Navigating Career Challenges: Lessons from Jackie Santayana’s Journey

Ever feel like you’re doing everything right, but the job search—or career growth—still isn’t working out?

Jackie Santayana knows that feeling well. She graduated during a financial crisis, faced multiple rejections, and had to take roles that weren’t quite what she envisioned. But instead of getting stuck in frustration, she focused on what she could do—one step at a time.

I had the chance to sit down with Jackie to talk about her journey—how she navigated uncertainty, built resilience, and ultimately grew into a leadership role in tech. If you’ve ever wondered “Should I just settle for this job?” or “How do I actually get to the role I want?”—you’ll want to hear her story.

📺 Watch the full interview here.

Every Job Has Something to Offer—Even If It’s Not “The One”

Jackie’s first few jobs weren’t ideal. She worked as a cashier and in a nonprofit before transitioning into tech. At first, it felt frustrating—like she was falling behind while others were moving forward.

But instead of dismissing those experiences, she asked, “What skills can I take from this?” She learned to manage different stakeholders, handle unexpected challenges, and communicate effectively—all of which later helped her stand out when applying for leadership roles.

I see this all the time with my coaching clients—women who feel like their experience “doesn’t count” because it doesn’t follow a perfect, linear career path. But leadership isn’t about checking off the right boxes. It’s about how you use what you’ve learned to create impact.

The Power of Conversations (Not Just Resumes)

One of Jackie’s biggest turning points came from talking to people who were just a few years ahead of her. She reached out, listened to their experiences, and gained valuable insights on what actually helps in a job search.

She wasn’t just trying to network in the traditional sense—she was building relationships and learning from others’ journeys.

If you’ve ever felt like networking events are a waste of time, here’s something to consider: Instead of trying to “sell” yourself or ask for a job, start with curiosity. Who’s doing work that interests you? What did their path look like? What advice would they give? You never know what doors might open from a genuine conversation.

Mindset Matters More Than You Think

At one point, Jackie was applying for jobs and not getting the results she wanted. She started to wonder, “Am I just not good enough?”

But then she flipped the script. Instead of seeing every rejection as proof she wasn’t qualified, she saw them as data points:

• Where am I getting stuck?

• What patterns am I noticing in feedback?

• What adjustments can I make next time?

This shift made a huge difference—not just in her job search, but in how she showed up in interviews. She stopped trying to prove herself and started owning her value.

I see this transformation happen with my clients all the time. The moment they shift from “Am I good enough?” to “Here’s what I bring to the table,” everything changes—how they speak, how they carry themselves, and ultimately, how others see them.

Taking Action—Even When It’s Not Perfect

One thing that stood out in Jackie’s story is that she didn’t wait until she felt “100% ready” to take the next step. She applied before she felt fully qualified. She reached out before she knew exactly what to say. She tried different things to see what worked.

Too many talented women hold themselves back, waiting until they feel completely prepared before they take action. But clarity comes from doing, not just thinking.

If you’re feeling stuck in your job search or career, ask yourself: What’s one step I can take today—even if it’s small?

Final Thoughts

Jackie’s journey is a powerful reminder that career success isn’t about luck—it’s about taking intentional steps, learning from every experience, and staying open to opportunities in unexpected places.

If her story resonates with you, I’d love to hear—what’s your biggest takeaway? And if you’re feeling stuck and want support in navigating your own career transition, let’s chat. Sometimes, the shift that changes everything is closer than you think.

📺 Watch the full interview here.

Why I Hiked in the Dark?

Last Wednesday was Lunar New Year, and I did something unusual—I hiked in the dark to see the first sunrise of the year.

I’ve never been one to celebrate New Year’s traditions. I don’t stay up until midnight, and I don’t put much weight on an arbitrary calendar date. 2024 and 2025 are just numbers for convenience. So why did I do it?

Because last year, I learned an important lesson: Don’t wish for good luck—make it happen.

Looking back, I realized that while I always worked hard and tried different things, I never fully embodied the mindset of I will make this happen. I was moving forward, but not always with the conviction that I was in control of my future.

This year, I’m shifting that. No more “let me try and see what happens”—I’m owning the outcome. It may seem like a small difference, but my mindset feels completely different. To mark this commitment, I decided to hike and watch the first sunrise of the year.

What’s your mindset for the new year? Are you taking the wheel—or just hoping for a smooth ride?

P.S. The sunrise was completely hidden behind clouds. So technically… I hiked in the dark, in the cold, for nothing. But hey, commitment is commitment, right? 😂

Ready to take control of your career and life? Here’s how I help people turn their aspirations into reality.

The Missing Key That Unlocks Your Future: Peer Energy

Have you ever walked into an interview or an important conversation, feeling like you had to prove yourself over and over again, but wondering why the opportunity still feels out of reach? You know you’re capable, but somehow it just doesn’t feel like others see it too.

If this resonates with you, you’re not alone. Many women experience this frustration. But here’s the key you might be missing: how you show up. And the secret lies in showing up with peer energy.

The Three Types of Energy You Can Bring

There are three kinds of energy you can bring to a conversation, interview, or any professional opportunity: Predator energy, Prey energy, and Peer energy.

