Uplifted Living
Uplifted Living is a podcast for thoughtful, growth-oriented people who want to live with more clarity, intention, and presence—without burnout or overwhelm.
Each episode offers grounded reflections, practical insights, and gentle reframes to help you simplify self-development, reconnect with what matters, and make steady, sustainable progress in your life.
This is not a podcast about hustle, perfection, or constant optimization.
It’s a space for learning, slowing down, and becoming someone you trust—one small step at a time.
If you’re seeking growth that feels aligned, meaningful, and human,
you’re welcome here.
Uplifted Living
Why You Feel Behind (And Why It’s Actually a Lie)
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Have you ever looked at someone else’s milestone and wondered why you aren’t further along? A new job, a home, a relationship, or a sense of certainty can make your own life feel late, even when nothing about it has changed.
In this episode of Uplifted Living, Nick Gilbert explores the invisible timeline: the expectations we absorb about when life is supposed to happen. Through personal stories about growing up alongside his brothers, recovering from an eye injury, and taking a teaching certification exam seven times, Nick reflects on what comparison leaves out: the terrain each of us has traveled.
If you’ve been telling yourself you should be further along by now, this episode offers a chance to question whose timeline you’re following, reconsider what success means to you, and notice the direction you’re moving in.
Reflection question: Finish the sentence “By now, I thought I would…” Where did that expectation come from, and does it still belong to you?
You can’t be late to a life that never had an official schedule.
Live uplifted.
For a long time, I felt like I was playing catch-up. I have older brothers, and growing up, it seemed like certain things came easier to them. School, sports, confidence. There were times when I would look at where they were and wonder why I wasn't there too. Of course, when you're young, you don't always understand everything that goes into someone else's success. You see what they're good at, but you don't necessarily see the work it took for them to get there. You see the result without understanding the process. And I think somewhere along the way, I started using their progress to measure mine. If they were good at something, I thought I should be good at it too. If something seemed easy for them, but difficult for me, I wondered whether there was something wrong with me. As I got older, the people I compared myself to changed. The milestones changed too. But that feeling of needing to catch up followed me into different parts of my life. Maybe you've experienced something similar. You look around and see people getting married, buying homes, moving up in their careers, starting families, traveling, building businesses, or simply seeming more confident about where their lives are headed. Then you look at your own life and you wonder, why am I not further along by now? But I want you to think about the question for a second. Further along compared to whom? And perhaps more importantly, according to whose timeline? Welcome back to Uplifted Living, the podcast for Living Uplifted. Today, I want to talk about something I've struggled with throughout different periods of my own life: the feeling of being behind. I think most of us have some picture in our minds of where we thought we would be by now. Maybe it's related to our career or finances, maybe it's marriage, family, confidence, health, or some personal goal we thought we would have accomplished years ago. And there's nothing wrong with wanting those things. The problem begins when the things we hoped would happen eventually become the things we believe should have happened already. At that point, the dream becomes a deadline. And suddenly, we're not thinking about the life we want, we're using an imaginary schedule to determine whether the life we have is good enough. That's what I call the invisible timeline. I want you to think back to when you were younger and imagine what you thought your life would look like today. Maybe you pictured where you would live, what kind of work you would be doing, who you would be with, or what kind of person you would become. I think dreaming about our future is part of what makes life exciting. It gives us something to work toward. But somewhere between imagining that future and actually living our lives, those hopes can turn into expectations. I'd like to own a house someday becomes I should own a house by now. I want to find someone to spend my life with, slowly becomes everyone else is getting married. Why haven't I? Or maybe you thought you would have had your career figured out, feel financially secure, know exactly what you wanted from life, or finally become the confident version of yourself you always imagine. When reality doesn't match that picture, it's easy to believe that reality is the problem. But how often do we stop? Stop and ask where the deadline actually came from? Was it something we consciously chose? Did our parents give it to us, our friends, the people we grew up around, social media? Or did we simply see enough people reaching the same milestone at a similar age and started assuming that was when it was supposed to happen for me too? I think we absorb more of these expectations than we actually realize. And eventually they become so familiar that they start sounding like our own voice. That's why I call this the invisible timeline. There isn't actually a calendar somewhere telling us we need to have our career figured out by 25, get married by 30, own a house shortly after that, and somehow, somewhere in between, discover our purpose. Life doesn't come with those instructions, and yet we carry those deadlines around as if it