Optimizing Friendships: Build Deeper, Healthier Connections | Ft Ashley Negron
28 Jan 2026 · 28 min
In this episode of the Optimizing Beyond podcast, host Josh Negron sits down with his wife Ashley Negron to explore why meaningful friendships are increasingly hard to find and how to cultivate deeper, healthier connections. They identify modern obstacles such as the superficiality of online relationships, constant busyness, and unhealthy relational patterns like performance‑based friendships, love‑addiction, score‑keeping, access expectations, and trauma bonding. The conversation introduces the “closest five relationships” framework as a diagnostic lens for assessing the quality of one’s core circle, and provides a self‑audit checklist (energy, honesty, challenge, consistency, etc.) to spot red and green flags. They stress the importance of being selective, setting boundaries, and recognizing when a relationship no longer serves growth. Practical strategies are offered for building new friendships: engaging in shared spaces (volunteering, gyms, classes, religious groups, hobby clubs), maintaining repeatable interactions, asking thoughtful questions, and truly listening. Ashley shares personal anecdotes about honest feedback from a college roommate and the value of friends who push you toward the best version of yourself, while Josh reflects on personality type dynamics and the law of positive intent. The episode concludes with actionable advice—initiate invitations, be consistent, avoid chronic complaining, and prioritize personal growth—to turn connections into lasting, supportive friendships.
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Welcome to the Optimizing Beyond podcast. I'm Josh Negron, and this show is all about sharing lessons, ideas, and strategies that sharpen your thinking, strengthen your habits, and push you to grow beyond comfort zones. Let's dive in. Welcome back to the show. Today I'm back with my wife, Ashley, and we'd like to discuss optimizing Friendships. So right now is obviously a time where meaningful connection seems to be something that is more and more difficult to find. In this most connected time we've ever had, people describe being more lonely, anxious, and depressed than ever before. And so we'd like to walk through some of the challenges of connection these days, and then go into some practical steps on how to find and optimize meaningful relationships. So Ashley, welcome back to the show.
Hello, excited to do this again.
Yeah, absolutely. So we want to walk through some of the modern challenges of friendships and connections these days. I mean, obviously, the, the number one glaring thing is the, the convenience of online relationships, not that they can never be meaningful, but it seems to be pervasive of this like surface-level, context-dependent, seasonal-type relationship. How do you think that, that, that kind of hurts us in connection?
Yeah, it's easy to think like, you think about like, oh, Facebook says you have this many friends, right? So it's kind of like rewired the definition of friends. I've always heard like friendships is like the rings or ripple effect in a circle, right? So on the inside you have your most intimate friends and then you have maybe another set of friends outside of that and then you have acquaintances and then you have like people you're connected with because of other people. And so I think because of things like Facebook, it's easy to think that you, Um, have more relationships and have more friends than what you really do have. Friendships can mean a variety of different things. Sometimes, you know, people come into our lives for seasons, for certain reasons. And, you know, I'll never forget a friend of ours saying that, you know, she knows that there's certain people that came into her life for only a certain season, and that was the reason that they were brought in. Or maybe there was some lesson to be learned from that relationship. And so we have to look at friendships differently and, and be sure that we have and prioritize the right people in our lives.
Yeah, absolutely. And obviously right now you can't mention social media without mentioning the extreme divisiveness on social media, especially Facebook. There's some other mediums that are a little bit less that way. I know Instagram is your choice because it's not as divisive, right?
Correct.
Yeah, for sure.
Correct. And so, and I just stay off of X altogether.
That's probably wise. So also there's additional obstacles like busyness. Now this is, this is just the life that we're in, you know, that the empty space gets filled by so many And so carving out time for friends is just as difficult and important though, as carving out time for fitness and other important habits and things like that. There's also challenges of unhealthy relationships and expectations. We all have baggage of some sort, and that baggage extends into our relationships. So we have all sorts of dynamics like performance relationships where people are in relationships specifically to get something out for them. And you have other people who are people pleasers and what some therapists call love addicts. And so they, they give love and they give of themselves. They don't say no so they can get approval, affection, and those kinds of things. The need and search for validation. There's also things like scorekeeping, which can happen even in a marriage where it's like, well, I did this last time, or I've done all these things. And that's really just unhealthy type of behavior. And there can even be dynamics in relationships such as, you know, access expectations. There's those people who get offended if you don't respond to their text message immediately and they expect to have access to you 24/7. And then that's some measure of importance in the relationship. And finally, there's things like trauma bonding. So there's unhealthy relationships that are forged through complaining and drama and gossip and those kinds of negative things, right? And so those relationships are really kind of forged in those negative emotions. So when you're looking to optimize your life, when you're looking to grow and improve yourself, those don't tend to be the most fruitful relationships. And then when you do grow, those are the kinds of friends that guilt or punish you for your growth and say things like, well, Ashley, you've changed. Yes. Yes, I have. And so there comes out that phrase where, show me your closest 5 relationships and I'll show you who you are or who you will become. And so we're starting to recognize that these are extremely important things to consider when you're looking to grow, improve yourself, and become the best version of yourself that you can be, like Glenn Lundy says. said in the last episode. That's what we were meant to be, the best version, not an average version, not an okay version, not a worst version, but the best version that we can possibly be. So Ashley, can you share with us what that 5 closest relationships phrase has taught you in your relationships?
