179. Playing It Safe Is Costing You More Than You Think

Playing it safe can feel responsible, but it often quietly limits our growth and fulfillment. By recognizing when our pursuit of security becomes a trap, we can begin taking small, intentional steps that reconnect us to our curiosity and purpose. Through experimentation, self-trust, and the willingness to embrace discomfort, we give ourselves the chance to create a career and life that truly feel like our own.

These small acts of self-abandonment build up. One day you look up and realize the life you’re living is technically fine, but it feels pretty hollow.

Are you clinging to the comfort of stability even though it’s leaving you feeling stuck and unfulfilled? Are you downsizing your goals to make others more comfortable with your choices? Are you waiting for the “perfect” plan before taking action toward what you really want?

You’ll learn that playing it safe might feel responsible, but it can quietly erode your ambition and potential, and that the real path to growth often starts with small, curiosity-driven experiments that build self-trust and momentum.

WHAT YOU WILL DISCOVER

• Why redefining safety helps you navigate uncertainty and create a career that truly excites you

• 3 practical tips to break out of the safety trap

• Why shifting from seeking approval is essential for reclaiming your potential and avoiding long-term regret

SUBSCRIBE: APPLE PODCASTS | SPOTIFY | AMAZON | PODBEAN | POCKETCASTS

DOWNLOAD GUIDE TO LIVING MORE BOLDLY

DOWNLOAD TRANSCRIPT

TRANSCRIPT

Welcome to the Stop Sabotaging Your Success podcast, episode one hundred and seventy-nine. 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. 

It's completely natural to want to feel safe. In fact, we're wired for it – our brains are designed to seek comfort, predictability, and protection from risk. But, in today's world, especially for women navigating careers in demanding environments, that instinct to play it safe can slowly turn into a trap. We stay in roles that no longer challenge us, silence our own ideas that feel too bold, and prioritize being seen as competent over feeling truly fulfilled, all under the guise of making the smart choice. But, clinging too tightly to stability doesn't always keep us secure – it can quietly erode our ambition and keep us from living up to our potential. 

In this episode, we want to challenge the belief that playing it safe is protecting us, because often, it's contributing to what's holding us back. And yet, you don't have to blow up your entire life to change it. Small, low-stakes experiments, fueled by curiosity, can help you reconnect to your intuition, uncover new possibilities, and start building a career (and a life) that feels like it's actually yours. It's not about being reckless or impulsive; it's about recognizing when our desire for safety and security has become a trap. 

We are designed to seek stability. It's part of how we survive in a world that sometimes feels uncertain and, at times, overwhelming. So, when life gets hard or unpredictable, of course we lean toward the familiar. We look for the safest option – the secure job, the stable income, and opting for the 'sensible' solution. But, did you ever stop to think that clinging too tightly to what you think is safer can hold you back from what you actually want? 

We don't seem to talk about how our instinct for safety, while protective, can also quietly confine us. That mindset can convince us we're being responsible when we're actually just staying stuck. It whispers things like, "Now is not the time", "Don't rock the boat", or "You should be grateful for what you have". And over time, those whispers grow louder until we adopt them as our beliefs. The belief that maybe this is as good as it gets, that we shouldn't ask for more, and that we don't really need to feel fulfilled as long as we feel secure. 

I'll admit, safety feels good... until it doesn't. It feels like we're in control, and like everything is okay – until one day, it begins to feel like numbness, like you're boxed in, and it feels like you're living someone else's version of your life and you don't remember exactly when you stopped making your own choices. And, so we stay. We play small. And we keep ourselves safe by avoiding risk – which often means we're also avoiding growth. The world today feels chaotic, so it's easy to justify it. But shrinking your world doesn't make it safer; It just makes it smaller, less vibrant, and less yours.

We often mistake survival mode for success. That packed calendar, that sense of control, that exhausting to-do list – it can feel like achievement. But, if you're emotionally disconnected from your own ambitions, from your sense of purpose, and for what lights you up, that's not success.

What's even more insidious are the tiny betrayals. You know the ones. Those moments when you wanted to try something new but didn't, because someone else told you it wasn't practical. Those times when you chose the safer path instead of the one you felt drawn to, because you didn't want to disappoint anyone. The dreams you buried, little by little, because someone said, "People like us don't do things like that". These small acts of self-abandonment build up. One day you'll look up and realize that the life you're living is technically fine, but it feels pretty hollow. 

