Episode 4: Zigging when you're told to zag: A new career strategy

In this episode of Little Moves, Big Careers, Caroline Esterson gets gloriously real about the messy truth of career paths, emphasising that success is not linear, no matter what the old-school career ladder crowd wants you to believe. Instead, we’re talking zigzag moves, surprise sliding doors moments, and the wild power of zigging when you're told to zag.

Caroline takes aim at the myth of the straight line and hands you a better map, one where detours, pivots, and “Wait, how did I end up here?” moments are actually rocket fuel for personal and professional growth. If you've ever felt like you took the long way round, good news: you’re not lost, you’re levelling up.

You’ll walk away with practical advice, a dash of cheek, and full permission to define success on your own (gloriously unpredictable) terms.

Key takeaways

• Careers are not straight lines; they are weather systems.
• Success is often found in unexpected pivots.
• Recognising sliding doors moments can change your career trajectory.
• The traditional career ladder is becoming obsolete.
• Zigzagging through your career can lead to valuable experiences.
• Chase experiences rather than titles or positions.
• Curiosity and awareness are key to spotting opportunities.
• It's important to trust patterns over rigid plans.
• Don't let conventional wisdom limit your potential.
• Progress is not always perfect, but it is still progress.

Sound Bites

"Progress doesn't always look like sunshine."
"Chase experiences, not jobs."
"Start trusting pattern over plan."

Quick Fire Career Moves You’ll Learn

• Stop asking “Is this the right move?”, start asking “What will I learn?”
• Trust the pattern over the plan. Your instincts are wiser than your CV.
• Ask people how they really got where they are. Note to self: it’s never the five-year plan.

Listen if You’re:

• Second-guessing a job change that doesn’t look neat
• Tired of chasing titles and ready to chase truth
• Trying to explain your zigzag to your Dad, your boss, or your inner critic
• Ready to make the brave, weird move… and own it

Resources + Extras

Download the Bold Moves Brief for this episode

Download The Career Story Prompt Pack

Run the Big Conversation session with your team

Want to bring this energy into your organisation? Let’s talk. caroline@inspireyourgenius.com

Subscribe + Share
Love this? Forward it to someone who’s quietly plotting a bold pivot.
Please rate & review so the algorithm sends it to the brave ones.

Because success doesn’t come from staying put, it comes from knowing when to zag.

Ready to make your next bold move? Grab the free Bold Move Audit and join the insider crew.

Stuck, simmering, or onto something juicy? I want to hear it. Drop me a line at caroline@inspireyourgenius.com - I read them all.

Chapters

• 0:00 Navigating Career Chaos
• 3:00 Embracing Ziggy Victories
• 5:55 Recognising Sliding Doors Moments
• 8:37 The Broken Career Ladder
• 11:48 Zigzagging Your Way to Success
• 12:19 Jonna's Story
• 14:37 Practical Career Moves
• 17:44 Redefining Career Quotes

Transcript

Speaker 2 (00:00.334)
So let's talk about careers. They're not straight lines, are they? They're weather systems. Sometimes you drift, sometimes you're thrown. There are swells, storms and the occasional lightning bolt of clarity. And if you're measuring success by neatness, well, you'll miss the power in a pivot. Not every step up is progress and not every detour is disaster. Sometimes what looks like a weird move is just you refusing to play a rigged game. You're not lost.

You're just not following a map that was never made for you. Thank you for joining me at Little Moves, Big Careers. I'm Caroline Esterson, career strategist and sticker of brilliant people and your co-pilot through the chaos of real world careers. And this podcast, well, it's for you if you've ever done everything right and still feel stuck, overlooked or like you were shouting into a team's call on mute. Without further ado, welcome to episode four.

Speaker 2 (00:59.778)
This isn't a pep talk, it's a practical guide with a glitch in its eye. Smart moves, slight chaos. Welcome to Little Moves Big Careers.

Speaker 2 (01:13.29)
And today is all about zigging when you're told to zag. Because the fastest way to get where you're meant to go might just not be in a straight line. It might be a zig, a zag, a sideways shuffle or a chaotic leap into the unknown with only a dodgy wifi connection and a suitcase of snacks to guide you. Picture this, some days at work are crisp and clear, other days it's all fog, static and the emotional equivalent of being caught in a surprise hailstorm.

with no coat and a paper thin umbrella from the office Christmas party. When that thunderclap hits, it might sound like we're pivoting the business or we don't see a future for your role or just slow rumbling realization that you've outgrown your job. Progress doesn't always look like sunshine. It often sounds like a storm. Sometimes you're not blown off course. You're just finally catching the wind in your sails and other times

