Why Your Dreams Aren't Big Enough (And What It's Costing You)

Have you ever set a goal, worked toward it, achieved it—and then stood at the finish line wondering, is this it?

Maybe you aimed for a director role and got it. Maybe you finally hit the salary number you had in your head for years. And yet, there's something quietly unsatisfying about it. Not because it wasn't real. But because somewhere along the way, you made your dream small enough to feel safe. And safe, it turns out, doesn't always feel like enough.

There's a reason for that. And there's something worth doing about it.

The Running Lesson That Changed How I Think About Goals

When I started running, a 5k felt impossible. I couldn't imagine running 10k. It seemed like something other people did—people with a different body, more time, more discipline than me.

When I started learning from experienced runners, every single one of them said the same thing: if your goal is 10k, train for 13k. Don't practice running the distance you want to finish. Practice running further than you need to.

The reason stuck with me. If you can run 13k, then 10k becomes your floor, not your ceiling. It means that on the days when everything is off—it's too hot, the course has more hills than you expected, you didn't sleep well, your legs feel heavy—you still finish. Because you've built capacity beyond what the moment demands.

Your career works the same way.

If you only aim for exactly what you want, you have no buffer. Every obstacle, every setback, every unexpected challenge threatens the goal. But when you dream bigger than your target—when you build toward something beyond what you think you need—you create reserves. Resilience. Room to still succeed even when conditions aren't perfect.

And conditions are never perfect.

Dreaming Big Isn't About the Title or the Money

Let's be clear about something. When I talk about dreaming big, I'm not talking about chasing status for its own sake. I'm not talking about a specific title or a number in your bank account—unless that's genuinely what matters to you.

Dreaming big is about designing a life that feels like yours.

It's about work that energizes you instead of draining you. It's about relationships, time, creativity, and impact—not just output. It's about waking up on a Monday and feeling something other than dread. It's about building a career that reflects the full range of who you are, not just the most practical version of yourself.

That's what's at stake when you don't dream big enough. Not just a missed promotion. A missed life.

When you consistently undershoot your own aspirations, you end up building someone else's vision instead of your own. You optimize for "good enough" when "remarkable" was always available to you. You settle into roles that fit, rather than roles that stretch you toward what you actually want. Over time, that gap between where you are and where you know you could be becomes a quiet frustration that's hard to name—but impossible to ignore.

Why Women Leaders Resist Dreaming Big

In my work coaching high-achieving women, I've noticed that the resistance to big dreams is rarely about capability. It's almost always about something else.

1. Guilt: Dreaming big feels greedy.

Many women have been raised to prioritize others—their families, their teams, their organizations. So when a bold desire rises up ("I want to run this company," "I want to work from anywhere," "I want to be known for this work")—it can immediately be followed by a pang of guilt. Who am I to want so much? Isn't that selfish?

It isn't. Wanting a bigger, more meaningful life doesn't take anything away from anyone. In fact, the more you build a life aligned with what you truly value, the more you have to give—with clarity, energy, and intention rather than quiet resentment.

2. Fear of what success demands.

This one surprises people, but it's one of the most common patterns I see. Many women are not afraid of failing. They're afraid of succeeding.

Because success brings visibility. It brings attention, expectation, more responsibility—professionally and socially. It means stepping fully into your power in a world that doesn't always make that easy for women. And so the subconscious mind does something clever: it keeps your dreams modest enough that you never have to find out what happens if you actually get there.

3. Fear of losing yourself.

Underneath the ambition, there's often a quieter worry: Will I still be me? Will my friendships change? Will people treat me differently? Will I become someone my family doesn't recognize?

This isn't just about workload or responsibility. It's about identity. It's about belonging. Stepping into a bigger, bolder version of your career can feel like stepping away from the version of yourself that the people you love have always known. And that's a loss many women aren't sure they're willing to risk.

How to Actually Dream Bigger

Dreaming big is a practice. And like any practice, it starts with concrete steps.

Step 1: Allow yourself to want what you actually want—without thinking about how.

