How To Know When It’s Time To Leave (And Why It Feels Impossible)

Hey everyone, welcome back to OnPurpose. Today I want to start with something. that may sound simple, but I think it. explains why so many of us feel stuck in. seasons of life we know we've outgrown. Here's the thing. Most people don't. struggle with starting over. They. struggle with letting go. We think the. hard part is beginning again, taking a. risk, stepping into a new chapter. But. more often than not, the real hardship. comes from having to release the chapter.

that came before it. Think about it. Most of us already know when something. in our life isn't working. We know when. a relationship has become more draining. than enjoyable. We know when a job no. longer fulfills us. We know when we've. lost excitement in a path we once. thought we wanted. The challenge isn't. usually recognizing that something needs. to change. The problem is that every time we get. close to moving forward, attachment.

pulls us backward. We're attached to the. years we've already invested, the. identity we've already built, the story. we've been telling ourselves, and the. future we once imagined so clearly that. it almost feels impossible to move away. from. We are attached to what we hoped. our current situation would become. And. that can be even harder to release. because you're not grieving what. happened. You're grieving what you. thought would happen. This is why.

starting over can feel so confusing. On. the outside, people might look at your. life and say, "Just leave. Just quit. Just move. Just try something new." But. inside, it feels much more complicated. Because letting go is rarely just about. changing a circumstance. It's about. changing the story you had about your. life. And that story may be more central. to your identity than you've realized. So today, I want to talk about the. psychology of letting go and how to.

start over in your life even when it. might feel impossible. We're going to. look at why your brain holds on to. things you've already outgrown, how to. let go of an identity that no longer. fits, how to know when a risk is. actually worth taking, and how to begin. a new chapter the right way. By the end. of this episode, I want you to see that. letting go is not failure, weakness, or. a sign of giving up. Instead, sometimes. letting go is the bravest form of. growth. Let's start with why we hold on.

to things we've already outgrown. One of. the biggest mistakes we make is assuming. that if something is hard to leave, it. must still be right for us. We think. difficulty to move on is evidence we. shouldn't. We think emotional attachment. to something is proof it's a part of us. But the pain of loss doesn't always mean. something is still meant for you. Psychologists help explain this through. something called loss aversion. Loss.

aversion is a cognitive bias where the. emotional impact of a loss feels roughly. twice as intense as the joy of an. equivalent gain. This explains why. people strongly prefer avoiding losses. even if it means missing out on other. gains. And it heavily influences. decisionm under risk. In other words, when applied to real life, you simply. aren't able to comprehend the awaiting. joy on the other side of giving. something up. This is why your brain may.

resist a decision even when that. decision would make your life better. Your brain is not always asking, "How. will this help me?" Sometimes it's. asking, "What am I about to lose?". And when the answer is familiarity, comfort, approval, status, predictability, or a version of yourself. that feels safe, your brain naturally. becomes protective. It would rather keep. you in a familiar place than lead you. into an unfamiliar possibility.

That's why people stay in relationships. long after the connection has. disappeared. That's why people stay in. careers that drain them because they. don't know who they would be without the. title. That's why people keep chasing. goals they no longer want because. abandoning the dream feels like. admitting failure. We tell ourselves. we're being loyal, committed, or. responsible. But sometimes we're simply. afraid to lose the story we have already. spent so much time building. This.

connects to another idea in psychology. called the Sunkost fallacy. The sun cost. fallacy is when we continue investing in. something because we have already. invested so much even when continuing. may no longer make sense. You see this. in small ways like reading the rest of a. book you don't enjoy because you already. read the first 40 pages or eating a meal. you're no longer hungry for because you. already paid for it or staying at a. concert long after you're tired because. it was the hard to get tickets. But we.

also do this with our lives in much. bigger ways and the cost becomes much. higher. We say, "I've already spent 5. years in this relationship or I've. already spent 10 years building this. career. I don't know who I am outside of. this. So, how can I change now?" But the. years you've already spent are not the. only years that matter. The years you. still have ahead matter more. And. sometimes the most loving thing you can. do for your future is stop making it pay.

for your past. So here is the first. question I want you to sit with. Think. about the relationship, job, friendship, goal, commitment, or situation in your. life that you're struggling to let go. of. If that exact thing walked into your. life today exactly as it is right now, would you choose it again? I don't mean. the version of it from the beginning. I. don't mean the version you hoped it. would become. I don't mean the version. you still find yourself reminiscing. about when you're feeling nostalgic. I.

