216. Embracing Possibility Rather Than Settling For What's Probable

In our careers, we often limit ourselves by pursuing only what seems probable based on past patterns rather than what might be possible. This probability-based thinking keeps us stuck, undermining our momentum and widening the gap between who we are and who we could be. By shifting our mindset and applying six practical strategies, we can begin pursuing possibility and creating careers that truly reflect our capabilities.

Probability is about pattern recognition. Possibility is about pattern creation.

Are you basing your next career move on what you've seen other women achieve in your organization, rather than what you truly want? Are you waiting to feel fully qualified before pursuing a promotion or high-visibility opportunity? Are you playing it safe while watching others advance by boldly pursuing what seems improbable?

You'll learn that shifting from probability thinking to possibility thinking is a mindset change that requires committing to ambitious goals without knowing exactly how you'll achieve them—and that the discomfort you feel is actually a sign you've entered the growth zone.

WHAT YOU WILL DISCOVER

• Why relying on backward-looking probability thinking to make forward-looking career decisions keeps you stuck well below your true potential

• 6 practical strategies to shift your mindset from settling for what's probable to actively pursuing what's possible in your career

• Why staying in your comfort zone may feel safe but actually erodes your self-trust, motivation, and long-term career momentum

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DOWNLOAD GUIDE TO BREAKING FREE FROM PROBABILITY THINKING

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TRANSCRIPT

Welcome to the Stop Sabotaging Your Success podcast, episode two hundred and sixteen. 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. 

What if I told you that the biggest obstacle standing between you and your next promotion isn't your qualifications, your boss, or even the old boys' club culture at your company—but the fact that you're only pursuing what seems probable instead of what might be possible? I know, I know, this sounds like something you'd see on one of those motivational posters, but stick with me here because there's a critical distinction that many of us completely miss. We're great at solving complex technical problems with incomplete data. We can troubleshoot systems, debug code, analyze failures, and develop solutions that didn't exist before. Yet, when it comes to our own careers, we suddenly become incredibly conservative, basing our next moves entirely on what we've already seen other women achieve in our organizations. We're using backward-looking probability calculations to make forward-looking career decisions, and it's keeping us stuck in positions way below what we're actually capable of achieving. 

In this episode, we're diving deep into this mistaken idea that we should only pursue what seems realistic based on past patterns, and it's quietly sabotaging our success in ways we probably haven't even noticed. We're going to talk about why we chronically understate our goals, how we're tricked into believing we don't deserve more, and what happens when we mistake our current reality for the only possibility.

There are specific beliefs that keep us playing small, but this is really just a mindset. We look at some practical strategies we can use right now to shift your mindset from what's probable to exploring what might be possible. This is going to require you to get uncomfortable, question some things you've accepted as facts, and probably feel some feelings you've been trying to avoid. 

Let's start with the problem, because I'm guessing some of you are already thinking, "But being realistic is good! I'm an engineer. I deal with facts and data." And you're right—to a point. The issue is that you're treating incomplete data as if it's the whole story, and then making major decisions based on temporary circumstances. 

Here's what I mean: when you look around your company and see that no woman has ever made it to Director or VP level, or that the one woman who tried to negotiate her salary got labeled as 'difficult', or that female engineers consistently get assigned to support roles instead of leading the high-visibility projects, you're observing patterns. That's probability. That's what has happened up until now. But here's the thing—you're taking that historical data and using it to determine what's possible for you, and that's where everything goes sideways. 

Probability is about pattern recognition. Possibility is about pattern creation. And we have become good at recognizing patterns and then limiting ourselves to them. 

Think about it: 

• How many times have you not applied for a position because you didn't meet all of the qualifications, only to realize that your male colleague applied, when you know it's a stretch to think he even meets most of them?

• How many times have you accepted a lateral move instead of making it known you wanted a promotion? 

• How many times have you stayed quiet about a compensation gap you became aware of just because you weren't supposed to know that kind of information? 

