Ep. 166: When Your Life Doesn't Follow the Expected Script

In this episode of the Maybe I Can Podcast, I talk about what happens when your life doesn’t follow the expected script.

After hearing someone younger than me share that she plans to retire at 63 — the same age I’m about to turn — I noticed how quickly my mind shifted into self-judgment. I started replaying financial decisions, questioning myself, and telling myself I should be further along.

That reaction made me realize how often we measure our lives against someone else’s timeline — without knowing their full story.

In this episode, I share:
 • Why comparison ignores context
 • How life chapters like infertility, caregiving, loss, and reinvention shift our timelines
 • The emotional cost of measuring ourselves against others
 • Why different does not mean delayed

There is no universal life schedule. There is no single script we’re all supposed to follow.

If you’ve ever felt behind, late, or like you missed something, this conversation is for you.

You are exactly where you need to be — based on the life you’ve actually lived.

Maybe we can put down the measuring stick together.

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...

Chapters

• 0:00 A Rocky Start And Blizzard Woes
• 1:41 When Plans Derail And Why That’s Okay
• 3:03 The Myth Of Life’s “Expected Script”
• 4:32 Retirement Comparisons And Self‑Critique
• 7:10 Milestones, Kids, And Pressure To Keep Up
• 10:35 Social Timelines Vs. Your Real Life
• 13:24 Business Comparisons And Hidden Backstories
• 16:10 Reinvention, Caregiving, And Delayed Dreams

