Building a Strategy That Moves With You
I tend to have a “strange” habit of combining concepts in my mind that – at first glance – have nothing to do with each other.
That’s exactly what happened the other day, when I found myself thinking about two seemingly unrelated topics: my career trajectory and my next moves in investing and portfolio management.
Out of nowhere, a question popped into my head: What if we borrowed a concept from investing – specifically, “alpha”- and used it to reframe how we approach our careers? Let’s call it Career Alpha.
When we talk about careers, we’re often handed the old-school playbook: pick a profession, climb the ladder, collect titles. But for many of us, that linear approach no longer applies. Today’s career paths twist, pause, accelerate, re-route – often unexpectedly. To stay ahead, we need something more – something that creates value beyond simply doing our day jobs. That’s where Career Alpha comes in.
In investing, alpha is the excess return generated beyond the benchmark. Translated into career terms, it’s the unique value you build through intention, experimentation, and self-awareness. It’s not just about money or promotions – it’s about shaping a professional life that compounds over time and reflects who you are, what you care about, and how you want to grow.
So how do you generate alpha in your career?
Define Your Benchmark: What Are You Comparing Yourself Against?
In investing, before you can generate alpha, you need to know what your “market return” is. In traditional investing, that might be the S&P 500. In careers, it’s obviously trickier.
To figure that out, you need to know who you’re comparing yourself to. Are you benchmarking yourself against peers in your field? Your own past performance? An imagined version of success? Defining your benchmark is personal, but crucial. Without it, you won’t know whether you’re outperforming or just moving.
Maybe your benchmark is a comfortable, well-paid corporate job. And that’s fine — just be honest about it. But then ask: What does “better” look like for me?
From Linear Planning to Strategic Positioning
Building on the above, the climb-the-ladder model is outdated. Careers today are like portfolios — diverse, flexible, and multidimensional.
Instead of planning every step, it makes more sense to think in themes: Are you optimizing for learning, leverage, lifestyle, or long-term impact? What problems do you want to be known for solving? What spaces do you want to play in — tech, sustainability, finance, design?
Positioning is about placing yourself in environments where you can gather relevant experience, relationships, and insights — even if they don’t come with a neat job title.
Spot the Asymmetry: Where Are the Positive Optionalities?
In investing, great returns often come from asymmetric bets: high potential upside with limited downside.
In careers, those look like projects that stretch you, platforms that amplify your voice, secondments that broaden your exposure, or people who pull you into new circles. They often don’t come with guarantees – but they open doors.
Ask: What can I do today that could unlock something bigger tomorrow – even if I don’t know exactly what that is yet?
Design for Compounding Returns
Alpha builds over time. So does your career.
The content you create, the relationships you nurture, the ideas you explore, the systems you build – those are all assets that can grow if you keep showing up with intention.
Instead of chasing every shiny title, think: What can I build now that pays off for years to come – professionally and personally?
Protect the Downside: Manage Risks Like a Portfolio
No growth comes without risk, no matter the area. But not all risks are equal.
In a career context, risk management means knowing the difference between productive risk (taking on a new challenge, switching industries) and destructive risk (burnout, misalignment, reputational damage).
Diversify your bets: build multiple skills, explore adjacent fields, maintain professional relationships outside your current role. If one area underperforms, another can carry you forward. Hedge yourself against the unexpected.
Keep Rebalancing: Evolve Your Strategy as You Grow
Life changes. You change. So should your strategy.
Borrowing again from investing, you should revisit your career thesis regularly. And in practice, that means asking yourself: Is your current setup still aligned with your values and goals? Are you over-indexed on comfort and under-invested in growth? Are you optimizing for someone else’s version of success?
Career Alpha isn’t a one-time calculation — it’s a mindset. You experiment, adjust, and realign as your life and the world around you evolve.
The Bottomline
Your career is your most important long-term investment. It deserves more than autopilot or borrowed benchmarks.
By thinking like an investor – curating your experiences, placing asymmetric bets, compounding your assets, and protecting your downside – you can create something more valuable than a stacked résumé. You can build something uniquely yours.
That’s Career Alpha. And it moves with you
