As we explored in our previous article, "Why Strategic Reinvention and Your Unique Talent Stack Matter More Than Ever," the modern career requires continuous adaptation and strategic thinking. Building on that foundation, let's dive deeper into how the approach to reinvention should evolve at different life stages. The strategies that serve you well in your twenties require significant adjustment as you move into your thirties and beyond.
In Your 20s: Try, Fail, Repeat
Your 20s are the laboratory years of your career. This is the time to embrace experimentation over optimisation, breadth over depth, and learning over earning.
Curiosity Is Your Best Asset—Explore Widely
The pressure to find your "passion" or "calling" in your 20s is not only unrealistic—it's counterproductive. Instead of searching for the perfect fit, focus on developing an insatiable curiosity about how the world works. Take the marketing coordinator role even if you studied engineering. Say yes to the startup opportunity, even if you had planned on a corporate life. Join cross-functional projects or volunteer for assignments outside your job description.
This exploration isn't random wandering; it's strategic reconnaissance. You're gathering intelligence about industries, company cultures, work styles, and your preferences and strengths. Each experience adds another data point to help you make more informed decisions later.
Think of Jobs as Experiments to Learn From
Here's a game-changer: reframe your early career moves as experiments rather than permanent commitments. When you're evaluating opportunities, ask yourself, "What will I learn here that I can't learn anywhere else?" This mindset shift takes the pressure off making the "right" choice and makes you more willing to take calculated risks.
Document what you learn from each role. Not just technical skills, but insights about what energises you, what drains you, what types of people you work best with, and what environments bring out your best performance. This self-knowledge becomes invaluable as you start making more strategic career decisions in your 30s.
Build Resilience Early by Taking Smart Risks
The cool thing about being 20s is that the recovery time from career missteps is shortest. You probably have fewer financial obligations, more geographic flexibility, and literally decades ahead to course-correct. This is your window for taking smart risks.
Smart risks aren't reckless gambles, though. They're calculated moves where the potential downside is manageable and the upside—in terms of learning, network building, or skill development—is substantial. Starting a side project, joining a high-growth startup, or moving to a new city for an opportunity all fall into this category.
Work Hard, Meet People, Stay Open
Your 20s are when you establish your reputation for reliability and excellence. Work hard not just to advance quickly, but to build that foundation of professional credibility that'll serve you throughout your career. Show up consistently, deliver quality work, and go beyond what's expected.
Just as important? Building relationships across industries and seniority levels. The connections you make in your twenties often become the most valuable parts of your professional network. Stay genuinely curious about others' career paths and be generous with your own time and expertise.
Most critically, stay open to opportunities that don't fit your original plan. The career you end up loving might not even exist today, or it might emerge from some unexpected combination of your various experiences.
In Your 30s and Beyond: Go Deeper
By your 30s, the experimentation phase gives way to a more strategic approach. You have enough data points about yourself and the working world to start making more intentional choices about where to focus your energy.
Start Narrowing Your Focus
You've likely discovered patterns in what types of work engage you most, which environments bring out your best performance, and where your natural strengths lie. Use these insights to begin narrowing your focus.
This doesn't mean locking yourself into a rigid career path, but rather choosing to deepen your expertise in areas where you have both interest and aptitude. The goal is to become known for something specific while maintaining enough flexibility to evolve as opportunities arise.
Make More Intentional Choices—Know What You're Trading Off
Every career decision involves trade-offs, but in your 30s, these trade-offs become more significant and harder to reverse. Choosing the high-travel consulting role means less time with family. Accepting the startup equity offer means forgoing the steady paycheck. Pursuing a graduate degree means delaying other goals.
Make these trade-offs consciously rather than by default. Before making major career moves, explicitly identify what you're gaining and what you're giving up. Consider not just the immediate impact, but the compound effects over time. This level of intentionality helps ensure your choices align with your evolving values and circumstances.
Balance Building Expertise with Staying Adaptable
Your 20s are when you start building the deep expertise that can differentiate you in the marketplace. This might mean becoming a recognised authority in your field, developing a valuable speciality, or building a track record of success in a particular type of challenge.
However, deep expertise shouldn't come at the expense of adaptability. The skills that are valuable today may be commoditised tomorrow. Stay curious about adjacent fields, continue learning new technologies and methodologies, and maintain relationships outside your immediate speciality. The goal is to be deeply skilled but not narrowly trapped.
