I Became a Director at 29—Here’s What No One Tells You About Being Effective

I became a Director at the age of 29.

On paper that might sound like a straightforward career trajectory—like I followed some well-planned path to leadership.

But in reality?

I spent six years figuring it out—failing fast, switching lanes, and building the foundation I needed without even realizing it at the time.

I started as a media assistant—a role that wasn’t quite right for me.

Then came grad school, but I wasn’t sure where it would take me.

After grad school I tried working for myself—for a year, I convinced myself I was going to be the next jewelry mogul. Spoiler alert: I was not. That business failed spectacularly. But in the process, I learned how to pitch, how to market, and how to bet on myself—even when it didn’t pan out.

Then I spent six months managing digital media at a nonprofit. There, I also had to email my boss every single time I left my desk to go to the restroom. Her rules, not mine. And…that’s why I only stayed for six months. 😭

After that, I landed at a charter school network, where I joined as an Associate Director.

I felt like I was back on track. My meandering path had finally led me to where my peers were.

Then after a year and a half, I did something crazy.

I left. I left my title behind. I pivoted industries. I took a more junior role.

It felt like I had finally caught up only to turn around and willingly start from the bottom again.

I felt equal parts excited and terrified.

What if this was a mistake? What if I had just thrown away all my progress?

But deep down, I knew it was the right decision for me.

I joined my new company as a Program Producer. Not only was I starting over, but I was suddenly in charge of the company’s two most technical offerings—with zero technical experience.

I could’ve flailed. I could’ve let imposter syndrome eat me alive and that would’ve been understandable.

But instead, I did the only thing I knew how to do: I mastered it.

And you know what? Mastery opens doors.

My first promotion came just six months later.

And a year after that? I earned the title of Director.

I was 29.

The transition that no one tells you about from expert to leadership novice, overnight

Previously, I was in rooms where I was decisive, commanding, and sure footed. Where I was confident that I knew the right path forward, where I felt comfortable amongst my peers.

My new title came with expectations.

I was sitting in meetings with seasoned leaders who had decades of experience and suddenly, I felt like I couldn’t measure up.

Yes, I worked damn hard to earn my spot. But I felt like I had no idea how to be a “leader”. So, I made myself small.

I focused on things like dressing “older” to look more professional.

I deleted my graduation years off of LinkedIn, because I didn’t want anyone to know how young I was.

I held back in meetings, afraid of saying something wrong.

I worked twice as hard as everyone else to prove I belonged in the room.

But here’s what I learned: brilliance doesn’t come from age or experience—it comes from persistence.

When you climb quickly, you assume that once you prove yourself, things will just start happening. That your ideas will be implemented, that people will listen the first time, that change will come easily.

But real leadership? It’s not about proving yourself once. It’s about proving yourself over and over again. That’s the job.

If you’re a high achiever, you’re used to hearing something once and getting it.

But in leadership, the people around you don’t work like that. There’s an old marketing adage that consumers need to hear things 5-7 times before it sticks.

Let that sink in.

Now to be clear, it’s been proven that those exact numbers are somewhat arbitrary, but in my experience saying something one time in the workplace isn’t nearly enough. So 5-7 times illustrates the point that repetition is necessary.

So what this means for you is:

• You don’t just say something once in a meeting and assume people get it. You reinforce it—repeatedly.

• You don’t suggest an idea, hear "no" once, and drop it. You refine it, reposition it, and bring it up again.

• You don’t wait for the system to work in your favor. You work the system—until you get what you need.

The most effective leaders aren’t just brilliant. They’re relentless.

Here are my top 3 lessons no one tells you when you climb the ranks quickly as a young leader. My advice isn’t just based on my own leadership journey, it’s shaped by 500+ hours coaching high achievers in the past year alone. I’ve seen firsthand what actually moves the needle.

You’ll want to bookmark this post.

Lesson 1: stop waiting—start reinforcing

One of the biggest mistakes young leaders make is waiting for their ideas to be recognized instead of actively reinforcing them. I know this all too well, I did it myself. And, you guessed it, it comes up in my coaching all the time. I’ll say it again—people need to hear something 5-7 times before it sticks.

Think of leadership like marketing.

People don’t buy a product the first time they see it. It takes repetition. Your ideas work the same way—you need to repeat them, refine them, and make them stick.

Let’s get tactical - the power of repetition in self advocacy:

• Track your ideas: Every time you introduce a new idea or initiative, log it. Keep a note of how you framed it, who you spoke to, and what the response was.

