208. You Need Challengers Not Just Cheerleaders
- 2 days ago
- 17 min read
Support networks that only validate our frustrations can keep us stuck in echo chambers that feel comfortable but don't move us forward. When everyone around us simply cheers us on without questioning our direction, we risk repeating ineffective strategies while getting better at explaining why they aren't working. Building a challenge network gives us the external perspective we need to identify blind spots and develop the cognitive flexibility that drives real career growth.
But if you're only surrounded by people who help you justify why your current approach isn't working rather than people who push you to try something different, you're not moving forward.
Are you surrounded by people who only validate your frustrations instead of pushing you to try something new? Are you repeating the same career strategies and expecting different results? Are you so committed to how things should work that you're struggling to adapt to how they actually work?
You'll learn that a traditional support network can quietly keep you stuck by reinforcing your existing beliefs and blind spots, and that building a challenge network of thoughtful critics is what creates the growth and forward momentum you're looking for.
WHAT YOU WILL DISCOVER
Why relying solely on a cheerleader support network can be career-limiting, leaving you overconfident in strategies that aren't actually working in your favor
6 practical tips to build and use a challenge network effectively
Why developing confidence in your ability to learn matters more than confidence in what you already know, making adaptability your sustainable competitive advantage
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TRANSCRIPT
Welcome to the Stop Sabotaging Your Success podcast, episode two hundred and eight. 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.
We've all been told the importance of having a support network—those people who believe in us, who champion our work when we're not in the room, who celebrate our wins, and encourage us when things get tough. And look, I'm not saying that's bad advice. Having people in your corner matters. But here's what no one tells you: if everyone in your corner is just cheering you on without ever questioning whether you're running in the right direction, you might be heading straight for a wall. Also, having a support network that only validates your frustrations isn't going to get you to where you want to go.
In this episode, we're talking about why the traditional support system might actually be keeping you stuck, and what you might need instead. We're going to explore the problem with surrounding yourself only with people who think exactly like you do, why that echo chamber is particularly dangerous when you're trying to navigate workplace dynamics that weren't built with you in mind, and the consequences—both professional and personal—of never having your assumptions challenged. Then, we'll dig into what a challenge network actually looks like, how to build one without surrounding yourself with people who just want to tear you down, and the strategies that will help you use feedback to move forward instead of getting stuck in analysis-paralysis, or becoming someone who changes their mind for all the wrong reasons.
The conventional wisdom goes something like this: find mentors who believe in your potential, cultivate relationships with colleagues who've got your back, and build friendships with people who validate your experiences. And honestly, all of that is important. When you're navigating a workplace where you're frequently overlooked or underestimated, having people who see your value and remind you of it can be the thing that keeps you from walking away entirely.
But here's where it gets tricky. When everyone in your support network just validates your perspective without ever challenging it, you end up in an echo chamber. And echo chambers are particularly insidious because they feel so comfortable. Everyone agrees with you about what the problems are. Everyone shares similar frustrations. Everyone reinforces the same narratives about why things aren't working. You get together and commiserate about how unfair it all is, how the system is broken, and how you're doing everything right but still not getting the results you deserve. And you know what? You might be absolutely correct about all of it.
But is being right, in this case, actually getting you any closer to your goals?
Because when there's no one to challenge you, you keep using the same strategies that haven't been working, hoping this time will be different. You keep approaching workplace dynamics the same way, advocating for yourself the same way, and positioning your contributions the same way. And when it doesn't work, your support network helps you explain why—the system is biased, your boss doesn't get it, or the company doesn't value technical expertise the way they should. All of which might be true.
But if you're only surrounded by people who help you justify why your current approach isn't working, rather than people who push you to try something different, you're not moving forward. You're just getting really good at explaining why you're stuck.