Consider Your Long-Term Values and Responsibilities
This doesn't mean compromising your ambitions, but rather ensuring they're sustainable within the context of your broader life goals. Consider what success looks like, not just professionally, but personally. How do you want to spend your time? What kind of example do you want to set? What legacy do you want to build?
The Art of Strategic Reinvention
Mastering reinvention isn't about constantly changing direction—it's about continuously evolving in response to new information about yourself and the world around you. The specific strategies that work best will vary by life stage, but the underlying principle remains constant: stay curious, stay flexible, and stay intentional about the choices you make.
Your 20s teach you what's possible. Your 30s and beyond are when you decide what's important. The magic happens when you can hold both truths simultaneously and remain open to new possibilities while being selective about which ones you pursue.
At Wild & Wise, we help progressive HR and business leaders take a fresh perspective on leadership and career development for the new world of work. Through strategic facilitation and strengths-based coaching, we support teams and leaders to grow and thrive.
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The Uncomfortable Truths of Leadership: How to Make the Right Decision and Bridge the Generational Gap in the Workplace
Being a leader isn't just about keeping things the same. It's about figuring out how to handle a fast-moving landscape where tough calls are often the right calls, and where understanding how leadership has evolved across different generations is super important. Paul Soon, a seasoned pro in the creative business, recently shared some thoughts that really connect these two ideas on the Offscript, part of the Wild & Wise Podcast.
The Core of Modern Leadership
One of Paul's most honest moments was talking about the "uncomfortable truths" of being a leader. He especially highlighted those tricky times when leaders have to deliver tough news. He stressed that taking the easy way out is rarely the best way. "When a decision is too easy, sometimes it may not be the right decision," Paul pointed out. This really hits home when you think about how it impacts your team. For example, telling long-time employees their time with the company is ending takes a huge amount of empathy and bravery. It's more than just a severance package. Leaders need to put the individual's dignity and future first, even if it goes against typical corporate goals focused purely on profit.
Authenticity, Empathy, and the New Leadership Paradigm
This dedication to making principled decisions, even when they're not popular, directly relates to how younger generations see leadership today. The old "do what I say" style, common in the past, is quickly being replaced by a demand for authenticity, transparency, and empathy. Young leaders, often thrown into positions of power as founders or quickly promoted, might not have as much experience as those who came before them. They're living in a world where information is instantly available, and they might even get leadership advice from AI tools like ChatGPT.
But Paul makes a key point: while AI can offer a "cheat sheet" for certain situations, it can't give you the real-life experience that builds true resilience and determination. Today's generation values leaders who are vulnerable yet strong, willing to own their mistakes, and consistent in their values. This is quite different from the past, where leaders might have felt they had to appear perfect. "If you commit to the journey of wanting to lead, then you've got to live. You're going to make your mistakes," Paul says.
The challenge for leaders today, no matter their age, is to find that sweet spot. It's about having the courage to make tough choices that might be uncomfortable or go against the grain, while also creating a workplace built on psychological safety and trust. This means looking beyond just revenue and growth, and asking deeper questions like: "How have your people developed?"
Ultimately, bridging the gap between generations in leadership isn't about one group copying another. It's about all leaders recognising that the heart of good leadership is about being consistent, empathetic, and ready to make hard decisions from a place of genuine care. When leaders show these qualities, they not only get things done but also inspire and develop the next generation of leaders to do the same.
Speaking Your Dreams Out Loud: How Vocalising Your Desires Helps You Get There
In a perpetual state of evolution and collision, finding clarity and direction can feel like navigating a maze. Yet, a recent episode of the Wild & Wise Podcast featuring singer-songwriter and DJ Daphne Khoo explores navigating this complexity through the simple act of vocalising your desires.
When Your Words Become Reality
It might sound a bit like magic, but giving voice to your goals actually makes them more real. Daphne explained it perfectly: when you speak your desires, you're not just thinking about them anymore; you're bringing them out into the real world. It's like writing things down; it helps you get super clear on what you truly want.
Daphne shared her trick for getting things like new music gear or a guitar. She'd write down what she wanted and stick it on her laptop so she'd see it all the time. And guess what? She noticed something amazing:
There is nothing that I've written down that I have not been able to achieve. It's not just about wishing; it's about telling yourself, constantly, what you're working towards, and your brain starts figuring out how to make it happen.