So, how do you know when your so-called safety has actually become a form of complacency? Watch out for these three clues: 

• You constantly ask for permission or wait for validation before making a move. 

• You feel 'safe' but also stuck – like nothing is going terribly wrong, but nothing is lighting you up, either. 

• You find yourself downsizing your goals to make other people more comfortable with your choices. 

These are the telltale signs you've settled into a version of life that prioritizes predictability over possibility. And while stability has its place – financial stability, emotional safety, supportive relationships – those things should be a foundation, not a ceiling. 

Unfortunately, basing our decision on stability often means reshaping ourselves to fit someone else's idea of success. And it's tricky because it's not always obvious. It can show up as doing work you're good at, but don't love. It can look like sticking with a job 'for the benefits', even though it drains your energy. It can look like following a well-worn path because it's safer than facing the uncertainty of heading out in a new direction. 

We convince ourselves we can't make a change unless we know exactly what comes next. We tell ourselves that unless we have a detailed five-year plan, complete with a backup plan should something go wrong, we're not 'ready'. But that's just our fear getting in the way. The truth is, you don't need to see the whole staircase – you just need to take that first step. And sometimes, the step is as small as asking yourself what you actually want, not what you think you're supposed to want. 

Playing it safe tricks us into thinking we're doing the right thing. But more often, we're just delaying the feeling of regret. The discomfort of growth will pass, but the weight of wondering what would have happened, if we'd only given ourselves a try, tends to linger.

So, what do we do instead? 

I'd recommend that we start small and run tiny experiments. Instead of committing to an all-or-nothing leap, try a 'limited engagement' like a side project, developing a new skill, or pursuing a short-term goal. Something that lets you test what excites you, without blowing up your life. These tiny steps don't need to be perfect, they just need to be an honest reflection of what you want to explore next.

Most importantly, stop asking others for permission to live your life in a way that feels good to you. Yes, it will feel scary. Yes, you might disappoint someone. But, you also might surprise yourself. You might reconnect with the part of you that's been buried under obligations and expectations. You might find energy, creativity, even joy where you thought there was only responsibility. 

Once we recognize that playing it safe can quietly sabotage our potential, the next step is to reframe what feeling 'safe' really means. Because playing it safe can actually be one of the riskiest things we can do. 

We tend to equate safety with security – job security, financial security – meaning a stable path we can count on. But, if the last few years have taught us anything, it's that there's no such thing as guaranteed job security. Teams get reorganized. Budgets get slashed. Managers change. Entire industries shift overnight. And that 'safe' plan you were banking on, it can disappear in the blink of an eye. If you've spent years clinging to the hope of security instead of developing your voice, your skill set, or your adaptability, you're now left without a backup plan and without a sense of what might be next for you. 

This is why redefining what safety means is essential. Safety doesn't mean avoiding discomfort. It means building trust in your own ability to respond to discomfort when it comes, because it will come. Growth and uncertainty are part of any meaningful career, and the more capable you feel navigating them, the less you need to cling to predictability as your only strategy. So, let's be clear: real safety comes from self-trust, not from a job title or a perfect five-year plan. 

And yet, we're taught to chase comfort and security, especially in my case, the steady paycheck. But what often gets missed is that comfort doesn't necessarily mean contentment. It can just as easily mean stagnation. That creeping numbness that sets in when every day feels like a repeat of the day before. When the work no longer challenges you, but you keep doing it because it feels easier than starting over or trying something new. But, I hate to tell you, easier is not the same as better. We're more likely to regret not having given ourselves a shot, than giving it a try and having it not work out the way we'd hoped.

In fact, that's the actual risk: regret, not discomfort. Discomfort passes, but regret tends to stick around. Especially the kind that sounds like, "I should have tried", "I could have done more", "I knew this wasn't for me and I stayed anyway". That's the real threat, not failure, and not even the fear we sometimes feel. It's more the slow erosion of our own potential, while we wait for the right moment to act.

