How To Let Go of the Timeline for Your Life

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. 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. 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. 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 coworker 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. 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. Psychologists have actually been studying this for decades. According to 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. 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 bench marks 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. In the span of three minutes, someone announces they're engaged, someone else just bought their first house, a friend from college shares their expecting their second child. Another person celebrates becoming vice president of 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. Psychologists 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 coworkers, 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 you're parenting to someone posting perfectly curated family videos online. No human brain was designed for that many comparisons. 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. 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 stop treating milestones as exciting possibilities and start to 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. 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 I.I.HS 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. 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've 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. 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. 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. 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 means 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. 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. The problem is your presence 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 grieve 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 carry the scar, but you also carry to 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. 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. You'll outgrow certain dreams. You'll discover new ones. Some goals you'll accomplish only to realize that 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 her. 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 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. 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. 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 onto 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, 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'd 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. 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. 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 a script. But many of us spend our lives judging ourselves by it. 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. 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 the 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. We're told to spend our 20s traveling the world and collecting. connecting 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. 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, all your zip code, what kind of life would you choose? Not the life that would impress people, not the life that would make everyone not an approval, the life that would make an ordinary weekday feel good to you. 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. 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 turned fold in one specific way in order to be fulfilling to you. 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. 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, the version of success you've inherited from friends, parents, society, or culture. Then in the second column, write down everything that you have been able to accomplish because that first column hasn't happened yet. Those two lists might surprise you. Maybe you haven't met your soulmate yet, but you just went on an amazing vacation with some of your best friends. Maybe you don't own the home yet, but you didn't have to dip into your personal savings last year when your apartment flooded. Maybe you aren't where you want to be career-wise, but you've learned an incredible amount of skill sets by jumping around and testing different opportunities. There is always a reason and a lesson to be learned along the path you didn't intend to travel. So give yourself permission to rewrite the blueprint. Today's happier, healthier habits are brought to you by Mazda. Consumer Reports' safest new car brand. Mazda's designed for what matters most to you. Here's your challenge this week. For the next seven days, I want you to turn your commute into intentional learning time. And I want to make this really simple. There are three steps. First, before your next commute, choose one thing you want to learn more about. Maybe it's relationships, maybe it's your health, your career, your finances, or a subject you've always been curious about. Second, find one podcast series or audiobook about that topic and save it right now. Don't wait until you're already on your way somewhere and start searching. Decide ahead of time what you're going to listen to. A number three, for the next seven days, make that the first thing you put on when you start your commute. And if you don't commute by car, that's okay. Maybe you take the train, walk, ride a bike, or simply don't have a traditional commute. Choose a regular part of your day when you're moving from one place to another and use that time instead. The goal isn't about how you travel. It's about taking time that normally happens on autopilot and giving it an intention. So that's the challenge. One topic, one podcast or audiobook, seven days. Thank you again to the sponsor of today's Happier, Healthier Habits, Mazda. Mazda delivers more confidence in control in every drive and consumer reports, safest new car brand designation proves it. Mazda's safety features are designed to bring more enjoyment to every drive, not take away from it. When you were 18 or 25, you made plans based on the information you had at the time. You had an experience failure, loss, unexpected joy, or the countless moments that shape us into who we become. Why would we expect a blueprint written decades ago to perfectly fit the person we are today? I always think about the way a GPS works. If you miss a turn, it doesn't stop the journey and tell you you failed. It doesn't spend the next 20 miles reminding you to turn around and fix the mistake you made. It simply recalculates, recalibrates, calmly, instantly without judgment. Life asks us to do the same exact thing. Every unexpected turn is an invitation to ask, given where I am now, what's the best path forward? Not how do I get back to the road I thought I'd be on? Maybe that's what this entire conversation has been pointing towards. It's trusting that the blueprint was never supposed to be perfect. It was simply a first draft and the first drafts are meant to be rewritten. So as we leave this episode, I don't want you to ask yourself whether your life looks the way you imagined it would 10 years ago. I want you to ask a different question. If you were writing your life for the first time today, knowing everything you know now, what life would you choose? Start fresh, start here today. Use the new information that's available to you because that's the incredible gift life gives us. We can't rewrite the past, but we can always rewrite the next chapter. And sometimes the life that's waiting for us is far more beautiful than the one we are trying to desperately hold on to. Think about the younger version of yourself one more time. Maybe they're 18 years old, maybe they're 25th, maybe they're sitting in a dorm room, driving to their first job or lying awake at night, imagining what life will look like one day. They have this beautiful blueprint in their hands and they're doing exactly what all of us do. They're dreaming, they're hoping, they're making plans with the limited information they have about who they'll become. What they don't know is that life is about to surprise them. The truth is your younger self wasn't wrong. They simply couldn't see what was ahead. They didn't know that some doors would close so that others could open. They didn't know that some prayers would go unanswered because life was making room for something that you would never have asked for. They didn't know that success, love, purpose and happiness would come to mean something completely different than they once imagined. One day, I think all of us will look back and realize something surprising. The life we spent worrying wasn't happening fast enough was actually happening all along. As you move through this week, I want you to stop asking yourself, why doesn't my life look the way I thought it would? Instead ask yourself, what is this version of my life making possible? What freedom do you have during these years without children? What flexibility do you have before your career stakes become too high? What adventures can you go on before your roots are firmly planted somewhere else? If you stopped mourning the life you expected, how much more deeply could you appreciate the life you're living? Maybe one day years from now, you look back at the season. The season you were convinced you were falling behind and realize it wasn't the chapter where your life stopped unfolding. It was the chapter where it truly will begin.