Start with the wildest, boldest version of your dream. Not the responsible one. Not the one you'd say out loud in a meeting. The one that makes you feel a little exposed just thinking it. Write it down. Don't edit it. Don't justify it. Just let it exist on the page.

Step 2: 10x it.

Whatever you just wrote—make it bigger. Not because you're committing to it, but because reaching for 10x forces your brain out of its habitual limits. You start to see possibilities that "realistic" thinking actively hides from you. This is exploration, not obligation. Let yourself roam.

Step 3: Build your roadmap.

Now, come back to what's genuinely yours. What resonated in all of that? What felt true, even if it's still a little scary? From everything you've been exploring, identify the top three things you want to set as goals for the next two years—and what needs to happen to get there. These become your direction. Not a fantasy. A plan.

Final Thought

You've already proven you can set a goal and reach it. You've already proven you can do hard things. The question worth sitting with now isn't can I do this? It's what am I not letting myself want?

Dreaming big is not reckless. It's not naive. And it's certainly not greedy. It is the courageous act of deciding that your life—not just your career, but your whole, actual life—is worth designing with intention.

Train for 13k. Run your 10k with ease. And then dream bigger again.

This dreaming-big exercise is one we do together in the Women Leaders Club—a space where accomplished women support each other in building careers and lives they're genuinely excited about. If it sounds interesting, come check it out.

7 Pillars of Career Success for Women: Where Do You Stand?

Over the years, I’ve coached many women through their leadership journeys. These women are smart, capable, and deeply committed to their growth. Despite their differences in background and industry, I’ve noticed the same core pillars that determine how fulfilled and successful they feel in their careers.

I’ve summarized these seven pillars here and created a quick self-assessment to help you measure where you are right now. Think of it not as a test, but as a mirror, a way to see what’s working well and what might need more attention.

Rate yourself for each pillar:

1️⃣ = Needs your attention | 2️⃣ = Making progress | 3️⃣ = Thriving

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1. Define Your Own Success Plan

• 1️⃣: You’re chasing what others expect of you, not what truly fulfills you.
• 2️⃣: You have some direction, but your path feels fuzzy or reactive.
• 3️⃣: You know what success means to you and intentionally align your work and growth around it.

2. Visibility & Self-Advocacy

• 1️⃣: You do excellent work but rarely talk about it. You hope it speaks for itself.
• 2️⃣: You share results occasionally but not strategically.
• 3️⃣: You consistently communicate your impact and let key people see your passion and strengths.

3. Networking & Support System

• 1️⃣: You avoid networking or only reach out when you need help.
• 2️⃣: You stay in touch with a few people but rarely invest in deeper connections.
• 3️⃣: You actively build a strong circle of mentors, sponsors, and allies who support one another’s growth.

4. Prioritization & Boundaries

• 1️⃣: You say yes to almost everything and often feel overwhelmed or resentful.
• 2️⃣: You’ve started setting limits but still struggle to protect your focus.
• 3️⃣: You’re clear about what matters, say no with confidence, and create space for meaningful work.

5. Time & Energy Management

• 1️⃣: You’re constantly busy, reactive, and running on empty.
• 2️⃣: You manage your tasks but often feel drained or scattered.
• 3️⃣: You design your days intentionally, matching energy to priorities and building in rest and renewal.

6. Confidence & Self-Belief

• 1️⃣: You often second-guess yourself or hold back from opportunities.
• 2️⃣: You push through fear but still question whether you’re “ready.”
• 3️⃣: You trust your experience, own your strengths, and take bold action from self-belief.

7. Authentic Leadership

• 1️⃣: You try to lead the “right” way, how others expect you to.
• 2️⃣: You’re partly authentic but still worry about being judged.
• 3️⃣: You lead from your values and strengths, creating trust, clarity, and genuine connection.

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Scoring

Add up your points (minimum 7, maximum 21):

17–21: 🌟 You’re Thriving.
You lead with purpose and confidence. Keep growing, and share your wisdom with others.

13–16: 🌿 You’re Growing Strong.

