‘Was It a Bad Idea to Work for My Friend?’

Esther Perel is a psychotherapist, a best-selling author, and the host of the podcast Where Should We Begin? She’s also a leading expert on contemporary relationships. This column is adapted from the podcast — which is now part of the Vox Media Podcast Network — and you can listen and follow for free on Apple Podcasts or wherever you listen.

When a childhood friend of this week’s caller opened a bookstore in 2019, he asked her to work with him and, at first, things went really well. But eventually, “things started to feel hard between us. We didn’t have any systems in place to talk about job performance or anything like that,” she says. “He started to make snippy comments about things he didn’t like, then I would get defensive.”

After a few blowups between the two of then, the caller left her job. They are still friends, but the caller is stuck wondering whether there’s any future scenario in which a professional relationship between the two of them could be smoother. In the course of their conversation, Esther Perel gives her advice for how to broach the idea of working together again with her former boss and revisit what they think worked well as a team, and what didn’t.

Esther Perel: There are many ways I could start this, but just to get a little bit more context, how is your friendship with him now?

Caller: I think it’s okay. We were able to talk a little bit after I left about how we were both sad, but I think that there are things that neither of us will say to each other. I haven’t said I left because I thought you were kind of being a jerk. I haven’t said those words. So there are definitely things unsaid, but in general, we’re in a good place and love each other and have no ongoing conflict.

Esther Perel: Have you had an actual debriefing conversation? What worked? What are things that we overlooked? What are things that we didn’t communicate about well? What are KPIs that we may have missed? How did we let the blending of the friendship and the feelings enter into a conversation that then could not address issues of competence and performance and outcomes and goals? You don’t tell your boss he’s a jerk, you know?

Caller: No, no, no.

Esther Perel: And he was your boss. And that does not say much. It just means you didn’t like what he had to say. Have you had a professional off-boarding conversation?

Caller: No, we haven’t. I think we tried to do something like that, but to hear you say the word professional was striking to me because I don’t think we ever figured out what our professional relationship was.

Esther Perel: Correct.

Caller: So we’ve talked about it more as friends than as colleagues or co-workers or professionals.

Esther Perel: You remind me of an episode that I did with three men who had been playing together since they were young children and that play turned into a production company. They, too, struggled with the formalizing of expectations, of boundaries, of accountability, of communication flow, of initiatives — things that are not necessarily defined in a relationship, even though they are often implied in a friendship, they’re not made explicit. If you ask me, “Do you think there’s a chance this could ever happen again, that I could work with him?” I would say, yes, potentially, but it requires this transition.

I was not very professional. I became defensive. I thought if we like each other, we should overlook these things. I didn’t really like the sudden shift in power dynamic. And now you get to evaluate me. I don’t get to tell you what I really think because you are my boss. All these things need to be formalized and clarified if you ever want to have a professional relationship with a friend. You’re trying to integrate these two things. It’s not just two friends working together.

Caller: I hear about couples who have businesses together, and I really can’t even understand how that could possibly happen. I do think there’s probably some resentment on my part. Since he was the leader, the boss, I think I was waiting for him to do things like establish job-performance systems, you know, stuff like that never happened. Maybe I used that as an excuse not to rise to a more professional level.

Esther Perel: Does he do it now with the next person?

Caller: Not that I know of. He’s been very slow to hire new people. He hasn’t really replaced me. He’s sort of drowning there at the bookstore by himself. He has a few part-time people.

Esther Perel: So if you came to him and you said, “I want to take accountability for my part. I kind of left it up to you. Since you didn’t come, I didn’t push. And I think we have a lot that we can learn from this. Should we sit down and just to do a debrief together? We can see if there’s ever an opportunity to try this again.”

I think it’s a very interesting thing to rehire people whom we let go or who left. It can work very well. I’ve done it. But it demands a clarification of defining the terms of the relationship, a clear set of expectations, and a willingness to be very professional and not to try to diffuse the professional because we are friends. Which I think is what I’m hearing you say.

Caller: I think I don’t really know how to do that. I don’t really know how to be professional with my friends.

Esther Perel: So tell me about you in the new job.

Caller: I work at a school now. I’m professional there, for sure.

Esther Perel: What is being professional for you?

Caller: I guess it means I’m always focused on the work and why I’m there, and acknowledging the hierarchies that exist in my place of employment.

Esther Perel: You show up.

Caller: Yes, right. I show up on time, I stay until I’m supposed to leave. Yeah, I do all those things. I did that at the bookstore too.

Esther Perel: Okay. So where would you say were your lags in the bookstore? Where were the leakages?

Caller: I think the power dynamic was a struggle for me. I wasn’t sure how much freedom I had to be creative and share my own thoughts and ideas and where I was meant to do as I was told.