does. Most of the time, we don't even notice the timeline until someone else reaches one of the milestones on it. For example, you open your phone and you've seen an engagement announcement from someone you went to school with, someone else bought a house, another person got promoted, someone younger than you started a business that seems to be doing incredibly well. You might genuinely be happy for them. But sometimes their good news still creates an uncomfortable question about your own life. What about me? I think that's the moment when comparison changes. You no longer simply are observing somebody else's journey. You're using their journey to grade your own. And perhaps that's why comparison can make us feel behind, even when we were perfectly content with our lives five minutes earlier. Nothing about our circumstances changed. We just changed the measurement. This is something I had to learn when I thought about my brothers. Growing up, I could see the things they were good at, but I didn't always understand what it took for them to become good at those things. I saw the result. I didn't necessarily see the process. And I think we make that mistake with people all the time. We see someone who seems confident without knowing what they had to overcome to build that confidence. We see the promotion without knowing about opportunities that didn't work out. We see a happy relationship without knowing the heartbreak that came before it. Even with people we know really well, there are parts of their journey we simply weren't there for. Yet we take what we can from their lives and compare it against everything we know about our own. Think about how uneven that comparison is. You know every mistake you've made, you know every time you doubted yourself, changed directions, procrastinated, struggled, or wondered whether you were ever going to figure things out. You don't necessarily know those things about the person you're comparing yourself to. You see their result and your process at the same time. Of course, your process looks messier. It's still being lived. There's another problem with comparing timelines. No two people are moving through life under exactly the same circumstances. Imagine two people traveling. They're going the same distance, but one person is walking across flat ground while the other person is climbing uphill. If all we measure is how far each person traveled, the person climbing is obviously moving slower. But once we understand the terrain, the comparison changes. Life has terrain too. We grow up in different families, we have different responsibilities, opportunities, strengths, fears, financial circumstances, relationships, losses, and experiences that shape the way we move through the world. Sometimes the terrain changes without us choosing it. When I was 13 years old, I was shot in the eye with a BB gun. After that, I spent countless times going back and forth to the eye specialist. I eventually needed cataract surgery and later a laser corrective surgery. For a period of time, I was legally blind out of my left eye. And because my eye was so sensitive to light, I had to wear sunglasses at school. At 13, being the kid walking around school wearing sunglasses when nobody else's tends to get attention. I dealt with name calling. There were times when I sat alone at lunch. My confidence changed. And some of the sports I enjoyed became more difficult. At that age, I didn't have the perspective I have now. I wasn't thinking about how that experience might affect the way I saw myself or how I compared myself to other people. I just knew that I felt different. And yet, when I looked at other people my age, I wasn't thinking about the fact that they were carrying different things. I was simply looking at where they were and where I was. I think we still do that as adults. We judge our pace without acknowledging our tarrying. And sometimes we become frustrated with ourselves for moving slowly without ever stopping to recognize what we've been climbing. Years later, I found myself struggling with another kind of timeline. I wanted to become a teacher. I'd finished my undergraduate degree and I knew what I wanted to do, but there was one certification exam I needed to pass. So I took it and I failed. I studied and I took it again, I failed again. Eventually, I took that same exam around seven times. After failing for the sixth time, I remember sitting on my kitchen floor and breaking down. By that point, it didn't feel like I had simply failed an exam. I started wondering: maybe I wasn't meant to be a teacher at all. And I think that's what can happen when something takes much longer than we expected. At first, we question the process. Eventually, we start questioning ourselves. This is taking longer than I thought. Slowly becomes maybe I'm not good enough to do this. This is a dangerous transition because now the timeline isn't measuring our progress anymore, it's measuring our worth. Sitting on that kitchen floor, though, didn't erase everything I had already done. It didn't erase college or the work I had put in my education, and it certainly didn't erase why I wanted to become a teacher. Eventually, I had to be truthful with myself. What I was doing wasn't working. But that didn't mean I couldn't do it. I needed to change the way I was preparing. So I approached the test differently, used different tools, and I tried again. On the seventh attempt, I passed. I think about that experience differently now because at the time, six failed attempts felt like evidence that I was behind. Looking back in retrospect, they were part of the process that eventually got me to where I wanted to go. Imagine if I had treated attempt number six as an official deadline, my timeline would have ended before my journey did. I think there's something else we need to give our younger selves a little grace for. When we imagined