You’ve built a great foundation! With a few focused shifts, you’ll feel unstoppable.

9–12: 🪴 You’re Ready for a Reset.

You’re doing many things right but may feel stretched or unfulfilled. It’s time to realign with what truly matters.

7–8: 🌱 You’re at a Turning Point.

You’ve outgrown your current way of working. Start small: one new boundary, one bold conversation, one act of self-belief. Small shift can spark big change.

Final Thought

Success isn’t a straight line. It’s an ongoing alignment between who you are and what you do.

The more your career reflects your values, energy, and authentic self, the more natural your confidence and impact become.

Take note of your lowest-scoring pillar. That’s not a weakness, it’s your next opportunity for growth.

If this reflection resonated with you and you’re ready to go deeper, join me and a group of accomplished women in the Women Leaders Club where we turn awareness into action and help you create the career and life you truly want.

Create Your Own Leadership Path: A Conversation with Kaitlin Liston

I had the pleasure of speaking with Kaitlin Liston for the Kim Coaching Group Interview Series, and I’m so excited to share her story and insights.

Kaitlin is a demand generation manager at RingCentral who has built an impressive and intentional career in tech marketing. She started at a small startup while still in college, held almost every type of marketing role you can imagine, and along the way co-founded a nonprofit and helped more than 100 students with their college applications. But what stands out most is how she consistently created leadership opportunities for herself and brought others along with her.

Here are some of the key takeaways from our conversation, in Kaitlin’s own words, with reflections and examples you can use right away.

Rethink What Leadership Means

“Being a leader is more leading by example… All of the best leaders that I’ve worked under have enabled us to be our best selves. It’s more of a collaboration, allowing for an environment where everyone feels like they have the abilities to do their best.”

Kaitlin grew up playing sports and described how the best team captains were the ones who led by how they showed up, not by barking orders. That same approach shaped her view of leadership at work. She’s not waiting to be given authority, she shows up with it.

We talked about how people often tune out during all-hands meetings or skip team calls because they feel too busy. But leadership means showing up anyway, asking questions, and treating those meetings like they matter, because they do. That’s where you get context, build trust, and show you care about more than just your own tasks.

Decide What Kind of Leader You Want to Be

“I love this quote that you are the sum of the five people closest to you. I started thinking about the kind of people I wanted around me and the kind of leader I wanted to be to them.”

Kaitlin discovered her leadership style by observing others. Some made people feel empowered. Some didn’t. That helped her reflect on what kind of leader she didn’t want to be and she built her own version from there.

You don’t have to pick from the leadership styles already out there. You get to define your own. Kaitlin leads by building trust, giving credit, and making people feel like they belong. That’s what people remember and follow.

Ask yourself: who are the people you admire most in your life and work? What do they do that makes you feel seen and supported? Start modeling those behaviors.

Build a Real Network, Not Just a List of Contacts

“Your network is your net worth.”

Kaitlin believes in building meaningful relationships that go beyond LinkedIn connections. When she joins a new company, she asks her manager to introduce her to 10 people across the org. She reaches out to new hires. She gets curious about what people do and who they are.

We talked about how real networking isn’t about keeping score, it’s about being generous. When you offer help without expecting anything back, you build reputation and trust. And over time, those people remember what you’re great at and want to work with you again.

If you’re wondering how to start, Kaitlin’s advice is simple: send a message that shows genuine interest. Tell someone what you admire about their work, ask one thoughtful question, and offer something specific you can help with.

Create the Opportunities You Want to See

“I didn’t wait for a promotion. I started leading book clubs, organizing events, and building community.”

At RingCentral, Kaitlin helped launch WISE, the Women in SaaS Empowerment group. She began by volunteering to run small programs like book clubs and lunch-and-learns. Eventually, she became the event chair, helping others grow their skills and confidence too.

Outside of work, she co-founded a nonprofit during the pandemic and continues to support students through college counseling. All of this started with small decisions to raise her hand.

We talked about how creating leadership opportunities doesn’t have to be big. You can volunteer to lead a 30-minute discussion. You can offer to review someone’s document. You can step in on something that fits your time and energy, and still have an impact.