mean the reality of it today with. everything you know now and everything. you've experienced. Would you willingly. choose it again? Because that's often. where clarity begins. So many of us keep. making decisions based on who we were. when we first said yes instead of who we. are now. We keep defending an old choice. rather than evaluating the life that's. actually in front of us. That question. can be uncomfortable because it removes. nostalgia from the equation. It stops.

asking you to defend what something used. to be and asks you to look honestly at. what it is. And sometimes the answer. will be yes. You would pick that. situation again. This means you may not. need to leave, but you may need to. recommmit with clearer intention. But. often the answer will be no. You. wouldn't choose this situation today as. it is if it were presented to you for. the first time. And if the answer is no, then the work now becomes learning how.

to let go without turning the past into. a present mistake. Letting go does not. mean the chapter was pointless. It does. not mean the relationship was a waste, that the job was a waste, the dream was. a waste, or the version of yourself who. wanted it was wrong. something can be. meaningful and still be complete. One of. the greatest signs of maturity is being. able to honor what something gave you. without forcing it to keep giving. The. second thing I want to touch on is this.

Once you've accepted what needs to. change, you need to accept that you will. have to adjust your own identity. accordingly. This may be the deepest. part of the conversation because often. what we're holding on to is not the. relationship, the job, the city, the. dream, or the plan itself. We're holding. on to who we got to be inside of it. We're holding on to the identity it gave. us. And identity is one of the hardest. things to release because it becomes the.

way we explain ourselves to the world. Maybe you are the person who is going to. be married by a certain age, successful. by a certain age, living in a certain. city or working in a certain industry. Maybe you were the dependable one, the. ambitious one, the spiritual one, the. strong one, the one who never gave up, the one who was in a perfect. relationship and then life changed or. you changed and suddenly the identity. that once helped you feel grounded. starts to feel like a cage. It's natural.

for the brain to start wondering, "Who. am I if I don't want this life anymore?". Yes, it can feel like betrayal to. outgrow something you once prayed for. But growth will often ask you to. disappoint an older version of yourself. so you can become honest with the. version of yourself that exists now. There is a concept in psychology called. narrative identity, which is the idea. that we make sense of our lives through. stories. Human beings are meaning making. creatures. We don't just experience.

events and move on. We organize those. events into a narrative that helps us. understand who we are, where we've been, and where we're going. Without even. realizing it, all of us are carrying. around a story about ourselves. Maybe. your story is, "I'm the person who had. to work twice as hard as everyone else.". Maybe it's, "I'm the person who always. puts family first." Maybe it's, "I'm the. ambitious one, or I'm the independent. one." These stories are incredibly.

useful because they create a sense of. continuity. They help us feel grounded. They help us answer the question, who am. I? But over time, the story that once. helped us understand ourselves can start. limiting us. Because once you've. repeated a story enough times, it stops. feeling like a story and starts feeling. like an obligation. That is why changing. your identity can feel so uncomfortable. It is not just that you are changing. your schedule, your relationship status, your address or your job. You are.

changing the explanation of who you are. You are changing the sentence you've. been using to introduce yourself, to. define yourself, and sometimes to. protect yourself. Suddenly, you're left. with a space between identities. This is. the gap between who you were and who you. are becoming. And it can feel. frightening because nothing is fully. formed yet. But the absence of an old. identity does not mean the absence of. self. It means you're in the process of.

becoming more authentic. We often think. identity is something we find once and. keep forever. But identity is meant to. evolve. The version of you who wanted. something 5 years ago may have been. completely sincere. But sincerity does. not require permanence. You can honor. what you wanted then and still choose. differently now. So the practice here is. not to ask who am I without this in a. frightened way. The practice is to ask.

what part of me is ready to step forward. now. That question. moves you from loss into curiosity. It. allows you to start treating change as. evidence that you're alive, that you're. growing, learning, and becoming more. aware. For anyone listening who feels. terrified of changing, I want to offer. you this. Sometimes the bravest thing. you can do is admit that the person. you're becoming wants something. different than the person you used to. be. That's not a failure of commitment.

