How to Navigate Non-Linear Career Progression

Your “chaotic” career might be the thing that turns you into an operator who can fix what others avoid. Most people think you need a perfect linear path to reach executive-level operations work. Not true. If you’ve jumped roles, industries, or departments, here’s the secret: You’ve been training in systems design without realizing it. I learned this the long way. I’ve worked in marketing, proposals, process improvement, healthcare ops, data analysis, enterprise automation, and now AI-enabled workflow design. At the time, it looked scattered. Now I see it clearly: Every role taught me how work actually breaks, and why systems crumble long before people do. If your path has been messy or nonlinear, here’s how to turn that into an advantage: 1. Stop defining yourself by your last job title: Your value is in the intersections. 2. Treat every job like systems training: Every broken workflow you’ve touched matters. 3. Shift your identity early: Show up like someone who designs better systems — not just someone who survives bad ones. 4. Use your range: Pattern recognition is an executive skill. You only get it by seeing many environments. 5. Focus on clarity: If you can fix fragmentation, reduce cognitive load, and make work make sense… you’re already operating above your title. That’s how I built my career.nAnd it’s how you can build yours. Your path doesn’t need to be straight. It just needs to be yours.

The most dangerous career strategy in 2025: Following a path that worked for everyone before you. Over the last few weeks, my inbox has been flooded with messages of strife and anxiety from brilliant people blindsided by layoffs. To be honest, there is very little I can say to many. Most played the game of life perfectly. They went to great schools, got good grades, landed prestigious jobs, and worked hard. Their stories raises a critical question: What if it's not just specific jobs disappearing, but a fundamental flaw in how we've viewed careers and success? The linear world we've grown accustomed to is abruptly being disrupted. The ladders that guaranteed safety and success no longer hold their promise. For decades, we've operated under the belief that: → Business success comes from perfect execution → Career paths follow logical progression → Expertise can reliably predict the future My friend Gaetan recently said: "What if success was always more random than we wanted to believe? What if strategic planning was always more about the illusion of control than actual causality?" Navigating uncertainty now requires us to: → Judge the quality of our decisions not just results → Embrace uncertainty over false certainty → Recognize success as probabilistic For individuals navigating this shift: → Build skill portfolios, not linear paths → Combine skills uniquely; avoid single specialties → Design for uncertainty, not control → Test multiple career options → Adapt quickly; don’t chase perfection → Diversify income streams Following these principles won't just help you withstand career shocks, it makes you antifragile, allowing you to grow stronger from volatility and stress. The human cost of layoffs extends beyond financial insecurity; it's the painful realization that playing by the rules perfectly was never a guaranteed protection. Yet within this destabilizing reality lies a massive opportunity: to redefine success itself. Success shouldn't be a singular path to follow, but the freedom to create multiple paths of your own design. The true cost of clinging to old models isn't just stalling your career; it's missing the chance to discover who you might become when you stop following and start creating.

Of non-linear career trajectories and paths...... I started my career as a full-time clinician (Paediatrician) and moved to become a clinician who worked in research. These days I see myself as a researcher who works as a clinician... 😊 I think non-linear career paths are a double-edged sword, they can be exciting, engaging, and many times fulfilling. They also can be froth with fear and anxiety because the pathways are usually nebulous and there are no manuals for progression or pre-defined steps to take for a successful career. Over the years, I have applied a few principles to my path and I thought to share- 👉 Learning from others Never underestimate the power of learning from those who are a few steps ahead of you. A 30-minute conversation with someone ahead of you can provide insights that can take you the next few years to learn on your own. I think knowledge is power and knowing how things work is always an advantage and brings clarity. There is a popular saying - "There is no favorable wind for a sailor who does not know where they are heading". I think clarity comes from knowing. Many times, you do not need to ask to know, at times just observing tells you a lot. People are also willing to help others who can show they have made an effort for themselves. 👉 Avoid building career silos Silos by nature are isolated from each other. I think when there is no linkage between career decisions, progress is minimal and career decisions can feel like we are starting all over (In some instances, this might be necessary). I think this can bring with it negative feelings of sadness, doubt, or feeling insufficient. I think one guiding principle for me has been to build on past experience and link the next experience to a previous one. At times it feels like weaving tapestry but it gives you a sense of fulfilment and a feeling of progress. 👉 Make career decisions that resonate with your values. I think one side effect of a non-linear career path is the multitude of possible career pathways that open up to you. Someone once said it brings with it the problem of many choices. The more I go down this part, the more I recognise it is important to mute the 'noise' around. Listen to yourself. What do you value, and what gives you fulfillment? 👉 Have a growth mindset I think I have always been guided by opportunities that make me grow and develop in a multitude of ways and those that drive me to bring more value to myself and my chosen field. I think growth brings a sense of fulfillment and calm when you navigate a non-linear career path If you see yourself as someone who has navigated the non-linear career pathway, please comment below on strategies you have used successfully throughout your career and join the conversation. Perhaps someone might find value in this 😊 #phdjourney #careerdevelopment #careertalk #career

