"Should I Tell My Coworker She Hurt My Feelings? Help!"

Summary

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

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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.

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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]

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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]

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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.

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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]

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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]

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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.

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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.

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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.

Transcript

[A]

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[B]

This is Help Wanted, the show that tackles all the big work questions you cannot ask anyone else. I'm Jason Pfeiffer, Editor in Chief of.

[A]

Entrepreneur Magazine, and I'm New York Times bestselling author and money expert Nicole Lapin.

[B]

The helpline is open.

[C]

All right, Jason, I'm going to read you a super, super embarrassing. I don't even know if I could do it. I might have to have Morgan read it because it's just like my armpits are already sweating.

[B]

I'm so excited. I don't even know what you're talking about yet.

[C]

It's an email draft for a hard work situation I was in that I smartly left in the drafts folder.

[B]

So this is something you wrote to somebody else?

[C]

I wrote to someone else and I didn't send it.

[B]

Great.

[C]

But I want to know what you think about it.

[B]

Okay.

[C]

And I want to know what of this. I don't know if I can do it. You would change or how you would make it better, which would be like starting over, I think. But here goes.

[B]

That sounds great. I'm very excited. I also, and I genuinely do not know what you're going to send me And I don't even know the hard situation. So I'm learning all this on the fly, folks. But I'm going to stand in praise before we go any further of writing the email and then not sending it.

[C]

Write it dirty, write it, write it nasty.

[B]

Yeah, Just get it all out. Just be the asshole. This is a powerful thing that people should do. Sending the email, almost always a bad idea. Writing the email emotionally, often a very good idea.

[C]

Okay. Yes, totally. For your own mental health.

[B]

Is there a question about whether to send this?

[C]

No, I know not to send it.

[B]

Okay.

[C]

But I wanted to. And so I think the question is where and when should you bring up feelings or emo in work situations? Like, I can't dissociate from how I feel. Like I feel very deeply. It's all very personal.

[B]

Yeah.

[C]

And so pretending that it's not is merely pretending and merely trying to up my bq, I guess.

[B]

Your eq. Are we talking about eq Emotional intelligence.

[C]

Yeah, but I made it like business intelligence.

[B]

Oh, you just made it confusing.

[C]

All right. Anyway, yes. In other words, when do we send emo emails? Are emo emails ever appropriate at work?

[B]

Or maybe the question is, we agree, don't drop the email bomb. Like don't, don't send that first thing that you write. But when there are things to talk about, what do you send?

[C]

Yeah.

[B]

Okay, great. Let's hear this email. What context do I and our listeners need for understanding this?

[C]

So here's what you should know. This was a potential business partnership where the contract was almost signed. There was a ton of back and forth with lawyers, but we had already put time, money, and energy, like more money than I would do now into this project in good faith.

[B]

Yeah.

[C]

That the contract was going to be signed. So we had agreed, like on a handshake to the spirit of the deal, but we hadn't figured out, like the long form, which often happens in entertainment type working relationships where you're like, okay, cool, we will get the lawyer stuff done. Let's start the project.

[B]

Yeah. And not just, not just entertainment, for whatever it's worth. I mean, I, I have been involved in many a business transaction where a bunch of work happened before the paperwork came along. And you're doing that because there's some amount of mutual trust that's been built that both sides are committed to getting this thing done. So I could. I understand. So this, you put a lot into it and clearly it went south.

[C]

Right. And we were friends.

[B]

Which is even more complicated.

[C]

Which is more complicated.

[B]

And I just want to note the way that you phrase that we were friends. Are we talking in the past tense?

[C]

I caught it as it was coming out of my mouth. I don't know if we would go hang out right now. I wouldn't call her an enemy, but we're friends for context of this and potentially past tense.

[B]

Okay.

[C]

And so she in. After almost a year of us working on this in good faith, she was like, actually, I can't accept your offer. And it wasn't an offer at that point. We're already half pregnant. We were already in this. It wasn't like we're going on a first date.

[B]

Right. Okay. I hear it. A lot of disappointment. A lot of like lost resources. Lost emotional energy.

[C]

Yes.

[B]

Lost possible friendship. Okay. Here. All of which is going to get crammed into a real barn burner of an email. Okay.

[A]

I don't.