That's the natural result of living, learning, and growing. Many of us. secretly believe there is one correct. version of our lives. one right career, one right relationship, one right city, one right timeline, one right path. And. because we believe that, every ending. feels catastrophic. If the relationship. ends, then maybe I missed my chance. If. the career doesn't work out, maybe I've. fallen behind. If I change direction. now, maybe I'm walking away from the.

life I was supposed to have. But when. psychologists study happiness, fulfillment, and life satisfaction, they. don't evidence that there is one perfect. life waiting for each of us. What they. find is that human beings are remarkably. adaptable. We create meaning wherever we. go. One of the most freeing realizations. you can have is that there isn't one. version of your future capable of making. you happy. There are many. The life you. imagined at 20 could have been.

beautiful. the life you're building now. can still be beautiful, too. These ideas. don't compete with each other because. sometimes what keeps us stuck isn't our. attachment to the past. It's our fear. that letting go means losing our only. chance at a beautiful future. Now, I. want to move on to something I think is. very important to consider, especially. when making very large life choices. We. need to unpack how to know when a risk. is worth taking. I want to be very clear.

here because sometimes when we talk. about starting over, people can mistake. it for impulsivity. When I'm talking. about letting go, I'm not saying to. destroy your life every time you feel. uncomfortable. Taking a risk does not. mean you abandon wisdom, responsibility, patience, or discernment. Not every hard. season is assigned to leave and not. every exciting opportunity is assigned. to jump ship. So how do you know when a. risk is actually worth taking? The first.

thing I want you to look at is the cost. of staying. Most people only calculate. the cost of leaving. They think about. what they might lose, what might go. wrong, who might judge them, how much. money it might cost, or how uncertain. the future might be. But they rarely. calculate what staying is already. costing them. Staying may be costing you. confidence. It may be costing you. energy, creativity, health, peace, selfrespect, or time you will never get. back. Staying may be teaching you to.

ignore your own instincts. Staying may. be making you feel smaller, more. resentful, or more disconnected from the. person you want to become. And sometimes. when you really calculate the cost of. staying, you realize that the safe. option is not actually safe. Research on. regret gives us something powerful here. Studies have found that in the short. term, people often regret actions more. intensely because the consequences are. immediate and visible. But over the long. term, people tend to regret inactions.

more deeply because the mind keeps. returning to the life that might have. been. The change you made may sting for. a moment, but the change you never tried. can haunt you for years. Simply put, a. risk is worth considering when the. downside is survivable. The upside is. meaningful and the lesson would still be. valuable even if it didn't work out. If. the worst case scenario is painful but. recoverable and the best case scenario. could expand your life in a way that.

deeply matters to you, then that can be. a risk worth exploring. And if staying. exactly where you are is dimming. something important inside of you, then. avoiding the risk may already be the. risk. One of my favorite questions is. this. What would I regret more 5 years. from now? Trying and failing or never. giving myself the chance. The question. doesn't give you a perfect answer, but. it changes the timeline. Suddenly, the. pain of temporary discomfort becomes.

smaller than the pain of permanent. self-abandonment. So let's say you decide the risk is. worth taking. You're ready to let go of. your past identity. You're ready to. detach from the life you were previously. living. Now we need to touch on how to. start a new chapter from the beginning. One of the reasons people delay starting. over is because they want certainty. before they move. They want proof that. the new relationship will work. Proof. that the new career will succeed. Proof.

that the new city will feel like home. proof that the new version of themselves. will be accepted, admired and safe. But. life rarely gives us certainty at the. beginning of a chapter. So to start a. new chapter, you need to deeply engage. in a concept called psychological. flexibility. Psychological flexibility. is the ability to stay present with. discomfort as you adjust to changing. circumstances. It means taking action. that aligns with your values even when.

you feel uncomfortable or afraid. It. means you can feel uncertainty and still. move in the direction of what matters. The first step in developing. psychological flexibility is learning to. stop treating your emotions as. instructions. Just because you feel fear. doesn't mean something is wrong. Just. because you feel uncertain doesn't mean. you're making the wrong decision. Just. because you feel grief doesn't mean you. should go back. One of the biggest. mistakes we make during periods of.

change is assuming that our emotional. state should determine our next move. Psychological flexibility asks us to. separate the feeling from the decision. The second step is learning to get. comfortable with the concept of both. Many of us believe we need to choose. between fear and action, uncertainty and. confidence, grief and growth. But. psychological flexibility teaches the. opposite. You can be terrified and still. move forward. You can miss the old.