There's this thing called the consistency principle—we want to see ourselves and be seen as consistent people who act in accordance with what we say and believe. And your support network often reinforces this. They expect you to stay consistent with who you've always been. If you've always been 'the person who doesn't play politics', they might actually discourage you from building strategic relationships, because that wouldn't be the 'you' they know. If you've always been someone who 'lets their work speak for itself', they might validate that approach even when the evidence clearly shows that, in your workplace, people speak for their work, and if you're not doing that, you're invisible.
Here's what's particularly problematic: we often build support networks primarily with other women facing the same barriers. Which makes sense—these are the people who get it, who've experienced the same frustrations, who don't need you to explain why being interrupted in every meeting is exhausting. But, if everyone in your circle is facing the same challenges and using similar strategies to address them, you're all reinforcing the same approaches and the same blind spots.
You're not getting exposed to different ways of thinking about the problem. You're not hearing from people who've successfully navigated the system using approaches you haven't considered. You're just validating each other's frustration, which feels supportive in the moment, but doesn't actually change anything.
And then there's the approval-seeking trap. When you're trying to make a bold move or do something differently, you naturally want to run it by your support network first. But here's what happens: if they're all committed to seeing you as the person you've always been, they might encourage you to stay in your comfort zone. Or worse, you might water down your convictions to maintain their approval.
You change your mind at the wrong moments for the wrong reasons. Not because you've encountered better information, but because you want to fit in or you don't want to lose their support. And once you've changed course to get that validation, it's really hard to walk it back.
The other issue with traditional support networks is that they can actually make you overconfident in approaches that are undermining your goals. Everyone agrees that you deserve that promotion, that your work is excellent, and that you should be recognized. So, you become confident that you're doing everything right. Which means that when you don't get the promotion, the only explanation must be external—leading you to believe that it's bias, politics, or someone else taking credit for your great work. And look, those things might be true.
But, what if your approach to making your work visible is also part of the problem? What if the way you're advocating for yourself isn't landing the way you think it is? If nobody in your network is willing to question whether your strategy is effective, you'll never know. You'll just keep doing the same thing, getting increasingly frustrated when it doesn't work, and your support network will keep reassuring you that you're right and everyone else is wrong.
So, what's the alternative? That's where I invite you to shake things up a little and find people who challenge you to consider whether there could be a different way to look at things. This is a fundamentally different way of thinking about who you need around you.
The challenge network isn't made up of people who are trying to bring you down or rain on your parade. These aren't the naysayers or the people who don't believe in you. They're people who care enough about your success to point out your blind spots. They're thoughtful critics who enjoy playing with ideas and are excited to figure things out with you, even when they disagree or they have an entirely new take on things. They're skeptical in the best possible way—interested in stretching your thinking, questioning your assumptions, and helping you see the holes in your reasoning that you're too invested to notice.
Here's the key distinction: these are the people who challenge you because they want you to succeed, not to tear you down. They're not trying to further their own agenda or use you as a pawn. They're not criticizing you just for the sake of being destructive. They're pushing back because they can see things you can't see about your own work, your own approach, or your own strategy. And most importantly, they're interested in seeing who you could become.
Think about it this way: you may not be the most objective person to evaluate your own work or your strategy. You're just too close to it. You're too attached to your own thinking. And there's actually research showing that people who occasionally experience imposter syndrome—who sometimes doubt themselves and second-guess their decisions—often perform better than people who never question themselves at all. Why? Because that doubt makes them follow-up, verify that their decisions are working in the way they expected, and course-correct when needed.
A challenge network serves a similar function. They are the external check on your thinking when you can't be objective about it yourself.
But here's what people get wrong about this: they think a challenge network means surrounding yourself with people who are harsh or hypercritical, or who enjoy poking holes in things. That's not it. You want people who are genuinely curious about whether your approach is working, who ask questions like, "I'm noticing you've tried this strategy three times now and haven't gotten the results you wanted—what does that tell us?" or "You say you want to be seen as a technical leader, but you turn down speaking opportunities because you don't want to self-promote. How do those two things fit together?". These aren't attacks. They're invitations to examine whether what you're doing actually aligns with what you're trying to achieve.