Esther Perel: Is that a question that you ever were able to bring to him? Did you have regular meetings set in the calendar where you looked at things from inventory to work culture to store culture—

Caller: We didn’t have regular meetings because it was just the two of us, so all of our conversations were just folded into while we were both just standing there.

Esther Perel: Stacking the books.

Caller: Exactly, yeah.

Esther Perel: And this question — in between conversations, were you able to ask him? Is there an opportunity for me to share some of my ideas? I have some thoughts about how we could do this or …

Caller: I’m trying to think. I’m not sure how to answer that. I think I feel intimidated by him. He’s very smart. He’s one of the smartest people I’ve ever met. I think sometimes I just defer to him. Then he was my boss, so I defered to him. Sometimes I would have ideas that he would sort of pivot away from and just end up doing his own idea instead. I think I just got the message or interpreted some message that maybe my ideas weren’t so valued.

Esther Perel: Imagine that you have an opportunity to meet him and to just start the conversation. “I was talking to this lady on her podcast. And the reason I brought this up with her …”  What would you say?

Caller: I would say I brought it up because I wish things had gone differently. I wish we could have figured out how to be friends and work together.

Esther Perel: And that was really sad and a disappointment to me.

Caller: It was very sad. It was sad to him too. He was very sad when I left. And very surprised when I told him I was leaving.

Esther Perel: So he may not even know half of what went through your head. “As I was talking to her, I thought, we really need more conversations about this. It’s a pity. We’ve known each other our whole life. If we can’t have this conversation, who can? So, here are things that I’ve been thinking about that I really would like to think out loud with you and I would love for you to talk to me as well because I think there may have been many misunderstandings, many unspoken moments, many things left on the cutting room floor. Here we are, a little bit dazzled at this thing just unraveling like this. Neither of us have actually really done a post-mortem. So I told this woman, Esther Perel is her name …”

Caller: We have your book at our bookstore, so he knows you.

Esther Perel: All right. “Remember that woman in the book? I went to talk to her. And here are the things that stood out for me that I realized that I have not really had an opportunity to share with you.”

Caller: Then it’s my turn? Okay. I never figured out how to be a professional with you, I never quite figured out our roles, our boundaries, how our relationship needed to evolve to be a healthy working relationship. So consequently when you tried to talk to me about things that you wanted me to work on, it felt like my friend criticizing me, and I felt defensive and didn’t act my best.

Esther Perel: When I did what?

Caller: When I snapped at you. When I got mad at you for giving me instructions.

Esther Perel: I’m going to role-play him: Did you hope that when you said I’m leaving that I would beg you to stay? And put our friendship above our collaboration and run after you?

Caller: I was hoping that you would try to figure it out with me, that we could figure out together how to make it work. I wasn’t playing a game. I wasn’t hoping that you would talk me out of leaving. But I did somewhere hope that it would be the impetus for change between us.

Esther Perel: But you didn’t come to me saying, “We need to talk. This isn’t working out very well. We can do better.” You had a fit, then you told me “I think I should go.” That was your dramatic exit. I don’t like to force people to do things they don’t want to do. So you didn’t give me a sense that you wanted to work something out. You gave me a sense that you are upset.

Hot or cold?

Caller: So here’s what I did. This sort of last instance, when he snapped at me about something, it was Black Friday. It was a stressful day anyway, so I give him that, but I blew up. I got very angry. A couple days later, I came to him and apologized and said, “I should not have spoken to you that way. I was very stressed out.” I sort of took responsibility for my part of it. And he didn’t really say much. I just got the impression that it wasn’t going to be possible for us to have in-depth conversations like I wanted to based on his response to my apology. He just doubled down on his initial complaint. That is when I thought, I don’t think things can change. I think I should leave.

Esther Perel: Because?

Caller: I didn’t say it right then.

Esther Perel: So he reminded you why you had snapped rather than showing you appreciation for your taking responsibility. And what did that represent for you?

Caller: I wasn’t looking for appreciation, but I was looking for him to say something about, maybe I shouldn’t have said that in the way I said it, or perhaps like we could have talked about it at a different time — just some acknowledgement that the communication between us on both of our parts was not excellent. When it didn’t even seem that he could see that, I lost hope.

Esther Perel: But you’ve known this man your whole life. Is this the first time you have a misunderstanding, a skirmish? A moment when you do something that you think is for the benefit of the relationship and you feel that he’s talking for the benefit of the point he’s trying to make rather than protecting the relationship?

Caller: I think we had never had an opportunity to really have a skirmish like that where we both were so invested in something.

Esther Perel: In being right. When two people are invested in being right, then what? Finish the sentence.

Caller: I don’t know, someone has to, someone has to say “I was wrong.” Both people can’t be right, I guess. I don’t know the answer.

