244. Your Next Chapter May Not Look Logical
Too often, we measure our careers against a straight-line script of bigger titles and pay that we never actually chose for ourselves. When we separate real ambition from outside pressure and weigh choices by what our seventy-five-year-old selves would regret, we can make moves that truly fit us. Staying curious and treating lateral moves as experiments helps us learn, even when our next chapter looks illogical to others.
Nobody questions the person with the new, bigger title, even if that person is feeling gutted by the job that goes along with it.
Are you wondering whether you should be further along in your career by now? Are you considering a lateral move, industry switch, or pay cut that might not make sense to the people around you? Are you chasing titles and approval more than the work that actually energizes you?
You’ll learn that exploration and experimentation aren’t signs of indecision. They’re how capable adults gather real data to make good long-term career decisions under uncertainty.
WHAT YOU WILL DISCOVER
Why a lateral move can do more for your career than the obvious next step ever could
3 practical questions to ask at your next social gathering to tap into other people’s hard-won expertise
Why using anticipatory regret can pull you out of reactive decision-making and bring clarity to your next career move
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TRANSCRIPT
Welcome to the Stop Sabotaging Your Success podcast, episode two hundred and forty-four. I'm your host, Cindy Esliger. This is the podcast focusing on what we can do today to take control of our careers and overcome the inevitable barriers to success that we encounter along the way.
You're sitting in your car in the parking lot of your office building with the engine off. You submitted your resignation letter twenty minutes ago. You have another offer that you've accepted, but it doesn't come with a bigger, fancier title. It doesn't even come with a raise. In fact, it's actually less money than you're making now. It's with a smaller company nobody's even heard of, for a role that's actually one rung lower than the one you just left, and a job description that, on paper, doesn't sound even close to impressive. And yet, you're happier than you've been in a long while.
Your old manager has already texted, asking you, "Are you sure about this?". Your parents are going to ask, "What happened?". Your friends are going to do that thing where they say "good for you" a little half-heartedly because they are also wondering if you know what you're doing. And you're probably going to have to explain this decision that took you eight long months to make, in a conversation that will last maybe ninety seconds, to people who are going to measure it against a scoreboard you are no longer playing by.
You're not panicking. That's the strange part. You're just sitting there, keys in your lap, feeling that weird kind of relief, that's kind of peaceful in a way, that shows up after you've done something that's right for you, even when it seems wrong in everyone else's eyes.
In this episode, we're talking about why the next chapter of your career does not need to look logical to anyone else—not to your manager, and certainly not to your parents. We're going to get into why exploration and experimentation can be a good strategy, even when everyone else is chalking it up to immaturity. We're going to unpack those self-judgments, saying you should be further along by now because it's important to figure out where that timeline came from that you're judging yourself against. It probably wasn't your idea to begin with and yet, here we are, feeling like we aren't measuring up, again.
This isn't me giving you permission to blow up your life for no reason. I'm hoping that with all that we're going to cover, you'll have a clearer way to evaluate whether to make the move you've been thinking about—the one you haven't told anybody about, yet.
Somewhere along the way, we seem to pick up a script for what our careers are supposed to look like. We expect that it will be a straight line trajectory, up and to the right, with bigger titles every two to three years, along with the corresponding boost in pay that tends to go along with it. And that script isn't wrong exactly—because it works for some people and it can feel pretty satisfying when it does. The problem is that that script gets applied to everyone, as a default setting, whether or not it had anything to do with what they actually wanted for themselves.
We think our choices need to at least appear to be logical, which usually means understandable and approved of by an outside observer. It means someone glancing at your resume or your online profile for a few seconds can decide that your choices seem to track with what they somehow expected for someone like you. And yet, that might mean absolutely nothing because while what you've accomplished to-date might be what's expected, it does not mean that path is actually working for you.
A career path can look completely logical from the outside and be quietly killing you on the inside. And another can look like a complete mess on paper, maybe with a few lateral moves, maybe a switch of industries or what appears to be a title downgrade, or even a brief unpaid detour to learn something new. And yet, even just one of those might be the smartest thing you've ever done for yourself and your career going forward. Who's to tell?
Contrary to popular belief, doing what some might call some exploration and experimentation may not necessarily work in opposition to your career strategy. They can be part of a very strong plan for your future. Testing a hypothesis about what kind of work actually energizes you, gathering data by doing the thing instead of simply theorizing about it from the outside—that's not indecision. That's how competent adults make good long-term decisions in conditions of uncertainty, which, by the way, is what a career is. There is no one perfect way that any career should unfold. Nobody is going to be handing you the answer key.
But, if you're not following what might seem to be the tried-and-tested career path, you are bound to be second-guessed by others and, more than likely, by your own inner critic. Maybe it shows up around a milestone birthday, or right before a college reunion, or when someone your age gets tagged on social media in a promotion announcement, and it starts to make you wonder whether you should be further along by now.
Further along than what, exactly? Or further along than whom? That's the question almost nobody stops to ask, because this timeline seems to be something that is universally understood. And yet, it doesn't seem to apply to many of us. It's more of a social expectation that you've adopted over time. It might have come from watching how your parents' careers unfolded, but my guess is that was a completely different era with completely different economic drivers. It might have come from someone in your friend group, whose career path seems to be going full-throttle at the moment. It could also have come from some highlight reel that landed in your feed.
