I was chatting with someone on my team the other day. She’d been listening to Episode 149 (why we should all want our friends to have robust social lives, even if it’s without us).
She said, “Yeah, you know, it IS so great that you want your friends to have other friends. And I love that idea. It sounds like the dream. But I really don’t know how you go from where I am now—where that’s not really acceptable in our friendships, where there’s some jealousy under there—to what you describe in that episode. It just seems like it would be so hard to get there. And it feels like we’d really rock the boat.“
Basically, she was telling me: there’d be conflict. It would be uncomfortable. She just couldn’t imagine the journey to get there and still stay friends.
And of course, I did what I tend to do. I dropped into what people call my “friendship mode.” I’m analyzing what she said. Clicking all the pieces together in my head. Thinking through her situation.
And my first response was: “Hey, if my episodes make it sound like every friend transition I have is seamless, then I really messed up here. My apologies to you. Seriously.”
Because these transitions are NOT seamless at all.
There are definitely hurt feelings sometimes. There are definitely frustrations sometimes. There are fights. There are periods where two friends really aren’t talking to each other until a bigger conversation happens. Sometimes it’s uncomfortable.
Now, this isn’t ALL the time. That’s why I think I don’t push it. It’s not like we’re having blow-up fights. But there are definitely times where I show up to a friend hangout and I can tell that some sort of shift happened. Somebody has some thoughts about it. Maybe they’ve been staying up a little too late at night thinking, ruminating on whatever this shift was. And they have something they want to say.
And it’s like, “Okay, we gotta say it. Tell it to me. What is your frustration? What do you not think is right? How are you feeling?”
Maybe they agree we need to make this shift in our friendship, but they still don’t like how it feels. They’re dealing with maybe some jealousy. Or it’s giving them a hit to their self-worth. They feel like they’re not a good friend.
I don’t know what it is. Could be anything.
And we talk about it. We have a civil conversation. Normally, it’s just a PIECE of our hangout.
If I think back to the last one of these I had, I was out shopping with a friend. We were wandering through a store. We’d spent over an hour just having a normal hangout. I could tell she really wanted to talk about something. I asked her what it was and said I was open to hearing anything.
She gave her perspective. We probably talked about it for 20-ish minutes. Just as we’re wandering the aisles. We’re having a “Hey, this is how I feel. This is how you feel” conversation. And then we were like, “Okay, let’s check back in on how we feel about this next time.”
We probably checked in for five minutes the next time we hung out. Then we checked in again the next time.
The point is: if I have made it sound like all these transitions, all these changes in friendship culture are seamless and there’s no conflict, that’s not true.
But it’s also not these big fights all the time.
The Unspoken Rule We All Follow
I think there’s this unspoken rule that a lot of us have. Somewhere along the way, we started to believe that a GOOD friendship, a TRUE friend, a REAL friend is one that always FEELS GOOD.
Those transitions, changes in our friendship culture, growth should always be seamless. Conversations should be easy. No one should ever be upset.
That’s what I mean by “feel good.” Easy transitions. Easy conversations. No one should be upset.
And I think that for a lot of us, that has become the filter for our interactions.
When I was listening to my teammate talk, she was like, “To get from this place where we have some jealousy about hanging out with other friends to what you’re talking about—where it’s okay to even just say, ‘Hey, I hung out with one of our closest friends without you last night’—it just feels like I don’t know how we get there without a bunch of conflict.”
And I said, “Well, there probably WILL be some conflict. It doesn’t need to be these big blow-up fights. But there will probably be some conversations you have to navigate. And if our filter is that we never want to have those conversations, that’s going to make it really hard to shift anything in our friendship.“
The more I dig into this, the more I think there’s something SPECIFIC to friendship here.
Because I don’t think we apply this standard to romantic relationships or familial relationships.
In romantic relationships, there’s almost this BADGE OF HONOR when you talk about doing the work. It’s very common to say, “Yeah, we’ve been together 16 years. It’s had its ups and downs. We’ve had periods where we’re the most in love we’ve ever been, and periods where we feel like roommates. Hard periods and really great moments. But through it all, we have worked SO HARD with each new version of ourselves.”
If I told you that, you would celebrate me. You’d probably be like, “Yeah, that’s how a relationship SHOULD be.”