The interesting thing in having people challenge you is that it helps avoid the trap of overconfidence. We talk a lot about how women need more confidence, and there's truth to that—lack of confidence can prevent you from aiming high enough or advocating strongly enough for yourself. But there's another side to this coin. Overconfidence is just as problematic when you're so certain you're doing the right things that you can't see what needs to change. It's the difference between confidence in your existing knowledge and skills versus confidence in your ongoing ability to learn. One makes you rigid. The other keeps you adaptable.
So, what happens if you don't build a challenge network? As you might have guessed, the consequences can be significant over the long-term. Professionally, you keep using ineffective strategies to advocate for yourself. You keep approaching workplace dynamics the same way, but expecting different results. You might think you're good at navigating these situations when you're actually missing crucial signals or opportunities.
You don't know what you don't know. And in today's workplace, not knowing what you don't know can be career-limiting in ways you won't even recognize until years later.
You also stay attached to beliefs about how things 'should' work, rather than adapting to how they actually work. Maybe you believe promotions should be based purely on technical merit. Maybe you believe that if you just do excellent work, recognition will follow. Maybe you believe that playing politics is beneath you. And, perhaps things should work differently than they do. But if you're so committed to how things should be that you refuse to adapt to how they actually are, you're fighting a battle against reality. And reality wins that fight every time.
There's also an identity piece to this. When you're never challenged, you stay attached to an identity that might be limiting your growth. Telling yourself, "I'm someone who doesn't play politics" becomes who you are, not just a strategy you've chosen. And when something is connected to your identity—to who you see yourself as being in the world—it becomes almost impossible to change, even when clear evidence shows it's not serving you. When you do get to a point where you need to make this type of identity shift, you end up grieving not just the loss of a belief, but the loss of who you thought you were.
And if you don't have people challenging you along the way, that realization comes much later, after years of sticking with an approach that wasn't working. And what has it cost you?
Personally, the consequences can be even more painful. There's a resentment that builds when you watch others advance using strategies you refuse to consider. The frustration of realizing that your commitment to doing things 'the right way' meant you were playing a different game than everyone else.
The regret of looking back and seeing all the opportunities you missed because you were so certain about your approach. And often, there's this painful moment of reckoning when you realize that the people who were just validating your frustrations weren't actually helping you. They were enabling you to stay stuck while feeling self-righteous about it.
What makes this even worse in professional settings is avoiding feedback from people whose success you don't want to emulate. Maybe there's someone who advanced quickly, but you didn't like how they did it—maybe they were too political, too quick to brag about their accomplishments, or too willing to compromise. So you dismiss anything they might tell you about what works. But here's the thing: they might actually see your blind spots more clearly than the people who think exactly like you do. They might notice that your unwillingness to build strategic relationships is being interpreted as aloofness, and that your commitment to 'letting your work speak for itself' means nobody in leadership actually knows what you're working on.
Or you confuse perspective-taking with perspective-seeking.
Perspective-taking is when you try to imagine what someone else is thinking—so you sit there and guess at their motivations, their reasoning, or their perspective. And research shows this doesn't actually work very well, especially when someone is different from you. The further someone's experience is from yours, the more likely you are to be wrong about what they're thinking. You end up just projecting your own thoughts onto them in ways that don't capture their actual opinions.
Perspective-seeking, on the other hand, is when you actually ask people what they think and why. In this way, you find out what their perspective actually is rather than assuming you know. This is something a challenge network forces you to do. You can't just imagine what someone did that helped them succeed or what they're thinking in that moment; you have to engage with viewpoints that might be different from your own.
So, how do you actually build and use a challenge network? Let's get practical, because this isn't just about accepting all feedback indiscriminately or letting people tear down your hard-earned confidence.
First, think like a scientist about your career. Treat your beliefs about career advancement as hypotheses to test, not truth to defend. If you believe that doing excellent technical work will lead to recognition, that's a hypothesis. So, as good scientists, we need to test it. What's the evidence? If you're doing excellent work and not getting recognized, that's data that doesn't support your hypothesis. A scientist doesn't double down on a disproven theory—they pivot. They develop a new hypothesis and test that one.