chapter and still know it's time for a. new one. You can be unsure about how. things will unfold and still be. determined to try anyway. The goal isn't. to eliminate difficult emotions. The. goal is to expand your capacity to hold. them while continuing to act in. alignment with your future. This. practice asks you to shift your focus. away from certainty and toward values. When people are trying to make a big. decision, they often ask, "What outcome. can I guarantee?" But life rarely offers.

guarantees. A more useful question is, "What choice best reflects the person I. want to be?" One question is rooted in. control. The other is rooted in values. And when you're standing at the edge of. a new chapter, values tend to be a much. more reliable compass than certainty. So, how do you begin when you don't know. how the future ends? You treat the next. chapter like an experiment, not a. verdict. One of the biggest mistakes. people make is believing every decision.

has to be forever. We think choosing a. new direction means guaranteeing the. outcome. But some of the most successful. people approach change differently. They. don't ask what if I choose wrong. They. ask what can I learn regardless? Instead. of committing to a new career, experiment with one. Maybe this will be. your job for life or maybe it won't. Maybe this new relationship will be your. forever person or maybe they won't. Embrace the liinal space between.

identities and allow yourself to explore. without attaching to the next set. version of your life. The goal is not to. be right 100% of the time. The goal is. to learn. And often times the. information you need to make a. life-changing decision only becomes. available after you start testing. possibilities. You can't know for 100%. certainty that you're on the wrong path. until you find yourself on a new one. that finally feels right. This takes me. to the final thing I want to touch on.

today. Let's go over how to let go of a. chapter of your life without becoming. bitter towards the time you spent there. This is important because sometimes once. we finally move on, we try to make the. ending easier by turning the old chapter. into something that was bad. We convince. ourselves the relationship was all bad. or the job was a waste or the person we. used to be was naive. We think if we can. make the past feel wrong, it will be. easier to detach from it entirely. But. bitterness will only hinder you from.

further growth. You can let go with. gratitude. You can leave without hatred. You can accept that something is. complete without needing to destroy its. meaning. This is one of the most healing. shifts you can make because it allows. you to move forward without carrying. resentment as proof that you were right. to make the choices that you made. Of. course, sometimes a chapter ends because. it was harmful. And in those cases, anger may be part of the healing.

process. Anger can be protective. Anger. can help you recognize where a boundary. was crossed or where your dignity was. not honored. But even then, the goal is. not to live inside anger forever. The. goal is to let anger give you. information without taking it into your. new identity. Because the fact of the. matter is, even as you grow and evolve. and shift identities, you are still you. And you need to hold love for every. version of yourself that you have been.

and will become. Changing your. circumstances does not mean abandoning. yourself. You are the same person you've. always been. What's changing is where. your values now align. I think this is. one of those fears people have when they. start over. They worry that changing. means losing themselves. They worry that. if they leave the identity they have. now, their future self will become. unrecognizable. But real growth does not ask you to. abandon yourself. Real growth asks you.

to return to the parts of yourself that. have been waiting beneath an identity. you outgrew. You are not a fixed thing. You are not one title, one role, one. relationship, one mistake, one. achievement, one plan or one season. You. are a living evolving person and you. will grow and survive through many. different chapters. So instead of asking. who am I once this chapter ends, ask. what parts of this chapter are coming. with me into this new version of myself. Maybe it's your kindness or your work. ethic or your compassion for others.

Starting over just means you are simply. releasing what no longer belongs so that. the truest parts of yourself have more. room to breathe. Maybe the old chapter. taught you resilience. Maybe it taught. you what love is and what love isn't. Maybe it taught you what kind of work. energizes you, what kind of people. nourish you, what kind of pace your. nervous system can sustain, or what kind. of life you no longer want to build. If. you leave with the lesson, then nothing. was wasted. This is how you start over.

with wisdom instead of panic. You don't. pretend the past didn't happen. You. integrate it. You allow yourself to. become someone more whole because of. what you've lived through. As we come to. the end of this episode, I want to bring. you back to where we began. Most people. don't struggle with starting over. They. struggle with letting go. And maybe the. reason that line feels so true is. because deep down many of us already. know the next step. We know what. conversation we've been avoiding, what.