• Follow up strategically: If your idea didn’t gain traction, bring it up again in a new way. Find a different angle, tie it to a pressing business priority, or loop in key stakeholders who can reinforce it.

• Get visible: Post-meeting, follow up with an email. Ask to put your initiative on the next agenda. Bring in data to strengthen your point. Keep pushing.

Check in with yourself:

• Are you repeating key ideas across multiple conversations?

• Are you refining your messaging to match your audience?

• If you’ve done the above, are you gaining more traction over time?

Think of it this way, you’re not being ignored. You’re just not being heard yet.

Lesson 2: confidence is a practice, not a feeling

After 500+ hours coaching high achievers, one thing is clear: confidence isn’t a feeling, it’s a habit. You don’t need to feel confident to act with confidence. And in leadership, the most confident people aren’t the loudest or the flashiest—they’re the ones who keep showing up, even after setbacks.

Let’s get tactical - how to show up as a self assured leader:

• Own your expertise. At the end of each week, write down three moments where you provided value in meetings, during problem-solving sessions, or contributed to decision-making. If you can’t list three, you may not have been vocal enough.

• Speak before you’re ready. Challenge yourself to voice your perspective in at least one meeting per week—especially if it makes you uncomfortable.

• Reframe doubt. If you find yourself hesitating to speak up, ask yourself: What would I do if I were 100% sure of myself? Then do that.

Check in with yourself:

• Are you contributing in meetings without second-guessing yourself?

• Are you reinforcing your ideas even when met with resistance?

• And if you’re doing the above, are you seeing a shift in how people respond to you over time?

Confidence isn’t a personality trait. It’s a habit. Build it.

Lesson 3: own your brilliance—then be relentless about it

The biggest shift for me was realizing I didn’t have to copy anyone else’s leadership style.

My strengths—strategy, empathy, and execution—were enough. Here’s something I tell my clients all the time. Being a leader doesn’t have to look like wearing a power suit or being commanding like [insert whatever male corporate leader figure from pop culture in the last 20 years]. It just doesn’t. Your job is to be effective and to exude confidence.

Knowing your strengths isn’t enough. You have to use them—relentlessly.

Let’s get tactical - how to make sure people see your value:

• Get credit for your work. If you solved a tough challenge, loop in leadership with an update. Visibility matters.

• Show patterns of success. If you’re known as a problem solver, highlight the repeated impact you’re making. Being a problem solver worked miracles for my career. Years later, some people still know me as a person who can be put on the most challenging problems and who will find a way to solve them.

• Be consistent. Know your strengths and lean into them repeatedly. If you’re a visionary, keep reinforcing the broader direction. If you’re analytical, keep showing where the data leads. Make your strengths undeniable.

Check in with yourself:

• What do I do better than anyone else on my team?

• What’s one situation this month where I leaned into my strengths?

• Where am I playing small when I should be doubling down?

Never assume people see your value just because you see it. Show it. Repeat it. Reinforce it.

Lead like a high achiever, but think like a CEO

Being a high achiever can feel like walking a tightrope between confidence and doubt. But the secret isn’t in pretending to be older, wiser, or someone you’re not.

It’s in realizing that your persistence is what makes you unstoppable.

So here’s my challenge to you:

• Stop waiting for recognition. Instead, reinforce your value.

• Stop assuming “no” is permanent. Instead, keep testing different ways to make it a yes.

• Stop believing that one shot is enough. Instead, keep showing up and keep proving it.

Remember: your job isn’t to wait until the perfect conditions to act, it’s to be effective.

Whatever you say, don’t just say it once. You say it 5-7 times. And then? You say it again.

Because the most effective leaders? They don’t just get it right. They don’t stop until it sticks.

You have all the skills. Go after it.

See you next week!

Ashley

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You’re a leader now, but do you feel like one?

Maybe you’re the youngest in the room. Maybe you’re second-guessing yourself. Maybe you thought once you got the title, things would just click—but now you’re realizing leadership is about more than just doing great work.

I help high achievers like you:

• Lead with confidence—even when you feel out of your depth.

• Make your ideas land—so the right people listen, act, and remember.

• Position yourself as the leader in the room—without waiting for permission.

My clients have gone from feeling overlooked to being seen as power players in their organizations—earning senior promotions, bigger opportunities, and high 5- to 6-figure salary increases.

Book a free 30-minute consult with me and let’s talk about where you are, where you want to be, and what might be getting in the way.

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