[C]

I have a few of these email drafts, but Morgan sent me one that we were contemplating, so. Hi. Let's just say, Jen, I've been thinking a lot about you and this. I am personally pretty bummed it has gotten here. I have been a longtime fan and friend who has always aimed to support you in any way I can. As a self funded female owned and run business, I was hoping to receive the same support. While business is not a sorority, I believe there should be a level of trust and respect for relationships like this. While I think a conversation is the best next step so nothing is lost over email. I will say this. Since we started working on your project, I've already incurred about $10,000 in costs. That is a lot of money for us. In parentheses. I used my life savings to fund this company and was spent on the basis of the good faith that the legalese would be worked out. I believe it still can if we both feel like that's the best way to move forward. I've added notes to all of your points below which seem very figureoutable. It's just factually not correct that we haven't compromised on this. Not only do we have one of the most generous talent friendly contracts in the business, I often negotiate against myself for the talent's greater good because I understand the nuances better than anyone. I believe strongly in the power and need for brilliant, airtight contracts, but I believe more deeply in the power of relationships. I am not in this to screw anyone over, especially you. I am not a big network yet. And the person on the other side is me. Hi. I would play in traffic for my friends and my people if anything were to happen that you were Unhappy about. I am confident that we would talk about it, work it through fairly without lawyering. Part of starting a network was that I got to choose who I work with. So I picked a team with that level of respect and trust. Top of mind, I promise. I'm almost done.

[B]

No, this is great. Keep going.

[C]

At this point, this is too much lawyering for what it is. If these points are an actual breaker for you, most of which I'm happy to tweak or strike in your legal favor, I can eat the upfront costs I put in with all the good faith I thought we agreed on and all my heart and move on. Hopefully we can part as friends. I do believe working with friends can be amazing. And I'll never regret reaching out to you for this. You. Even though it's gotten complicated, I contemplated my response to this every day since you sent it. I vacillated between including and not including emotion in it. I finally concluded that not including any emotion wouldn't be honest. And while some people might not care for that style, it's just not how I want to do business. Emotion, heart, and the rest of it don't have to be mutually exclusive with running a killer company, which we have and will undoubtedly do. Wow. So many feelings.

[B]

So many feelings. Okay, so first of all, that was not the email that I expected. The last time that I wrote an angry email and hit send was in college and it was to Marty, who was my co editor at the student magazine, who had done. I can't even remember what. And I was very angry about it. And. And the only thing I remember about that email is that it contained the words, you have fucked me. And. And you know, I. I did not feel good about having to see him when I saw him next after having hit send on that. So I was expecting that, Nicole. I was expecting the email to open up. Dear Fuckface, you have fucked me. Fuck you, Nicole fucking Lappin. It wasn't that, though. It was actually kind of lovely. Like I. Tell me, tell me what the. Tell me about this email.

[C]

So this email came from a place that I felt, you know, personally screwed by this woman that I respect. And I don't put money into people's projects or funds or companies very often, but I actually gave her money. Yeah, for her company, which was quite a lot of money. And honestly, I don't know why I did it at the time, but it was one of those situations where I believed in her, I was friends with her, I felt like it would be fun to work with her and I thought that when I signed her contract, I was in the hospital. I had that weird throat thing. I remember during the pandemic, she called me personally to expedite it. Like it was over Christmas and it needed to be done by the beginning of the year or whatever. And I ended up not even sending it to a lawyer and just signing it, which is bad on me. These are like things that I live, learn and I'm not proud of in hindsight. But for the context, I felt so crushed that fast forward we were doing a project then I also invested money. You know, we don't have a huge coffer.

[A]

Right.

[B]

Sure. Not made of money.

[C]

And then when we were going through the contract, it couldn't have been further from the experience that I had where I just signed it.

[B]

Yeah.

[C]

Probably the sweet spot was somewhere in between. She could have not nitpicked on every little thing and, and had us incur lawyer fees, which is hard for a startup to incur anyway.

[B]

Yeah.

[C]

And so I just felt screwed. And I felt like, yeah, Jen, like you fucked me. I wanted to say that, but I was so. I was like crying. I was hurt. I would just. So I would like I bled on the page.