where we would be at at 30, 40, 50, or whatever age we had in mind, we were making predictions with incomplete information. We didn't know who we would meet, we didn't know who we might lose. We didn't know which opportunities would appear or which ones would fall apart. We didn't know what we would discover about ourselves, what responsibilities we might take on, or which things we thought we wanted would eventually stop mattering to us. And yet, years later, we can judge ourselves for failing to fulfill a prediction made by someone who couldn't possibly have known any of that. Think about how unfair that is. Your younger self was imagining. They weren't signing a contract. And perhaps some of the deadlines we feel guilty about missing were never deadlines in the first place. They were hopes. There's a difference. I want you to imagine your younger self again. Think about what success meant to you then. Now compare that with what matters to you today. Has anything changed? Maybe there was a time when success meant making as much money as possible, and now having enough time to enjoy your life matters more. Perhaps you wanted the impressive job title, but now meaningful work means more to you than what appears underneath your name. Maybe you once thought you needed to have everything figured out, and now you're beginning to realize that just having some direction might be enough. We change. So it makes sense that our definition of success would change with us. But sometimes we continue judging ourselves using an old definition long after we've outgrown it. We tell ourselves we're behind because we haven't reached a destination we aren't even sure we want anymore. So before trying to catch up, maybe, maybe we should ask this where exactly am I trying to go? Because moving faster isn't very useful if the destination no longer belongs to you. If there's an area of your life where you've been feeling behind lately, I want you to try something. Finish this sentence. By now, I thought I would. Whatever comes to mind, let it. Maybe you thought you would be married by now. Maybe you expected to have more money saved, own a home, have a different career, feel healthier, or simply feel more certain about yourself. Then ask yourself where that expectation came from. You might discover that it genuinely represents something you still want. If it does, that is okay. The point isn't to stop wanting things simply because they haven't happened yet. The question is whether you can continue moving toward them without using the delay as evidence that something is wrong with you. And you might discover something else. You might realize that the deadline never really belonged to you. Maybe the goal doesn't either. If nobody else could see your life, would you still want the same thing? I think that's worth sitting with. For a long time, I liked instant gratification. If I was putting effort into something, I wanted to know it was working. I wanted to see progress. And if I'm being truthful, there's still part of me that wants that. But I've learned to appreciate delayed gratification more than I used to. I'm learning to trust the process and perhaps more importantly, to enjoy more of what the journey has to offer while I'm still on it. Because there will always be another milestone. You finally get the job and eventually you start thinking about the promotion. You reach one financial goal and you create another. You accomplish something you once desperately wanted, and after enough time passes, it becomes normal. There's nothing wrong with continuing to grow, but if we spend our entire lives waiting for the next milestone before giving ourselves permission to feel successful, I'm not sure we ever really arrive. Maybe pace isn't the measurement that matters most. Direction might tell us more. You can move incredibly quickly toward a life you don't actually want, or you can move slowly towards something that means everything to you. So perhaps the question isn't, why am I not there yet? Maybe it's do I still like the direction I'm going? If the answer is yes, keep going. You don't have to apologize for the pace. Years ago, I wrote something called How do we measure up? I opened it by asking a question. How do we measure the life of a man? Do we judge someone by their successes or their failures? Do we compare one person to another based on what we can see? Or do we somehow account for the journey that brought each person there? I was much younger when I wrote it, but I think I was wrestling with some of the same questions we're talking about today. How do we know whether we're doing life correctly? And what are we using to measure it? The older I get, the less convinced I am that speed tells us very much. Maybe a meaningful life isn't measured by how quickly we reach each milestone. Perhaps it has more to do with what we learn along the way, who we help, how we grow, the people we become, and whether we actually take the time to live the life we're so busy trying to improve. Your journey isn't supposed to look exactly like mine. Mine isn't supposed to look exactly like yours. We can even be working towards similar milestones and take completely different roads to reach them. So if you've been feeling behind lately, I want you to remember something. You can't be late to a life that never had an official schedule. You can take longer than expected, you can change your mind, you can rethink the destination, you can learn something about yourself halfway there and choose a different road. And you can appreciate where you are while still wanting something more for yourself. I think both of these things can be true. After all, maybe the goal isn't to spend our lives trying to catch up to everyone around us. Maybe the goal is to make sure that wherever our journey takes us, we actually take the time to live it. Until next time, live uplifted.