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Saying Goodbye podcast episode cover The Life Coach School

Ep #185: Saying Goodbye

When you have things in your life that you don’t love and you don’t use, you start to feel burdened by them.

Many of us have things that aren’t serving us—things that we don’t really want—yet most of us don’t want to let them go…

On this episode of The Life Coach School Podcast, we dive into why goodbyes can be so heart-wrenching for us and why, at the same time, they are so necessary. Join me in this session as I share a simple-but-challenging process for saying goodbye to things in your home, your relationships, your jobs, and thoughts—those things in your life that no longer serve you and are holding you back. It’s time to bid those things farewell.

Grab your copy of our new Wisdom From The Life Coach School Podcast book.  It covers a decade worth of research, on life-changing topics from the podcast, distilled into only 200 pages. It's the truest shortcut to self-development we have ever created!

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What You will discover

  • How to measure whether something in your life is no longer serving you and you no longer need it.
  • Why these things tend to wear you down.
  • The importance of letting go of certain things and people in your life.
  • The wrong reasons to continue holding on to something.
  • Why goodbyes are so difficult for us.

Featured on the show

Get the Full Episode Transcript:

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Episode Transcript:

Welcome to The Life Coach School podcast, where it’s all about real clients, real problems, and real coaching. And now your host, Master Coach Instructor, Brooke Castillo.

Well, hello, hello my friends. You guys are stoked for this podcast. So many of you have been asking me for it, and I'm thrilled to be able to offer it to you. We get a good sense of what our students are struggling with because of the section in Scholars called Ask Brooke, and so when so many people ask the same question and so many people want help with something, I determine that it's something I should discuss on the podcast.

So today we're going to talk about how to say goodbye, and I started this off in my notes, it says, "Saying goodbye is difficult and most of us don’t do it enough." And here's what I mean by that, and what I'm going to give you in this podcast is a process to say goodbye to the things in your life that no longer serve you, that are outdated, and that you don't truly want.

So this month in Scholars, what we're working on is organizing the clutter in our lives, organizing the things that share space with us. And for many of you, that is actual physical tangible items, but it is also relationships, it's also habits, it's also experiences, things you do, all of it.

So we're going to talk about when we go through the process, and I've talked about this with so many of my students. Going through the process of let's say, just cleaning out a cupboard or cleaning out an office. A lot of people will say to me, "I want my office to look like yours, I want my house to look like yours. You have no clutter, you have no extra things, it just looks so clean and clear." And one of the things that I say is that the things in my life are things that I love and things that I use, and there's a very productive, powerful feeling to that.

And when you have a lot of things in your life that you don't love and that you don't use, you start to feel burdened by those things. That includes the stuff that you have in your house, and not just the stuff you can see, but all the stuff you have jammed in the closets, the stuff you have jammed into your attic, into your garages. It will wear on you, and so many of us have things that aren't serving us, that are outdated, things that we don't truly want.

One of the best ways for you to measure this is to think about, would I buy this again? Would I invite this into my life right now? Would I be friends with this person right now? Would I go to this gym? Would I buy this car? Would I - all of those things that are in your life you have to re-decide to have them there.

And too often, we're holding on to things just because we had a relationship with them in the past, and a lot of us feel like if we don’t continue the relationship, if we don't maintain the relationship, that somehow, we're invalidating the experience that we've had. And what I want to offer is that a lot of times, our relationships with things and with people are complete, and we're now just dragging them along with us because we don't want to say goodbye.

And I know for sure dragging things along with you because you don't want to say goodbye to them will slow you down, will wear you down, will not ultimately give you what you need in your life. And so, in this podcast, I want to teach you hopefully how to say goodbye to things, to items in your home, to relationships, to jobs, and to thoughts, because goodbyes allow for hellos. And if you want to have a new version of your life, you're going to have to learn how to say goodbye.

So how do you know when to say goodbye? And here's a good rule of thumb. Would you buy it today? Would you start a relationship with this person today? Would you adopt this way of thinking today? And if the answer is no, you want to consider a goodbye.