•  Predator energy is like a tiger hunting its prey. It’s desperate and driven by hunger. Thoughts that come with this energy are, “I really need this role,” or “I need you more than you need me.” It’s a kind of energy that signals desperation.
•  Prey energy, on the other hand, is like a giraffe being hunted by a predator. They are constantly on guard, overly cautious, and they put the other person on a pedestal, thinking, “You have all the power; you’re more impressive than me.” It’s a kind of energy that signals insecurity.

Many people show up with either predator or prey energy. The problem is, neither of these energies works in your favor. Predator energy comes off as desperate, while prey energy feels unappealing and lacking in confidence.

The Power of Peer Energy

So, how should you show up? Peer energy is the answer. Peer energy sends the message, “I see you, I’m here to help, but I don’t need you, and you don’t need me.” This energy is calm, confident, and deeply attractive. It signals leadership presence and confidence—traits that are incredibly important when it comes to opening up new opportunities.

Think of it like this: a consultant or a doctor. They show up not with desperation or insecurity, but with confidence in their expertise. They know they can help solve your problem, but they don’t need you. And you don’t need them either—you can always go to someone else. But they’re offering a solution because they believe in their skills and experience.

When you show up with peer energy, you bring a sense of partnership to the table, not pleading or desperation. You’re not here to be judged; you’re here to see how you can help each other.

How to Shift to Peer Energy

Now, you might be wondering: How do I show up with peer energy?

The first step is to change your thoughts before the conversation or interview. Here are some thoughts you can have to embody peer energy:

•  I am an expert, and they need my expertise.
•  I know how to solve their problems, and they want what I offer.
•  I’m here to be a strong partner for them, not to please them.
•  I am perfect for this role, but I don’t really need it.

These thoughts will help ground you in your confidence, so you show up as a peer, not someone desperate for approval or validation.

By thinking this way, you’ll notice a shift in your energy. You’ll approach the conversation as an equal, ready to collaborate and add value. This subtle shift can completely change the dynamics and the way others perceive you.

Now, you might wonder when you can ask them about their challenges while you’re busy answering their questions. There are many ways, but here’s one way you can shift that. Let’s say the interviewer asks if you have experience with X. You can respond with, “Yes, I’ve used X to solve Y problems before. However, for your company, if you have Y problem, in addition to X, I’d suggest considering Z solution because [your reasoning].”

This is a major shift from just answering their question in a yes or no format and waiting for them to decide what to do with your answer. By doing this, you start a conversation to discuss their challenges and how to address them together.

Take Action and Make Your Dream Role a Reality

It’s simple, right? But it requires practice. And practice makes perfect.

If you’re struggling with how to show up with peer energy or need help shifting your mindset, I can help. I’ve helped countless women break through these barriers and land their dream roles. One woman, for instance, was ready to settle for a lower-level job after being laid off. After working together, she applied for the same level and ended up with a job offer one title higher, along with a higher salary. She showed up with peer energy, and it worked.

If you’re ready to start showing up with that same energy, I invite you to book my special first-timer offer. We’ll dive into your unique situation, get crystal clear on what matters most, and map confident next steps toward your dream career and life.

Do You Know What Truly Brings You Joy?

 Many people know they should do something about their careers but aren’t sure where to start or how to make a meaningful change. Sound familiar? Last month, I hosted a workshop focused on exactly this—how to gain the clarity needed to take meaningful steps forward in your career.

The first step in any career change is gaining clarity. Without knowing exactly what you want, progress can feel directionless—even if you’re working hard. You might be putting in effort, but if you’re unsure of the goal, that effort may not bring you closer to what you truly want.

During the workshop, we focused on gaining clarity around what truly brings you joy. This is so important yet often overlooked. Many of us have been guided by others—parents, teachers, and peers—telling us what success looks like, often involving good grades, landing great jobs, and having a stable career. We follow these predefined paths without always reflecting on whether we truly enjoy what we’re doing.

Some people are comfortable following the traditional success path. They’re doing well, getting good grades, landing great jobs, and feeling fulfilled. But for others, even with success in terms of grades, jobs, and a stable career, they still feel unfulfilled or unsatisfied. They feel disconnected from what truly matters to them.

The exercise helped participants gain clarity on what really brings them joy. Based on this newfound awareness, everyone created a plan for how to bring more of that joy into their career and life.

“It was helpful to take the time to make connections about my past and bring it to a tangible action item!”

Then, one participant shared her challenge with the group. She had clarity on what she wanted to do, but wasn’t sure how to implement it. The group offered insights, suggestions, and shared experiences, which she found incredibly helpful. It not only helped her, but it also benefitted the group. They shared feedback like, “It’s helpful hearing other people’s experiences compared to my own,” and “It reminded me that everyone struggles with their own fears, and sometimes the answer is just to talk to someone else.”

Does this resonate with you? We’re continuing this clarity journey, and you can join us. In our next session on January 23rd, we’ll take a holistic look at your life, helping you identify how different areas of your life influence your goals. We’ll also explore the guiding principles that define who you are and what truly drives you. With this clarity, decision-making becomes easier, and you’ll move forward toward your goals with confidence.