Esther Perel: What did you think when he continued to say why he thought he was justified in being upset or bad? What made you give up like this? You could have said, “I know this guy, I know how he gets” or “It’s not worth it, our relationship is more important.” What parts of each of you got uncovered there that it became so reactive?

Caller: I think he is not that willing to talk about his inner life. It’s weird because the way I responded to him when he would tell me things was not the way I would respond to someone who I hadn’t known for 30 years. I would not have snapped at someone who was only my boss, not my friend. So the repair I had to do with him was also not the kind of conversations I would typically have with someone who I only had a work relationship with. I had never had such intimate conversations with him. His stubbornness, the wall he put up — I didn’t see how it could work. I couldn’t imagine a scenario where we could go forward and the wall would be down and we would act like professionals but could still be friends. I couldn’t figure out how that could be possible. I didn’t think he was ever going to fire me. So I thought, “I think I have to leave. It’s not going to get better.”

Esther Perel: And none of that has been part of the conversation yet. That is not a conversation that you have had even ever since. Correct?

Caller: Yep, that’s correct.

Esther Perel: See, that’s the conversation I imagine. Many of us wonder, Can you work with your life partner? What is the essence of family business? What’s it like when two close friends join forces and start working together and they suddenly realize that co-parenting the store brings out many differences between them? How do we straddle superposing different relationships that have different rules and different frameworks?

It’s a real challenge and an act of creativity and it demands tremendous communication skills. I think all work relationships do, but there is something even more unique when you have an overlap. One minute I talk with you about some very personal things, the next minute you’re evaluating my returns. So lots of us want to know, How do we do this? What’s interesting is that you used your familiarity to allow yourself to react strongly, but you didn’t use your familiarity to actually have the difficult conversations. When I say familiarity, I mean the level of trust, the reliance on the solidity of the relationship. Suddenly you acted as if this relationship is über-fragile. I am curious about that.

Caller: I think I did try to use my familiarity to have conversations with him. But in retrospect, I don’t think I did it in a way that was productive. It didn’t lead to the outcome that I was hoping for.

Esther Perel: For example?

Caller: For example, him saying, “This is hard to be friends and to be a boss and employee. We’re gonna need to come up with some rules or boundaries or go to therapy or take a course.” I really don’t know, but just some acknowledgement that things can’t keep going the way they’re going. Because I didn’t know a way forward. This is all so new to me. We learned about selling books but we didn’t learn about this.

Esther Perel: Yep. And if he was here today, what do you think he’d say right now?

Caller: I think he would say that he’s sad that I don’t work there. That he never could figure out how to talk to me in a way that was productive about performance stuff. In a way that would lead to meaningful change—

Esther Perel: So he was more focused on criticizing than improving. He would tell you what was not right or what he didn’t agree with or didn’t like. But he wouldn’t tell you, “Expect this. You have that many days to do that. This should be the result that we’re hoping for.” Setting projections and goals.

Caller: Yeah. And I think he would probably say something self-deprecating, like that he was a bad boss or something, because he has a lot of negative self-talk.

Esther Perel: Do you think you’re going to use this conversation as a springboard to actually finally have the chat you’ve never had with him?

Caller: Yeah, I think it would be a real waste if I didn’t. I don’t know what my goal is, though, at this point. When I wrote to you, I really wanted to work there again. And now I feel a little bit less clear that that’s what I want. Regardless, we should still have the conversation.

Esther Perel: In order to?

Caller: In order to be better people? In order to learn from things like this. I’ve learned so much from having hard conversations with people where I thought I’m gonna die if I have this conversation, then didn’t die. Being able to talk to someone who you’re close to is an important skill.

Esther Perel: And maybe that’s how you want to start a conversation: I’d love for us to learn from our collaboration. Each of us for our own future but also one in our friendship.

When you started, what did you imagine? What are the things that you felt actually flowed nicely? What are the things that became hurdles? And what did you wish you had done differently; what did you wish I had done differently? What have you done differently since? Because you’ve actually learned something. I think your line about, “We learned a lot about selling books, we didn’t really learn much about being co-founders of the bookstore and to nurture the relationship that was needed in order for the bookstore to continue to grow and establish itself.” The conversation at some point can include: Have you ever thought that we could fix this? Did you think it was defunct? Do you think it was moot? Did you think you would never fire me because you didn’t have the guts to? Or did you actually think this should be able to work?

If you’re my friend and I know you well and you know me well, I shouldn’t have to tell you what to do because if you know me that well, you should know it. That’s one of the things that often happens — we presume the deep inner knowledge that we have as friends and we transport it into the workplace, and it doesn’t work like that.