Now, so many of us say, "But I've put so much time in", "But it was so expensive when I purchased it." Those are not good reasons to continue a relationship that you wouldn't choose today because here's the thing for most of us who are growing, most of us are in Scholars, most of us who are regenerating ourselves, evolving ourselves, moving towards more of what we want in the world, we're letting go of the past.

You can't hold space for both of those things. You can't be the person that used to be afraid of doing anything and the person who's courageous doing everything, all at the same time. You have to be willing to let go of parts of your own identity, parts of that thinking, people.

And I think people believe that the only reason to say goodbye to something is if something's gone terribly wrong, if we're terribly upset about it, if it's broken. And this will hold you back more than anything in your life. You take like the extreme version of this, which is hoarding, which is keeping pieces of paper because there's nothing wrong with that piece of paper, why would I throw it away? There doesn't have to be something wrong with something for you to say goodbye to it. In fact, you can love that thing and just not need it or want it in your life anymore, and that's okay.

I recently did this with one of my very long friendships, and I didn't say to this person that I didn't want them in my life anymore, I just basically told them that the way our relationship had been in the past was not going to work for me moving forward, and that I wanted to talk about letting that version of our relationship be complete, and starting a new version of it.

And for those of you who lose a tremendous amount of weight, you have to be able to say goodbye to the fat and I'll tell you, for so many of us that's such a huge part of our identity and how we've associated ourselves that it's much more challenging than you would think.

And we have to be willing to say goodbye to courses of action, like for example, when I stopped drinking, there were so many activities that I had to say goodbye to, so many things that I didn't need or want in my life, there were friendships of people that I would just drink with that no longer served me.

So why are goodbyes so hard for us? I think the first reason is we use it as a reason to feel regret, especially - and this is so fascinating - especially if we've hung onto it for too long, if we let go of it then we can often beat ourselves up for not letting go sooner. I've watched this happen with so many clients, when they finally decide to get a divorce or quit a job, they're angry at themselves for not doing it sooner. And so, to prevent that regret, we just stay in the relationship, which of course makes no sense. We stay in the situation, we keep that thing.

Another reason why saying goodbye is hard is because you have to make a decision and that requires adulthood. If you're anything like me, you don't want to have to make decisions, defining decisions and deal with the messiness of that. It's easier just to hold on to everything and not have to decide to let it go.

Many of us are afraid of the regret we will feel. So we don't make a decision because we will regret not having done it sooner, and then sometimes we won't make that decision because we're afraid that we will regret letting go of that thing or throwing that thing away, or ending the relationship or quitting the job. We're afraid of regretting it so then we don't do it.

The other reason why saying goodbye is hard is because of our brain's desire to avoid pain, seek pleasure, and be efficient. Our brain likes to keep doing what its always done. It's much more efficient just to keep all this stuff around, much more efficient for the brain not to have to say goodbye, not have to clean it up, not to have to change.

Saying goodbye is hard because we have a fear of the unknown. We like what we know, we like the familiar, even if we know it's not serving us, there's comfort in it.

And the last reason why most of us don't like saying goodbye to anything is because we would rather avoid. We would rather avoid any stimulus that causes us to have any flavor of a negative emotion. So many of us believe that our lives should be happy all of the time, why would we say goodbye? Goodbye is a sad thing. "I don't want to say goodbye, I don't want to end things, I don't want to anticipate the regret that I might feel. I don’t want to experience loss. That's why I will avoid all of that and stay in stale situations because I don't want to experience any pain."

Now, let's talk a little bit about why goodbyes are necessary. The first reason I have is constraint. So many of us are so overwhelmed by our lives. We have so many friends and so many social obligations and so many opportunities and invitations, and people to call back and birthday cards to write, and stuff to dust and clean and store and buy more of.

We don't know how to constrain and simplify our lives by letting go, and so I believe that constraint is what provides for progress and in order to have constraint, which means you constrain your attention to just a few important things, you have to be able to say goodbye to all the other things.