So, what's the alternative? Start by recognizing that you don't have to be brave, all at once. Courage isn't taking a giant leap off a cliff – it's usually a series of tiny, shaky steps in the direction of something that matters to you. It could be as simple as saying, "I'm curious about this" even when you're still unsure. It's applying for that new role that feels like a bit of a reach. Maybe it's speaking up in a meeting, even when your voice trembles a little. You don't need to feel ready, you just need to be willing to give it a try. 

That willingness is everything. It creates momentum. It turns ideas into experiments. Because the goal isn't to have all the answers before you act – the goal is to take action so you can discover the answers. So many of us wait until we've mapped out every detail, until there's no risk left, and we're guaranteed a win. But, that's not how progress works. You learn by doing. You build confidence by taking action. 

It also means dropping the myth that someone else is coming to rescue you from your safe-but-uninspired career. No mentor, manager, or leader can hand you a life that feels meaningful, if you haven't decided you're ready to claim it. That part is on you. And while it might sound daunting, that's also empowering. Nobody else gets to decide what success looks like for you. You get to redefine it, on your terms. 

The mindset shift that makes everything else possible is reframing safety and reclaiming courage. Part of this is understanding that discomfort isn't danger – It's just a signal. It's a sign that you're bumping up against your current limits. And that's usually where the growth happens. If you think about it, your best memories, and your most significant accomplishments probably came from times where you took a risk, not when you played it safe. 

Those moments when you said yes, even though it scared you. When you trusted your gut over someone else's opinion. When you acted before everything was perfectly lined up. These are the experiences that shape us – not the ones where we played it safe, but the ones where we were willing to feel a little vulnerable by putting ourselves out there.

And, contrary to popular belief, vulnerability doesn't have to feel like weakness. When we approach change not with fear, but with curiosity, we make bold moves feel exciting instead of terrifying. Curiosity is what turns, "What if I fail?" into "What could I learn?". It lets us try new things without demanding perfection from ourselves. And that small shift, from critical to curious, makes risk-taking feel a lot less like recklessness and a lot more like strategy.

Trusting your intuition is one of the most under-utilized leadership tools we have. It's pattern recognition. It's the sum of your experience, insight, and awareness bubbling up before you can consciously explain it. When your body tenses up during a meeting, or you get that subtle flutter of excitement about an opportunity, it's not random. It's worth listening to. And the more you practice tuning into those intuitive signals, the more precise your decision-making becomes.

Still, it's easy to ignore our intuition when we're so used to outsourcing our choices. We're conditioned to seek the approval of others – to do what makes other people proud, comfortable, or impresses them in some way. But at some point, you have to ask yourself, "Who am I willing to disappoint in order to stop disappointing myself?". That's not a small question. In fact, that could be a career-defining question.

Because you will disappoint people. That's unavoidable. The more you grow, the more likely it is that someone won't like it. And, the more you start living for what actually lights you up, the more you'll disrupt the status quo – whether that's within your workplace, your friend group, or even your family. But the alternative – staying quiet and playing it safe – will undoubtedly slowly cause you to unravel from the inside out. That's the real danger. 

So no, you don't need to be fearless. You don't need to have a detailed five-year plan. You don't even need to know exactly where this road is going. What you do need is a willingness to begin to get a little uncomfortable, and to move before you feel ready. Because, the truth is, the version of your career that feels bold, fulfilling, and fully yours is just on the other side of your comfort zone.

So, now that we've established that playing it safe isn't always the best move, that it can in fact quietly limit your potential, the next logical question becomes: now what? What's the actual path forward when you're ready to stop playing small, but don't want to torch your career, abandon your responsibilities, or leap into the unknown. 

I want to assure you that you don't have to burn it all down to build something better. The real path out of the safety trap is far less dramatic and far more doable than we're often led to believe. It's not about making one big, bold move. It's about experimenting, exploring, testing, and making adjustments. The same way you'd troubleshoot a project at work – not with reckless abandon, but with curiosity and iteration. 

That's why it's smartest to start small. Think micro-experiments, not sweeping life changes, but low-stakes time-limited trials that give you real data about what excites you, drains you, or might actually open new doors for you. Try something for thirty days – whether it's a new creative pursuit or a different way of working. Frame it as a 'limited engagement'. There's no need to commit to forever. If you hate it, you've learned something. If it works for you, it might create some momentum you can build on. Either way, you're moving forward – and that alone breaks the spell of feeling stuck. 