[B]

I have to say. Stick around. Help Wanted. We'll be right back. Welcome back to Help Wanted. Let's get to it. I thought that was a very nice email. It was very well composed, it was thoughtful, it wasn't defensive, but it explained where you're coming from. It was generous towards this person and continued to show throughout that you wanted to make this work. You, it was, it was a door, I thought a door opening email. Which is why I am very interested in why you would. I'm not saying that you should hit send on this exact email right now, but like, it, it, it wasn't the, you know, I made this joke before you started reading it, like we were going to read a barn burning email. Nothing was burned down by this email. And this is an email that tries to build things. So before we get to this kind of next question of, well, what do you, you know, you had said we want to get to. Well, how do you introduce how you're feeling to another person that you're working with? Like, when is it appropriate to do that in this case? I really do feel like you were trying to respect every part of what was happening here. This wasn't just a business interaction. This was a personal interaction. You had to deal with the parallel strains of a friendship and of partnership, potential partnership. And you were consistently saying, I will compromise I will compromise. I will compromise. I will compromise. This is valuable to me. One of the markers I think, of whether or not to hit send on an email is if that person forwards the email to other people. Do you look terrible? And in this case, I just kept picturing her forwarding the email to people. And you just keep looking good. Like, I just don't see how someone would be like, Nicole, definitely don't work with her. Writes an email like this, like there was nothing in there. I mean, I really do think, because I've used this for myself when I've written emails, and I thought, if this person forwards this to anybody, am I unhappy about that? And that's. That's a good filter. That's usually when I say this will never be sent. What is the part of that email that you would be afraid for people to see?

[C]

Yeah, I had an ex who would never put anything in writing, whether email or text or something, if he wouldn't feel comfortable with it being printed in the Wall Street Journal or something like something like that. Where, you know, whatever industry you're in, like, having a benchmark for sending anything, I think is really important. And, like, the farther you get in your career, the more litigious people are.

[B]

As you know, I. I do.

[C]

And discovery happens and all sorts of stuff.

[B]

All the same, I thought that you wrote a really thoughtful email, so. Oh, wow. Thanks, Jason. I don't know. Tell me about why you're not sending that.

[C]

I just felt like it was tmi. It was really emotional. It was really in my feels. Yeah, it didn't connote, I guess, like, power and bq. Like, I didn't. It felt. It felt like it was. It was a BS type, like something you would send to, like, a person you were breaking up with, like, significant other before you got a lot of therapy.

[B]

Well, yeah, I mean, if you. This is why, like I say, it's a. It was a really good email. I wouldn't hit send on it just like that, but because it is. It is quite a lot. And I would want to spend. If I were you, I'd want to spend time, read it fresh. A couple different. At a couple different points. I'm channeling another gen here, a real gen, which is my. My wife, not the hypothetical Jen that you just wrote to. Because I have shown her many an email of something that I ultimately didn't send, and a good piece of feedback that she gives me is, what do you want to happen as a result of this email? And then let's stick to that. The really useful thing about that framing is it eliminates emails just for the sake of telling somebody you're pissed or whatever, because that doesn't get you anything. There's no. Nothing happens because of that. And certainly once a door is shut, there's no point. If somebody screwed you and it's over, why send the email? What do you want to happen from this? They feel bad. They're not going to feel bad, so it doesn't matter. But in this case, at least based on this email, you tell me if it's incorrect. But based on this email, what I was hearing was maybe there's still a way to get this deal done. And if that's true, then maybe there's a reason to send some version of this pared down because there's. Yeah, there's a lot of drunk crying Nicole in there, but I think that some of. I think that some drunk crying Nicole is okay. Because you're. You're respecting, in doing that. You're respecting that you guys are friends, too. It wouldn't be an email to send to a total stranger who you were trying to work a contract out with, but you guys are friends and she knows that. I think it's perfectly acceptable that that is part of the conversation. And so I don't mind some of that emotion, but what I want to make sure you're focusing on is what is a realistic potential outcome that could be driven towards. Because ultimately that's the only reason to send something like this.

[C]

And that's. After a few days, what I thought I needed to fast forward the videotape or however we watch videos now, the Netflix show, and say, like, okay, well, what's like the next move from her after that? Like, what are her now choices? And then do I like those choices? And maybe I just don't want to work with this person at this point. And so to. To sort of echo Jen's point, but in a different way. Like, something I've been thinking a lot about is like, keep the main thing. The main thing. Like, what is the main thing that I wanted to get out of this? And I needed to decide that for myself. And so the first draft of this, yes, was drunken emojis, like feelings, all the rest, but it was devoid of what my goal was. And so I needed to figure out what the goal was first and then reverse engineer to figure out how to get that goal as quickly as possible.

[B]

Yeah.

[C]

And ultimately what I decided was success from this next exchange was not working together and trying to get the money that I Invested pay back to me.

[B]

The $10,000 that you reference in the email. Yep. Okay.

[C]

Because in the course of business, that would have been fair if I. I put, you know, production costs or whatever into this project with the understanding that it was in good faith. I wanted to also leave it in a. In a way that we are cool. That was another goal of mine, so that's what I ended up doing. Should I read the one that I sent?