decisions we've been delaying, what. career we've outgrown, what truth we've. been minimizing, or what chapter has. been ending for a long time. The work is. grieving the future that will no longer. happen, so you can stop missing out on. the future that still could. The work is. loosening your grip on the version of. life you expected, so you can receive. the version of life that is actually. meant for you. And I know that can be. painful. I don't want to make letting go. sound easy because it isn't. Letting go.

can feel like loss even when it leads to. freedom. It can feel like failure even. when it leads to success. It can feel. like uncertainty. even when it's rooted in alignment. But. I want you to remember this. The chapter. you're leaving is not the only chapter. capable of holding meaning. The version. of you that existed there is not the. only version capable of being loved, successful, fulfilled, peaceful, or. whole. There is more life beyond the.

identity you built, more possibility. beyond the story you planned, and more. of you beyond the part you are being. asked to release. Maybe for you, letting. go looks dramatic. Maybe it's leaving a. relationship, changing careers, moving. cities, or finally pursuing something. you've spent years talking yourself out. of. But more often than not, letting go. happens in much quieter ways. Maybe it. looks like releasing the timeline you. thought your life would follow. Maybe it. looks like leaving behind a friendship.

that hasn't been real in years. Maybe it. looks like letting go of the belief that. success has to look a certain way, that. love has to arrive in a certain way, or. that family has to show up for you in a. certain way. Letting go just means. accepting that a version of yourself. you've been trying to get back in. alignment with no longer exists. I think. that's an important one. So many of us. spend years trying to return to a. previous chapter of our lives. We tell. ourselves, I just want to feel the way.

we did in the beginning or I want to get. back to who I was when I first moved. here. Or I want my life to look the way. it did before I lost that person. But. life doesn't move backwards. We don't. get our old chapters back. What we get. is the opportunity to build something. new from what we've learned. And that's. why letting go matters. Because every. ounce of energy spent trying to recreate. a chapter that's already ended is energy. that can't be invested in the chapter.

that's trying to begin. The future. doesn't ask you to forget your past. It. asks you to stop living there. So this. week, I want you to ask yourself three. questions. What am I holding on to only. because it feels familiar? What identity. am I afraid to release because I don't. yet know who I'll become without it? And. what is the next honest step I can take. toward the chapter that is trying to. begin? You don't have to change your. whole life in one day. You don't have to. know exactly where the next chapter will.

lead. You don't need to feel completely. ready, completely confident, or. completely fearless. You just have to be. honest enough to admit when something is. complete, brave enough to release what. no longer fits, and willing enough to. take one step toward what may be waiting. for you next. Because here's what I've. learned. Every person I've ever met who. was terrified to take a leap is always. ultimately grateful that they did. Every. person who found the relationship,

career, purpose, city, community, or. version of themselves they were meant to. grow into had a moment where they stood. exactly where you might be standing. right now, looking at an ending they. didn't want facing. Uncertainty they. couldn't control and wondering if they. were making a terrible mistake. The. difference wasn't that they had more. clarity. It would all work out. The. difference was that eventually they. stopped asking what if this doesn't work. and started asking what if there's more.

for me than this. And that is the real. invitation of every new chapter. Not the. promise that everything will work. perfectly. Not the guarantee that you'll. never experience loss, disappointment, or heartbreak again. The invitation is. simply the possibility that your life. may be bigger than the story you've been. clinging on to. The life you were afraid. to lose was never the only life. available to you. There are still people. you haven't met, experiences you haven't. had, places you haven't seen, and.

versions of yourself you haven't grown. into yet. And that's what letting go. ultimately makes room for. The. possibility of what lies ahead may be. even more meaningful than what you've. been holding on to. When I look back at. the pattern of my life, I noticed so. many moments where I took a leap, when I. didn't know what was next. whether it was leaving my career, changing countries, changing cities, relationships, and I remind myself that.

yes, it was difficult. Yes, it was hard. Yes, it was excruciatingly painful. But you will always regret what you. didn't do more than what you did. Remember this. I'm forever in your. corner and I'm always rooting for you. I'll see you soon. If you love this. episode, you're going to love my. conversation with Matthew Hussie on how. to get over your ex and find true love. in your relationships. Make a list. of the things that are truly important.

>> for you to finding a partner and then be. that.