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 a free consultation call with me. Let’s discuss your unique situation and how you can get on the path to your dream role with confidence.

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.

How to Show Who You Are and Your Full Potential in Interviews

 If you’re not getting interview call backs after applying for jobs, check out my previous article for tips on turning applications into opportunities. But if you’ve made it to the interview stage, congratulations! That’s a big first step. Now let’s focus on how to make the most of this chance and land the role you want by standing out and building strong connections with the hiring manager.

This is not a full guide to interviews but a spotlight on key strategies that many candidates overlook. These tips will help you showcase your strengths, align with the company’s goals, and demonstrate why you’re the right fit.

1. Know what you want—and connect it to what they need.

Many candidates go into interviews focused solely on showing they fit the job description, but the most memorable ones share their aspirations and explain how they align with the company’s goals. This combination of personal vision and alignment with their needs makes a strong impression.

For example:

• Instead of saying: “I am ready to work hard in your marketing team,” 
• try: “I want to have my own business one day, and I’d like to gain marketing experience in a company like yours, where the marketing team is strong. I’m excited to work hard in your marketing team.”

• Instead of saying: “I’m happy to be an individual contributor,” 
• try: “Ultimately, I want to lead a team that provides scalable solutions for data-driven decisions. This role offers an opportunity to build experience in areas I haven’t been exposed to yet, and this is a very important part of building scalable solutions for your team. I’m excited for this opportunity, and I’m happy to work as an individual contributor and learn.”

Being honest about your aspirations and how they connect with the role demonstrates authenticity and motivation. Hiring managers know candidates who are excited about both their personal growth and the company’s success will be eager to learn and contribute.

Once you’ve shown how your goals align with theirs, the next step is to turn the interview into a collaborative conversation that explores how you can solve their challenges.

2. Treat the interview as a conversation, not an exam.

Many candidates approach interviews like an oral exam, where they feel the need to give the “right” answers. But interviews are more effective when they feel like collaborative discussions, where both sides explore how to address challenges and succeed together.

Ask thoughtful, conversation-starting questions that highlight your strategic thinking and help hiring managers envision your contribution. For example:

• “Teams your size often face this challenge. Is that something your team has dealt with?”
• “I’m passionate about building a knowledge base for the team to keep everyone aligned and ensure they can access information anytime. I’m curious—how are you maintaining your knowledge base?”

When asked a question, don’t just respond—use it as an opportunity to ask follow-up questions or share your perspective. For example:

• If they ask if you have a specific skill or experience, 
• you could say: “Yes, I’ve used this skill to solve [specific problem], and it worked well. We also noticed this limitation. Did you face this problem as well?”
• If they ask about your approach to challenges,
• you could respond with: “I focus on building alignment and finding scalable solutions. How do you typically approach challenges like this?”

The key is to avoid making your questions purely inquisitive, like, “I want to know if you have this problem.” Instead, treat them as conversation starters where you can discuss how to address the challenge together. Prepare to share your experiences and thoughts and don’t hesitate to ask evaluative questions before offering solutions—just like a doctor would run tests before deciding on treatment.

This kind of exchange helps hiring managers see you as a proactive and thoughtful problem-solver while turning the interview into a meaningful discussion.

3. Share what you want them to know about you.

Behavioral questions like “Tell me about a time you…” are more than just opportunities to tell a story. They’re your chance to highlight your skills and principles in a way that aligns with what the hiring manager is looking for.

For example, if they ask about handling a difficult colleague, they’re likely assessing whether you can handle interpersonal challenges effectively. Your answer should reflect that.

Instead of simply recounting an event, share your principles and how you applied them. For instance:

• “I believe most conflicts stem from misunderstandings. I always try to align goals through open conversations. One colleague I worked with was often challenging. When I tried to have open conversations, they would sometimes get angry and even yell. I stayed calm and focused on identifying the gaps in our understanding. Eventually, we agreed on a solution, and that person became highly collaborative and high-performing.”

This shows not only your ability to handle difficult situations calmly but also your effectiveness in turning them around positively. Even if you lack a strong example, sharing your philosophy and smaller experiences can still highlight your approach and strengths.

Additionally, prepare what you want them to know about common themes of behavioral questions:

• Teamwork, Collaboration — Will you work well with others?

• Problem Solving, Decision Making — Can you solve problems without needing step-by-step instructions?

• Adaptability, Flexibility — Can you handle when things change often?

• Communication — Will they feel comfortable putting you in front of stakeholders?

• Leadership, Influence — Can they delegate work to you in the future?

• Time Management, Prioritization — Can you handle workload and pressure?

• Conflict Resolution — Can you handle disagreements effectively?

