How To Let Go of the Timeline for Your Life

0:00Jay Shetty:This episode is brought to you by Whole Foods, where your back-to-school eats are sorted. First off, they have amazing quality standards with 300 food ingredients banned store-wide. No hydrogenated fats, nothing in store, has high fructose, corn syrup, and there's a great selection of allergen-friendly options too. Pick up your easy breakfast of frozen waffles, pack the lunchboxes with organic seedless grapes and baby carrots. Then plate up thin crust pizzas and a family-style salad for dinner after a long day of learning. Shop back to school must-haves at Whole Foods Market, in-store or online.

0:33This episode is brought to you by Amtrak.

0:36Jay Shetty:You know that feeling when you're already tired and you haven't even gotten there yet? That's where Amtrak comes in. Leave the driving behind and settle into a comfortable seat with plenty of room to stretch out. Catch up on work with Wi-Fi, grab a snack at the cafe car, or just sit back and enjoy your favourite podcast. Choose a cellar or northeast regional and get there without the stress of getting there Visit Amtrak.com to plan your next trip Hey, it's Jay I don't know what your day's been like but I was just thinking about you for a minute and I hope you're being a little patient with yourself because you deserve it and yeah, I'll talk to you soon

1:28Jay Shetty:I know many of us had certain expectations for how we thought our life would turn out. And a lot of us get down on ourselves for not reaching certain dreams or milestones by the time we wanted them done. But here's my take. The biggest thing holding you back isn't your past. It's the future you thought you'd have. When you were younger, you probably had a picture in your mind of what your life would look like by now. Maybe you imagined you'd be married or you'd have children running around your home. Maybe you thought you'd finally have your dream job, own a house, live in a different city, or simply feel like you'd figured everything out.

2:09Jay Shetty:Whether you realized it or not, somewhere along the way, you started writing a blueprint for your future. Then life happened. Maybe some parts of that blueprint came true, but others didn't. Maybe you found yourself in a career you never expected, living somewhere you never planned, healing from a relationship you thought would last forever, or wondering why everyone else seems to be moving through life while you're still standing still. And without even noticing it, you began comparing the life you're living to the life you thought you'd be living. I don't think we talk enough about how painful that comparison can be.

2:50Jay Shetty:We spend so much time comparing ourselves to other people that we overlook an even more common comparison. The comparison between who we are today and who we expected to be by now. Sometimes the person we're competing with isn't the influencer on Instagram or the co-worker who just got promoted. Sometimes it's the 20-year-old version of ourselves who confidently believed they knew exactly how life was going to unfold. You're measuring your real life against an imaginary one, and reality almost always loses to that comparison. So today, I want to talk about letting go of the expectation of what you thought your life would be.

3:35Jay Shetty:I think there are five ideas we need to understand if we're ever going to make peace with that. We'll go through each concept, and by the end of this episode, I hope you'll have a completely different perspective on how you think about your future. So let's dive in. Because holding too tightly to one version of your life can stop you from seeing the beauty, meaning and possibility in the life that's already unfolding right in front of you. Now, if this is you, don't get down on yourself. Because the fascinating part is, psychology shows us that our brains are wired to create this exact struggle.

4:16Jay Shetty:Psychologists have actually been studying this for decades. In cognitive behavioral therapy, there's a concept called should statements. These are the invisible rules we create about how life is supposed to unfold. I should be married by now. I should have my career figured out. I should own a house. I shouldn't still be living with roommates. I should be happier than I am. The word should seems harmless, but it quietly turns hopes into obligations and milestones into deadlines. Here's the problem with should. Every time you tell yourself your life should look different, you're arguing with reality.

4:58Jay Shetty:You're taking the life that's actually in front of you and comparing it to a standard that may have been written 10 or 15 years ago by a younger version of yourself. And when reality doesn't match that expectation, your brain doesn't conclude. Maybe the expectation needs updating. It concludes, something must be wrong with me. So here's the first thing I want to address. You need to be honest with yourself about where these should benchmarks in your life are actually coming from. Imagine this, it's a Wednesday night, you've finished dinner, you're lying in bed scrolling on your phone before you go to sleep.

5:37Jay Shetty:In the span of three minutes, someone announces they're engaged, someone else just bought their first house, a friend from college shares they're expecting their second child. Another person celebrates becoming vice president at work. You put your phone down, and suddenly the life that felt perfectly fine just 20 minutes ago now feels like it's somehow behind. What's fascinating is that you're probably not thinking, I wish I had her exact life. You're thinking something much more personal. I thought I'd be there by now. That's a completely different comparison. The truth is, the concept of comparison itself has changed dramatically over the last generation.

