Welcome to the Stop Sabotaging Your Success podcast, episode one hundred and sixty-four. I’m your host Cindy Esliger. This is the podcast focusing on what we can do today to take control of our careers and overcome the inevitable barriers to success that we encounter along the way. 

I’m finding that there’s a fine line between honesty and encouragement when offering career coaching. It sometimes feels like a delicate art. It’s easy to fall into the trap of trying to help by pointing out every obstacle or potential pitfall, believing we’re preparing someone for the real world. But too often, what feels like helpful realism can come across as unnecessary pessimism, deflating someone’s confidence before they even get started. The truth is, no one needs their dreams crushed prematurely. Life has a way of doing that all on its own. 

In this episode, we delve into how to best handle this opportunity we have to encourage others to explore their bold ideas while, at the same time, offering constructive insights to hopefully help them refine their path forward. In my opinion, this doesn’t mean ignoring challenges or sugarcoating reality; it’s about reframing the conversation. By replacing criticism with curiosity and shifting from ‘why it won’t work’ to ‘how it could work’, we empower others to see potential where doubt might otherwise thrive. 

Encouragement builds momentum, while prematurely applied realism tends to stop it in its tracks. Whether we’re offering advice to colleagues, mentees, or friends, choosing to validate their aspirations and explore their ideas fosters that much needed sense of possibility – one where creativity and progress can truly flourish.

This can feel a little tricky and many of us are prone to missteps, myself included. On one side, there’s the fear of giving someone false hope, setting them up for a fall. On the other, there’s the equally uncomfortable reality that crushing someone’s dreams doesn’t make us look wise, it just makes us look, well, terrible. 

So, how do we strike a balance? How do we become the kind of person who inspires others to reach for their potential without glossing over the harsh realities of life in male-dominated fields like engineering? It starts with unpacking our own tendencies and reframing how we approach these conversations.

When someone asks for your advice, they’re offering you a vulnerable moment. Maybe they’ve just decided to pursue a new role, go back to school, or finally leap into an ambitious project. They’re testing the waters with you, hoping for some validation – or at least a little less skepticism than usual. 

Here’s where it gets complicated. You have two choices: 

1. Be the person who listens, encourages, and validates their potential. 
2. Be the person who dumps a bucket of cold water on their dreams because you’ve been there and you know better.

The truth is, they’re not asking you to predict the future or sign off on a guarantee of success. What they need is someone to hear their excitement without immediately shutting it down. The ‘how will you actually pull this off?’ conversation can come later. 

I don’t think anyone sets out to crush dreams on purpose. Well, most people don’t, but it happens anyway. Maybe you’ve done it yourself, thinking you were being helpful by pointing out all the potential pitfalls. “You know that field is really competitive”. Or, “Don’t get your hopes up – it’s harder than it looks”. 

Why do we do this? It could be for a variety of reasons like: 

• Fear of false hope: We convince ourselves we’re protecting someone from disappointment by being realistic. 
• Our own insecurities: Sometimes their ambition shines a light on what we didn’t achieve, or what we’re afraid we still can’t do.
• Cultural conditioning: Professional environments often reward skepticism over optimism, making negativity feel like the safer route. 
• Trying to prepare them: We think we’re being noble by warning them of every challenge, as if knowing what’s coming will make the struggle any easier. And yet, I’m not sure it does. 

While these motives might feel justifiable in the moment, the result is often the same: we deflate their confidence, dim their enthusiasm, and send them away questioning whether they’re capable of the very thing they were excited about just five minutes ago. Not exactly a job well done, I don’t think. 

So, here’s the thing about dreams: they’re supposed to be bigger than what we’ve already achieved. Telling someone all the reasons why their idea won’t work might feel like a public service, but it’s usually just a waste of energy. Here are three possible reasons why: 

1. They’ll figure it out for themselves: If it truly can’t be done, life will show them soon enough.
2. You might be wrong: The world is constantly changing, industries evolve, and what seemed impossible yesterday could very well be possible tomorrow. 
3. You’re robbing them of growth: Struggling, failing, and figuring it out is all part of the process. Skipping straight to the ‘no’ denies them the chance to prove their resilience and realize their potential. 

Think back to when you were starting out. You didn’t know what you didn’t know, and honestly, being a bit naive probably worked in your favor. You took risks because you didn’t realize how hard things would actually be, and that’s how you grew. I know I did. I really didn’t know what I was getting into in the beginning with being a woman in engineering. Would I have wanted someone to tell me it was impossible before I even tried? I really don’t think so. Honestly, I’m not sure I would have listened. At the time, I was more the type to see that as a challenge to prove them wrong. 

Finding a balance between honesty and encouragement is definitely where the nuance comes in. Honesty doesn’t have to be synonymous with negativity, and encouragement doesn’t mean sugarcoating everything. The trick is finding that balance that empowers rather than deflates. 

Realism isn’t inherently bad. There’s a time and a place for a grounded discussion about the challenges, risks, and practical considerations. The key is knowing when to have that conversation and how to frame it constructively, without squashing their enthusiasm. 