Caller: I also think starting a small business is so hard and stressful and isolating. He was going through all of that at the same time, not to mention COVID, so all of these things were happening during the first few years of the bookstore. There was just a lot of naïveté on both of our parts about what it would take, emotionally and spiritually, to do this work together.

Esther Perel: The conversation will be a lot more useful if you don’t do it as a blame session, if each person basically looks at themselves and looks at the other and says, “I wish we had … I would have loved it if …” It’s a very different conversation than “you never did … you didn’t tell me …” As a rule, I think between friends, between partners, between colleagues, you can have a breach, then at some point people work their way back into a different collaboration that is much better. So I don’t think once gone forever. But sometimes there’s something very interesting in having created the cut that allows people to actually reflect back on what happened here. Why did this totally derail? What was our naïveté? What have we learned? Then from there, it’s not the same conversation between “should we do it again” or “what happened.” First one is a clearing of the slate.

It would be a lovely thing if you use this session, our conversation, and you say, “I would love for us to listen to it together and use that to start the conversation that we haven’t had.” It becomes a transitional object that you put in the middle. “We both listen to it, and we start this chat.” How is this?

Caller: It’s great in theory. I don’t really know what steps to take next, like, “Hey, do you wanna go for a beer?” I don’t know how to get to the point where we’re talking about logistics, you know?

Esther Perel: “What’s happened to us has been on my mind. I don’t know if you think about it often, but I do. And so I reached out to Esther Perel. It was interesting to revisit it now. And I would love for you to listen to my conversation with her and for us to use this as a springboard into a clearing of the slate together. Would you be open to that? I think we kind of left a lot of things hanging. We have a lot of things unspoken between us. I think both of us care deeply about our friendship and we don’t want it to suffer. If we really trust our relationship, then we need to trust that it’s solid enough that it can tackle this experiment that we had together and help each other understand the other side. We probably have a good idea of our own side, but it’s not clear that we have a good sense of what happened on the other side. If you say no, it’s totally fine by me. I know you’re not a guy who likes to delve deep into your … But I also think that it’s a good thing to do an off-boarding, a kind of a summarizing of what happened here. Because I think we stand to learn a lot together. So I brought you this tape, here’s the link. Here are my three questions for you and I’d love for you to come back and you start next time with your three questions for me.”

So what would be your three questions?

Caller: Oh boy, okay. Will you critique them after I say them? I’m asking seriously, because I don’t know that these are the right ones.

Esther Perel: They can change. I actually think that they can be the broader ones. What are the things that you think actually worked really well? Because we could start with everything that didn’t work. But is that the best way to start? There are a lot of things that worked quite well. How long did you work with him?

Caller:  Four years.

Esther Perel: Okay, that’s a chunk. That is a chunk. It’s not like you stayed there four months. I had no sense it was that long. In the four years, we overcame a lot of things. We actually learned a ton of things. God, opening a bookstore, it’s not like an easy, easy thing to do. So maybe we start with what we did well. Then we continue with what we think we could have done better. Then we continue with what we think we really flunked at.

Caller:  Yeah, I like that. I really like starting with what we did well.

Esther Perel: Yeah, and “what of what we did is still present in the way that the things that the stores run. How much did the launch really solidify the existence of this store? We launched it together.” Those are not questions about “what did you feel when you said this.” We’re not going into that zone at all. It may unfold there, but that’s not where you start. The store is in the middle of the discussion. “The store was our project. The store is what we co-parented and co-founded. We start by talking about our contributions to the store. The store was a dream for each of us. So it’s our contribution to our shared dream. If we were to write a book about the story of two people with a long friendship who want to build a bookstore together, how would we start the story? You came on a day, I was honored that you asked me, it really touched me, and I had tremendous hope that this would work, that this would succeed. I think you’re one of the brightest guys I know.” And from here you continue. It’s a lot of what you’ve already told me, by the way.

Caller: Yeah, I can do that.

Esther Perel: But the recording of our conversation is part of being a stress diffuser because he will already have heard a part of it. And then you basically say it in person.

Caller:  I hope I didn’t say anything that was, I don’t know, offensive to him.

Esther Perel: I haven’t heard anything that was offensive. I heard maybe things that he may say, “That’s not how I see myself, but that’s okay.” Otherwise he’d be standing in front of a mirror rather than in front of another person. They see other things than we see. I don’t know the person, but I didn’t hear anything that was in any form blatantly aggressive, hostile, at all.

Caller: Okay, good.

Esther Perel: But you will listen to it again first. And if you do find something there, you’ll say, “There may be things that I, as I hear them, I’m not so sure that that’s all I think. I said it then, but this is one conversation.” You’re not defined by these words. Neither is your friendship defined by this narration of the story of your friendship and your professional collaboration.