Yeah, it's so important to have people who are in your corner as your closest friends, you know, be sure that those closest friends are people who align with the direction that you want to go in life, but aren't afraid to call you out when they see you making a mistake, or maybe having an attitude or an approach to something that they're like, hey, have you ever thought about this from another, from another angle? You don't want just people who are going to be all yes-men in your life. You want friends who are going to help you to grow. You want friends who are willing to walk through the deepest valleys with you. You know, life is, is going to be hard, and so you want people, those 5 closest people, to be people who you know are going to show up and who you will show up for. You want it to be like this push-pull in a Right? We've talked about that push-pull in other, um, in other ways, you know, in marriage and in those kinds of things. But you also want that in friendships as well. You know, you're gonna have seasons where you have more to give than what they may, and then there may be times that they have seasons, um, you know, where they have more to give and you need them to show up and you need them in your corner. And so, um, you, you want— yeah, gonna be there for you, who are gonna show up And then who aren't afraid to say the hard things to you. And I think those are the things that have struck out to me and in building our closest friendships.
I totally agree. And so if you're thinking there, man, I, I, I don't know what that particularly looks like for me, there are some audit questions that you can ask yourself. You know, do you feel like those relationships call you to be better, to improve? Do you feel like they are honest with you? Do you have conflict with them where they challenge you, where they tell you where you were wrong? Or do you feel like they're agreeable, like Ashley said? Do you feel Do you feel like they're just yes-men? They constantly agree with you and don't challenge you. And then do you— an easy gauge is, do you feel energized when you're with them or do you feel drained? Now I get it, some of you are extreme introverts out there and you're like, I feel drained anytime I'm with anybody. And that's not a constant gauge for each interaction with everybody doesn't always either energize or de-energize you.
Mm-hmm.
I'm talking more overall in that specific relationship over time. And are they consistent in character, right? Like, is this somebody that, that you can depend on in multiple avenues? Like Ashley said, if you have a lot of no answers to your circle, then you may need to reconsider. Yeah. And so as a result to that, it is important to be selective, right? I mean, if those people are going to shape your future and who you are, Then that's going to be important in a lot of avenues. Who you are is going to affect your work, going to affect your personal life, your finances, a lot of these decisions that you're going to make throughout your life. And so it's pretty critical to be selective, and it's not wrong to be selective. So it's funny because I've, I've been a part of a lot of people's lives where they have made the decision to make their lives better, and there comes a time frequently where I've walked through this with people where they realize there's particular relationships that they have to either establish some clear boundaries with, decrease time spent, or worst of all, eliminate them entirely. I've walked through several people who have had these conversations with me. And they're like, man, I— it's become clear to me that this person is not going to grow. They're not going to change despite previous conversations.
Mm-hmm.
That I think they should, and it would be best for them, but also us and really anyone around them. And they realize that that's not gonna be a reality for them in the near future. And unfortunately, they're going to have to decrease their proximity to that individual. And so as a result, boundaries are not punishment. They are a protection for you and your family. And so that's something that's really important to remember because that's probably the hardest thing when you have somebody that you've been close to for a long time. And you're realizing that maybe the sun has set on that relationship because it's no longer a blessing to you and to anyone else. And so, you know, you need to ask yourself, do I need to adjust access? Do I need to have a conversation with them? Or do I need to just end that relationship because it's no longer beneficial? So in that conversation, we've done a lot of focusing on the other person, right? Like that's looking at ourselves like, you know, are you worthy to be My friend. So I'd like to flip the script here too. Like, can you actually handle a good friend? Because a good friend is going to be somebody that can contend with you, that has their own opinions, that is going to have boundaries and challenge you to be better, tell you the truth when you don't want to hear it, probably especially when you don't want to hear it. And it's going to be likely somebody that will hurt you at times. I know Cody Walker, our pastor, said in, in a message recently that the distinguishing factor when someone you care about hurts you, that he learned from his mentor a long time ago, was did they say things that hurt? Or did they say things to hurt? I thought that was a really cool distinction to be able to tell the difference, you know, using the law of positive intent and things that we've discussed before. But all of those things take some mental strength to, to understand, to not react to someone who is a formidable, strong-willed friend? You know, are you able to receive feedback and engage in that kind of relationship? Ashley, walk us through, you know, you've, I mean, you've had all sorts of friendships over the years. So what does this look like to be able to handle having a healthy, good friend for us?