Career mistakes I made so you don't have to. I've made plenty of missteps over 20 years across my roles with Big 3 Consulting firms such as Boston Consulting Group (BCG) and Fortune 50 companies such as Procter & Gamble. But looking back, each of those mistakes exposed blind spots. They taught me great lessons that helped me ‘level up’ each time. So I'm sharing three whoppers - and how to navigate them better: ❌ Thinking it’s linear, when it’s actually chess No two paths are the same because they don’t have to be. Each step you take guides the next. Each role buttresses your future skills. ✅ Rather: Ditch assumptions about linear progression. Embrace adaptability and open-mindedness to what comes and how it may be unique versus others. ❌ Chasing success rather than experience Failures forged me more than wins. In my two-decade long career, I missed fiscal targets only two years - yet those 10% failures were more formative than those 90% successes. ✅ Rather: Don't fear flops - extract learnings from scar tissue that makes you stronger. ❌ Undervaluing self-care Careers are a marathon, not a sprint. Unsustainable sprints that many of us ‘buckle down’ to compromise your long-term endurance. ✅ Rather: Prioritize your wellbeing. Nurture mind, body, spirit - that's how you gain staying power for the long haul. My early missteps taught me invaluable lessons to steer my working life and career. What career pitfalls tripped you up and how did you course-correct? #CareerMistakes #LeadershipAdvice #CareerWisdom #NavigatingSuccess #lLinkedinnewsasia

Gone are the days of a linear career path. Not long ago, the idea of a successful career followed a simple formula: Choose a study field > land a job > climb the ladder > retire. But today, career paths are anything but linear. More professionals are weaving between industries, blending their passions and redefining success. I went from climbing the corporate ladder as an Accountant, to taking a leap into tech and creativity — aligning my career with my passions and purpose. At school, I gravitated towards structure and logic, which led me to study accounting. It seemed like a practical and stable choice — one that promised job security and a clear trajectory. But at the same time, I craved the creativity I found through studying art, IT and photography. So I decided to pursue a double degree in business and design. While studying at uni I kickstarted my career at an accounting firm, getting a head start in the corporate world. Meanwhile on the design side, a Fine Arts assignment led me to launch my photography side hustle. I soon found myself fitting creativity into the margins of my finance career and defying the belief that Accountants couldn’t be creative. I knew I had more to give beyond a traditional corporate career, but I wasn’t sure how to blend my skills and passions in a way that felt authentic. Then came the opportunity to work at Canva. This was one of those sliding doors moments. I found my sweet spot at a company that is values-driven and where I could contribute to doing good in the world, while seamlessly merging my analytical and creative skillsets. The transition from corporate to tech was huge, but it unlocked a whole new level of growth. I now apply my financial expertise while being surrounded by creativity, innovation and a culture that encourages out-of-the-box thinking. If you’re feeling stuck or considering a career pivot, here is some advice: — Your passions matter. If you feel pulled in multiple directions, explore your intuition. Unexpected opportunities may follow. — Skills are transferable.  The analytical thinking I developed in public practice helped me thrive in tech, just as my creative background has shaped my approach to problem-solving. — Side hustles can open doors.  My photography business isn’t just a creative outlet — it has built entrepreneurial skills, connections, and confidence. — Growth happens outside your comfort zone.  The world of tech was unknown, but taking the leap led to profound learning and career development. — You don’t have to have it all figured out.  Each challenge offers learning and adds to your story. You know I love a unique personal brand! Your career doesn’t have to fit into a box — there’s value in taking the unconventional path. If you’re currently navigating a career change or thinking about one, I’d love to hear your story and help unblock your next step. Photo taken on my third day at Canva — which seems like a lifetime ago!