What many of us don't realize is that momentum matters more than motivation. Motivation is sometimes fickle; it shows up when it feels like it. Momentum, on the other hand, is built by taking action, and just one small step makes the next one easier. And, that's what these experiments are really about – generating motion so that you can stop overthinking and start learning what works for you, and what doesn't.

Another piece of this puzzle is learning to trust your intuition, even if it's rusty. We're so used to relying on logic and external validation that we sometimes forget our bodies have been collecting data all along. Intuition isn't mystical – it's practical wisdom gathered from years of lived experience, stored in your body, quietly waiting for you to tune in. 

When you start paying attention to how your body responds to certain situations, projects, or people, you begin to build the habit of attention. And, that's a skill worth developing. Because, when you know what energizes you and what doesn't, you're far better equipped to navigate your career with clarity. 

Next comes questioning your need for approval. Many of us spend our entire careers trying not to disappoint anyone – our parents, our mentors, even our peers. We wait for permission to try something new or different, or even to want more. But, at some point, you have to decide whose disappointment would actually matter. Are you willing to disappoint someone else if it means you stop disappointing yourself? 

That's not easy – but it is essential. Because the fear of judgment or disapproval is often the single biggest barrier between us and the work we actually want to do. And it's not always about career moves. It could be about wanting to work differently, speak more honestly, or lead more authentically. Whatever it is, the need for external approval can quietly dilute our boldest ideas before we've even uttered them out loud.

So, what if we ditched the perfectionist pressure and reframed the entire process? Sometimes, thinking of these experiments as a type of quest can be helpful. Instead of rigid, high-stakes goals, think of what you're doing as a quest – something you're genuinely curious about, that might also be fun. Maybe it will be something that will change your life (or not). The best part? A quest doesn't have to last forever. You can start one, see how it goes, and pivot when it stops being meaningful. This flexibility removes the fear of failure and opens the door to experimentation. And, that's where there's real growth potential. 

Of course, all of this involves getting comfortable with discomfort. We often interpret discomfort as danger but, more often than not, it's just uncertainty, unfamiliarity, or maybe a bit of awkwardness that comes with trying something new. Normalize that. Expect it. Plan for it. Because, if you're waiting for the fear to go away before you begin, you'll be waiting a long time. 

That said, you can absolutely make this easier on yourself. Start by expecting resistance, both from your own mind and the people around you. That inner voice that tells you it's too late, too risky, or too selfish is simply doing its job to protect you. You don't have to silence it, but don't let it hold you back. 

Progress is progress, even when it's messy. Celebrate those small wins. Don't wait until the entire vision is realized to feel proud of yourself. And please – focus on the process, not just the end result. So much of what you'll learn about yourself, your values, and your capacity come while you're doing the thing, not after it's done.

Another way to lighten the load? Find allies. You don't need a massive support system, just a few people who meet your dreams with curiosity and encouragement, instead of skepticism or pessimism. People who can say, "That sounds interesting, tell me more" instead of, "That can't possibly work". These kinds of people are the good ones, so keep them close. 

And finally, you don't have to know the whole plan before you start. You're allowed to change your mind, to pivot, and to try something new, and then try something else. What matters is that you're not just going through the motions of a life that no longer fits. You're actively choosing to show up. You're experimenting, learning more about yourself, and evolving. 

So, identify one tiny experiment that you can start this week. Something low-stakes, limited in scope, but aligned with the curiosity you've uncovered. What if you gave yourself permission to just explore, without it needing to be perfect? 

Playing it safe might seem like the responsible choice, but if it leaves you stuck, playing small, or feeling disconnected, it's not protecting you, it's costing you. The real question is: are you willing to trade a little discomfort now, for the possibility of a life that feels more bold, more fulfilling, and more yours? 

Because if you are... you might just discover that the safest thing you can do, is to finally take that risk.

And that's it for this episode of Stop Sabotaging Your Success. Remember to download your Guide to Living More Boldly at cindyesliger.com/podcast, episode one hundred and seventy-nine.

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.