Yeah, I think a lot of times it's those things that you mentioned, right? Like it's assuming the law of positive intent and that they have your best interests at heart and they want you to grow and they want to push you to be better. And they're They're not just trying to be mean. I also think that, you know, that comes with time and with trust. And trust is really only built with time and investment, right? So it's gonna take like years to forge friendships, right? Those aren't gonna happen overnight, you know? And it's things like spending time breaking bread together. It's things like playing games. It's taking trips, going on adventures, you know, whatever that looks like for you in your current stage of life. Maybe it's that you know you became friends because your kids were friends, and so you know that that is your connection. And it could be friendships over a myriad of different things. But I think that people want to rush the deepness straight into these deep friendships. But really, like like any relationship, it just takes time. And so I think that's the biggest thing to to realize and to know that it just it takes investment, intentional investment. Just like any other relationship, good friendships take intense. You know, one of the things that we've tried to do with, with people that we've been friends with for years is to try to make sure that we hang out at least a few times a year, right? That maybe before we, we leave the dinner table this time, we're gonna already put another date on the, on the calendar, or we're gonna do, um, you know, we're gonna try to hang out in 3, 4 months because that's how busy that most of us are. You know, you start texting your friends, you're like, hey, when can we hang out? When can we have dinner? And it's like, oh, No, because of all the things, it literally is like four months from now, right? And so you just you have to be intentional and you have to invest time. We have a set of friends that we have been doing one night a week of dinner and games or just conversation for years now. Like I think we're on like a decade, and the night that we do it has shifted and changed, right? But there is this consistent night that has been set aside to invest in our friendship and to invest in our relationship, and those are people that. we know that no matter what are going to show up, they're in our corner, they're here for us. And so invest, be intentional, just like you would be in any other relationship.
And I'd say that in asking the question, can you handle a good friend? There's this thing that I recognized in myself in the different relationships that I've had over the last 2 decades, being a blue on the color code personality type, a lot of my A lot of my closest relationships over the years have been dominant Type A relationships. And I think as a general rule, Type As tend to be much lower on the emotional reactive scale than my personality type. I don't know if it was super intentional, at least initially, but I think subconsciously I recognized that the emotional volatility of those types of people was lower and they were willing to be more direct and transparent and honest with me. I mean, you're that way. And I think about a story back when I was in college almost 20 years ago, shout out to Matt Johnson, the best man at my wedding many, many years ago. And he was a very brutally honest person. And that's something that I super valued, but definitely did not always enjoy. There's a, there's a memory that stuck out to me and still, still sticks with me in my transition to be more financially responsible. And it was a time when I was not managing my money properly in college. I wasn't paying my student bill like I should have. And he knew, being my roommate in college, he knew all the stress that I had financially and trying to make ends meet and working and also doing school. We went to Walmart together one night and I was getting ready to— you remember the cheap giant boxes at Walmart full of DVDs, you know, where you could pick up a whole bunch for a— people are like, what's a DVD? I'm like, I get it. And so, uh, and I remember him saying, Do you really need that? And he was like, man, the way you've been talking about all the stuff going on, you know, obviously a lot of shared context there. He didn't really have to say very much. But what he said was like, very, very honest. And it was said out of care. It wasn't, it wasn't said like Cody said, it wasn't said to hurt. It was what he said did hurt, because he was definitely onto something. And, and that's not something that I wanted to hear.
Right.
And so that's something that I think about when I think of can you handle being a good friend? And can you handle a good friend in your life? Those are two very, very important things.
Very important.
important questions, 'cause everyone wants a good friend.
Right.