What if you wake up in five years and realize you built the wrong career? In this economy?? That is what so many young professionals are afraid of. Last week, I was chatting with a college senior who was feeling completely stuck. She had several options in front of her but had no idea how to decide. She asked me, “You have had such a non-traditional career path. How did you know each step was the right one?” The truth is, I didn’t (and still don't) always know. But looking back, my career does not feel as “non-traditional” as she made it seem. Strategy consulting, human resources, coaching, all fed into an underlying narrative of wanting to help people. The pattern was simple. I would start with a hypothesis about what I thought I wanted. Then I would test it. For example, I once thought I wanted to work in healthcare strategy. So I took on healthcare-focused consulting projects. One night, I was working late on a proposal, sitting next to an analyst who genuinely loved the industry. She read about healthcare trends in her free time. She debated industry news with enthusiasm. I envied that enthusiasm and used it as motivation to find something I was equally as excited about. Though healthcare wasn't my calling, I did not regret taking those projects because they gave me data. They helped me pivot with confidence instead of guessing. This is why I believe in treating your career like a series of hypothesis tests. Instead of waiting for the perfect answer, test your way into clarity. You do not need to quit your job or take a huge risk to start experimenting. A few ways to test: ➡️ Take on a project at work that aligns with an industry or function you are curious about. ➡️ Use informational interviews to learn what people actually do all day in different roles. ➡️ If you are job searching, apply to a variety of roles and notice what excites you during interviews. You do not have to make the perfect decision today. But you do have to start gathering real-world data. I wrote more about this approach in my latest piece. Drop a "send me the link" in the comments, and I will send it your way. 👉 Have you ever realized a job wasn’t for you? What gave it away?

I recently spoke with a rising star executive who said, “I am not interested in running a bigger business.” His sentiment - a clear departure from the traditional path of “moving on to the next big thing” - surprised me. The executive then explained that his desire was not to follow a typical career path; he craved something more meaningful and impactful. He was even willing to make a financial sacrifice to do something that energized him. This interaction sparked a realization for me: Top talent is no longer exclusively motivated by the next step in a linear progression. Many candidates seek non-traditional paths that align with their broader personal and professional goals. As leaders, we need to ask the right questions and take a more holistic approach to effectively manage our top team. Understanding what our people are truly solving for will allow us to unlock their best performance while maintaining their long-term commitment. Here are a few ways to think about managing talent: 1️⃣ Have broader conversations with your top team. Learn about their professional goals, such as: -testing a new function -mentorship from a more senior leader -professional development -coaching opportunities This approach will help you align their career goals with your organization’s vision in a more meaningful way. 2️⃣ Focus on multi-dimensional rewards. Beyond financial outcomes and status, other dimensions of benefits are increasingly important to your employees: -time -mental health -physical health -personal development -recognition -pride Take real steps to incorporate these goals while maintaining their professional growth. As we work through an evolving landscape of career progression, I encourage you to think about how your own leadership can evolve - and recognize that a linear trajectory is not the only way to advance. More importantly, if you are a leader, don’t make assumptions about what someone wants; ask them. Take the time to understand what your top talent truly values, both professionally and personally, and how you can help them reach their fullest potential, even if their path is not what you would expect.

"Should I take a career break?" I’ve led a non-linear career that included multiple breaks: when I had my first baby, when I left management consulting after burn out, when I went through cancer treatment, when I left my first start-up in search of more mission-driven work, and when I decided to take a longer sabbatical after I got laid off. I’ve also moved between full-time and part-time, as well as employed, unemployed, and self-employed. Here are the three simple questions, which have complex answers, that helped me clarify my intentions and move forward with confidence at key decision points: 1. What are my feelings telling me? Have a pulse on not just “how” you’re feeling, but “what” emotions you’re feeling and what they’re signaling to you about the change you need to create in your life. It’s ok and normal for change to feel hard and uncertainty to be paralyzing, but recognizing what mental roadblocks (e.g., guilt, an outdated sense of identity, fear, etc.) are holding you back is critical to being able to break free of them. 2. What am I optimizing for? What I was solving for changed significantly at various periods in my life. What are you solving for at this stage in your career? Time with family and friends? Mission-driven work? A stable income? Opportunities for learning and career growth? The answers to this question help you clarify your intentions and define your must-haves vs the tradeoffs you’re willing to make. 3. What’s my “path of least regret?” Understand the options in front of you and how you feel about each, but don't let them limit you. Your intentions inform your aspiration or North Star, so work backwards from there to identify what might be a “third option” that mitigates your risks and concerns, and not only minimizes your regret, but maximizes your peace of mind. Which of these three questions will be the hardest for you to answer? #decisionmaking #careerbreak #executivecoach #personalgrowth #pathofleastregret