I really love the imagery of a rose bush, and if you've ever seen someone who takes beautiful care of their roses, who is a gardener, who knows if you've ever gone to a rose garden, well, you will notice what's so fascinating is them pruning roses. Cutting perfectly good roses off of the rose bush.

And I went to Santa Clara University and they had a beautiful garden there and I always wondered like, why would you cut off a blooming, beautiful rose when it's fine, it's good? And it's this idea that you have to prune what's good in order to allow for what's great. In order for the rose bush to be great, you have to prune anything that isn't up to greatness.

And I think that's the most challenging thing for us in our lives because it's a perfectly good spoon. It's a perfectly good shirt. It's a perfectly good friend. And when you allow for so much good in your life, you can't constrain for great. You can't make room for it.

It's so much better to have one great ladle that you want to use all of the time versus having five kinds of good ones. And think about if your life was constrained to only those things that are great, only those things that are beyond good.

I have a really good friend, Tanya Lee, she just sent me the most beautiful scarf, and I watch in her life how she has things that are great only. She has like five gorgeous dresses. Beautiful things that she wears, and I know that they're very expensive and she wears them so beautifully and takes such good care of them, and I think that can be true for all of the areas in our life.

Another reason why it’s really important for us to focus on the things that are great in our life is because of our energy. It takes energy to own things. I learned this from the minimalist. It takes energy to take care of them, to repair them, to store them, to clean them, to focus on them.

And so many times we're dragging so much stuff along that we no longer need or use or even want, so it's just so important to think about if you have a limited amount of energy and everything you own is pulling at that energy and that includes your relationships and your stuff, then are you making conscious decisions on what you want in your life and what you're actually dragging?

Let's talk about completion versus failure. Let's talk about throwing things away. Let's talk about ending relationships from a place of completion, instead of feeling like they were fails. I've watched people do this in divorces, it makes such a huge difference when they feel like I love you, but this relationship is complete. This relationship has fulfilled me to the maximum amount that I can be fulfilled within this relationship, and I love you, and goodbye; versus creating a huge fight about it.

I think that it's really important to complete relationships instead of just letting them fade away. Having conversations and meaningful decisions about relationships and where you want them to go and the forms you want them to take instead of simply deleting people from your life or avoiding people in your life.

And I'm talking about relationships with things. I'm talking about your relationships with thoughts, with beliefs, and with people. Everything can have its season, and then you can let it go. Goodbyes can feel loving and good and they don't have to be filled with conflict.

So here's the process I want to give you. It's simple and it's clear and it's very challenging to learn how to do. First, you want to take an inventory of what you currently have, become aware. I want you guys to do this with things in your life, things in your cupboards, with your bathroom drawers, with your friendships, with your lovers, with the people that are coming over, with everything. The habits in your life, take an inventory and become aware of it. Make a list. Pick a category and make a list.

All the things you have in your office, all the things you have in your drawers, and go through and decide on purpose if you want to say goodbye. And remember the way that you do that. Would I buy it again? Do I love this? Do I want it? Is it serving me? Is it outdated? Is it something you used to love that used to serve you and it no longer is? And then you say goodbye.

And let yourself feel the loss. So many people say, "I don't want to throw that away because I might use that again, I don't want to throw that away because I loved it so many. I don't want to throw because it reminds me of my grandma." And when you say goodbye to those things, you will feel that loss but I want to tell you that people are not things.

When you have something that reminds you of someone, remember that that someone is not in that thing, especially if they've passed away. I've had people that have loved someone that passed away so much that they don't want to throw away any of their stuff, and I say, "Why don't you just keep the one thing you love the most and put it somewhere where you see it all of the time?"

And then once you've said goodbye to those things, then create what you want. As with all decisions, you need to commit to the goodbye and not look back. Make the decision clearly and definitively. Allow an ending to be what it is. Choose not to regret. That is a decision that you get to make.