When someone shares an idea or ambition, they’re often in the early, fragile stages of excitement. This is not the time to unleash a list of potential obstacles. Save the realism for when they’ve moved into planning mode or are actively seeking your input. 

Instead of immediately pointing out why something won’t work, perhaps it’s worth starting with a little curiosity by asking a few questions, like: 

• What excites you most about this?
• Have you thought about how you’ll approach the possible challenges? 
• What would success look like for you? 

These questions might invite a little reflection without shutting them down completely. They also show that you’re interested in helping them figure it out, not just predicting their downfall. 

Another option is instead of saying, “That’ll never work”, try framing honesty as a bit of constructive insight. Try saying: 

• Here’s what I learned when I faced a similar situation.
• This part might be tricky, but here’s how I’d approach it. 
• It’s not easy, but it’s doable if you focus on this aspect first. 

This approach acknowledges the challenges without shutting them down. Honesty presented as a guidepost feels much more supportive and not so dismissive. 

No one can predict the future accurately. So, if you’re going to try to make a prediction, why not choose a positive one? We’re all pretty good at getting to the worst-case scenario without any help, so it might be refreshing to try to foster a belief in possibility, if only for a little while.

I’d really like to be the kind of person who empowers others to pursue their bold ideas, so here are five strategies I try to keep in mind as I’m coaching others: 

1. Be the ‘yes’ in a sea of ‘no’s’: Most industries, including engineering, have no shortage of naysayers. My encouragement could be the one thing that keeps someone moving forward in pursuit of their dreams. 
2. Flip the script: Instead of thinking, “There are so many reasons why this won’t work”, I try asking, “What would you need to have happen for this to work for you?”. This small shift can open the door for them to see new ideas and solutions. 
3. Normalize dreaming big: At some point, I started to think that having a lot of ambition was a liability for me. But, I don’t think that way anymore – now I believe that it is a superpower. I think there’s a real benefit to dreaming bigger, so I encourage others to do the same. 
4. Know when to step back: It’s not up to me to evaluate every idea that is proposed. Sometimes, the best thing I can do is to say to someone, “That sounds exciting – go for it!” and leave it at that. 
5. Lead by example: When I pursue my own bold ideas, I can show others it’s possible. My actions can inspire far more than my words ever will. 

I don’t want to be the dream crusher, the bearer of bad news, or the unwelcome reality check. My intent is to be helpful, maybe even provide some wisdom, steering someone away from the potential pitfalls. But, I’m realizing that my version of ‘help’ can sometimes be less of a lifesaver and more of an anchor dragging down someone else’s dreams.

So, let’s explore how I’m trying to balance honesty with encouragement. Because, shifting my mindset from finding all the reasons ‘why it won’t work’ to considering ‘how it could work’ was a key point in my own healing process. 

Dream crushing comes in many forms, some subtle, others painfully blatant. Perhaps you’ve heard some of these over the years, or maybe even coming out of your own mouth, as the well-meaning ‘reality check’ disguised as advice:

• That industry is impossible for women to break into.
• It’s still an old boys’ club.
• Have you considered a backup plan?

While these comments might feel like practical guidance, they usually land like a lead balloon. Instead of helping someone prepare, they often leave them questioning whether their ambitions were ridiculous to begin with. The fallout? Deflated confidence, diminished motivation, and a potential career trajectory stalled before it even starts.

I’ve also learned that crushing someone’s dreams prematurely doesn’t actually protect them – it just undermines their belief in what’s possible. It can be tempting to want to prepare them for what lies ahead, but it’s often unnecessary. Most people already know the risks. If someone is pursuing a big goal, they’re likely aware of the challenges they’re bound to face. It’s rarely helpful because, unless you’re offering actionable advice, pointing out obstacles just adds unnecessary negativity. And, beware that it often puts you in the line of fire because people tend to resent the bearer of bad news, even if your intentions are good. 

Sometimes, though, delivering bad news is unavoidable, like when you’re asked a direct question, or it’s genuinely important to provide clarity. Don’t get me wrong, I don’t advocate trying to pretend the issues don’t exist. But, more often than not, you can sidestep the doom and gloom narrative by redirecting the conversation. Instead of focusing on why something might fail, ask them to share more about their vision or try to turn their attention to potential solutions. 

If someone asks for your opinion, emphasize what’s possible before addressing any concerns. For example, “This sounds like an incredible opportunity for you. What’s your plan for navigating the competitive aspects?”. When in doubt, try to remain neutral. A perfectly valid response could be, “That’s an interesting path – let me know how it unfolds”. 

Recognizing my default to criticism or dismissal was the first step in breaking this habit. The second step was actively choosing curiosity over cynicism. I had to remind myself to pause before responding. When someone shared an idea with me, I had to resist the urge to evaluate it immediately. Instead, I started asking myself, “Am I being helpful or am I just being negative?”.

When you shift from ‘why it won’t work’ to focusing more on ‘how it could work’, you do more than support someone’s dreams – you empower them to think creatively and act boldly. It’s not just about them; fostering a belief in possibility benefits you, too. 