So, maybe the new hypothesis is: "Doing excellent technical work, plus making sure key stakeholders know about it, will lead to recognition." Then, test that. See what happens. This mindset shift—from defending what you believe to testing what you believe—is fundamental to being able to think differently.
And here's the amazing thing about thinking like a scientist: it separates your identity from your strategies. You're not 'someone who doesn't self-promote'; you're someone who's testing different approaches to see what works. That's a completely different psychological frame. It gives you permission to experiment without feeling like you're betraying who you are.
Second, assemble your challenge network intentionally. You want three to five people who've achieved what you want to achieve, even if their paths look different from yours. Actually, especially if their paths look different from yours, because that's how you'll encounter different strategies and approaches.
Look for people who've successfully advanced in your field, but took unconventional routes. Seek out people who are skeptical enough to question your assumptions, but invested enough in ideas to engage deeply. And, most importantly, make sure you're including people who think differently than you do about workplace navigation and interpersonal dynamics.
This might mean including someone who's more politically savvy than you're comfortable being, someone who's more assertive in self-promotion, someone who's made trade-offs you're not sure you'd make. You're not looking for people to tell you who to be—you're looking for people who will expose you to different ways of thinking about the problems you're facing.
Third, create distance from your own thinking. One of the best ways to get perspective on your own approach is to put it away for a while and come back to it with fresh eyes. If you're stuck on a problem, stop focusing on it for a while and do something else. Then, revisit it later. You'll often see things you missed before. But we can't always wait for that natural distance, so this is where your challenge network comes in. Explicitly ask them to identify what you're not seeing by saying something like, "I've been trying to get promoted for two years and it's not happening. What am I not seeing?". Then, actually listen to their answers without immediately defending your approach.
And practice perspective-seeking, not perspective-taking. Don't assume you know why someone succeeded or what they're thinking. Instead, ask them. If there's someone who got promoted and you don't understand how, don't just decide they played office politics or knew the right people. Ask them what they think made the difference. You might learn something that challenges your assumptions about how advancement works in your organization.
Fourth, know when to rethink and when to commit. This is the balance everyone struggles with. If you rethink everything, you'll never actually do anything. You'll be permanently stuck in analysis-paralysis, always second-guessing, and never committing. Some people do overthink things more than they should, but honestly, most of us are too good at justifying the choices we've already made and clinging to the opinions we've already formed.
So, the question is: when should you rethink your approach?
I would suggest you rethink things when you're repeatedly confronted with evidence that your approach isn't achieving your goals. If you've tried the same strategy three times and it hasn't worked, that's a signal. If you're telling yourself the same story about why things aren't working, like "My boss doesn't get it" or "The system is biased" or "They don't value technical expertise", and using that story to avoid changing anything about your approach, that's also a signal.
Stay committed when you're making actual progress, even if it's slower than you'd like. The key is being honest with yourself about whether you're actually moving forward or just getting better at explaining why you're not.
Fifth, manage the identity shift. This is the part nobody prepares you for. When you change your approach, especially if it's a significant change, you might need to change how you see yourself, and that can feel like a loss. If you've always been 'someone who doesn't play the game' and you realize you need to build more strategic relationships, that might require letting go of that identity. And there's often a grieving process in accepting that the thing you thought and believed in, or the way you identified yourself—it's now it's now time to let that go.
But rethinking things is only a loss if you're attached to your old belief. If you test your opinions as hypotheses instead of taking your beliefs too seriously, you can experience the joy of being wrong. You can be excited about discovering something you didn't know before. The grief of losing who you thought you were gets replaced with the joy of learning something new and growing from it.
In my own experience, it was a game-changer to learn that I didn't have to believe everything I thought because not every opinion that enters my head is right. If I wanted to keep evolving in my knowledge and in my career, I actually had to be more open to changing my mind. And yes, I learned that that's easier said than done. But being open to possibility—to the idea that maybe there's a better way I hadn't yet considered—is what kept me from continuing to get stuck.