But I don't think everyone recognizes what a good friend actually does. And if they're willing to tolerate you not being the best version of yourself. If you're a drama queen, if you're constantly looking for blame or affirmation or looking for validation in others versus in the ways that you actually should, that we discuss in other episodes, then I don't know if a lot of people are gonna wanna be your friend. Think of it this way. If everyone's looking for the top 5 best people that they can have in their circle, the responsibility on you is to be the best version of yourself that you can possibly be. Why? Because otherwise, you're probably not going to be chosen by somebody who's going to be a good friend to you. Does that make sense? And so, how do you look and how do you find a good friend? I think something that is very often overlooked in this age of no responsibility is it starts with you. You have to strive to be the friend that you're looking for. So again, that means if people are selectively looking for their top 5, are you somebody who's worthy to be chosen? So that's a super heavy question. We'll just leave that back there and then transition into, you know, what are some practical ways that people can find others to connect with? And so the first place is going to be what I'm going to label as practical arenas where you can find people, right? So those are like shared spaces. And so places of like shared mission where you can find people who are into service or volunteering into the same things that you care about. Or maybe it's a shared discipline. This will be like gyms and training groups. This doesn't necessarily have to be something as crazy as CrossFit, but I do find that those kinds of things that we've discussed before, like a type of fitness class, yoga class, fighting class, jiu-jitsu, stuff like that, any kind of like group class is going to be something that can bond you with others very quickly, particularly if it's high stress, High effort, those kinds of suffering bonding kind of things can be super, super powerful. Then there's also shared values, right? So if you're a religious person, this is in your church or your religious groups, you can have a men or women's group or even a family group that meets regularly that you can forge relationships with. And then finally, shared interests, shared hobbies. So what are things that you can do in the local community to find people of similar interests, whether that's painting, dancing, pottery. I don't know what it is, but in this day and age, there's more and more of these communities that you can find online to really find people with similar interests to connect with, right?
Yeah, I love that concept of finding, um, you know, shared spaces together. Some of our dearest friends we met because we started going to the gym together, right? And so what started as this, oh, we're going to show up in the mornings and we're going to suffer together, Um, and then it was like, oh, hey, we think you're cool. Do you guys wanna hang out? Do you wanna come over? Part of what really took that friendship to the next level was because during COVID time, we turned their barn garage into a gym and we all worked out together and we spent time together. Right. And so that was forging a different— forging through, um, one would say like a traumatic season of our lives, one that, you know, completely flipped it on its head. But then it turned it into this deeper friendship as the years have gone on. And so, you know, We've been friends for the last 7 years. And as that time has gone on, like that friendship has just grown deeper and sweeter. And there are people that I know that I could call in an instant who would show up if they at all possibly could. But people who also like love us and care about us and are invested in us. And we can have hard conversations. We don't agree about a lot of things, right? But that doesn't mean that we don't— care deeply for each other. Um, and that we, um, that we don't just continue to show up. And so I think, you know, tied back to our episode on grief, like you show up and you tell people that you love them.
Mm-hmm.
And so find people in those shared spaces. Don't be afraid to be the person to initiate, like, hey, would you guys like to go to dinner sometime? Like, be the person to ask. Don't be afraid to take that next step and to initiate that. You never know that those people may have just been waiting for someone to ask, right? And so be, be the first one. Don't, don't be afraid. Find, find things to go do together. You never know what friendship will come out of just asking.
And there's some, uh, there's some practical things that you can do to try to grow. So if you go to these type of gatherings or groups, there's some additional practical things that you can do to kind of start to foster and develop these relationships. And there are 3 that I want to touch on. The first one being repeatability and consistency is going to be something that really makes a difference. Like Ashley said, there are certain relationships that we've done things weekly with for now going on a decade, that evening dinner that we set up. And then additionally, our CrossFit class. I mean, we've been going now for 7 going on 8 years, and that's 3 to 4 days a week. And those are the same people, the same class, the same time of day.
And so, So you're—
that repeatability, whether it's every day, every week, or even once a month, those kinds of things are gonna grow that over time. We talk about like daily anything changes everything, right? And so even in the proximity of relationships, speaking in that way, those are gonna be things that help you develop that over time. Number 2 is gonna be asking great questions. I think this is super, super critical. The 3rd one ties into that, really dovetails. But asking good questions, you know, those types of people that are, that you get such a good feeling about when you're with them because you're like, man, they're really interested in me. When they're like, man, what do you, you know, what do you like to do? What are you learning? What are you doing? And they're just very interested in, in you. And that makes all of us feel important, feel like, like someone cares about us. And so that's a super powerful thing if you can figure out a way to ask really good questions. Now, there's a balance when you're getting to know somebody. There are questions that would, I would classify as a little bit too, a little bit too nosy, a little too forward to be, uh, to be ones that are appropriate to ask. But if you show a humble heart and curiosity about someone, that can be really powerful in building a really good relationship. And the third one being, you need to shut up. And listen, right? I think, I think everyone knows what it feels like when you're trying to share something about yourself and you get cut off by a know-it-all or a one-upper or someone that doesn't have the social awareness to listen, right?
