We're constantly told to "reinvent" ourselves, but what does that really mean? It sounds like a massive, overwhelming task. Instead of a complete overhaul, what if you thought about it like upgrading your personal operating system (OS)?
Just like the software on your phone or computer, you have a personal OS, a set of core beliefs, habits, and values that shape how you navigate the world. For many of us, this is the "out-of-the-box" system we've used since we were young, shaped by our upbringing, friends, and early experiences. It's a default setting, but it might not be the most effective for where you want to go.
Why an Upgrade is Essential
In the fast-paced world of the future of work, where careers and identities are constantly evolving, relying on an outdated OS can hold you back. An upgrade isn't just about learning new skills; it's about making a deliberate choice to examine and improve how you manage your time, attention, and energy.
Think about a prodigy athlete or a musician. They don't just hope for success; they develop a personal OS built on discipline, consistent practice, and a focus on their goals. This system allows them to be deliberate about how they use their resources to achieve what they want. You can do the same.
What to Look at When Upgrading
So, what are the fundamentals of a personal OS upgrade? It's about taking a good look at your current system and identifying what's working and what's not.
- Your Beliefs: Your operating system is built on your beliefs. Do you believe you're not a good leader? Do you believe you're too old to change careers? These stories you tell yourself can be limiting. The first step is to recognise them and decide if they're still serving you. An upgrade starts with changing the narrative in your head.
- Your Strengths: Your personal OS is also shaped by your innate strengths, the things that give you energy and allow you to thrive. Understanding your natural talents helps you work with, not against, your core self. An effective OS allows you to lean into these strengths and recognise when you need to adapt.
- Your Habits and Routines: The daily rituals you follow are the software applications of your OS. Are they helping you achieve your goals, or are they draining your energy? Simple changes, like prioritising sleep or dedicating time to focused work, can have a domino effect on your overall system.
The Goal of Upgrading
The goal isn't to become a different person, but to become a more authentic and effective version of yourself. Upgrading your personal OS is an ongoing process of self-awareness. It's about knowing your limits, understanding what gives you energy, and making purposeful choices.
The best leaders in the world aren't living two separate lives—one for work and one for home. They have one authentic OS built on consistent values. While the reality is that businesses move quickly, and you have to adapt, having a strong personal foundation makes you more resilient and able to navigate change with purpose, rather than just reacting to it.
Ready to dive deeper into this topic and hear more insights from the Offscript, part of the Wild & Wise Podcast co-hosts? Tune in to the full episode “The Power of Reinvention and The Future of You” on YouTube, Spotify, or Apple Podcasts to hear the complete conversation.
And for more on taking control of your life and career, check out our related article: "Stop Following and Start Building Your Life by Design."
Be Wild & Wise Today
Are you ready to unlock your strengths and achieve personal or professional growth? Whether you need help with personal branding, team alignment, or strengths-based coaching, Wild & Wise is here to guide you. Book your free consultation and take the first step towards your transformation.
Subscribe to our newsletter
Lorem ipsum dolor sit amet, consectetur adipiscing elit. Suspendisse varius enim in eros elementum tristique.
Related posts
Explore more articles from Wild & Wise
The Missing Playbook: How Founders Navigate Identity Shifts
When Derek stepped down from ViddSee after nearly a decade, people kept asking: "What's next?" He couldn't answer. Not because he lacked ideas, but because he didn't know who he was without the company that had consumed his identity.
"It didn't even feel like just a work identity," Derek told the podcast hosts. "It was a very personal identity that became work. And to be stripped away from that, I was like, Who am I really?"
The Identity Fusion Problem
Derek's story reveals why typical career transition advice fails founders. This wasn't losing a job—it was losing an extension of himself. For years, people had said, "Derek is ViddSee, ViddSee is Derek."
When well-meaning friends advised, "your work is not your identity," Derek found it impossible to accept. "It wasn't work," he explains. "It was my existence there. What I built."
This fusion between founder and company creates unique grief when separation occurs. Unlike other professionals, founders aren't just leaving a role; they're severing from their vision, values, and years of emotional investment.
What Founders Actually Grieve
Derek's experience illuminates the multiple layers of loss:
Loss of Purpose: VidSee represented Derek's mission to empower Asian storytellers. Losing that vehicle meant losing his primary source of meaning.
Loss of Identity: Being known as "ViddSee's founder" shaped how Derek saw himself and how others saw him.
Loss of Structure: The consuming daily rhythm of running a company suddenly vanished, leaving him unmoored.
Loss of Community: Teams, investors, and industry peers formed his primary social network.
Loss of Future Vision: His imagined trajectory—for himself and the company—required complete rebuilding.
Why "Getting Over It" Doesn't Work
Derek initially gave himself a deadline to sort everything out by year's end. When December arrived without resolution, his frustration compounded the sense of being lost.
The breakthrough came when he stopped managing his grief and started feeling it fully. "If you're sad, feel sad. If you're angry, feel angry," he reflects. "Why are we suppressing what we're supposed to feel?"
This meant waking up at 3 AM with anxiety, writing in caps lock when frustrated, and sitting with the full weight of loss. Rather than pathologising these responses, Derek began understanding them as necessary.
The Turning Point
Derek's perspective shifted after watching a simple YouTube video with the message "everything ends." This basic truth helped him contextualise his experience within natural cycles rather than personal failure.