You're the bloody storm. You come in, shake things up, rattle a few windows and leave the place fresher than you found it. So if your path looks messy, chaotic or suspiciously like a detour, that's good. It means you're reading the actual conditions, not clinging to a forecast from three years ago. These moves might not look like progress at first sight, but often they turn into something really exceptional. I call them Ziggy victories.

and they look like the job you take to get you unstuck. The pivot that makes no sense on paper, the left turn that leads to magic. And that brings me to an interesting truth. During our research, we started noticing a pattern. Many of the people we interviewed had a defining career moment, a chance encounter, a conversation, or a moment of unexpected look that catapulted them forward. Things like slipping into a lift as the door closed.

or a casual chat at an event that led to an unexpected collaboration. A project they almost turned down but ended up changing their entire career path. It seemed too common to be a coincidence. So we asked more people and we found the same story. Turns out sliding doors moments are happening all the time, but only to the people who are aware enough to notice them. You've got to be attuned to them before you can step through them.

Speaker 2 (03:36.32)
Sliding doors moments are shaped by how you see them. And if you're only looking for the obvious clear-cut, career-defining milestones, you might miss the real action. Let me give you a proper sliding doors moment. Maria was working in store for a big luxury brand, but had her sights set on the buying team. Zero experience, just a gut feeling and a back pocket full of big ideas. Then comes the twist. They're running a new store opening in Barcelona.

and Maria gets the chance to be part of the team. Most people would have treated it like a glamorous detour, tapas, sangria, and folds in cashmere at a slightly jauntier angle. Not Maria. She clocked that a few of the buying team would be flying in to support the launch. So instead of just doing her job and soaking up the sangria, she got strategic. Asking smarter questions. She spent time with the buyers in a way that felt genuine, not showy, it was just real.

She casually dropped product insights like breadcrumbs at a Fashion Week picnic. And the next thing, a job opens up in buying. The director says he wants someone with on-the-ground store experience. Hmm, who pops into his head immediately? Yeah, of course it was Maria. It didn't matter that she had the Excel skills of a distracted squirrel because of course that's trainable. She'd made herself memorable, credible and likeable.

She got the gig and hasn't looked back since. And you know what? She's even mastered Excel, which is no small feat in a world where pivot tables and VLOOKUPs are practically a second language. It turns out that Ambition is a great shooter when your formulas control millions in stock. So I want to ask you this question. Do believe that sliding doors moments could exist? How would this change the way that you show up every day? Because sometimes things get in the way.

If you

Speaker 2 (05:34.2)
You assume opportunities come scheduled and labeled. You tell yourself you're not ready. You probably are. You don't see the point of a chat unless it leads somewhere immediately. It often leads somewhere later. You just don't know it yet. You might edit yourself out before you've even begun. You might say things like, I won't say that. It's too obvious. Obvious to you maybe, but not to others. I won't bother asking. They'll just say no.

Is that just your excuse? I won't introduce myself. They don't care who I am. Most people will actually be quite interested to meet you. You're pretty amazing. To spot a sliding doors moment, you need three things. Presence. If you're mentally in tomorrow's meeting, you'll miss today's moment. Curiosity. Ask questions, be nosy, but in a charming way. And awareness.

Who's in the room? What's the vibe? What's not being said? You can't win a game you've already benched yourself from. So let's play a game you aren't benched from.

Now, welcome to the chaos. It's game time! Zero prizes, mild embarrassment, but hopefully excellent fun. This one is all about choices. Your choice is about what you're prepared to do to get on. So let's examine some of these by playing a cheeky quick game of Would You Rather? The Career Curveball Edition. Use it to consider exactly what you're prepared to do.

And please welcome my great friend Sonia Allen, who is this week's special guest. Hey Sonia. Hi. Right. Go for it. Let's do a couple of examples first, Sonia, before I unleash you on the team here.

Speaker 1 (07:19.79)
everybody.

Speaker 1 (07:28.75)
Okay, would you rather take a job in a new sector you know nothing about or stay where you are but slowly disintegrate into your desk chair?

come on, son, you've seen my desk chair. You know what that's like. So I'm not going to answer that one. Give me another.

Would you rather be brilliant at something nobody understands or average at something everybody crazes?

Ooh, interesting. You know, after all, shiny mediocrity is often very well funded, but you know me, Sonia, I'd want to be brilliant and try and help people understand. Now, I guess that's been my life, right?

Okay, so now you're warmed up. These are for you. Would you rather be the go-to person everyone relies on or the person that's seen at the right moment who gets the promotion? Would you rather lead every project but get none of the credit?

