This week, you’re hearing one of the most important podcast episodes I’ve ever done. It’s a lesson I’m still learning and will continue to for the rest of my life, and if you’re here to do the work of personal growth in any area of your life, this is one you cannot miss. 

As humans, we want a black-and-white rule that says the hardest things to work on are the most valuable or worthwhile. But what if it’s not that simple? How can you discern when something that’s hard is worth it because you’re evolving, growing, and healing in the process, or when there’s no real redemptive value to it? 

Join me this week to hear how to discern when emotional difficulty is worth it, and why it’s always your choice to decide whether you want to continue to pursue working on something or not. I’m sharing my thoughts on why we fetishize difficulty, and offering questions you can ask yourself to develop your discernment around the challenges you want to experience and why. 

Joining The Clutch is easier than ever! Text your email address to 347-934-8861 and we will text you right back with a link to all the information you need. Hope to see you inside The Clutch soon!

What You’ll Learn From This Episode:

  • How I think about my own personal growth.
  • Why it’s your choice to decide what problems you want to solve, and what you’re no longer going to pursue in your life. 
  • The difference between giving up because it’s hard, and changing paths because something else is more important to you.
  • Why emotional growth often doesn’t feel good.
  • How to discern when emotional difficulty is worth it. 

Listen to the Full Episode:

Featured on the Show:

Full Episode Transcript:

Welcome to Unf*ck Your Brain, the only podcast that teaches you how to use psychology, feminism, and coaching, to rewire your brain and get what you want in life. And now here’s your host, Harvard Law School grad, feminist rockstar, and master coach, Kara Loewentheil.

Hello, my chickens. Today we are re-airing one of the most important podcast episodes I’ve ever done. And I felt it was one of the most important when I created it and based on the download and listening numbers you all feel that way too. So if you haven’t heard this episode you obviously need to listen to it but even if you have I want you to listen to it again because honestly, this is a lesson that I still am learning and I am sure that I will continue learning.

This episode is all about how to know when emotional difficulty is worth it. One of the most common things that happens when we start doing thought work and we start taking responsibility for our emotions is that we can basically take the tools and use them in a perfectionistic way just like we do everything else. I see this sometimes leveled as a sort of accusation at thought work itself or at coaching itself but coaching is just a set of tools. You can use a hammer to build a house or to hit yourself in the face. It’s not the hammer’s fault. It’s not your fault in a blaming way either.

The point is just that it’s a tool that can be used in different ways. And that’s the same with thought work. So if we come into learning thought work and coaching from a place where we are used to blaming and finding fault with ourselves and punishing ourselves, we will totally use thought work to do that and that’s why so much of my work focuses on what I always say, literally my main goal is just for you to be nicer to yourself and if we get that done I don’t care what else happens.

So this episode is kind of all about how to know when an emotional difficulty is worth it. And how to kind of discern that because one of the things that happens is that we start to almost in a masochistic but not a fun masochistic way think that the right answer is to always go through the most emotional difficulty possible.

And then we won’t change a circumstance even if it’s easy to change, not a problem to change or maybe it’s challenging to change but whatever it is we start to use thought work in this very absolutist way of I’m never allowed to ever decide to not do thought work on something. Or I’m never allowed to decide not to do the emotional work on something. I always have to do it all. And the way that I think about coaching and thought work and my own kind of personal growth, is that I have a limited human lifespan and I’m never going to finish it all.

There are infinite things in my mind that I could work on. There are infinite ways of growing and evolving that would be interesting and I can’t get to them all. So if I decide not to pursue the work on something that’s a decision that I’m allowed to make. And in fact, I have to make, to be responsible in my own life I have to decide which work am I going to do and what work am I not going to do.

What problems in my life am I going to solve and what problems in my life or patterns of myself am I just going to make peace with because I just don’t think they are worth the amount of emotional energy it would take to solve them? But here’s this really important distinction and there’s more on all this in the episode but I’m not sure I talked about this particular little bit of it because this is kind of maybe a new way of thinking about it or just a piece that I maybe didn’t include the first time.