People are more likely to involve you in exciting projects when you’re known as someone who believes in potential. Seeing the possibilities instead of the limitations opens doors to new ideas and potential opportunities. Encouraging others isn’t just good for them – it’s a boost to your own morale, too. 

With all that I’ve endured over the years, I had become pretty jaded. I had to remind myself that not every workplace is toxic, and not every industry is a battleground. Sure, some environments are rough – where you seem to have to fight for recognition and navigate office politics to get ahead. I was hoping that a lot of the old attitudes would have retired by now. And yet, the next generation seems to be reviving them. But, to paint all workplaces or industries with a broad brush of awfulness does a disservice to those dreaming of a better professional future. 

When providing career coaching or advice of any kind, it’s important to leave room for possibility. Sure, they might land in a challenging environment, but they could just as easily find a place that’s supportive, innovative, and encourages growth. Instead of warning them about the potential pitfalls of their choice, I now try to reframe the potential challenges by saying something like: 

• There are tough places, but there are also great ones. Let’s focus on how you can position yourself to find the right fit for you.
• Every workplace has its quirks, but they are also where you have the potential to learn the most. What do you think you’ll need to thrive where you are?

Encouragement isn’t about denying the challenges – it’s about reminding us that there’s more to the story. 

If you find yourself dreading these conversations because you don’t want to sugarcoat the truth, here are four strategies to make it easier on you to answer honestly, while also making it easier on them to take it all in: 

1. Validate First, Prepare Later: When someone comes to you with their dreams, lead with an equal dose of enthusiasm, “That’s an exciting idea. Tell me more!”. This doesn’t mean you ignore the challenges entirely; it means saving them for when they’re further along in the process and more ready to heed your warnings. 
2. Frame Feedback Constructively: Instead of, “That’ll never work”, try, “What do you think it would take to make this happen?”. This shifts the conversation from dismissal to problem-solving, fostering their belief in themselves and their ability to navigate obstacles.
3. Encourage Self-Reflection: Help them clarify their own wants and needs by saying things like: “What resources or support would make this easier for you?” or, “What challenges are you anticipating and how might you address them?”. By encouraging reflection, you empower them to take ownership of their career path. 
4. Resist the Urge to Overprepare Them: Some of us can’t help but try to prepare people for every possible hurdle, but overloading someone with warnings and contingency plans can often do more harm than good. Trust that they will learn and adapt along the way. 

I have to say that curiosity beats criticism every time. When faced with someone’s aspirational plans, your gut reaction might be skepticism – especially if their plan seems unrealistic. But, criticism shuts down possibility, while curiosity can open the door to exploration and experimentation. So, try to ask thoughtful questions, avoid snap judgments, and encourage more brainstorming. By engaging with their idea instead of rejecting it immediately, you create space for them to refine their vision and gain confidence in their ability to pursue it. 

Encouragement isn’t just about making someone feel good in the moment – it creates a ripple effect that spreads far beyond a single conversation. When someone believes in themselves, it shows in their actions and inspires others. A positive mindset encourages people to think creatively and take bold steps. Encouragement fosters trust and openness, making people more willing to seek advice and share ideas. 

The professional world needs more dreamers and fewer critics. Dreamers are the ones who push boundaries, disrupt industries, and create solutions to problems the rest of us didn’t even see coming. By fostering a belief in possibility – both in ourselves and others – we create a professional world where progress thrives. 

Provide encouragement by asking open-ended questions to empower them to reflect, refine, and take ownership of their ambitions. This shift not only avoids the pitfalls of criticism or dream-crushing, but also creates a collaborative space where possibilities can grow organically. 

This approach also relieves you of the pressure to have all the answers. It positions you as more of a supportive guide. This can create a conversation that fosters belief in possibility while still leaving room for practical insights, when they are ready. Encouragement doesn’t mean ignoring challenges; it means helping someone discover their own capacity to overcome them. This simple shift can transform how we approach these types of conversations and inspire others to pursue meaningful progress with confidence. 

What I’ve learned is that navigating the fine line between honesty and encouragement is less about getting it right and more about staying mindful of how my words land. When someone shares their dreams with me, they’re trusting me to handle them with care. I’ve learned the importance of being curious, supportive, and letting life reveal the obstacles in due time – because fostering possibility isn’t just good for them, it’s good for all of us. 

So, the next time someone comes to you with a bold career idea, resist the urge to criticize or over prepare them for every possible hurdle. Instead, choose curiosity, offer encouragement, and trust them to figure out the rest. 

And that’s it for this episode of Stop Sabotaging Your Success. Remember to download your Guide to Empowering Possibilities at cindyesliger.com/podcast, episode one hundred and sixty-four. 

Thank you to our producer, Alex Hochhausen and everyone at Astronomic Audio. Get in touch, I’m on Instagram @cindyesliger. My email address is info@cindyesliger.com. 

If you enjoy listening to this podcast, you have to come check out The Confidence Collective. It’s my monthly coaching program where we dig a little deeper into what’s holding you back in your career and we find the workarounds. We help you overcome the barriers and create the career you want. Join me over at cindyesliger.com/join. I’d love to have you join me in The Confidence Collective.  

Until next week, I’m Cindy Esliger. Thanks for listening.