6:24Jay Shetty:Psychologist Leon Festinger introduced social comparison theory in the 1950s, explaining that we naturally evaluate ourselves by comparing ourselves to others. Back then, your comparison group was relatively small. It was your siblings, your co-workers, your neighbors, maybe a few friends from school. Today, before you've even had your morning coffee, you can compare your career to a founder in Silicon Valley, your fitness to a professional athlete, your finances to an entrepreneur who just sold their company, and your parenting to someone posting perfectly curated family videos online. No human brain was designed for that many comparisons.

7:05Jay Shetty:We've gone from comparing ourselves to a handful of people to comparing ourselves to thousands. And because social media shows us everyone's milestones, but almost none of the ordinary days it took to get there, we begin to believe that everyone else is arriving while we're somehow standing still. The irony is that millions of people are having that exact same thought at exactly the same time. These comparisons become a mirror to where you expected your life to be. Maybe 22-year-old you were certain you'd be married by 30. Maybe you assumed you'd have children by now or that you'd finally feel confident, financially secure or sure about your purpose.

7:49Jay Shetty:Every birthday that doesn't match that internal blueprint can start to feel less like a celebration and more like a report card. The question I want you to sit with is this. Who wrote that blueprint? Was it truly you? Or was it your parents, your culture, your friends, your school, the movies you watched, the messages you absorbed growing up? Because somewhere along the way, many of us stopped treating milestones as exciting possibilities and started treating them like deadlines. And once milestones become deadlines, every detour starts feeling like failure instead of simply another path. This episode of On Purpose is presented to you by Mazda.

8:35Jay Shetty:Peace of mind doesn't happen by chance. It's created through the habits we build before we ever need them. That's the philosophy behind every Mazda. With proactive safety features that help keep you more aware, more connected and more engaged, Mazda helps you feel ready for whatever the road brings. It's why Mazda has been named Consumer Reports' safest new car brand. And as of July 2026, Mazda has won more 2026 IIHS Top Safety Pick Plus awards than any other car brand. Visit www.iihs.org to learn more. A lot can happen when an accident doesn't. Visit MazdaUSA.com to learn more. Consumer Reports does not endorse products or services.

9:20Jay Shetty:Here's what I want you to remember before we move on. The reason you feel behind isn't because your life is behind. There's no way to truly ever be behind in life. It's all arbitrary. You're measuring your real life against an expectation that may no longer fit the person you become. But that raises an interesting question. If these expectations can make us so unhappy, why do we become so attached to them in the first place? The answer has a lot to do with the way our brains imagine the future. Because here's something fascinating. Long before your future ever arrives, your brain has already started living there.

10:03Jay Shetty:I'm sure at some point in your life, you caught yourself daydreaming about your future wedding. You picture who's standing beside you, who's sitting in the front row, or what song you'll dance to. Or maybe you've imagined walking into your dream home for the first time, decorating your children's bedrooms, and moving to the city you've always dreamed of living in. We don't just think about the future, we rehearse it. We visit it over and over again until it starts to feel strangely familiar. That's one of the reasons it hurts so much when life takes another direction. You're not just letting go of a possibility, you're letting go of a future you've already spent years emotionally investing in.

10:45Jay Shetty:Psychologists Daniel Gilbert and Timothy Wilson have spent decades studying something called effective forecasting, which is simply our ability to predict how future events will make us feel. the surprising discovery is that human beings are remarkably bad at it. We consistently overestimate how happy positive events will make us. Think about how often we tell ourselves, I'll finally be happy when, when I get married, when I work out more, when I get the new job, when I move cities, when I have a family, when I finally make enough money. We place so much emotional weight on these future milestones that they begin to feel like the gateway to a better life.

11:29Jay Shetty:Then something interesting happens. You finally get the promotion you've wanted for years. For the first few weeks, you feel incredible. You celebrate with your family, your confidence grows, and you think, this is it. I've finally made it. But slowly, the new job becomes your job. The meetings become your new normal. The excitement fades. Before long, you're chasing the next title. Or maybe you've dreamed about moving to a new city. You imagine walking down beautiful streets, making amazing friends, becoming a completely different version of yourself. The first few months feel exciting because everything is new.

12:08Jay Shetty:But eventually you get rained on rushing to your apartment. You get locked out doing your laundry. You get lost on the subway. You have moments where you feel lonely. The city you're in may have changed, but life didn't suddenly become perfect. Now, there's also another reason we're so bad at predicting the future. But this one, I actually find empowering. Experts have found that we consistently underestimate our own resilience. Psychologists call this immune neglect. Just as your body has an immune system that helps it heal after illness, your mind has an emotional immune system that helps you recover after disappointment.