There’s a big difference between I’m not going to work on this because it’s just too hard so I’m going to give up and I’m not going to do anything instead. And I’m not going to work on this because this other thing is more interesting and important to me. It’s a choosing what to work on versus a giving up and just not doing anything. So I think that’s an important piece of this to keep in mind.

So keep that in mind as you’re listening to the original episode which starts next and revisit this as many times as you need, the answer for what’s worth it for you is going to change over time but it’s really important to make that decision on purpose. Have a beautiful week my chicken and let’s dive into the episode.


So, I moved to Brooklyn which as a nearly lifelong Manhattanite I did not ever think I would do. Even more unlikely I moved here for a boy, I mean for a man, for my partner who lives nearby. And I’m telling you that because it’s actually relevant to today’s podcast because I want to talk to you about when your feelings are not a kind of good guide. And how to know when something being really difficult is actually worth it and good for you. And this concept and topic kind of came to me as I was thinking about what I’ve learned so far in this relationship and what the experience has been like.

So, I have been in this relationship for about a year now. And I have dear lord, learned a lot about myself even at my ripe old age, having been in many relationships before. It’s been a real year. First of all, I learned I would move to Brooklyn which I definitely didn’t think was the case. I live in a house now that has stairs, that feels extremely suburban. I have a backyard. I feel like I’ve moved to the country. But this relationship has been an enormous growth and learning opportunity for me, a lot of which felt fucking terrible because sometimes growth is not that fun.

So that’s why I want to talk to you about it today. So, I was thinking about this because there have been a lot of big identity shifts for me in growing into this relationship and this new phase in my life. And that is why I’m talking about this because I think it’s so relevant to all of you whether your kind of context is going to be a relationship or something else in your life. And no matter what happens with this relationship those lessons and that journey is going to be something that I always have with me which is one of the nice things about growth.

So, I want to talk about this today because my experience of the kind of first year of this relationship was so different from what the stereotypes are and what internet psychology tells us things should be about. I mean I guess I’m internet psychology also but pop psychology like social media psychology. And so, I really want to talk about that because again your thing might not be your romantic life, it could be your professional life, it could be some kind of physical goal you have. It could be your family, whatever it is.

There is all of this social stereotyping for instance that the beginning of relationships are when it’s easy. That you have a honeymoon phase when you meet. You fall in love, it’s so easy. It feels amazing in the beginning. Our social narrative about relationships is that they’re fun and easy in the beginning and then they get hard and boring. And that’s such a bullshit narrative. First of all, that comes from having an unmanaged mind. Your relationship is going to feel the way your thoughts about your relationship feel.

So, if you have shitty thoughts about your relationship then you’re going to feel terrible. And if you have positive thoughts about your relationship you’re going to feel good no matter how long you’ve been together. But the story that there’s this honeymoon phase, it feels amazing and then it gets boring and hard. What we’re really saying is sometimes it’s that people are infatuated when they first meet. They have positive thoughts more easily. And then they’re not managing their mind to create their emotions that they want as the relationship goes on.

But I also think that we have sort of digested and spit that back out in a weird way in a lot of the sort of social psychology I see going on which is all of these sharable quotes that are those little quote squares that are like trust your feelings. And if something feels hard it’s not meant for you. And if you’re with the right person it will feel easy. And love means never having to apologize. And love means never having to explain yourself. Love means someone meeting and exceeding, and anticipating your needs.

And if it’s a struggle or it’s hard, or if you don’t feel good then that means the person is bad or wrong for you, or they’re toxic, or it’s not the right fit or whatever. And all of that is just bullshit. I mean if you fell in love and it just was perfectly easy then kudos to you, that was not my experience. And maybe this just isn’t an area you struggle or maybe you were just high on the validation and finally kind of achieving the goal you thought you wanted. But emotional growth often does not feel good. And that’s why most people don’t do it.