Speaker 2 (08:34.062)
Step back and let your name be remembered for one bold win.

Would you rather be on back-to-back Zooms all day or have time to think but constantly worry you're not looking busy?

Would you rather say yes to more work to prove your value or say no and risk being seen as not a team player?

Would you rather be respected by your boss but invisible to everyone else? Or well liked by your peers but underestimated by decision makers?

Speaker 1 (09:21.75)
And finally, would you rather play the game to fit in, even if it means shrinking a little every day, or take the longer messier road and back yourself loudly, clearly and on purpose?

Ooh, interesting. I liked some of those. Because in the end, it's not about which door opens fastest, it's about which version of you is prepared to walk through. So, you know, just have a think about your answers. It is obviously just a bit of fun, but maybe your answers will also tell you something about how you view work and what you want from it. Don't dismiss this data. Time for Brain Food, the research bit.

But make it cheeky. Because we all love evidence, especially when it supports our own experiences. So this next segment is about where we go deep to explore the facts behind the challenge of career advancement. For this episode, it's called The Ladder's Broken But You've Got Legs. And that gives you a hint about what we've uncovered in our research. Let's just say it, the career ladder, as you already know, is a bit of a myth these days.

Actually, scratch that. It's not a myth. It's more like a prop in a badly designed escape room. Technically still there, but not very helpful. You climb up one rung and realise someone's outsourced the rest of the structure to a freelancer in a different department. In a different country even. Cheers for that. In a cracking article for The Guardian, Andre Spicer lays it out. Jobs are still out there. In fact, graduate hiring's up. But actual progression?

Good luck with that. A recent SHRM research study found that only 29 % of employees are very satisfied with their available career advancement opportunities. And according to Cornferry, 33 % of employees jump ship because they feel bored in the workplace and want to find new challenges. Women in particular get stuck on the broken rung. There are enough early promotion opportunities, which means not enough leaders later on. Makes sense, right?

Speaker 2 (11:39.67)
If lower down people don't have the stepping stones, then there's less of a talent pool further up. No wonder organizations say that they're struggling with the challenge of keeping their talented people. Big firms are shrinking internal pathways, slicing out the middle bit between, well, entry level and oops, accidentally becoming the CEO. And Gen Z, well, they're not even pretending to want the ladder. I guess they figure why fight for something that's so elusive. It turns out...

they'd rather have a life. So what's your alternative? Zigzagging. That's not flaky, it's strategic. It's how you collect skills, dodge dead ends and keep your brain alive. Spicer Cites Career Research, as you say, is actually the smartest way through the maze now. Sideways, diagonally, sometimes chaotically, but always learning. So if your career path looks more like snakes and ladders than neat little promotions,

you're doing it right. Keep on zigging. Yonah, another of our wonderful interviewees, actually took a step down to help her get unstuck and it was the best move she ever made. Yonah was a manager in store but found she was losing her mojo. I'll let Yonah take it from here.

was amongst all these amazing general managers and store managers. And I looked at them and I saw their kind of grit and motivation and passion and I didn't feel it. I did well, but I didn't excel. And I didn't really want to. I was like, this is not for me. I can't get super excited about all these kinds of customer service initiatives. I can't get super excited about...

the new ways of merchandising the store or these training programs. Like it just wasn't for me. Something wasn't clicking. And I felt like I can't compete because I don't want to. Like the passion isn't there. So I felt pregnant, went on maternity leave and didn't think I was going to return. And then a job came up when I was on maternity leave and Annie was a step down. It was an operations coordinator in head office.

Speaker 1 (13:47.918)
And it was for someone that liked end-to-end solutions, someone that was organized, someone that liked problem solving. And I read the briefing, I thought, this is perfect. It fits me to a T. Yeah, it's not a management position, but you know, this is probably the right thing. And I went to the interview and I remember them saying to me afterwards, cause I knew I was up against someone else that I thought, well, she's brilliant. I'm never going to get this. And they call me the next day and they said,

If someone can talk so passionately about repairs and maintenance, they have to have the job. That's kind of probably like one of the defining career moments for me. like deciding to take the step from a secure management position in store, which probably would have been okay for me, but which never have made me particularly happy to taking a step down and starting something completely new. And the more I was doing it, the more I saw,

Why don't I take this on? Why don't I take this on? And how can I get to management and how can I do this? And it was just, it was wonderful. I loved every minute of it. And I did it for a couple of years before I then got made manager at the European level.

made a choice that allowed her to enjoy her work again and in doing so she created a brilliant boomerang. She left, learnt and came back stronger with new clarity and fresh momentum. Sometimes the smartest move isn't up, it's out and back in with purpose. Because let's be honest, the ladder's wobbly, the escalator's jammed and most of us are quietly rewriting the rules as we go. So what does a smart zigzag actually look like in practice? Let's dig in.