When you frame your answers with these questions in mind, you can show the hiring manager that you’re not just qualified—you’re an asset to their team.

4. Don’t fear your weaknesses—embrace the challenge.

It’s natural to feel uneasy about gaps in your experience, but they don’t have to hold you back. If you meet every single requirement for a role, it may not be challenging enough to help you grow. Confidence in your ability to learn and adapt is more important than ticking every box.

Think about a time when you successfully took on a challenge outside your comfort zone. For example:

• “When I started in my last role, I didn’t have experience with [specific skill], but I dedicated time to learning it and became proficient in just a few months. I’m confident I can do the same here.”

You can take it further by showing how you go beyond learning to create impact:

• “In my previous role, I noticed a new tool gaining popularity in the industry. Out of curiosity, I learned it and began applying it at work. It turned out to be incredibly useful, and I eventually taught my team how to use it. That experience taught me how important it is to stay proactive and ahead of trends.”

This approach not only demonstrates your ability to learn but also your proactive, resourceful mindset.

Remember, interviews aren’t about passing or failing—they’re about finding the right role that meets what you want and what they need. Do your research to understand their goals and challenges, but don’t forget to show what matters to you as well. By doing this, you’ll not only stand out as a candidate but also position yourself for better opportunities and offers.

Many candidates who approach interviews this way have landed their dream roles—sometimes with higher titles than they originally applied for. You can do it too. Keep going—you’ve got this!

How to Get That Interview Call Back

 With the current economy and uncertainties in the world, many people share that they’re not getting callbacks for jobs they used to secure interviews for with ease. This can lead to doubt: “Maybe I’m not good enough for this role?” And with discouraged confidence, even when they do get a callback, they struggle to show up with confidence.

But the truth is, the reasons you’re not hearing back are most likely about them—not you. The hiring process has become more complex:

• Job openings may be on hold or even in the middle of discussions to be canceled.
• Companies might still be refining the role’s requirements or debating whether to adjust job descriptions.
• With fewer hires allowed, hiring managers have to be more strategic than ever, carefully considering who their ideal candidates are.

This is why it’s more important than ever to talk to someone on the team. Ideally, this is the recruiter or hiring manager, but even connecting with someone who works on or near the team can offer invaluable insights. These conversations can help you learn about their challenges, what they’re trying to achieve, and how you can help. This insight not only informs your approach but also helps you show them you’re the right person for the job.

Here are five steps to help you effectively connect and stand out:

1. Prepare your questions.

Before reaching out, decide what you want to learn from the conversation. Avoid broad, vague questions like “How do you like working here?” Instead, tailor your questions to uncover useful insights.

For example:

• If you’re curious about work/life balance, ask: “What do you typically do in the evenings or weekends?”
• If you want to know about autonomy, ask: “What’s a project you’ve initiated with your ideas recently?”

Each question should have a clear goal—what do you want to know, and why?

2. Prepare your selling points.

Selling points are the things you want them to know about you—specific skills or experiences that align with their challenges or goals.

For example, do you have a skill you think they’ll find impressive? Instead of simply stating that you have the skill, be ready to share how you’ve applied it to solve similar problems in the past.

• “I’ve worked on a similar problem before and used [this skill] to solve it. It worked really well.”

This shows not only that you have the skill but that you also know when and how to use it effectively.

3. Conduct informational interviews.

Reach out to people who can provide insight into the team or company. Use LinkedIn or ask your network for introductions. When you connect:

• Be respectful of their time—keep it brief and focused, and appreciate their help.
• Do not ask for referrals or connections unless they offer.

Remember, this is part of the interview process—if you make a strong impression, they’ll want to help you become their colleague.

4. Show up as a consultant (like a doctor).

When talking to hiring managers, act like a consultant. Think about their challenges and explain how you can help solve them.

Imagine visiting a doctor, and the doctor says: “I can use any medicine you want—what do you want to take?” You’d lose confidence in their expertise, right? Instead, you’d want the doctor to assess your situation and recommend the best course of action.

Similarly, hiring managers want someone who can diagnose their team’s challenges and propose solutions. Show them you understand their needs and can be trusted to deliver results.

5. Ask for help.

Don’t hesitate to seek support from your network. Practice mock interviews or mock informational interviews with a trusted friend or colleague. It’s a great way to gain feedback, build confidence, and feel prepared for real conversations.

Consider joining the Women Leaders Club, where you’ll find a community of people supporting one another through these challenges and beyond.

This process has become more challenging, but it’s far from impossible. Many people who approach job searching this way have landed the roles they wanted—even some with higher titles than they originally applied for. You can do it too.