Sixth, use feedback without becoming a people-pleaser. When you start getting input from your challenge network, you may not always like what you hear. You might want to push back. You might feel attached to your own perspective and resistant to their questions. That's normal. But pay attention to whether you're dismissing their input outright or actually engaging with it.
Over time, if you've chosen your challenge network well, you'll start to value what you're learning from them, even when it's uncomfortable. You'll want them to keep challenging you because you'll see how it helps you improve.
But—and this is crucial—the goal is not to cater to their opinions. You're not trying to please them or get their approval. You're using their perspective to stress-test your own thinking.
There's a huge difference between changing your mind because someone's challenge revealed a flaw in your reasoning, versus changing your mind because you're seeking their validation or approval. One is growth, the other is just a different version of being stuck.
Now, what some people overlook is the difference between confidence in what you know and confidence in your ability to learn. We're constantly told that women need more confidence, and there's truth to that. A lack of confidence can prevent you from aiming high enough, from advocating for yourself, or pursuing opportunities. But the kind of confidence we're usually encouraged to build is confidence in our existing knowledge and skills. Confidence that we're doing things right. Confidence that we know what we're doing.
And I'd argue that's actually the wrong kind of confidence to cultivate in this case. What you need is confidence in your ongoing ability to learn. Confidence that, even if you don't know exactly what to do right now, you can figure it out. Knowing that you can experiment, gather data, adjust your approach, and improve with consistent effort. This kind of confidence keeps you humble and curious. It allows you to be flexible instead of rigid. It lets you rethink things without feeling like you're admitting failure.
Think about all the times you've initially struggled at something and then gotten better with practice. You're remarkably good at learning. We all are, but we tend to discount that and focus only on the things we've already mastered and the things we're already confident about. But when we encounter something new or something that's not working, we interpret that as evidence that maybe we're not good enough, rather than evidence that we're still in the process of learning.
Seeing yourself as a learner, rather than expecting yourself to already be an expert is a fundamental distinction. It's the difference between being satisfied with what you know and being excited to rethink everything you thought you knew. And in male-dominated fields, where the landscape is constantly shifting, where the unwritten rules are often opaque, where what worked for previous generations of women might not work now, being a learner is your sustainable competitive advantage.
Here's what you can actually control in all of this. You can't control whether your workplace recognizes your contributions fairly. You can't control whether rewards are distributed equitably. But you can control whether you're getting feedback that actually helps you grow. You can control whether you're testing the effectiveness of your strategies or just defending them. You can control whether you're learning from people who think differently or just seeking validation from people who think just like you do.
And that matters more than you might realize. Because the people who advance in any profession aren't necessarily the most talented or the hardest working. They're often the ones who are willing to rethink their approach when the evidence shows it isn't working. They built challenge networks that helped them see their blind spots. They developed confidence in their ability to learn and adapt, rather than arrogantly assuming that they already had all the answers.
That cognitive flexibility—that willingness to rethink things—becomes your competitive advantage in environments where the rules aren't clear and the path isn't obvious.
So, take a look at your current support system. Are these people only cheerleaders, or are they also willing to challenge you? Are they helping you justify why you're stuck, or are they pushing you to try something different? Are they so invested in you staying who you've always been that they discourage you from evolving? And if the answer to any of those questions make you uncomfortable, it might be time to rethink who you're learning from and what kind of input you're actually seeking.
Because at the end of the day, you deserve more than just people who believe in you. You deserve people who believe in you enough to tell you the truth, even when it's hard to hear.
That's what a challenge network gives you. And that's what might finally help you move forward.
Choose growth over validation. Choose learning over certainty. And watch what becomes possible when you do.
And that's it for this episode of Stop Sabotaging Your Success. Remember to download your Guide to Building Your Challenge Network at cindyesliger.com/podcast, episode two hundred and eight.
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.