It's time for What Would Caro Do? Like a career agony aunt but with less cardigan and more fire. Because sometimes you don't need permission, you just need better advice. This week's dilemma is from My Dad is a Wedding Dancer from Matlock.

Speaker 1 (15:47.254)
Auntie Caro, I've been offered a sideways move. Less pay, weird title, but it sounds fun. My dad says I should stay put. What would you do?

Look, dads mean well, don't they? But they also think that dad dancing is a feast for the eyes. Your dad's coming from a different generation. Things were simpler, more structured back then. If the job expands you, excites you and stretches what you can offer, that's not a step down. That's a step through. I remember when I first decided to set up my own business, money was tight and we were quietly struggling. Bill's mum started to clock on.

Mainly because we were raiding her fridge more and more and Friday night dinners became an actual thing. She meant well, she'd scour the local paper, leaving me post-it notes with numbers on them or cutting out ads for waitress jobs, nursery support and once a dental assistant gig, even though she knew I hated the dentist. She didn't get what I was trying to build. She wasn't dismissive. She was just scared for me. Kind of like Dancer's Dad.

So think about what would happen if you stopped trying to impress LinkedIn with your progress or your dad or mom-in-law and did the thing that makes you curious again. Let's get clever. Let's get bold and start playing the game differently. Here are a few cheeky moves to help you zag with confidence.

Speaker 2 (17:14.445)
Small shifts, sharp impact. These quick fire career moves, real things you can do before your next coffee refill. First, stop asking, is this the right move? Start asking, what will I learn? Sideways doesn't mean backwards. Even downwards doesn't mean backwards if you're going to learn something. Let that shame go. As Yonah says, chase experiences, not jobs.

The

Speaker 2 (17:43.532)
And here's a big one. Number two, start trusting pattern over plan. Why? Because traditional career plans assume that life is linear and sensible. Promotions every two years, a tidy CV, no sudden left turns. But life's rarely that cooperative. Patterns on the other hand, they're gold. They tell you what really works for you if you're paying attention. So ask yourself what kind of roles light you up.

When have you felt most alive at work? What kind of opportunities seem to find you again and again, even if they don't fit your plan? If every great thing in your career has started with a weird coffee, a rogue opportunity or a gut feeling you couldn't explain, that's not chaos. That's your career strategy trying to get your attention. So maybe it's not about having a five-year plan. Maybe it's about spotting the pattern instead and choosing to follow it on purpose.

And thirdly, ask people how they actually got where they are. Ask them to share their story. I bet you'll find it wasn't a five-year plan. It was a weird dinner, a risky email and a lucky lift ride. Remember, ask people you respect, not the ones that hold you back. All right, now you've got your radar back online. Let's wrap this up with a little wisdom for the road, one career quote crime that needs gently, but firmly putting in the bin.

Speaker 2 (19:12.846)
This quote has the right vibe and the completely right advice. So let's fix that before someone puts it on a mug. This week is a real treat for you. I got told it regularly when I was younger and I still hear it knocking around. It's a classic.

Stay in your lane.

Ugh, this one gets thrown around like it's deep, man. The translation is don't try new things, don't question the system, know your place and wait your turn. It's the kind of phrase that kills curiosity, flattens potential and quietly maintains the status quo. Here's the thing, if someone dares to tell you to stay in your lane or any of the similar sayings like that's not your responsibility or let's not reinvent the wheel, let's stick to your area of expertise,

Let's not rock the boat or don't overstep. Stay in your lane. Baby, I'm building the motorway. Or better yet, I was in a lane. I zagged. Now I've got a better view. Zagging means you notice the rules don't work for you and you chose to make your own. That's not off track. That's leadership. Until next time.

Speaker 2 (20:33.4)
So that's a wrap on this episode of Little Moves Big Careers, where progress isn't perfect, but it is happening. If your brain's buzzing and you want more magic like this, head to inspireyourgenius.com forward slash podcast for the show notes, cheeky extras and the kind of tools your career has been crying out for. Share it, steal it with pride, start a movement. So if you did enjoy this episode, please subscribe, share.

and send me your dilemmas for what would Caro do and any ideas that you've tried to caroline at inspireyourgenius.com. And if you want to bring fresh thinking into your team or company, that's literally what we do. Drop us a line, we'll make it sing for you. Until next time, make the move. Even if it's tiny, especially if it's tiny.