You can always start the relationship again anew later. You can buy a similar version later or you can start thinking the same thought again. But most likely, you will learn to stay true to your goodbyes so you can move forward to many more hellos.

Goodbye, my friends, I'll talk to you next week.

Hey, if you enjoy listening to this podcast, you have to come check out Self-Coaching Scholars. It's my monthly coaching program where we take all this material and we apply it. We take it to the next level and we study it. Join me over at the Make sure you type in the I'd love to have you join me in Self-Coaching Scholars. See you there.


  1. Great Podcast Brooke! Thanks for taking your time to enlight us with say goodbyes to things aren’t serving us! That was a powerful message. Always looking forward to hearing more podcast like this! Thanks again!

    1. This is a Fantastic podcast!! Opened up my eyes about letting go and saying goodbye! I’m so ready to make more room in my life great thinngs! Thank you Brooke you are amazing!

  2. This is great stuff!! About a year ago, I pretended I was moving, went through every drawer, bin, garage, attic and got rid of so much stuff!! I am 27yrs old and married for 8 years now and in that amount of time my husband and I had accumulated so much stuff!! I felt so free every time I filled my car up to haul away! I needed to hear this podcast because I still have so much that doesn’t serve me, its just “stuff” that clutters my mind.

  3. This podcast came at such a good time for me!! Thank you Brooke you are seriously the most inspiring person to me in my life right now and pretty much have been for the past few years. My question to you. I have journals…lots of journals that I have filled with everything about my life. I am 27 now and have been writing for 10 years everyday about a lot of different things goals, dreams, relationships, daily reflection also good and bad times. Do I throw all of these away…? Yes they are my past and not my life anymore. I feel sad that they are awesome memories I would have never remembered if I wouldn’t have wrote it down so long ago and then reread it… Do you think it is really ok to let all of this go…? I think the further back ones are ok to let go but this past year I have been in a relationship that is a forever keeper I feel at this point and I really dont think it is best to let those memories from this past year with him go yet. I understand we are not meant to remember or relive everything. I also ask myself why would I want to use time on thinking about the fun and the bad in the past when I want to create better memories for my future and do more productive things in the moment….am I on the right track of thinking here? Also what do you think about haven shoe boxes full of pictures… especially ones of my ex-boyfriends or even ex-friends? I have thought about going through all of those and just keeping the good ones….what really defines a good picture? Obviously the clarity and who the people are in it? Any kind of tips on going through this stuff is so appreciated. Thanks for your awesome work. I aspire to be a life coach one day and do the amazing work you do!

    1. Hi Brittany, Thank you for your question. Brooke will be responding to questions in an upcoming Questions and Answers episode. Stay tuned! –Rebekah

  4. Hello my friend!
    What’s up??
    Is someone translating your podcasts into Portuguese? Many of my Brazilian comrades would LOVE this. One friend actually wanted me to translate these concepts into Portuguese for her mother. What??? Yes. You are quite literally changing the world! If you need a translator, let me know!
    Best, and THANK YOU,

    1. Hi Emily, Glad you and your friends are enjoying the podcast! We’re not looking into translation at this time, but Brooke appreciates the offer. –Rebekah

  5. Hi Brooke,
    This podcast came at just the right time for me. Had to say goodbye to an ex today for the second time after he got in contact with me. Feel like it’s a constant choice to say goodbye to him after 6 years of our relationship being on and off. It’s tough saying goodbye to the dream I had for us but I know this relationship no longer serves me.
    All the best,

