email were forwarded to others?
- Nicole shares that she didn’t send the draft because it felt like “TMI" and too emotionally raw.
- The importance of outcomes: Both agree you should ask yourself: What do I want to happen as a result of sending this?
- The value of emotional honesty vs. strategic communication: Save emotional unpacking for a time and context where it serves a concrete purpose (e.g., restoring a relationship).
Memorable Advice:
“What do you want to happen as a result of this email? And then let’s stick to that...it eliminates emails just for the sake of telling somebody you’re pissed, because that doesn’t get you anything.”
– Jason Feifer, [16:22]
3. Honing the Message: Stripping Back to the Essentials
[18:32 – 21:13]
- Nicole refines her goal: She doesn’t want the business partnership to continue, but she does want her money back and to keep the relationship civil.
- She crafts and sends a concise, emotion-free email requesting reimbursement for incurred expenses.
Nicole’s Actual Sent Email:
“Hey, Jen,
Totally understand that you need to get out of our agreement. Super exciting about how much you have going on. I obviously have a vested interest in you doing well with this project that I invested in, so go get them. I’m attaching our hard costs for production and development to date so that we’re not out of pocket here. Hope all else is well and look forward to seeing you soon.”
– Nicole Lapin, [20:41]
- The partner wires her the money the next day, keeping things amiable and professional.
4. Lessons & Strategies for Difficult Work Conversations
[21:13 – 26:29]
Takeaways:
- When hurt at work, first clarify your goal before communicating.
- Emotional venting can be valuable for drafting but is rarely useful in the message you actually send.
- Keep personal communication proportional to the context: Save emotionally honest conversations for times when you can repair, not break, relationships.
- Emails should be written with the assumption they might be shared—the “Wall Street Journal” or “forward” test.
- Sometimes, the feelings conversation is best tabled for a future, face-to-face discussion once emotions cool.
Memorable Quotes:
“There was no reason to go full crying, Nicole. But maybe a year from now you guys will get together and you will have a heart to heart and that will be a great opportunity for you to say, ‘you know, I was really hurt by that whole thing.’”
– Jason Feifer, [23:39]
“People make the mistake of just trying to bundle it all together…if I’m hurt or if I’m angry…the other person needs to know about it. But you know what, they may not need to know about it. What they need to know might just be binary...”
– Jason Feifer, [24:06]
Notable Quotes & Memorable Moments
-
On Writing Angry Emails:
“Write it dirty, write it nasty...getting it all out is a powerful thing that people should do. Sending the email, almost always a bad idea.”
– Jason Feifer, [02:54] -
On Emotion in Business:
“Emotion, heart, and the rest of it don’t have to be mutually exclusive with running a killer company.”
– Nicole Lapin, [09:36] -
On Professional Reputation:
“If you write ‘you fucked me’ to everybody…you’ll become known as the person who is irate…that people don’t want to work with.”
– Jason Feifer, [25:20]
Timestamps for Important Segments
- [02:10] — Nicole introduces the dilemma and reads the unsent emotional email draft.
- [06:35] — Detailed reading of the feelings-laden draft.
- [09:38] — Jason reacts, discusses “forward test” for emails.
- [16:22] — The question: “What do you want the outcome to be?”
- [20:41] — Nicole reads the pared-down, successful email.
- [21:32] — Result: Her money is quickly reimbursed.
- [24:06] — Jason on separating feelings from business outcomes.
Episode Tone
Candid, practical, and empathetic; conversational with moments of humor and authentic vulnerability. Both hosts balance emotional intelligence with hard-won business lessons, encouraging a healthy boundary between feelings and professional communication.
Summary for the Busy Listener
Jason and Nicole help listeners navigate the tricky intersection of hurt feelings and professional life. Through Nicole's real work quarrel, they unpack how to process emotion privately and communicate strategically, reminding us that the best outcomes rarely come from impulsive, emotional emails. The key: Know what you want, wait before you send, and keep the “forward test” in mind. Save the rawest truths for trusted, private moments—or perhaps, never at all.