From Quiet Wish to Confident Shout
Going from just thinking about a dream to actually saying it out loud takes courage, and it usually grows with your confidence. Daphne admitted that when she was younger, winning a Grammy was just a secret thought she'd never dare to say. But now? She confidently declares, "I'm manifesting right now, I'm manifesting winning a Grammy."
This shift doesn't happen overnight. It's built on small wins. Imagine you set a goal to work out this week, and you actually do it. That small success builds momentum. It tells your brain, "Hey, you did that! You can do it again!" This boost of confidence then makes it easier to voice those bigger, seemingly impossible dreams. Speaking your desires out loud really kicks things into gear, creating pathways in your mind that help you see how to reach your goals.
Your Amazing Subconscious: The Universe Within
The power of vocalising your desires is totally tied into your incredible subconscious mind. As they talked about on the podcast.
The subconscious mind is extremely powerful. It's so powerful. The mind is a universe, and if you're able to anchor and find clarity, it's amazing what comes out of it.
When you speak your desires, you're essentially sending a clear message to your subconscious, pointing your inner compass directly towards your purpose. And then, every decision you make, even without realising it, starts to move you closer to that goal.
It's not just about being overly optimistic. It's about sharp, intentional focus. Saying what you want out loud helps you define it clearly, making it easier for your mind to spot and grab opportunities that bring you closer to your aims. It turns fuzzy hopes into solid plans, kicking off a powerful internal process that can lead to some seriously cool results.
Tuning into Strengths to Build Cohesion in Turbulent Times
Political shifts, economic pressure, and workplace volatility are challenging leaders across Asia to rethink how they lead and how teams thrive. In boardrooms and offsites alike, a key question sounds something like this: “How do we stay cohesive and engaged when everything with how the current world is shaping up”?
The answer isn’t found in process maps or performance dashboards. It’s found in people and specifically, how well we understand and use their strengths.
Strengths Help Support Performance and Build Resilience
Strengths is a powerful anchor for individuals and teams. Especially when the external environment is uncertain, teams need something to anchor them. That’s where CliftonStrength® can offer valuable perspectives. By helping individuals and teams identify what they naturally do best, it shifts attention away from firefighting and toward a more intentional form of collaboration.
We are not here to ignore weaknesses or pretend that challenges don’t exist. The approach with Strengths is amplifying what energises people.
As author and researcher Tom Rath puts it, “What great leaders have in common is that each truly knows his or her strengths, and can call on the right strength at the right time.”
CliftonStrength® is not just a feel-good philosophy. Backed by decades of Gallup data, the data shows that when people use their strengths at work, they are more engaged, more productive, and more likely to stay.
The Strongest Leaders Know What and When to Lean In
Across Asia, I’ve worked with leadership teams from the media, tech, and energy sectors. In every case, the most resilient leaders aren’t the ones trying to be everything to everyone.
They’re the ones who have clarity on their own strengths and trust others to bring complementary perspectives.
That awareness fosters interdependence and collaboration. In one team I coached, a leader with Futuristic and Strategic strengths was able to cast a compelling vision during a restructuring. But it was a teammate with high Responsibility and Consistency who ensured daily operations stayed grounded and stable.
Strengths creates a shared language that helps people see where they fit, where they add value, and how they can count on each other when it matters most.
Culture Is Reinforced in the Micro-Moments
Strengths-based leadership often begins with a one-off workshop, but it comes to life when it shows up in everyday conversations.
When a manager says, “I saw how your strength in Communication helped clarify that situation,” or asks, “What’s been giving you energy lately?”. It is in these moments that’s when the culture starts to shift.
They say consistency is key. When it comes to Strengths, it’s about repetition, reinforcement, and recognising people for what they naturally bring. Done well, strengths work moves beyond coaching and into culture-building.
Gallup’s own research highlights this responsibility. “If, as a leader, you are not creating hope and helping people see the way forward, chances are, no one else is either.”
Strengths provide a practical way to do just that. They allow teams to see progress, recognise what’s working, and move forward with purpose, even if the environment remains complex.
The Human-Centred Shift Is Already Happening
HR leaders across Asia are already making the pivot. Strengths strategy is now being used not only in leadership development but in onboarding, change management, and even team conflict resolution.
The shift is subtle but powerful: from diagnosing problems to activating potential.
In a time where traditional leadership models are being redefined, strengths offer a more sustainable, human-centred approach. They help you sail through a storm together.