There is this great Emily McDowell quote and image goes around about self-development that basically says, “If we told people that self-development felt like dying, they wouldn’t do it. That’s why we call it self-development instead.” That’s what it feels like sometimes. So, the idea that if something feels hard, or if it’s challenging to communicate, or if you are ‘triggered’, that automatically means that something’s not right for you, or that something has gone wrong. It’s just not true. And that’s not true whether it’s a job or a partner or anything else.

Because that would mean either that emotional growth always feels super fun and pleasurable, which we know is not the case. Or it would mean you have zero emotional growth to do. Something feeling perfectly easy and pleasant all the time basically means you’re not growing, you’re just trying to create an echo chamber where somebody never triggers anything unresolved in you. And that’s not really true intimacy. Or it’s not looking at yourself with a real eye and being honest about what’s going on with you. That’s not being really vulnerable and coming up against yourself.

And I’ve been thinking about this so much in the context of my relationship because now a year into it this is about when I’m starting to feel the honeymoon phase kick in. It has taken me about a year to actually work through all the shit that came up for me in the first part of this relationship. And I am sure it’s not over. There will be more later on but I have gotten through the first round of it. And it’s taken until now to really feel a lot more of my daily experience of it be all those positive emotions that we hear about and that we think romantic relationships are supposed to bring us.

Of course, they’re created by our own thoughts. It’s never by the other person. But it’s only now that I’m even really starting to be able to relax and think enjoyable thoughts about it because I have a fucking human brain. And especially if you have attachment issues intimacy is challenging. And again, it’s my relationship but for you, it could be starting a business or trying to go back to school, or trying to get into a new career, or whatever. The idea that if it’s meant for you it will feel easy. And if it feels like a struggle it’s just not the right fit is just so misguided.

If you have self-esteem issues then a promotion can feel really hard and challenging, or a new job could feel really hard and challenging. Trying to start and build a business can feel really hard and challenging.

If you don’t think you’re good enough if you have imposter syndrome and you don’t think you’re good enough for your role and then you get a promotion that is not going to actually feel good. It’s going to feel really hard and challenging after the initial high wears off because your self-concept is in conflict with what you’re trying to do now and that will make your brain hurt. That will bring up all your shit. If you have attachment issues, intimacy can be hard, whether that’s a new friend or a romantic relationship, or whatever.

If you experienced complicated family dynamics growing up, intimacy can be hard. If you’ve had a lot of negative thoughts about yourself in your romantic life you may have worked on them enough to get into a different kind of relationship and be able to actually receive the kind of partner you want. But then there’s a whole new level of cognitive dissonance and stuff that gets stirred up once you’re in the relationship that you have to work on. So, whatever the area where it’s so much less important it can be in a lot of different areas of our lives.

But understanding that the idea that whatever’s for you will feel easy and anything that feels hard is just not right for you or it’s just not meant for you is so inaccurate and incorrect. And it makes me very mad because [inaudible]. So, if you are not interested in emotional growth and development then sure, follow whatever feels easy.

But if you are and you just kick anything out of your life that doesn’t feel easy right away, or you kick anyone out of your life. Where you have some trouble communicating or where negative emotions come up, or where intimacy is making you uncomfortable. You are missing out on so many opportunities to get to know yourself and learn about yourself and love yourself at a deeper level.

So, all of that being said of course this idea that’s sort of things that are challenging are good for us can be taken too far. Because the way I just said it, things that are challenging are good for us, is not necessarily true. It is not true that anything that’s hard is good for us. It is just also not true that anything that’s easy is good for us. So, it’s not that anything that’s hard is good for us. It’s that some things that could be good for us are also hard. So, it’s not that anything that’s hard is valuable. It’s that some things that are valuable are also challenging.

There can be a tendency I think to sort of fetishize difficulty, to think that the hardest things are the most worthwhile. And it’s not that simple either. If you’re in an abusive relationship, doing thought work to be okay with that would be very difficult and challenging. That’s very hard thought work. That’s probably not worthwhile thought work. That’s not a useful way to use thought work. So, it’s not that whatever is the most challenging is the most worthwhile.

And I think this is why people want it to be one way or the other. They want it to be if it’s for you it’s easy or they want it to be the hardest things are the most valuable because we just want a simple rule. When really what you have to learn is how to discern when something is hard because you are growing or evolving or healing, or confronting something.