• How many times have you shied away from going after a major role on a high-visibility project because you haven't seen another woman be given that chance to lead one?

Every single one of those decisions was based on probability thinking. You looked at the data, you saw the pattern, and you concluded that what happened before is what will happen again. 

But here's what you're missing: every single innovation you've ever worked on, every technical breakthrough, every new product or process or solution—it all started as impossible. Nobody had done it before. There was no pattern to follow. There was no probability calculation that assured you that, yes, this will definitely work.

Someone had to decide it was possible even when it wasn't probable, and then they had to figure out how to make it real. You do this in your technical work all the time. You're just more reluctant to do it in your career. And I get it—when it's a technical problem, the worst-case scenario is that you'll learn what doesn't work. When it's your career, the worst-case scenario feels like public humiliation, being labeled as 'difficult', or seen as having ambitions. The stakes feel higher, so you default to what feels safer. 

Except it's not actually safer. You get comfortable and comfortable feels like safe, but what you're actually doing is slowly killing your career momentum. You become known as reliable but not promotable. You're the person who gets things done, who takes on extra work without complaining, who mentors junior staff, and who keeps the team running smoothly. But you get absolutely zero credit for it when promotion time comes around. Because none of that work is high-visibility enough, none of it is deemed strategic enough, and frankly, none of it proves you're ready for leadership. Meanwhile, your colleague, who delivered one flashy project (that honestly, you did half the technical work for) gets tapped for the senior role because he had the audacity to pursue something improbable and claim credit for it.

So, let's talk about four of the beliefs that tend to perpetuate this pattern: 

Belief #1: "I need to see how it's done before I can do it." This one is particularly insidious in organizations where there aren't a lot of female role models in senior leadership. You're waiting for a roadmap that doesn't exist and using its absence as evidence that the destination is unreachable. But consider the fact that every woman who's currently in a leadership role in your field most likely didn't have a roadmap either. She figured it out. Was it messier and harder for her than it was for the men? Absolutely. Does that mean it's not possible for you? Absolutely not. It just means the how isn't going to be handed to you. You're going to have to figure it out for yourself. 

Belief #2: "I should wait until I feel completely qualified." If you're not careful, this one will keep you stuck forever. Here's the thing about qualifications for leadership roles: they're often written by people who already have the job, describing what they think made them successful. And guess what? Those people are usually men, and they usually overestimate their own qualifications while underestimating everyone else's. You could wait until you have every single bullet point on that job description, but I promise you, even then, the goalposts will move. There will be some new requirement, some new concern, some reason why they think you're not quite ready yet. Meanwhile, others will get promoted into roles they're only partially qualified for and then expected to learn on the job. Stop waiting for permission to be ready. You're ready enough right now. 

Belief #3: "If it hasn't happened for other women here, it probably won't happen for me." This one can be particularly painful. You're taking the company's past failure to promote women and internalizing it as your own personal limitation. Do you see how messed up that is? The system is broken, but you're making it mean something about you. The company may have a track record for not recognizing or rewarding female talent, and instead of using that data to decide this company isn't aligned with my career goals, you're using it to decide that you're not good enough. Stop that right now. The fact that no woman has achieved something at your company yet doesn't mean you can't be the first. It might not happen in your timeframe, so that might mean you need to leave the company and find somewhere that deserves you, but it definitely doesn't mean you're not capable. 

Belief #4: "I need to know the how before I can commit to the what." This is the belief that really ties all of this together. We want the algorithm, the formula, or the step-by-step instructions. We want to know exactly what we're up against before we commit. The problem is, when you're doing something you've never done before—like breaking into senior leadership in a male-dominated field—there is no how. Not yet. The how only becomes clear in the rearview mirror, after you've done the thing. You're going to have to commit to the 'what' without knowing the 'how', and that's going to feel uncomfortable, because your brain is going to scream at you that this is reckless, irresponsible, and you're going to fail spectacularly. But that discomfort you're feeling—that fear and uncertainty and doubt—those aren't warning signs that you're headed for disaster. They're indicator lights telling you that you've entered the growth zone. You're supposed to feel uncomfortable here. That's how you know you're pursuing something worth achieving. 