[B]

Oh, oh, oh. I didn't know that. I didn't even know that that was the next part of the story. Okay, so you wrote an. You wrote an email with an outcome that is unrealistic.

[C]

So spoiler alert, it worked out.

[B]

Oh, you're jumping all over the place. Okay. You didn't send that email. Instead, you sent a different email. I would love to hear that email.

[C]

All right. This was after, like, four other iterations of drafts going through, so then I ended up writing. 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.

[B]

That is a much tighter email. And on that, she reimbursed you.

[C]

And on that, the wire was sent the next day, which is the fastest I've gotten paid in a long time. And let me see, what. Is she right? Her response was, we will wire this to you on Monday. Meant to get it done this week. Keep rocking. Exclamation point.

[B]

Well, okay. How do you feel about that? Much shorter but more profitable exchange?

[C]

I feel great about it.

[B]

Good. I think you should.

[C]

Thanks.

[B]

The thing is, if we go back to the filter of what do you want to get out of this? What you wanted to get out of it when you sent that final email, the one that you actually hit send was two things. You wanted to maintain the relationship. It may not be as strong as it once was. It's going to require some work or time or something. And he wanted your money back. And what you wrote was perfectly acceptable. It was pretty to the point, but also it, you know, I mean, like another way of saying it was, hey, well, didn't work out. That's really too bad. I would have liked it to. I still like you. I hope you like me. Let's move on from this. Also, I need my money. Thank you, Nicole. Right. And she basically wrote, confirmed, confirmed, we're good, here's the money and everyone's going to move on. Now there's a missing piece here which is you telling her how hurt you felt and all that. And I think that in this case that can all come later if it serves a purpose. Like again, like, what do you want, you know, what do you want to get out of it, right at this point, what you wanted to get out of it was just keep the door open, do not create an enemy, get your money back. That was great. 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. And she will say, I am really sorry about that and here's what was going on in my life at that moment or whatever the hell she'll say. And, and that will be a time in which that information drives for the right outcome, which is a restoring of the relationship. But that kind of wasn't the moment that you were in right now. The moment that you were in right now was, let's just end this chapter and get it in a nice tidy bow and just keep the door open and like we'll get to the next chapter or some later time. And I do think that people make the mistake of just trying to bundle it all together where like they just feel like if I'm hurt or if I'm upset or if I'm angry or something, that 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 at the moment just be binary, which is like I, I would like to maintain a friendly relationship with you, or I don't, which, you know, could be fine. But you want to, you want to signal that. So I think that had you wanted a different outcome, had you wanted to throw yourself at the chance of making this thing work, then that other email in a pared down way with a little bit of, hey, I'm really bummed about this, but I also really want to make it work and I really care about whatever could have worked. But if that wasn't the outcome, you had a different outcome, then you served that outcome and I think you served it well. And my hats are off to you, all of them. I don't know what's the hats off to you? All the hats.

[C]

Is there ever a hat to be taken off for a you me email. Is that what you wrote? You fucked me.

[B]

You. Me, Marty, who is very nice.

[C]

There's a spectrum, it sounds like, of emotion to include. Yeah, you know, within business, it sounds like. But never, you fucked me, Marty.

[B]

I cannot think of a appropriate use case for you fucked me. Unless. Unless the outcome that you really want is driven by that language. Right? Like, think about it like, you want.

[C]

A lawsuit, you're just itching. It's on your bucket list. Like, I want to be sued.

[B]

You just want a person to not like you, and you want a reputation as someone who says that kind of stuff. And you know what? For some reason, there are people in this world who want that. But I think there are a lot of people who accidentally stumble into that because they just let their emotions lead and they're not stepping back and thinking, what do I actually want out of this? Because you will be and you will get whatever it is that you write. So if you write, you fucked me to everybody, then you'll become known as the person who is irate and says crazy stuff and that people don't want to work with. And if that's what you want, then by all means, go fuck yourself. But otherwise, I think you go with the Nicole Lapin philosophy. Help Wanted is a production of Money News Network. Help Wanted is hosted by me, Jason.

[A]

Pfeiffer, and me, Nicole Lapin.

[C]

Our executive producer is Morgan Lavoy. Do you want some help? Email our [e-mail] for the chance to have some of your questions answered on the show. And follow us on Instagram, Instagramoneynews and TikTokoneynewsnetwork for exclusive content and to see our beautiful faces. Maybe a little dance?

[B]

Oh, I didn't sign up for that.

[C]

All right, well, talk to you soon.

[B]

Sam.