Mm-hmm.
And so, and as you're talking to someone like that, there's usually multiple times where you try to get something in to connect with them. And if they just interrupt and keep talking about themselves, you kind of stop trying, right? You're like, okay, I know what this is like. I'm just gonna listen and they're gonna talk about themselves. Awesome. And so there's this thing where you don't wanna be that person, right? And so just be self-aware. Don't be the one constantly talking. I mean, just asking great questions and learning to listen are just so critical and important to building those kinds of relationships that I believe are gonna be fruitful for you.
I do think one other element that goes into that is, and this just came to me, but don't always the person who complains about everything, right? I think that goes back to the habits of gratitude that we've talked about before, about looking to see the world differently. People don't like to be around someone who complains all the time. So don't be that friend who complains about everything, that nothing's ever right, nothing's ever good enough. Don't spend your time blaming other people, blaming the world, whatever. Be the friend who is positive and uplifting and seeks to see the world in a different kind of way. And that's just gonna set yourself apart and help others to, like you said, pick you to be in their top 5.
And I think that's, that's some good distinctions too. So like, if we're looking at what are red flags in relationships versus green flags, so some red flags that I would look for in deciding who's in my circle, is it someone who gossips a lot, has a victim mindset, maybe someone who's flaky or jealous, or someone who maybe doesn't have good boundaries, or you get the sense that maybe is a little codependent, or is kind of maybe in it for themselves. Or selfish in some way. And so these things are important things to, to be aware of. Some good qualities that you can look for is, you know, are they consistent? Are they humble? Do they genuinely seem interested in you? Are they someone who's been working on themselves? Right. And, you know, are they accountable? Are they loyal? Those are some qualities that I would consider good things to look for. And in it, along that line, like Ash, you mentioned earlier that it doesn't necessarily have to be someone who's thoroughly aligned with you in every aspect of life, no matter what.
Yeah.
Right. I think that's super important in today's day and age. I think comedians are doing a good job of highlighting the binary nature of relationships right now, that in order to have a quality relationship, you have to agree with me in every way. And if you say something weird publicly or on Facebook or whatever, then, you know, just go ahead and unfriend me if I haven't unfriended you already. Those kinds of things. I think are just ridiculous. I have plenty of friends that I have amazing relationships with that we disagree fundamentally on a lot of things, and that's not something that's a deal breaker for me, to be honest. And just because I know what they believe in one area does not mean I assume what they believe in another area. And I think that's also very critically important, that just because that— I think assumptions do kill in that area. It's super important to remember that, you know, you told me a long time ago, like we talked about in our marriage episode, you're allowed to have your own opinions. And there are some that we don't have to reconcile even in our marriage, because they don't matter between the both of us. And so I think if you have a friendship, you should be able to respect the boundaries of their opinions and the things that they think. And that doesn't mean you can't discuss them or have a civil conversation or even a debate about it. But if you guys don't And if we don't arrive to the same conclusion, that's okay because I love actually getting to hear someone else's perspective, especially from someone that I love and respect. That's usually when I'd be most likely to listen to that perspective and try to understand it and go, well, that makes total sense. I can totally see why they view the world in that way. And that's super helpful. Doesn't necessarily mean that I subscribe to that perspective, but now I have an understanding. It's not just like, man, everyone who thinks that is stupid. What a shallow, assumptive way to see the world, right? So I hope this conversation has been helpful to you in evaluating your friendships. And maybe it's a blessing to be able to reflect on the healthy ones that have been very powerful and a blessing to you. If it's helped you shed light on certain relationships that you think you can help improve, or maybe set those boundaries to allow yourself to have more peace and get to the next level, especially this day and age where relationships Relationships seem to be a commodity that is more and more rare to find something of extreme value. Instead, it's more relationships of convenience that are not fulfilling and leave people feeling more lonely than ever. Thanks for listening to the Optimizing Beyond podcast. Remember, growth happens when you take action. So subscribe, share this with a friend, and most importantly, put what you learned into practice because as we know, Daily anything changes everything. Welcome to the Optimizing Beyond podcast. I'm Josh Negron, and this show's all about sharing lessons, ideas, and strategies that sharpen your thinking, strengthen your habits, and push you to grow beyond comfort zones. Let's dive in.
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