Or when something is hard because there isn’t really any redemptive purpose or value to it, it’s just you making your life harder by trying to thought work your way to put up with something that you don’t really want to experience or do. And that’s all subjective. That’s what’s so complicated about being honest about the kind of discernment and sophistication that’s required to do this work at this level. I can’t give you a blood test to know if what you are doing is a valuable challenge or not a valuable challenge.

The only thing you can do is ask yourself, why do you want to do the work and stay with the difficulty? What value are you connecting to for you? Why is it worth or not worth going through the discomfort of whatever the job or the person or the situation, or the relationship is bringing up for you? And you have to check in with your big-picture vision for your life. We can try to stick with things that are really hard and painful for us where we aren’t really growing or learning because we’re actually staying with them out of insecurity or scarcity, or ego.

If you are in a job that you don’t enjoy, doing work you don’t care about with a boss who screams at you all the time, and you’re working on widgets and you don’t care about widgets. It’s not that there might not be some value in learning to be happy even though those things are happening. That could be valuable. But you’ve just got to check, why is that what you want to do?

If your reasoning is that you believe that you’re not smart enough to get any other job, that reason doesn’t feel good. And so, the work is not going to feel good. You’re always going to be fighting against the sort of foundational reason you’re doing it. When we try to use thought work to get us through or change a reaction to something challenging, it will feel good and worthwhile when our reason is aligned with our values and things we care about. It will not feel good when the whole reason we’re doing it is out of scarcity.

So, for instance in my relationship even though it was bringing up a lot of stuff for me to work on, I knew that this was work I wanted to do for reasons that I liked. If my reason had been, I don’t think that anyone else will ever love me. I’m not good enough. Nobody will want to be with me. I’ve got to make this work. That reason would not feel good. It would not motivate actual growth. And it would not be aligned with my values and so I would just be suffering without really having a value-driven reason to do that work.

Whereas in my situation I wanted to stay and do this work because I could tell that what was coming up was something unseen and unhealed in me, thought patterns that I hadn’t been aware of before, ways that my nervous system had gotten patterns that I hadn’t really had to confront before. And I knew that even though the day-to-day I was having a lot of negative emotions.

When I looked at the values I had for a relationship, my partner and I kind of met those values. We shared important life values. We wanted the same kind of relationship. We had a lot of compatibility. There are things about our connection, our relationship that worked well together. I enjoy him. I respect him as a person. We had a lot of elements of things I wanted. So, I knew that this was a relationship that I wanted to be in. It was not out of scarcity or insecurity.

And that I was sort of discovering and learning new things about myself, a lot of that felt terrible because until I figured it out I mostly was discovering and learning how easily triggered I was into negative emotions around certain things. So that was not my favorite part. But I knew that that work was work I wanted to do and I liked my reason for wanting to do it. But I had to use that intellectual understanding to really carry me through the parts that felt so emotionally hard.

And I think that sometimes in this sort of swing – it’s not that emotions aren’t valid. They’re neither valid nor invalid. They’re just sensations in your body caused by your thoughts. So, I don’t think it’s even useful to ask if they’re valid or not but I think that there is this kind of sometimes kind of swing away that’s a reaction against just being too brain focused, which I totally understand when I discovered thought work like many analytical people I did not want to feel my emotions. And I just wanted to use thought work to get out of feeling negative emotion and that’s not useful.

So, there is totally a way in which you can overintellectualize and ignore your feelings in a way that isn’t helpful. But that doesn’t mean that all your feelings are always right. Sometimes I think it just gets misunderstood. When someone says, “Your feelings are all trying to tell you something,”, that’s true. They are information about what’s going on with you. But they’re not always telling you the truth. They’re not always an objective sort of reflection of reality or of what’s going on.

And so, your feelings are a clue that you’re having a thought you want to look at. And there’s nothing wrong with a negative emotion. But we can also kind of over-fetishize our emotions. And I think that’s kind of the point of this episode for me is that neither your emotions are always the answer nor your thoughts are always the answer. Neither is it true that anything difficult is worth it, nor is it true that everything valuable is easy. You have to develop the discernment to know and the self-trust to know when is this difficulty worth it.