Comparison can come from any direction these days. It convinces you that everyone is doing great and you're somehow falling behind. There's no one timeline for everyone. There's your life, and a bunch of other people's lives that are probably nothing like yours—with different starting points, different obligations, different opportunities, and different definitions of success.
This is where I want to draw a hard line between two things that get treated as similar but are not the same at all, which are ambition and pressure.
Ambition is self-generated. It pulls you forward. It's specific—you want that skill, that role, that particular kind of problem to solve—and even when the work is hard, it energizes you.
Pressure is external. It pushes from behind. It's vague—you just don't want to feel like you're behind, you don't want to feel judged, and you don't want to have to explain yourself or your choices during Thanksgiving dinner.
Ambition can feel like reaching for something, while pressure might feel like you're running from something else. So, when you picture the achievement you're chasing, are you excited about having attained it, or are you simply relieved because then you won't have to explain why you don't have it, yet? Don't confuse that second option with ambition.
And once you can see the difference, you can start setting your own pace. Proceeding slower to be sure you're headed in the right direction for you isn't necessarily going to cause you to fall behind. Sometimes, taking a pause to figure out what you actually want is the best thing you can do to ensure you're not climbing a career ladder only to find out it's leaning against the wrong wall.
Maybe you're someone who's been contemplating making a lateral move, but you've talked yourself out of it multiple times already.
Here's the reframe I'd like you to consider: think of the word "lateral" as just a resume word. It's a flat, two-dimensional way of describing a move that, in real life, is rarely flat. It's a move that might look like you're going sideways on paper but, in reality, it can set you up on a completely different trajectory—because it opens up for you the opportunities to acquire new skills, to become a part of a different team, or to step into a new industry, that what others would deem your "obvious" next step never would have.
Unfortunately, career clarity is not usually something you think your way into. You don't sit in a room with a whiteboard and suddenly you're certain about what you want next in your career. You get clarity by trying things and making course-corrections as you go, based on what you learn. Maybe you make the lateral move. Then after you've been in that role for six months, you realize that there's this one part of your work that lights you up, but there's also that part that doesn't. But you never would have known that from the job description. The moves you make don't just change your position, they augment your skill set and change what you thought you knew about yourself.
Think about what a lateral move could actually provide that a straight up promotion often can't:
a new skill set that makes you harder to replace instead of just becoming more senior in a narrowing lane;
a new network because you're suddenly in meetings with different people, solving different problems;
or broader experience on your resume that shows an expanded range instead of just tenure.
And sometimes, if you're being honest, it gives you much needed distance from a career ladder that was never going to take you where you wanted to go, anyway.
So, instead of asking yourself, "Does this look like progress?", try asking a better question like, "What might this teach me that the obvious path may not?". If you can answer that clearly, you're not being reckless; think of it as pivoting strategically. Call it what it is—not a setback, more of a repositioning.
Most people can only see the through line to their career in hindsight. When you're in the midst of figuring it out, it may not be easy to explain to a stranger at a dinner party, and that's okay.
A lot of what might look like ambition to others is simply you looking for approval. You're chasing a title you don't actually want, applying for a role that sounds impressive but would make you miserable, optimizing for a metric that means nothing to you personally—because it's what you think you should be doing at this point in your career. Because then, other people will see it and be impressed. Nobody questions the person with the new, bigger title, even if that person is feeling gutted by the job that goes along with it.
That's a version of a productivity trap where you're spending the bulk of your time doing work that looks impressive to others instead of work that means something to you. And perfectionism is one of its main engines, but not for the reason most people assume. Perfectionism isn't really about producing work of the highest quality. If it were, it would produce great work while feeling calm and confident. Instead, it usually produces exhaustion, procrastination, and a person who's feeling slightly behind on all the things that they care about most—because the real driver of perfectionism is usually fear. You try to look busy and impressive so nobody gets close enough to question whether any of this is actually working for you, or whether you even want it.
Busy and impressive might look good on the outside, but it does not build anything sustainable career-wise, because it was never designed to. It was simply designed to be admired, from a safe distance.
So, here's a question worth sitting with, uncomfortable as it may be: are you optimizing for what you actually want, or for what will be harder for other people to criticize? These are two completely different objectives, and most people are doing the second one, while telling themselves it's the first. Living what feels truer to you is quieter, calmer, and tends to feel more satisfying. It doesn't always come across as impressive to others. But it's the only version of success that will really matter, in the long run.
So, if the goal isn't the obvious next step on the career ladder, and it isn't simply having an impressive looking resume either, how do you actually make major career decisions? I went in search of something because, at least for me, "follow your gut" wasn't specific enough to be useful. This is the tool I found to be helpful that I began to trust more than almost anything else for making major career decisions, and that is anticipatory regret.