With family, we accept that “it’s complicated and sometimes it’s hard, but it’s worth it.” So again, it’s very openly acceptable to know there are probably going to be some rough patches. You’re going to have to do some work. You’re going to have to navigate some sticky conversations.
But with friendship? If it’s not fun, if it’s not seamless, if it’s not positive, then why bother? Almost.
The Scarcity Problem
This isn’t the first time I’ve brought up this idea that I think we have SCARCITY around our friendships.
And you can find this in the language we use every day.
“Friendships are like four-leaf clovers. They’re hard to find.”
“Making new friends is impossible as an adult.”
“It’s the hunt of a lifetime to find a true friend. When you find them, hold on tight.”
These are phrases you just hear. They’re pinned all over Pinterest. They’re going viral all over Instagram. People just throw them out.
If I was in a conversation with you and I told you I was struggling with my oldest friend, my friend I’ve had since I was five, somebody might turn around and say, “Well, that friend, that’s a REAL friend, so you should work really, really hard to hold on tight.”
But if I just tell you about a friend I met at yoga a year ago, a month ago, somebody might be like, “Well, I don’t know. If they don’t fit into your life like that, then I would just let them go.”
What is the switch? At what point is it worth it to do the work?
I don’t know. You tell me.
At the end of the day, I think there’s this underlying fear we have: If we rock the boat, our friends will walk away.
The joy of friendship is that we CHOOSE to be friends actively all the time. And the other person will just decide they don’t want to choose anymore because it’s not worth the work.
Maybe this is because we’re so overbooked, over-resourced, we just don’t have capacity. Maybe it’s because there’s no guarantee (like a marriage license or a blood relationship, these people are on your birth certificate type thing).
I think the question we need to sit with is: If the North Star shouldn’t always be that our friendships always feel good, feel easy, seamless, then what SHOULD our North Star be?
The complete episode goes so much deeper into how this scarcity mindset shows up in our everyday language and the stories we tell ourselves about friendship—including the real conversation with my teammate that sparked this whole episode and where it led us. If you’re someone who’s been holding back because you’re afraid of losing what you have, you need to hear this one.
The Work You’re Already Doing
I broke this down. I think there are THREE types of work we’re doing if we’re trying to make our friendships feel good.
Let me continue with the example of your friends having friends other than you (or if you’re in a trio of friends, hanging out with somebody else in the trio without you).
Option 1: Suppressing Your Urges
Let’s say you want to expand your social circle for whatever reason. Maybe your friend had a life change. They’ve been feeling really sick. They have really bad migraines, and they’re not able to go out and do as many things as you want to do.
You’re still supporting them. You’re still checking in on them. You’re still going over to their house. But you have things YOU want to do. You want to join some clubs. You want to get out of your house more on weeknights.
But you’re worried that if you do that, they will be jealous. Or upset. Or they’ll feel like you’re leaving them behind.
So you suppress your urge and you don’t do it. You just stay at home. Watch more Netflix. Get really into basket weaving.
You hold yourself back from joining that group, going to that event. You make yourself SMALLER to keep the peace.
And I would argue that is WORK. It’s work to sit there and know you are drawn toward maybe some community events or a speed-friending event. But you don’t do it.
You look at all these hobbies. You could sew. You could crochet. You could basket weave. You could get really into sourdough. You could rebuild car engines. And none of them really sit right because it’s not what you WANT to do. But you just keep forcing yourself to find a singular hobby because you don’t want to upset your friend.
That’s work.
Option 2: Hide and Calculate
Let’s say you DO decide to go to the speed-friending event. And when you go on your third time, you meet a couple people you really hit it off with. So you invite them to a local board game shop where you can play board games together.
You have a great time. You really enjoyed getting out of the house on a weeknight. It was fun to meet new people. You found out one of them also has an interest in basket weaving. You’re going to go take a class together.
But when you’re talking to your friend (the one who is at home trying to figure out how to navigate this new migraine diagnosis), you LIE about where you were the night before.
Or maybe you don’t lie, but you just… omit it. She’s like, “How is your week?” You talk about everything else but what you did last night. And she never really asked specifically what you did because she figured you just stayed at home. So you just omit it.
And then you have to start CALCULATING. Because maybe you get together again for board games. Or you go on a walk. Or you go to that basket weaving class. And you’re thinking, “Can I share that I went to the basket weaving class? Will they be jealous? Do I tell them I went to the class but not that I went with this person?”