  6. Hi Brooke, I love your podcast and all the content you provide. I’ve grown so much since listening to your podcast and gosh i would love to join your 6 day course but dont feel this is the right time yet. I do hope you will offer it again. I do have a question that i dont think you have covered yet having to do with the other person in the relationship. My husband who is a wonderful loving and mild tempered man usually except when he uses drinking to buffer his stress. When this happens he gets tired and grumpy (dehydrated and hungover etc) and I would be faced with his short temperness and bad attitude. He would sometime yell at me or says mean/rude things which I dont accept. I know that after listening to your podcast that I cant controll his reactions or feelings and that I can only love and accept that drinking is his way of buffering when he is stressed. Instead of nagging him now I do as you say and I tell him that this is not acceptable behavior to act this was towards me and I accept his apologies when he sobers up and realizes what a jerk he has been (he’s been good about this) and I continue to love him as he is. My question is however at what point is it enough if his drinking habits/aftermath doesnt ever change? What if he never takes responsibilities for his feelings and reaction on his own. I would love for him to come around on his own through my being supportive and loving of him. I hope this is how it would play out but my fear is that he might just see it as an “okay” way to act as long as he is sorry after. I am 31 weeks pregnant and the thought of having our child deal with this side of my husband also makes me sad. Is there anyway I can lead him to see his own actions and reactions as something he can improve from? How do i help him see that his drinking buffering isnt the best way to deal with stress? (Also, its not the drinking i mind just his bad attitude after) Thank you so much, Karen.

    1. Hi Karen, Thank you for your question. Brooke will be responding to questions in an upcoming Questions and Answers episode. Stay tuned! In the mean time, check the episodes on the manual. Ep #11: The Manual: and Ep #139: Someone to Love: Also notice, you are still trying to control him and thinking that he should change. This thinking is what is causing you pain, not his behavior. –Rebekah

  7. What a wonderful session. I’m so grateful to have came upon this in my journey of self-discovery and self realisation. I’ve been struggling to let go (say goodbye) to the people and relationships that no longer serve me in my life and in my becoming the person I keep saying I am but never showing myself to be. It’s a choice- an active decision that I keep making to subject myself to past behaviours and attitudes that shouldn’t have control over me. I am beginning to understand the power I have for my own life and the things that I allow into and out of it.
    Forever grateful for your reminders of the greatness that lies within myself.

  8. This is such a powerful episode! I haven’t done the inventory, but am loading up a bag or two for donation. I’m a bit of a hoarder.

    1. Thank you for sharing! So glad you enjoyed this episode. –Brecklyn

  9. Hello,
    I purchased the e-book. If I’m so smart why cant I lose weight and I haven’t received a link to download the content. Please let me know when I can expect it.

    Thank you,
    Cindy Forbes
    [email protected]

  10. hii brooke, as usual your podcasts comes at the right time.
    i loved it!

    I have a friendship, where she doesn’t open up to me like i would wish with other people/Friends.
    we have a superficial relationship. we do a lot of stuff togehter, travel etc.
    but I love having DEEP FRIENDSHIPS.. what i don’t have with her.
    what would you reccomend to do?
    it makes me really sad because we had some great times together and i think we would still do.
    but its just akward sometimes because she’s not opening up so i can’t really enjoy our friendships.

    and my boyfriend and i had a similiar time in our relationship where we recreated our relationship again and now we are happier then ever.
    when i notice i have to say goodbye to a person, can i try and recreate a new style of relationship with them?

    big hug and thanks for your help!

    1. Hello Debra, Thank you for your question! Brooke will be responding to questions in an upcoming Questions and Answers episode, so please stay tuned! –Lori

  11. Hi Brooke,
    I was just introduced to your podcast this summer and I’ve been intently listening through each episode. This one in particular I’ve listened to at least three or four times. Reason being is that I’m planning on completing a relationship with someone over the Thanksgiving holiday. It’s been a very long journey over the last year but I’m ready to peacefully complete the relationship without feeling hatred or regret. I learned a lot from my partner and there were certainly good and bad times. There’s been a lot of pain and I know I wouldn’t trade these experiences for anything else, but it’s time to say goodbye so I can open myself up to new hellos. Thank you so much again.

    Side note: I’m graduating college here in 28 days and I’m hoping to find a career out in Dallas. If you have any recommendations on where I should consider applying for a marketing or graphic design position I’d appreciate any guidance or counsel you have.

    All the very best,

    1. Hi Adam, I’m so glad you’ve enjoyed the episode. We wish you all the best in your transition. –Felicia