Now, let's look at what happens if you don't make this shift from probability to possibility, because the consequences are real and they compound over time.

You're going to experience chronic procrastination that you'll probably label as just 'waiting for the right time'. But here's what's really happening: you're not lazy; you're overwhelmed. You're carrying around this perfectionist pressure that says you need to have everything figured out before you can make a move, and that's paralyzing you. 

Every day you don't advocate for yourself, you're reinforcing the belief that you're not worth advocating for. You're teaching yourself that your wants and needs and your career ambitions are less important than avoiding potential discomfort. And each time you decide to keep playing small to stay safe, you lose a little more self-trust. Because deep down, you know you're capable of more. You know you're selling yourself short. And the gap between who you are and who you could be just keeps getting wider. 

Your motivation and energy levels are going to tank. There's actual science behind this that says when goals are set too low, people often achieve them, but then subsequent motivation decreases. You're not challenging yourself enough to stay engaged, so you achieve the thing—you get the lateral move, you complete the certification, or you deliver the project—and then you feel empty. You're wondering, "Is this it? Is this all there is?". Because you're capable of so much more, but you keep aiming for what's realistic instead of what might be possible, and deep down, you know it. 

You end up in this weird place where you're technically successful—you have a good job, you're respected in your field, and you make decent money—but you feel stuck and unfulfilled and you can't quite articulate why. It's because you're playing in your comfort zone, and comfort doesn't lead to happiness. Happiness comes from being challenged and feeling like you're making progress towards something that matters to you. 

While you're carefully calculating probabilities and waiting for the 'right' time to make your move, those around you are pursuing promotions they're not quite qualified for and getting them. They're negotiating compensation packages that might seem unrealistic and making a successful case for them. They're getting tapped to lead high-visibility projects they've never done before and building their reputations. And every time that happens, the gap between you and them widens. Not because they're more capable than you—but because they're willing to pursue what might be possible instead of only what they think is realistic. 

And I hate to tell you, your compensation gap is going to get worse, not better. The people who ask for improbable raises are the ones who get life-changing increases. Those who don't, get incremental bumps that barely keep pace with inflation. If you're only asking for what seems likely to be approved, you're leaving massive amounts of money on the table over the course of your career. And believe me, I know asking for an improbable number can feel ridiculous and embarrassing, like you're going to get laughed out of the room. But you know what? The worst they can say is 'no'. And then, you can counter with a number that's likely still higher than what you would have asked for if you'd started with what you thought was more realistic. 

Here's what you need to watch out for. These are four of the most common professional landmines that are going to try to keep you stuck in more realistic thinking: 

1. The qualification trap: This is where you convince yourself that you need one more certification, one more degree, one more skill before you're ready for the next level. It's a trap, because there will always be one more thing. I am in full support of lifelong learning, but if you're using more education as a way to avoid taking action, you're just procrastinating. So ask yourself, am I pursuing this qualification because it's genuinely required for the role I want, or am I pursuing it because I'm afraid to go after the role with what I already have?

2. Comparison quicksand: This is where you measure your next move based on what others in your company have achieved. If no woman has ever made it to Director level, you most likely assume Director level is off limits to you. Or, if the one woman who did make it had to work there for fifteen years and never took maternity leave, you assume that's the only path. Stop benchmarking yourself against the women around you and start believing in your own potential. What do you want? Not what seems achievable based on observing others, but what do you actually want? 

3. The false binary choice: This is the belief that you have to choose between being liked or being successful, between being a team player or being ambitious, or being yourself or being taken seriously. These are false choices designed to keep you small. You don't have to choose. You can create a third option that honors all of who you are, but you have to be willing to disappoint some people in the process, and that's where most of us get stuck. We'd rather disappoint ourselves than risk someone thinking we're wanting too much. 