Leadership grows with every action. Start where you are.

Think Like a Leader Before Anyone Calls You One

“When something doesn’t feel right, I don’t just let it go, I try to be part of the solution.”

Kaitlin once noticed something in the marketing org that didn’t sit right with her. She was a manager at the time, and it wasn’t her responsibility to weigh in on org-wide strategy, but she cared deeply about where the team was headed. So she sent a thoughtful Slack message to her VP, sharing her perspective.

Leadership often starts like this, not with a formal role, but with a mindset. Leaders treat everything like it’s their problem. When you care enough to speak up, offer ideas, or take initiative, even when it’s not in your job description, you’re already leading.

What’s something that’s been bothering you at work? Instead of venting about it, what would it look like to take action? You don’t have to fix everything. But you can start the conversation.

What’s One Thing You’ll Try?

Kaitlin’s story is full of small, intentional actions that added up to real leadership. She didn’t wait to be chosen. She chose herself.

What’s one thing from her story that you’ll try this month?

Pick something simple. Reach out to someone new. Offer to help. Show up differently.

And if you’re ready to take your leadership to the next level, check out the Women Leaders Club. We go deep into topics like these and support each other through every stretch and leap.

Why Your First 90 Days Should Begin at the End

The first 90 days at a new job are high-stakes—and not just for the reasons most people think.

You’re new, you’re being evaluated, and there’s pressure to ramp up quickly. Most people focus on learning how things are done, delivering results, and proving they were a good hire. And yes, all of that matters.

But there’s another reason the first 90 days are important:

They set the course for the story you’ll tell when you leave.

When Listening Too Well Leads You Off Course

Let me explain what I mean.

When I started one role, my new manager said, “This is how we do things here. Just focus on this for now.” So I did. I followed his advice exactly—and it quietly put me on a path that didn’t align with where I wanted to grow. By the time I realized it, I had to work really hard to change course and steer toward the direction I actually wanted.

I see the same thing happen with my clients.

Take Julie. She joined a company and quickly noticed that many things weren’t working—some were even quite bad. But she didn’t say anything because she was new. She didn’t want to come off as someone who thought she knew better. Two years later, she came to me and said, “I want to speak up and make changes—but how do I suddenly start saying something now? I’ve been fine with it until now—won’t it seem weird?”

She was stuck—not because she lacked clarity, but because she hadn’t anchored herself in a bigger purpose from the beginning.

When You Push Too Soon Without Context

On the other end of the spectrum, I’ve seen what happens when someone tries to lead change too quickly—before earning trust or understanding the full picture.

A new VP of Marketing joined a small company I worked with. Just one month in, she stood in front of the entire marketing team and presented—point by point—everything she thought they had been doing wrong. Right in front of the people who had been doing the work.

Naturally, the team pushed back. They admitted things weren’t perfect, but they had made tough trade-offs with limited resources. The VP agreed with many of their points—but the way she delivered her critique completely alienated the team.

She wasn’t wrong about the problems. But she failed to understand why things were the way there were—and that cost her trust and influence.

So How Do You Avoid Both Extremes?

You start by thinking about the day you’ll leave the role.

It might sound strange—but when you imagine the story you’ll tell at the end of this chapter, you gain clarity from the start. What will you have accomplished? Why did it matter? What will this role have prepared you for?

This mindset shift helps you lead with intention, especially if you’re in a leadership role. Your job isn’t just to maintain the status quo—it’s to create an environment where your team and company can succeed, even after you’ve moved on.

If you see room for improvement and don’t act, you’re not doing your job.

But if you try to change everything without understanding the context, you won’t get far either.

A Better Way to Start Strong

Here are three things I recommend to anyone starting a new role:

1. Observe and ask a lot of questions. You’re new—this is your best window to ask why things are the way they are. People are more open to explaining, and you can raise ideas in a way that’s curious rather than critical.
2. Start with your end story. Imagine the impact you want to make and what you’ll be proud to share when you leave. Let that vision guide your priorities and decisions.
3. Make a plan. Based on that vision, map out how you’ll create that impact. Maybe it means introducing ideas gently in meetings, building alliances behind the scenes, or making a bold change right away. The right approach will depend on the context—but having a plan helps you lead with intention.

