Why Playing It Safe Is Killing Your Career Confidence (and What to Do Instead)

What if confidence wasn’t something you’re born with—but something you build, one bold step at a time?

If you’ve ever felt stuck, misaligned, or like you’re shrinking to fit a role that no longer fits you—this episode is your permission to shift.

In this powerful and practical conversation, Siena Dean—Senior Manager of Alumni Engagement and purpose-driven career strategist—shares the confidence formula she’s used to guide 500+ professionals into roles that reflect their true value.

🎯 Inside this episode, you’ll discover:

• Why confidence isn’t a personality trait—it’s a product of repetition, clarity, and purpose.
• How to break free from “career autopilot” and re-align with what really lights you up.
• The mindset shift working women need to stop shrinking—and start owning their zone of genius.

🎯 Key Takeaways

• Confidence is crucial for career growth and opportunities.
• Connecting personal stories to purpose enhances career decisions.
• Many professionals struggle with self-trust and confidence.
• Modeling confidence starts at home and in the workplace.
• Small intentional steps can lead to significant career changes.
• Betting on oneself is essential for personal growth.
• Understanding one's value is key to overcoming challenges.
• Support from community can shift perspectives on career paths.
• Balancing personal responsibilities with career ambitions is possible.
• Continuous learning and connection are vital for professional success.

🔥 Hit play now to unlock the confidence to pivot boldly, lead intentionally, and build a career that aligns with your deepest ‘why’.

Transcript

Olajumoke Fatoki: Welcome to another episode of the Thrive Careers Podcast. Today, we’re diving into the confidence formula with career strategist and Senior Manager of Alumni Engagement, Siena Dean. Siena has helped over 500 professionals align their purpose with their work—and today, she’s here to help you do the same.

Olajumoke Fatoki: Siena, let’s start with something fun. If your career journey were a movie, what would the title be?

Siena Dean: I’d call it The Bold and the Fearless. I’ve taken some big leaps in my career—ones that wouldn’t have worked if I had let fear lead. Boldness has always played a huge role in my growth.

Olajumoke Fatoki: And that brings us right into today’s topic: confidence. You help people connect the dots in their careers. When did you first realize that betting on yourself was the key to purpose?

Siena Dean: For me, purpose is everything. Once I understood mine, I started seeing every role—no matter the industry or title—as a building block toward my bigger mission. Purpose gave me power and direction.

Olajumoke Fatoki: How does a sense of purpose actually help someone take bold career steps, especially when outcomes aren’t guaranteed?

Siena Dean: When you know your purpose, decisions become less about promotions or job titles. You start asking: “What skills do I need for where I’m going?” That shift gives you confidence to step outside your comfort zone because you’re moving with intention.

Olajumoke Fatoki: You've helped hundreds of professionals navigate misalignment. What do you notice in people who struggle with confidence?

Siena Dean: Many people let their roles define them, instead of shaping their roles around their strengths. Confidence comes from repetition in areas you naturally excel. Once you understand your zone of genius and create opportunities to operate in that zone regularly, confidence starts to build.

Olajumoke Fatoki: What does it really mean to bet on yourself, especially for women juggling work, parenting, caregiving—all of it?

Siena Dean: Betting on yourself is about having a purpose-aligned game plan. It’s adjusting your role to reflect the skills you want to grow. At home, it means having honest conversations with your loved ones about your goals. When everyone understands your mission, they support you—and it becomes a shared journey.

Olajumoke Fatoki: How can women learn to trust their value, especially if they’ve worked in environments that didn’t reflect it back to them?

Siena Dean: If over 60% of your job doesn’t align with your strengths, it’s hard to feel valuable. I teach clients to focus their energy on areas where they naturally excel—especially if those areas align with what the organization truly values. That’s where your contribution becomes undeniable.

Olajumoke Fatoki: Can you share a client success story that really illustrates this transformation?

Siena Dean: One client had climbed the corporate ladder by chasing promotions—not purpose. When she reconnected with her why, she left her job and launched a successful business. Another client realized she was in the right organization but had lost touch with her mission. Once she re-integrated purpose into her daily work, she rediscovered joy and motivation.

Olajumoke Fatoki: For listeners who feel like they’ve played it safe for too long—what’s one step they can take to start betting on themselves?

Siena Dean: If you don’t know your purpose, start there. Think back to childhood—what lit you up before money or status were factors? If you do know your purpose, share it. Speak it out loud to people who believe in you. That community support will open doors you didn’t know existed.

Olajumoke Fatoki: Final question—what’s one confidence booster that always works for you?

Siena Dean: My faith. I believe my purpose is divine, so I lean into the confidence God has in me. Even when I feel unprepared, I know I’m equipped for every room I walk into.

Olajumoke Fatoki: That’s so powerful. Siena, thank you for being here and sharing so openly. For listeners who want to stay connected, where can they find you?

Siena Dean: You can find me on LinkedIn at sienna.dean. I’ll be sharing updates and more resources there.

Olajumoke Fatoki: Amazing. And to our listeners—if you’re ready to stop shrinking and start owning your brilliance, this is your moment. Hit play, take notes, and take that bold next step. Until next time—keep thriving.