Here's how it works. Take the decision in front of you—maybe it's a lateral move, or maybe it's something scarier like making an industry switch—whatever that might be for you. Now, project yourself forward. Not five years, go further. Picture yourself at seventy-five, looking back over your whole career. From that distance, ask yourself: which decision would that version of me regret more—making this move and having it not work out, or never trying it and always wondering whether it would have?
That question does something important. It takes you out of panic mode that you might be feeling right now—the reactive job-hop to get you out of a bad week or a stressful month, or the staying-put out of fear of the unknown—and it gives you more of a long-term perspective on a short-term choice. Most bad career decisions aren't bad because the person was foolish. They're bad because the person was reacting to what they were feeling this week instead of looking at how it might set them up for the next twenty years.
Try this with whatever you're sitting on right now. Not the big, dramatic once-a-decade decision—start with something a bit smaller, like maybe making an internal move to a different team, having that conversation you've been avoiding, or submitting that application you've been feeling uncertain about. Run it through the seventy-five year old test. Most of the time, the answer gets uncomfortably clear, remarkably fast.
This is what regret-proofing actually means. It's not about avoiding every mistake, because you can't. It's about making sure the decisions that compound over decades are decisions your future self will actually thank you for, instead of decisions that are made by the most anxious, most reactive version of you that is feeling the pressure of somehow feeling behind everyone else.
If you look at people who keep getting better—year after year, decade after decade—they almost all share one trait, and it's not superior intelligence and it's not talent. It's curiosity. They're always looking for an edge. They are working with the belief that one new idea, or a new twist on an old idea, could be the thing that moves them to the next level. So, they keep trying new things in their search for it.
Most people take things at face value. Something works, they use it, and then they move on. Curious people tend to ask how and why. They're trying to determine the differentiating factors—those small, specific differences that might actually matter—instead of accepting only the surface-level explanation. It's more about finding what each experience can teach them, even in areas where they may already be the expert.
And here's the part that surprises some people: gaining expertise doesn't shrink your curiosity, it expands it. The more someone actually knows about their own field, the more clearly they can see what they still don't know. That's not imposter syndrome. That's an accurate read of how large their chosen field may actually be. People who stop being curious usually stopped because they mistook a small amount of competence for the whole picture.
It's about cultivating a beginner's mindset, long after you've stopped being a beginner. Genuinely curious people want to know what someone brand new to their field would notice that they're no longer seeing. They ask questions like, what looks obvious to me now that would look strange to someone seeing it for the first time? That question alone can identify potential blind spots that ten years of experience might shield from you.
And curiosity does something else that's easy to take for granted and that is that it lets you learn from other people's experience instead of just your own. Every good open-ended question you ask someone else compresses years of their trial and error into a five-minute conversation. The curious ones are tapping the expertise of everyone they meet, and most people never notice, because it just looks like they are interested in someone.
So, here's a practical challenge for you to consider. Next time you're in a social setting—a dinner party, an industry conference, or standing around at a kid's birthday party—pick one person and ask them as many questions as you can about what they do and why they do it, without making it seem like an interrogation. Get beyond the small talk, and see how many details they are willing to share, by asking some real questions like:
How did you get into that?
What's something about your job that people always get wrong?
What would you do differently if you started over?
What you might find is that almost everyone has some useful insights that almost no one ever asks them for. Most people are full of good suggestions about how to solve problems in their world, and they go their entire lives without anyone caring enough to ask. In those types of conversations, you might be privy to insights and solutions that took the other person fifteen years to learn the hard way, and it will cost you nothing but giving them your undivided attention.
Combine that kind of curiosity with a beginner's mindset applied to your own field, and you will find solutions you can use immediately, simply because you asked the question no one else thought to ask.
Before we close this one off, let's go back to you in the parking lot of your office building. You're still sitting there. Keys in your lap. Resignation letter submitted. You've accepted the new role that comes with what seems like a less impressive job title, at a smaller company, for less money. Your decision isn't going to make sense to anyone measuring it against the job you just walked away from.
Here's what's actually true about that moment, even though you might not be able to fully feel it, yet—the discomfort you're sitting in isn't a sign you did something wrong. It's the price of making a decision that was actually yours. Every real decision—the ones that come from ambition instead of pressure, from curiosity instead of what you think you should do, from what you'd want at seventy-five instead of what you can defend at this year's Thanksgiving dinner—might look a little strange from the outside.
Your next chapter in your career does not need to make sense to anyone, except you. Go make that bold move you've been sitting on, and see what that makes possible for you going forward.
And that's it for this episode of Stop Sabotaging Your Success. Remember to download your Guide to Writing Your Next Chapter at cindyesliger.com/podcast, episode two hundred and forty-four.
Thank you to our producer, Alex Hochhausen and everyone at Astronomic Audio. Get in touch, I'm on Instagram @cindyesliger. My email address is info@cindyesliger.com.
If you enjoy listening to this podcast, you have to come check out The Confidence Collective. It's my monthly coaching program where we dig a little deeper into what's holding you back in your career and we find the workarounds. We help you overcome the barriers and create the career you want. Join me over at cindyesliger.com/join. I'd love to have you join me in The Confidence Collective.
Until next week, I'm Cindy Esliger. Thanks for listening.