I used to think career success was a ladder – until life taught me it’s more like a winding path. Embracing detours has been one of the most valuable lessons in my career journey. 𝗛𝗲𝗿𝗲 𝗮𝗿𝗲 𝗺𝘆 𝟭𝟬 𝗸𝗲𝘆 𝘁𝗮𝗸𝗲𝗮𝘄𝗮𝘆𝘀 𝗼𝗻 𝗻𝗮𝘃𝗶𝗴𝗮𝘁𝗶𝗻𝗴 𝗮 𝗻𝗼𝗻-𝗹𝗶𝗻𝗲𝗮𝗿 𝗰𝗮𝗿𝗲𝗲𝗿: ➡️ Be Open to Unexpected Opportunities Growth often comes from roles you didn’t plan for. ↳ Say yes to projects outside your comfort zone – they may lead to your next big move. ➡️ View Setbacks as Stepping Stones A career “pause” or shift isn’t failure; it’s redirection. ↳ Reflect on what a setback taught you and how it prepares you for what’s next. ➡️ Build Skills, Not Just Titles Skills you pick up in one role can unlock opportunities in another. ↳ Focus on mastering transferable skills that keep you versatile. ➡️ Network Beyond Your Industry Career paths often connect through unexpected people. ↳ Invest in relationships outside your current role – it’s often who you know that opens doors. ➡️ Prioritize Personal Growth Over Promotions True career fulfillment comes from alignment, not titles. ↳ Ask yourself, “Is this role helping me become who I want to be?” ➡️ Accept the "Side Step" as Forward Movement A lateral move can be strategic if it brings you closer to your goals. ↳ Seek roles that build critical experience, even if they aren’t an immediate step up. ➡️ Stay Curious About New Fields Sometimes your passion doesn’t align with your degree or background. ↳ Explore areas of interest, even if they don’t “fit” your current role. Curiosity can lead to big shifts. ➡️ Create Value Where You Are Meaningful impact can open doors faster than climbing ladders. ↳ Focus on making a difference in your current role, even if it’s not your end goal. ➡️ Pace Yourself – There’s No Deadline Success is a marathon, not a sprint. ↳ Trust your timeline and avoid comparing your progress to others. Career paths are deeply personal. ➡️ Remember – Growth Can Be Nonlinear Each role and experience adds layers to your unique path. ↳ Embrace every twist and turn; they’re all part of your story. The straight-line career is a myth. Embrace the detours – sometimes, they’re where you find your greatest success. Quote: Gary Tan -- ♻️ Find this helpful? Repost to remind others that career paths are unique. ➕ Follow me Nico for tips on designing an intentional and fulfilling career path.

For those of you interested in management positions (and not everyone is) think of managing your career not as scaling a ladder, but instead as climbing a tree. Most ladders look pretty much the same with standard length progressions proceeding in a straight line. A colleague manning the base increases your confidence and as long as you don’t step on the rung labeled “unsafe to step above here,” there is little risk. Career paths rarely resemble a ladder. The best climbing trees are different, with branches extending in every direction. Some are thick, easily supporting your weight, others questionably thin. The distance between branches varies challenging you to stretch and the higher you go the more dramatic the consequences of a fall. The most popular ones are large with room for multiple climbers at the same time. Some of those who started upwards before you will assist you in moving higher and others will crowd your space, competing for the next move. From the ground you can easily see the very top of the tree, but once you are on the first branch your view is blocked. That’s actually good. It is way too soon to be thinking about the view you will get from the top branch. You first need to be comfortable on the one under your feet and then start looking for your next move. Down low there are many paths forward and you must decide which one works best for you. It could be that your first choice isn’t available, occupied by someone who is turning his branch into their personal treehouse. Stay patient – but not too patient – and consider the alternatives. When I helped others think about managing their careers, I always made three points: First, managing your career is your responsibility. My responsibility is to help you become more valuable to the company and to provide opportunities for you to grow Second, when you are ready to consider a move, identify a role that you would like to take on next and, most importantly, tell me why. Third, take the other tree dwellers to lunch. Learn about what others do and how they got to the branch they occupy. I suspect you will also learn that at some point they had to modify their planned path upward. The relationships you build may result in a hand reaching down to pull you up at some point in the future. I like my tree climbing analogy, but it needs a little more context to address the real-world dynamics of career management. Is the tree healthy? What happens when certain branches get trimmed unexpectedly? What happens when growth is stunted during a dry year? These may cause you to change your path or even change your tree. When you are young there is a certain excitement from climbing a tree. I expect you will feel some of that same emotion as you manage your career. Onward and upward!