Transcript

SPEAKER_00: 0:00

Hello everyone and welcome back to the Maybe I Can podcast. I'm your host, Debbie Weiss, and thank you so much for joining me today. Oh my goodness, I've got to be honest with you. This is my third time recording this episode. And I am pretty darn frustrated. Yesterday I tried to record. Today's Monday. I'm in New Jersey, so the blizzard has passed. And luckily, I am in western New Jersey, and this was a coastal storm. So I know that some areas at least got two feet of snow. I'd say we only got maybe, I don't know, I'm looking outside, maybe eight inches. Yesterday I came on to try and record, and I couldn't get on the website that I used to record. So I thought, okay, maybe there's a glitch and maybe they'll figure it out tomorrow, meaning today, which is Monday. And I couldn't get on again. And then whatever. I got on some alternate way and I recorded the episode. And then afterwards, I noticed that usually it'll say like transcribing, processing, whatever. And it didn't really say that. And I waited and I looked and it showed like the name of the recording, but it didn't show. I'm like, okay, let me try it again. And then I tried it again, and the same thing happened. Oh my goodness. So I've switched to a different platform. I'm recording this time third time, and it is what it is. But when I think about it, it's really funny that this is happening because this episode is titled When Your Life Doesn't Follow the Expected Script. Now, as we get into it, you'll understand that the script I'm talking about is more of a lifetime script. First thing this morning, I sat down. I filled out my morning sprinkle journal. And it's okay, what's my intention for today? And what's one problem I could face? And I said one problem I could face was being off track and being distracted by so many different things. And then the prompt says, Well, what are you going to do about it? And I said, Okay, here's what I'm going to do, and I'm not going to stray from this order. I'm going to record my podcast, then I'm going to answer my emails. Then I had some trading that I had to do for my insurance agency. Like I had a whole list down the line of what I was going to do. And so it's okay, that was my expected timeline for today, but it didn't quite work out the way I planned. That's okay. Nothing wrong with that. All the times, life just throws in unexpected little annoyances and challenges. And so that kind of leads me into the topic today, which is when your life doesn't follow the expected script, meaning like by a certain age you're not settled, or by an age you're supposed to be financially secure, retiring when you're supposed to buy your forever home. I don't know. When you're going to travel the world, whatever it is. And lately I've been around people who have been talking about retirement and their grandchildren. And yesterday, someone, this probably is like the third or fourth person recently, who is younger than I am, who talked about that they'll be retiring soon. And so this person just turned 60, and she said she's going to retire when she's 63. And here I am, 62. I'll be 63 this year. And there's no chance of me retiring anytime soon. Maybe by the time I'm 73. You know, actually, I don't even want to retire, but just the idea that it would be an option is kind of really appealing. And so, if I'm being honest, my immediate reaction when she said that and shared that she plans on retiring by the time she's 63, and then she started talking about the things that she wants to do. My first reaction was not resentment. You know, it wasn't like I resented her for being able to retire, not at all. Instead, it turned into self-criticism. I really started replaying all the decisions that I've made in my life. I started wondering, what should I have done differently? You know, what if I didn't spend my money and buy my house at that time? And kind of second-guessing, in this case, every financial decision that I ever made, and then start thinking, oh, I should be further along than I am. And I start kind of berating myself because isn't it my fault? It's my fault that I am not keeping up with this timeline. But yet, as I said in the beginning, this is life. We're all on the same but different journey. Who says that, okay, you're supposed to retire when you're 65? Maybe now people say when you're 67, you know, when you have a baby and it's okay, they're supposed to roll over by four months and sit up by six months and crawl by whatever it is, I don't even remember anymore, nine months and walk, you know, in a year and say their first word, like all of those milestones. And I get that it's a developmental thing and it's a measuring stick. I think about my own son, my oldest one, and how he was a little on the later side. And I remember starting to think back then, why is this? Why isn't he keeping up? And I know so many other parents that get stressed out by these timelines. But yet in Sam's case, my oldest son, I remember you're supposed to say your first word maybe by around a year, you're saying like mama, dad, like simple stuff like that. He didn't say his first word until he was 21 months old. And this is after having speech therapy and all the things. Let me tell you, he has no problem talking now. No problem at all. And I know so many other parents that are stressed and feel behind for their children because they're not re-meeting this criteria. But we take that same idea and we create in our minds our own timeline of our entire life. And when in our mind are we supposed to get married and have a family and buy a house and be financially secure and retire? And the list goes on and on and on. And when we do that, we aren't taking into account, we don't know what life is gonna throw our way. Each of us has a different journey. Life doesn't maybe follow the sequence that you quite expected when you were a little kid, right? You think, oh, this is exactly how it's gonna go. But nope, it typically doesn't. We all have our own timeline just because we all have our own unique journey. Different doesn't mean that we're delayed or we're behind. It just means different. And this script that we make up in our minds comes from our parents and social media and just maybe the idea that it's a linear timeline, you know, no bumps in the road, no change, like just a straight timeline. Thinking like when you're making a graph and you put, okay, age, I'm making it up, 27. Because when I was a little girl, I was like, I'm gonna get married at 27. Okay, boom, 27, get married. 29, I'm gonna have my first kid. Boom, 29, have my first child. It's almost like that makes me think also about people who keep talking about their grandchildren, which is wonderful. And believe me, I'm so happy for them. But then again, I feel behind. My brother's four years younger. He has three grandchildren and two on the way. My life just didn't take that path. I struggled with infertility for a really long time, and so I did not have my children until I was 37 and 39. And now they're 23 and almost 25, and they're not ready, nor should they be ready to have children. So believe me, I'm not rushing them. So what? So I'll be a grandparent when I'm in my 70s, when other people are in their 50s. Does it matter? No, it doesn't matter. That's just my life and my timeline. But there's such an emotional cost when we measure our own lives against somebody else's timeline. What does it do to us? I mean, it makes us feel horrible about ourselves, I think, or at least it does for me, because I always feel like I'm not good enough, I'm behind, I'm late. It's so funny how you take this piece of information that someone else is sharing, which was in my case, I am hoping to retire early. I should be able to retire when I'm 63. Now, good for her. Like I said, I didn't feel any ill will or anything towards the that person. But this is an acquaintance. So if she retires at 63, good for her. It does not impact my life at all. So it's really something neutral as far as I'm concerned. But nope, I didn't take it as neutral. Right away, I translated it into self-judgment. Oh my gosh, she's gonna be able to retire at 63. I'm gonna be 63 this year. There's no chance that I can retire. I did something wrong. Oh, I knew that I mishandled things early on. I'm late, I missed something. The shift from just listening and observing her statement to self-judgment happened in seconds. Seconds. And sometimes we don't even notice what's going on. When I measure or you measure the outcome, someone else's outcome, against your life, you're not really looking at the full picture, right? When I equate it to business and I look at other people and I see their social media following or their book sales or how many speaking engagements they get or what they're getting for their speaking engagements, and I compare myself and I am not on the same level, right away, my first reaction is I'm not good enough. I'm not as good as they are. What am I even doing this for? Maybe I should just stop. But am I comparing myself apples to apples? Absolutely not. I don't know what happened in their lives. Maybe they have training in being uh, I don't know, a podcast host or a public speaker or an author. Maybe they've been at it for the last 15 years. When I only just started five years ago. I'm not comparing apples to apples. I don't know their backstory. It's not a fair comparison. Who knows what has happened in your life that has maybe caused some of your dreams to be delayed? That doesn't mean that there's anything wrong with it. It's just your own timeline. And so I think about my infertility issues or my decades of caregiving. Not that I would change that, but did it change my timeline? Did it change my financial situation? Did it change everything in my life? Absolutely. It absolutely changed my timeline. What about the fact that I've started to reinvent myself when I turned 50? Now I'm 62. I've been at it for 12 years. It's a journey. Maybe that person never had to reinvent themselves because they've been doing what they were meant to do since they were 20, but I'm comparing myself. I lived through chapters that they didn't, and they lived through things that I didn't. So how could we all possibly have the same timeline? When I think about it like that, it really does change everything for me. Because then I don't feel like something's wrong with me. And when we measure, even when I can look and say, look at the good job I've done here. If I'm measuring, it's like, oh yeah, I did that, but I didn't do enough. It's exhausting, right? And when we do that, we are really saying, we didn't hit that milestone at the appropriate time. So we must not be good enough. It affects our self-worth, our self-respect. While we're measuring where we should be, we then often miss all the things that are happening in our lives right now. The tiny increments of growth that you are experiencing, the strength you've developed from things that you have gotten through in your life, the relationships you're nurturing, the reinvention that is currently unfolding. We forget about that because all we start thinking is we don't measure up. It makes us always feel late or like we're behind or we've made a mistake. Instead of feeling unique, because we are all unique on our own journey, on our own timelines. There is no one set standard. And when you try to fit your life into someone else's timeline, you start pushing, forcing things, overcompensating, and panicking, right? Because I can't retire at 63 or 65. I've had a very short period of time to make that happen. Says who? That's their timeline. It's not your timeline. The problem isn't that our lives look different, the problem is that we measured different against a standard that was never universal. In other words, who says there's a universal timeline that our lives are all supposed to conform to? No one. The work is putting down that measuring stick and trusting your own process. Before I wrap up, I want to share one quick thing. In addition to the podcast, I do also speak at conferences, organizations, community events on the themes that we talk about, as well as burnout, caregiving, grief, major life transitions, small shifts that lead to big change, all the things. So if you're involved in an organization or you know someone who is, I truly love the opportunity to bring this conversation to an event near you. So to learn more about my speaking and my workshops, please visit my website at debirweiss.com. And any information that you need, just reach out, either DM me on Instagram, Debbie.r.weiss, or email me at Debbie at Debirwiss.com. And don't forget, you are exactly where you're supposed to be. Okay, that's what I've got today. I'll see you all next week. Make it a good one.