You basically start to build this entire part of your life that you don’t feel like you can share with your friend.
And that is also work. It is work to calculate what you can and cannot share. It is work to try and make sure you’re going places where they won’t run into you or won’t hear about the fact that you were there.
Option 3: Navigate the Changing Culture in Your Friendship
This might look like having a hard conversation with your friend. And it doesn’t need to be this big blow-up thing.
It could just be telling your friend: “Hey, I know you’re really, really struggling with these migraines. And I feel awful for you. And I want to help you however I can. And I’m happy to come up with some ways we can still stay really connected. Is it easier for me to text? Is it easier to voice memo? Is it better if I come over and sit in your house? I’d love to come drop off dinner to you a couple times a month so you know I’m thinking of you. What can I do to still feel connected? But I also have some things I want to do. And normally maybe we would do those together. But you can’t do that right now. And I don’t want you to think I’m trying to leave you behind. But I have some things I want to explore. I’m lonely at home without you. I want to go check out this group and see if I can meet some more people who are interested in some of the hobbies I’m interested in.”
Maybe they’re sad about that. Your friend that they can’t join along. And you have to sit there and say, “Yeah, I’m sad you can’t join along either. I want to help you get rid of these migraines so we can go do fun things together.”
That conversation? Maybe it was a little hard to bring up. It feels like it’s rocking the boat. Because your friend is probably kind of sad now. Because they want to join along with you.
In their mind, when you were also sitting at home doing nothing, it made them feel a little better that they weren’t the only ones sitting at home miserable.
There’s probably gonna be some uncomfortable moments. Maybe there’s some growth. Maybe they tell you to go do it. Go check out those speed-friending events.
And then when you tell them about it, maybe they’re a little sad. And it feels like you backtracked. They told you to go, and now you feel uncomfortable because it almost sounds like they wish you didn’t go. Which might lead to more conversations.
And over time, this will be a slow shift of what’s normal between you.
The alternative? If you go with Option 1 or Option 2 (suppressing your urges or hiding and calculating), I think there’s an emotional undercurrent that builds over time. More lies to keep track of. More resentment building. More distance.
That is all work you are managing. But it’s work that I think is ERODING the foundation of your friendship.
Sometimes, I think people who have been doing this type of work for a really long time (that’s kind of eroding the foundation of their friendship), and then a year from now their friend finds out they’ve been doing all these hangouts and they never told them, the friend might get really mad. And it might actually be a blow-up fight.
And you might come back and blame your friend. Like, “Well, they just can’t handle that I’ve been doing all these things.”
And sometimes I think people don’t see their part in this. Like, “Hey, you CHOSE the work of hiding everything. You had a part in this too.”
The emotional toll of Option 3 (navigating the changing culture of your friendship) is that there is going to be some discomfort when you bring it up. When you have that conversation.
But the hope would be that over time, the discomfort DECREASES. Because you’re building repair skills. You’re building trust that you can work through things together. Eventually, it becomes easier and easier to just bring this stuff up.
And the biggest bonus? The biggest win? You get to be fully yourself in the end.
You get to go after your interests. You get to talk about your real feelings. You get to hear your friend’s real feelings. You might get CLOSER to that friend who has the migraines. Because now they’re really telling you what it feels like. They might tell you all about how they feel like the world is passing them by, and how sad that is. And they’re not blaming you for that. But you might get to hear this whole side of them you never would have heard if you’d gone with Option 1 or 2.
You’re not choosing between work and no work. You are always choosing WHICH work you’re going to do.
But one kind of work keeps you stuck. And one kind of work builds something more sustainable.
In the full episode, I walk through even more real examples of what these Option 3 conversations actually sound like—the stumbling, the awkwardness, the moments where it doesn’t go perfectly but it still moves the friendship forward. If you’ve been stuck between suppressing and hiding, this episode might give you the push (and the words) you need to try a different kind of work.
What Should the North Star Be?
If the North Star is NOT to have this friendship that feels good on the surface, then what SHOULD the North Star be?
I think it comes down to three parts.
1. Authenticity
We are trying to fully be ourselves. We are trying to share—I don’t think it’s ALL the parts of our lives—but whatever you decide to selectively share feels honest and real.
You’re allowed to still keep something close to the chest if you want to. You don’t have to share it. But whatever you DO share, you feel like it’s the real share.