"As much as the founder, building and building and building, you cannot have things end," he explains. "You got stakeholders, you got investors—you can't have things end. So I was never in that psyche or that language."
Rebuilding, Not Rejecting
Friends suggested Derek "throw away" his past and start fresh, but the healthier path involved integration. "There were people around me that were like, no, don't throw away, you rebuild. You stack on top."
This reframe helped Derek see VidSee as one vehicle for deeper values that predated the company and would continue beyond it. His current venture, BE (The Be Company), represents evolution rather than departure—still empowering creators but with expanded scope.
What Actually Helps
Derek's journey reveals what founders need during transition:
Permission to Feel: Explicit support to sit with difficult emotions without timeline pressure.
Protected Time: Derek describes his "adult gap year" as essential for reflection without productivity demands.
Story Sharing: Talking with strangers about his experience helped Derek realise he wasn't alone.
Community: Connecting with others navigating similar transitions provided validation and practical advice.
The Hidden Gift
Derek's grief forced examination of patterns he'd ignored during company building—overwork, neglected relationships, leadership blind spots. "If I were to work on myself better, then maybe it could affect how I show up in relationships with co-founders," he reflects.
This self-examination became the foundation for more sustainable approaches in his next venture.
Redefining Success
Rather than measuring how quickly founders bounce back, we might consider:
- Depth of self-understanding
- Quality of rebuilt relationships
- Development of sustainable practices
- Integration of learning into future work
By these measures, Derek's year-long process wasn't delayed—it was a thorough preparation for better leadership.
Confirmation Bias: The Invisible Blindspot in Leadership
I've just started my second degree. A Bachelors Degree in Psychology (Organisational Psych). Part time of course. And as I embark on this fun new chapter, re-inventing my new way of life - family, life, fitness, work, I've also decided to take what I learn in uni and apply it to my workshops, strategies, clients and work.
Here's a take on Confirmation Bias. I've seen it at work in the office. I've seen this at work in my own reflections. Let's get into it a little more, from the lens of leadership.
Ever you ever noticed how some leaders only listen to those who agree with them? Or dismiss ideas that challenge their assumptions?
That’s confirmation bias at work.
Confirmation bias is our tendency to favour information that confirms what we already believe and to ignore or downplay anything that contradicts it. It’s human. It’s subconscious.
And for leaders, it can be dangerous.
What does this look like at work?
Here are a few real-world examples:
- Hiring decisions
- Innovation blind spots
- Performance reviews
Why leaders need to care:
Leaders, you have the responsibility to shape culture. We are all humans and when confirmation bias goes unchecked, we limit ourselves and also the business.
- Diversity of thought gets stifled
- Innovation slows down
- Trust within teams may erode
What could be the biggest risk in leadership when Confirmation bias is in play?
Unawareness. Most leaders don’t even know they’re doing it.
What can you do?
As I begin my Bachelors in Organisational Psychology, here’s what I’m learning: self-awareness is everything.
Here are a couple of thoughts that could help you as a leader:
- Slow down your decisions. Ask yourself: What might I be missing?
- Encourage dissent. Invite voices that disagree with you.
- Keep a bias-check partner. Someone who’ll challenge your blind spots.
You don't need to know all the answers in leadership. You need to have a vision, a plan and more importantly, you need to be open.
If you found this helpful, follow me for more thoughts as I share what I’m learning on organisational psychology, leadership, and the mindsets that drive better work.
Unlearning Entrepreneurship: A Simple but Powerful Take on Career, F&B, and Life
Why F&B in Singapore Can Be Challenging
For many in the F&B industry, the dream is to find a profitable niche and then scale quickly. But as Chua Ee Chien learned, that strategy can be a fatal mistake, especially in Singapore. He argues that the country's unique market forces businesses to thrive at the extremes—either as a high-end destination for those with money to spare or as a low-cost hawker stall serving the masses. The "middle ground," where you compete with everyone and their mother, is a place where businesses "go to die."
His own experience serves as a cautionary tale. He admits that his business, which started with a single outlet, made the critical error of expanding too quickly, a common tendency in Singapore. This over-eagerness, he believes, is what "killed" the venture. He learned that being "fickle" is a Singaporean trait, and without an effective strategy to combat it, even the most promising concepts can fade away.
The Unsung Heroes of Success: Hard Work & Resilience
"Quiet Quitting," Ee Chien's message is a refreshing reminder of the old-school virtues of hard work and unyielding resilience.
He argues that these are the skills that ultimately allow you to adapt and survive. He recounts facing a 60% increase in cooking oil prices and a 30% jump in a chef’s salary in just six months—insurmountable challenges that demanded more than just a good business plan.
His philosophy challenges the idea that a successful pivot is an act of pure genius. Instead, he believes it is born from the gumption to push through and the wisdom to recognise a new opportunity when it presents itself. He learned that even if you have the intelligence and capital, without resilience, you won't be able to pivot and try new things.
The Maverick's Journey to Finding Joy
Ultimately, Ee Chien’s journey is about more than business; it's about personal growth. It's the story of a man who moved from a "good white-collar job" to a venture he found on a website and then back into the corporate world. His key takeaway is simple: don't do what your mother, father, or society expects of you. Do what you genuinely enjoy.
He reflects on how he learned more in three months at Uber than in two years at a prestigious bank because the work was "super fun" and provided an environment where he was constantly learning. This search for enjoyment and new experiences has defined his journey and continues to guide him as he explores new opportunities in the fast-paced world of AI and Web3.