These three steps can help you ramp up without losing sight of why you’re really there.

What’s the Story You Want to Tell?

Yes, learn how things work. Yes, deliver results quickly. But also remember: you’re not just there to keep things running. You’re there to make things better.

What’s the story you want to tell when you look back on this role?

Want More Support Like This?

Want support with finding the right balance, building the best plan, and following through? This is exactly the kind of shift we work on in the Women Leaders Club—a coaching program for women who want to lead with clarity and own their impact. Join us and build the career you’re meant to have.

5 Behaviors That Set Future Leaders Apart

As a people manager, there are certain individuals I naturally pay more attention to. They may not be ready for promotion yet, but I can clearly see them as future leaders. They don’t just do their jobs—they do them in a way that makes my life easier.

I hear similar stories during layoffs. Some individuals are the ones leaders fight to keep at any cost. On the surface, they don’t seem much different from their peers, and people often wonder, Why them?

These are the people who not only excel at their work but also anticipate what I need—sometimes even before I ask. They get things done faster than most. They don’t just focus on their own tasks; they engage in broader discussions, form opinions, and share them confidently. They understand how different teams fit together and are respected across functions. They show up to larger meetings like all-hands, stay engaged, and when asked, contribute meaningful insights.

I’ve noticed five common behaviors among them. Each one seems small on its own, but together, they create a powerful impact.

1. Building Connections

When they join a new team, they don’t just settle in—they actively seek out key connections. They meet people not only in their immediate team but across different functions, understanding their challenges and finding ways to help. They build relationships at all levels, from new hires to executives, gaining a broader view of how the company operates and where they can add value.

2. Creating Leadership Opportunities

They step into leadership roles—whether within the company or beyond. If no opportunities exist, they create their own, organizing book clubs, lunch-and-learn sessions, or casual networking events. These don’t require much effort but provide exposure to new people, spark valuable conversations, and establish them as leaders.

Even when they’re too busy to organize something, they contribute in smaller ways—offering feedback on strategy documents, volunteering for projects, or simply showing up with a helpful attitude. Leadership isn’t about a title; it’s about taking initiative.

3. Be Present for the Team

Most people tune out or multitask during all-hands meetings, seeing them as unproductive. These individuals think differently. They show up, pay attention, and even if they don’t speak, they stay engaged. When called on, they respond with thoughtful insights.

This not only helps them stay aligned with leadership’s priorities but also signals that they care about the organization as a whole—not just their personal tasks. Over time, this visibility makes a difference.

4. Lead with Curiosity

At some point, you’ll encounter people who don’t understand your work or even challenge it. It’s easy to get defensive and think, They should know this already. But these individuals take a different approach—they lead with curiosity.

Instead of reacting, they ask questions and seek to understand. This small mindset shift changes everything. Instead of being seen as difficult, they’re recognized as experts who bring value, as team players others want to collaborate with. What could have been a blocker turns into an opportunity for influence—and sometimes, a future sponsor.

5. Thinking Like an Owner

This mindset ties everything together. These individuals never say, That’s not my job. Instead, they take ownership of problems, big or small.

They think about challenges from a leadership perspective—If I were in charge, how would I handle this? When they see leaders make different decisions, they ask thoughtful questions and share their perspective. This does two things: it helps them understand leadership’s thought process (and any missing context), and it makes them memorable to senior leaders.

Leaders appreciate those who ask smart questions and push for better solutions. Over time, these interactions sharpen their decision-making skills and prepare them to lead at higher levels.

What about you?

Which of these five behaviors resonates most with you? Where do you see the biggest opportunity for growth? What questions do you have? Email me—I’d love to hear your thoughts.

And if you want to develop these skills alongside other women leaders, join WLC (Women Leaders Club).