4. The permission pattern: This is where you wait for your manager to offer you opportunities instead of deciding what it is you want and proactively asking for it. You're waiting to be chosen, to be tapped on the shoulder, or told you are ready now. And meanwhile, those around you are simply making the case for what they want, whether anyone thinks they're ready or not. Stop waiting for permission. You can ask for what you want. The answer might be no, but at least then you'll know for sure. And honestly, you're probably going to be surprised by how often the answer is yes, once you actually make the strong case to support it. 

And here's the big one that I think trips up a lot of us: confusing the discomfort zone with the delusional zone. There's a difference between a goal that's challenging but achievable, that tips you into the discomfort zone, and a goal that's actually impossible given your constraints, that's firmly in the delusional zone. 

• Discomfort zone goals are risky and make you feel fear, uncertainty, and doubt—but they're grounded in reality. You don't know exactly how you'll achieve them, but they're not completely out of the realm of possibility. 

• Delusional zone goals are the ones where the math just doesn't work—no matter how amazing you might think you are, it's just not going to happen, yet. 

The problem is, when you're not used to operating in the discomfort zone, everything that scares you feels a wee bit delusional. So you abandon goals that are actually perfectly achievable just because they make you uncomfortable. It's important for us to learn to tell the difference. 

So, how do you actually make the shift from settling for what's probable to exploring what might be possible? How do you start making career decisions that honor what you really want instead of settling for what seems more realistic? 

Here are six practical strategies that you can implement immediately: 

1. Start with your finish line, not your starting point. Most of us have been trained to set goals by looking at where we are and then identifying what seems achievable from here. Instead, I want you to start with what you actually want, even if you have no idea how to get there. Be very specific about the end result you're looking for. And then apply this test, because if you currently have all the financial, emotional, and physical resources you need to accomplish this goal, where you can easily imagine completing it with what you have right now, it's not challenging enough. A compelling goal should make you feel like you have no idea how you're going to pull this off, but you really want to make it happen. Then, identify three major milestones that, if you achieve them, would definitely get you to your goal. Again, don't worry about how you'll hit each milestone, because your brain is going to want to spiral into all the reasons why it's impossible, and you need to shut that down. Just focus on what these major milestones are, and not how you'll reach them. This is the beginning of your roadmap. It's not detailed yet, but you're beginning to see the big steps you'll need to take to get from where you are to where you want to be.

2. Make decisions from your future self, not your current circumstances. This is a game-changer. When you're facing a decision, don't ask yourself whether you can do this. Instead, ask yourself, "What would someone who has already achieved this goal do in this situation?". Because I guarantee you, the version of you who's already a Director isn't sitting around wondering if she's qualified enough to speak up in meetings. She's not agonizing over whether to ask for what she wants. She's making decisions from a place of confidence and self-trust, and then taking action from that place. You can start being that person right now. You don't have to wait until you've achieved the goal. Start making decisions as if you've already done it, and watch how quickly your trajectory changes. 

3. Integrate all your data, not just the external stuff. You're probably really good at collecting and analyzing information, and yet you might be completely dismissing the critical internal data, which includes your intuition, your lived experience, your desires, your emotions, and your body's wisdom. Your gut might be telling you something's off about this role or these people you'd have to work with, but you ignore it because the opportunity looks good on paper. Your body is screaming at you that you're burned out, but you push through because everyone else seems to be handling this workload just fine. Your deepest desires are whispering that you want something completely different, but you shut them down because that's just not realistic. Start trusting your internal data because it's just as valid as any other information you've gathered. Actually, it's more valid because it's specific to you and your situation, whereas external data is generalized and might not apply to your unique circumstances at all. 