And I have given you some questions I think are useful for you to think about like why am I going through this difficulty? What is challenging me? Am I being challenged in a way that is illuminating something new to me about myself that I didn’t realize or understand? Or maybe I’ve been aware of but have never really worked on that I’ve always run away from before. Why am I doing this? What is my end goal? How does that align with my values? Is it coming from insecurity or ego, or scarcity, or is it coming from a desire that feels aligned with the person I want to be and what my values are?

These are all useful questions to ask yourself but it is never as sort of black and white as this should feel easy or it shouldn’t feel hard, or everything should be hard. It’s neither one of those things. And when I was working through this in my relationship I really needed to have access to that kind of value-based thinking from my prefrontal cortex, the part of me that can do higher-order thinking. And I needed that to get through the part that was so emotionally challenging otherwise it would have just seemed like, this is hard and I feel terrible and why would I put myself through this?

So, it’s just so important to understand that if you tell yourself, I just want something that feels easy you’re not asking yourself the right question and you’re glossing over or combining two very different things. One of which is does this feel hard in a way that is worthwhile, that is important, it’s connected to what I value, it’s in pursuit of a bigger goal I’m trying to achieve? Then it may be a thing that is very right and good for you. I mean again this is all made-up thoughts, we don’t get a test on what’s good for you. We don’t get a certificate from the universe.

But within your own framework and the way you’re trying to live your life, it may be a place there’s growth for you and positive results if you keep with it and you’re willing to put that work in and feel uncomfortable. That’s very different from this sucks and I’m only sticking with it because I don’t think I deserve any better. I don’t think I can succeed on my own, I don’t think I’m good enough, whatever version of that you might be thinking. Those are two very different reasons.

Not everything that feels hard is inherently a valuable growth experience. But not everything that is sort of good for you or aligns with your highest desires and goals, or will produce, growth and change is easy. You can’t always do the easy or always do the hard. You really have to learn and practice the discernment of asking yourself, why is this hard, and is it worth it?

So, if it’s hard because I’m trying to coach myself to feel okay about somebody calling me names and cancelling with me all the time because I don’t think I can find another partner. That’s probably nothing redemptive coming out of that.

On the other hand, if something’s hard because I have some unhealed patterns, or unhealed trauma, or thought patterns I haven’t looked at that’s coming up, or I’m learning something about myself I didn’t really know. Or I’m just having a lot of emotions come up, I don’t even know why yet. But I’m doing this because I see this positive end goal that my kind of higher thinking self has then that’s a very different story. It’s different to say, I don’t think anyone else would want to date me and I want a relationship where I’m truly intimate and vulnerable. And so, I want to build this connection.

Or it’s very different to say, I want to stay in my job because I don’t think I can get another one so I’ve just got to make peace with this versus I really think it’s worthwhile to me to do the work to know I can feel proud of myself in any circumstance. And then I’ll decide later if I want to stay in this job.

So, all of that are questions that I recommend you ask yourself. But above all, do not drink the Kool-Aid that what is for you will always feel easy and that if something feels hard you should just walk away. Because those are not the correct questions to ask yourself, they don’t dig deep enough into what kind of challenge you’re experiencing and why. And those are two ways to never grow as a person for the rest of your life. And that’s not what we do around here, is it? That’s not why I work here.

If you’re loving what you’re learning in the podcast, you have got to come check out The Clutch. The Clutch is the podcast community for all things Unf*ck Your Brain. It’s where you can get individual help applying the concepts to your own life.

It’s where you can learn new coaching tools not shared on the podcast that will blow your mind even more. And it’s where you can hang out and connect over all things thought work with other podcast chickens just like you and me. It’s my favorite place on earth and it will change your life, I guarantee it. Come join us at www.unfuckyourbrain.com/theclutch. That’s unfuckyourbrain.com/theclutch. I can’t wait to see you there.

Enjoy the Show?