12:48Jay Shetty:The problem is, your present self can't fully imagine how resourceful your future self will become. Think about a heartbreak you survived. At the time, you probably thought, I'll never get over this. You grieved the future life you saw building with that person. You couldn't imagine laughing again, dating again, or feeling hopeful again. But here you are. Maybe you still carried the scar, but you also carried yourself through it. The version of you sitting here today knows things the version of you back then couldn't possibly have understood. The same thing is true in the opposite direction. When you're imagining your dream life, you're assuming you'll remain the same person you are today.

13:35Jay Shetty:But future you won't think like present you. Future you will have different priorities, different wisdom, different support systems, and different definitions of success. The person who desperately wanted the corner office at 25 might desperately want flexibility at 40. The person who thought success meant recognition may eventually discover that success actually feels like peace. That's why holding too tightly to one imagined future is quite dangerous. You're asking today's version of yourself to make permanent decisions for someone you haven't become yet. You'll love different things. You'll value different things.

14:17Jay Shetty:You'll outgrow certain dreams. You'll discover new ones. Some goals you'll accomplish only to realize they weren't actually yours in the first place. Others will quietly disappear, not because you failed, but because you changed. And maybe that's the most freeing realization of all. The future you're grieving may not even be a future that would have made you happiest. Think about that for a moment. Which brings us to the hardest part of this conversation. If your brain has spent years rehearsing a future that never arrived, if you've emotionally invested in a life that didn't unfold the way you imagined, then of course letting that go is going to hurt.

14:58Jay Shetty:And that isn't weakness, it's grief. When we think about grief, we usually think about losing someone we love. We think about funerals, breakups, divorce, or losing a job. But some of the deepest grief we experience isn't about losing what we had. It's about letting go of what we always wanted. This episode is brought to you by Indeed. I know how important every hire is for a business. If you need to make the right hire, this is a job for sponsored jobs. Indeed sponsored jobs helps find quality candidates when you need them most. You can reach who you need based on whatever criteria you're looking for.

15:35Jay Shetty:like skills, certifications, or location. In fact, people are finding quality hires on Indeed right now. In the minute I've been talking to you, companies like yours made 27 hires on Indeed, according to Indeed data worldwide. Spend less time searching and more time actually interviewing candidates who check all your boxes. Listeners of this show will get a$75 sponsored job credit at indeed.com forward slash podcast. That's indeed.com forward slash podcast. Terms and conditions apply. Need to hire? This is a job for Indeed Sponsored Jobs. This episode is brought to you by State Farm. We talk a lot about intentional decision making, and that extends to the practical stuff too, like making sure your coverage actually works for your life.

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17:14Jay Shetty:For ourselves. Think about someone whose relationship ends after five years. They're not just grieving the person they lost. They're grieving the holidays they already pictured spending together. The children they imagined having. The home they thought they'd grow old in. That future had already become real in their mind long before it ever became real in their life. The same thing happens when you don't get into the school you dreamed of, or when infertility changes the picture you had of becoming a parent, or when the career you spent years building suddenly disappears. The pain isn't only about the opportunity you lost, it's about the identity you were becoming and the life you had already started writing in your imagination.

17:59Jay Shetty:What's incredible is that many of the same brain regions involved in remembering the past are also involved in imagining the future. In other words, your brain doesn't treat the future as something completely separate. It begins building emotional connections to possibilities long before they ever happen. That's why an imagined future can feel almost as emotionally real as a remembered past. So when life changes direction, it makes perfect sense that shifting your view of the future often feels painful. You're not being dramatic. You're not being negative. You're not failing to move on. You're trying to release something your mind has been rehearsing for years.

18:41Jay Shetty:I think this is where many of us become unnecessarily hard on ourselves. We tell ourselves, I should be over this by now. We wonder why we're still emotional over a sudden life change. But maybe the reason it hurts isn't because you're holding on to the past. Maybe it's because you're still saying goodbye to the future. The truth is, we aren't just living our lives. We're constantly creating a narrative about who we are, where we're going, and what our experiences mean. That's why these moments can shake us so deeply. When your life doesn't go according to plan, it's not just the plan that changes.

19:19Jay Shetty:The story changes. This is why I think one of the most compassionate things we can do for ourselves is stop asking, why can't I just move on? And start asking a different question. What am I actually grieving? Because often the answer isn't the event itself. It's the story that ended. It's the chapter you thought would come next. But just because that story ended doesn't mean your story is over. Think back over your own life for a moment. I wonder how many chapters that once felt like endings eventually became beginnings. The breakup that introduced you to the person who changed your life. The job you didn't get that led you toward work you love even more.

20:04Jay Shetty:The city you never planned to move to that somehow became home. The friendship that only exists because your original plans fell apart. You probably couldn't see any of that while you were living through it. And maybe that's the first step toward letting go. Not pretending you never wanted that life you were imagining, not convincing yourself it didn't matter, not rushing yourself to move on, but honoring the future you thought you'd have, while leaving enough room for a future that might be even better. Some of the most meaningful chapters of your life are in the unknown, and they'll never fit inside the blueprint you created years ago, because they require becoming someone your younger self couldn't possibly have imagined.