This is all in contrast to performing a version of yourself.
2. Growth
Growth, both individually and together in your friendship relationship. Can you change and evolve? Can the friendship change and evolve? Can you share when you’re learning new things about yourself, even when you’re not even sure?
3. Building Resilience
Can you weather discomfort together? Do you have repair skills? Can you metabolize conflict? And do you trust that you’ll work through hard things?
I considered a fourth one: alignment on values. But as I thought through that in my own life, I realized there are definitely friends where I don’t align on every single value they have, and they don’t align on all my values.
But I DO think we can be authentic about our values. We can be honest if our values change, grow, and evolve. And we can build resilience when we don’t agree, by talking and listening about what each of us values.
At the core, I think a number of my friends and I have very, very similar values. But I value honest, direct, open conversation way more than maybe some of my friends do. I value pushing the boundaries and being bold a little bit more than some of my friends do.
I don’t think we necessarily have to be aligned on ALL of our values. But the places where I push them, the places where I make them a little uncomfortable, they can respect me. And the places where they push me, I can respect them.
That’s my goal.
Sometimes a Friendship Will Feel Bad (And That’s Okay)
Sometimes a friendship that is aligned on these North Stars—authenticity, growth, and resilience—will feel BAD.
Not even because either of you chose to bring up some sort of conflict or change.
I’ve mentioned on this podcast that I have a friend who lost her husband about seven months ago. And I think that together, we have navigated authenticity, growth, and resilience beautifully.
I think that unfortunately, this circumstance has brought us really, really close.
It did not feel good. No part of that felt good.
It was a lot of feeling bad together. It was a lot of sitting there and crying. It was a lot of sitting in sadness and watching her be at her lowest point, and wishing I could fix it all and knowing that I can’t. And all I can do is sit there.
It’s a lot of her depending on me, way more than she ever wanted to. And I constantly have to adjust, show up in different ways, sit in really hard stuff.
And we didn’t CHOOSE this. This is just by nature of the circumstances.
But the fact that we could go through the really, really, really bad together—I messaged her when I heard what happened from a family member of hers. I said, “I’m not offended. I just need your honest answer. Do you want me to get on a plane?”
Same day, I got on a plane. I flew to her. I stayed with her for weeks in her house.
The fact that we could do that together has completely changed our friendship. And none of that felt good at all.
The boat was absolutely rocked. It was overturned. It was thrown to the bottom of the ocean by circumstance, not by choice. But we chose to navigate it together.
When to Walk Away
If you’re like, “Okay, Alex, but when do I walk away?”
I think anyone can decide at any moment not to do the work. The real work. The Option 3 work. The out-in-the-open, messy work.
If the other person decides not to do that, and you’re forced to be like, “Okay, well, then the work I have to do is Option 1 or 2, and I don’t want to do 1 or 2,” that could be a moment to walk away.
If the work they want you to do (the out-in-the-open, messy work) just really doesn’t align with your values, you’re like, “That’s not me. I’m not doing that,” that could be a moment to walk away.
And that’s okay. Not every friendship is meant to survive.
But I do think that whatever above-the-surface work you do, the hope is that you can take some of those skills into your other relationships. Which will build more of that resilience and that trust.
You have less scarcity. You’re like, “Okay, when conflict comes up, I feel like I can have the hard conversation.”
The Hard Truth
If you are somebody who has listened to some of my episodes and you’re like, “I can’t comprehend how to get from where my friendship is now to what you are talking about,” I hope this episode has made you realize:
You are probably already doing work.
The question is: Which work actually is serving you and your friendship?
Because the hard truth is: If you want friendships where you can be fully yourself, where you can grow and change and share the real stuff, you’re probably going to have to rock the boat.
There are probably going to be moments that are uncomfortable. But it won’t be uncomfortable forever.
And the hope is that on the other side, you will see that work was WORTH IT. Because it made your friendship feel closer, feel easier, feel more authentic, true to yourself.
And is that work you think is worth doing? Or do you want to keep treading water endlessly, forever and ever?
Because I don’t think the treading water option will ever stop.
For the full conversation, including the raw, unfiltered version of these stories, the moments I couldn’t fully capture in writing, and a deeper dive into what it actually looks and feels like to rebuild after the boat has been rocked, listen to the complete episode. Sometimes hearing someone talk through the messy middle is exactly what you need to feel less alone in yours.