4. Focus on frequency, not just magnitude. Instead of saying, "I'll start asking for what I want when I'm feeling ready", commit to asking for something small every single day. Instead of telling yourself that you'll apply for a more senior role when you feel that you're qualified, commit to taking one action every day that builds toward that role. How often you show up for yourself matters more than how much you do each time. This is about building the habit of pursuing possibility instead of accepting what's more realistic. And when you focus on increasing the frequency, you take the pressure off each individual action. You don't have to hit a home run every time, you just have to do one thing that moves you forward every day. The consistency is what will create the transformation. 

5. Build your inner circle. This is critical, especially when you're pursuing something that feels slightly beyond the realm of realistic. You need people around you who see your potential, who believe in you when you can't believe in yourself, who respond with, "Of course you can!" when you share your ambitious goals. Because here's what's going to happen: you're going to have days when you can't see the path forward, when you doubt everything, when you want to retreat back to more realistic thinking where at least you know what to expect. On those days, you need to be able to look into the eyes of someone who believes in you and let them reflect back their trust in you. This isn't about surrounding yourself with only those who tell you what you want to hear. It's about surrounding yourself with people who can see what you're capable of, even when you can't. 

6. Reframe failure as a necessary part of the process. Whenever you try something new, it's not always going to go as planned. You're going to apply for roles and get rejected. You're going to ask for raises and get turned down. This is not evidence that you shouldn't have tried. This is simply data. What did you learn? What surprised you? What will you do differently next time? This helps you learn what works in your organization, with the power dynamics you're dealing with, on your path to figuring out the how. 

Don't get discouraged. Remember, you already know how to solve complex problems with incomplete data. My guess is that you do it in your technical work every day. You get the requirements, and while you don't know exactly how to build it at first, you figure it out. You try things, you test them, you learn what works and what doesn't. You iterate, you adjust, you bring in help when you need it, and eventually, it all comes together. If I had to guess, you've probably done this hundreds of times in your career already. 

So, what if you treated your career like you treat your most challenging technical projects? What if you approached your next promotion with the same experimental mindset you use when you're debugging a complex system? What if you're willing to try things, collect data, adjust your approach, and keep iterating until you get the result you want? You wouldn't give up on a technical problem after one failed attempt. You'd troubleshoot, you'd research, you'd ask for help, and then you'd try a different approach. Why are you giving up on your career goals after just one rejection? 

The women who came before you made your current position possible. Someone had to be the first. They didn't have a roadmap. They didn't know if it would work. They pursued something that seemed improbable and made it possible. 

What are you going to make possible for the women who come after you? 

Because staying stuck in realistic thinking doesn't just limit you—it limits everyone who's watching to see what's possible. When you play small, you're teaching the next generation of women engineers that they should play small, too. When you pursue possibility despite the fear, you're creating a new pattern for them to follow. 

I know this is uncomfortable. I know it would be easier if I just gave you a formula, a checklist, or a guaranteed path to follow from here to there. Possibility thinking requires you to commit to something without knowing how you'll make it happen. It requires you to tolerate uncertainty and discomfort. It requires you to trust yourself enough to believe that even if you don't know how to do it right now, you'll figure it out along the way. And honestly, that's risky and somewhat terrifying. But it's also the only way to create a career that actually reflects what you're capable of, instead of what others have historically allowed women like you to achieve. 

So, here's your challenge: identify one improbable goal, something you want but can't currently see how to achieve. Something that makes you feel scared and uncertain, and brings up a whole lot of self-doubt when you think about pursuing it. Commit to it anyway. And then, take one action this week from the perspective of someone who has already accomplished it. Just one. See what happens. See what you learn. See how it feels to pursue possibility instead of accepting only what you deem most probable. 

You might be surprised by what becomes possible when you stop limiting yourself to only what others tell you is more realistic. 

And that's it for this episode of Stop Sabotaging Your Success. Remember to download your Guide to Breaking Free From Probability Thinking at cindyesliger.com/podcast, episode two hundred and sixteen.

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.