20:51Jay Shetty:That's what I want to explore next. The idea that maybe the blueprints you're working off are outdated. Because if we're grieving futures that never happened, I think we need to examine who really decided those futures were the ones we were supposed to have in the first place. Most of us have inherited a timeline for life that we never consciously chose. Somewhere along the way, we absorb the idea that life unfolds in a predictable sequence. Graduate by this age, start your career by this age, get married by this age, buy a house by this age, have children before this age, retire by this age. Nobody ever handed us this script, but many of us spend our lives judging ourselves by it.

21:37Jay Shetty:This is referred to as the social clock. The cultural expectations we develop around when major life events are supposed to happen. Every generation has one and every culture has one, but what's fascinating is that they are constantly changing. The average age of marriage is older today than it was a generation ago. People are changing careers multiple times throughout their lives today when they used to stay in the same job. Families are being built in more ways than ever before. The timeline keeps evolving, yet somehow we continue treating it as if it were written in stone. This episode is brought to you by State Farm.

22:19Jay Shetty:We talk a lot about intentional decision making, and that extends to the practical stuff too, like making sure your coverage actually works for your life. State Farm is there to meet you where you are, and they know how sweet it is to feel good about your decisions. Talk to a State Farm agent today to learn how you can choose to bundle and save with a personal price plan. Like a good neighbor, State Farm is there. Prices are based on rating plans that vary by state, coverage options are selected by the customer, availability, amount of discounts and savings, and eligibility vary by state. I think one of the biggest reasons people feel overwhelmed today is because we've inherited multiple timelines that no longer fit together.

22:58Jay Shetty:We're told to spend our 20s traveling the world and collecting experiences, while also saving enough money to buy a home before prices rise even further. We're encouraged to build ambitious careers, but we're also reminded that fertility follows a biological timeline. We're told not to settle in relationships, but we're also warned not to wait too long. It's no wonder so many people feel like they're failing. We've been handed so many expectations and so many contradict one another. You can't optimize for endless travel and put down permanent routes at exactly the same time. You can't prioritize climbing the corporate ladder while also chasing self-care and free time.

23:38Jay Shetty:You can't build a billion-dollar company and be someone who intentionally chose a quiet life off the grid. These are all playing completely different games, yet we put pressure on ourselves to hit every single aspect. That's why I think one of the most liberating questions you can ask yourself is this. if nobody knew your age what would you actually be happy with today ask yourself that question right now if nobody could see your linkedin profile your relationship status your salary or your zip code what kind of life would you choose not the life that would impress people not the life that would make everyone nod in approval the life that would make an ordinary weekday feel good to you?

24:22Jay Shetty:Are you grieving the life you wanted or just grieving the life you thought you were supposed to want? That's a profound difference. Maybe you don't actually want the biggest house. Maybe you want more time with your family. Maybe you don't want the highest title. Maybe you want work that leaves you energized instead of exhausted. Maybe your definition of success changed years ago, but you've still been judging yourself by someone else's scorecard. I think one of the greatest signs of maturity is realizing that your life doesn't have to make sense to everyone else. It only has to make sense to you.

24:59Jay Shetty:Once you stop living by someone else's timeline, something remarkable happens. You stop asking, am I behind? And you start asking a much better question. Am I building a life that actually feels like mine? Now at this point of the episode, you might be wondering, okay Jay, I understand why I feel this way, but how do I actually let go? I think the first thing we need to acknowledge is that letting go doesn't mean giving up. It doesn't mean lowering your standards, abandoning your dreams, or pretending you never wanted the life you imagined. It simply means loosening your grip on the belief that your life has to unfold in one specific way in order to be fulfilling to you.

25:40Jay Shetty:Maybe you still want to get married one day. Maybe you still hope to become a parent, build a successful business, write a book or travel the world. Those dreams don't have to disappear simply because they didn't happen when you expected them to. We don't always need to release the destination. But sometimes, just simply, the arbitrary timeline we've attached to it. One of the most powerful questions I've started asking myself is this. What does this version of my life make possible? It's such a different question than asking, what am I not accomplishing? Every path closes certain doors, but it also opens others.

26:19Jay Shetty:We spend so much time staring at the doors that closed that we never appreciate the ones that have opened beside us. Of course, not every painful experience is secretly a blessing, but the fact is that human beings are incredibly resilient storytellers. We have the capacity to take detours, disappointments, and unexpected chapters and weave them into lives that are even more meaningful. There's an exercise I'd like to encourage you to try. Take out a piece of paper and draw two columns. In the first column, write down everything you think you should want. The career, the partner, the specific salary, the house.