Last month, I hit a milestone: 20 years of work. I still remember graduation like it was yesterday — and how we used to laugh at job ads asking for “20 years of experience,” imagining how ancient we’d be by then. Well, I’m here now. Definitely older. Slightly wiser. Or maybe just someone with thicker skin from facing change, ambiguity, and randomness.
In my first draft of this, I started down the LinkedIn path of “two decades of relentless battles against workplace evil, sleepless nights building the next big thing”… but that’s not me. Yes, I’ve worked hard to succeed — but I’ve also worked hard not to fail. They’re different.
I’ve worked in three countries, eight (or nine, depending on how you count) companies, and with hundreds — maybe thousands — of people from dozens of nationalities. I’ve taken wild, irrational decisions (we call them “risks” in professional jargon) that worked brilliantly, and I’ve made perfectly sensible decisions that blew up in my face. If there’s one thing I know for sure: every story has multiple angles, and you can almost always frame it as a success or a failure.
Anyway — enough philosophy. Here are a few notes for my future self. Writing them here means they might survive. (No promises I won’t delete them later.)
It’s Always Day One
If I learned one thing at Amazon, it’s this: It’s always Day One.
At first, it felt like one of those inspirational slogans you write but don’t follow. But after more than five years at Amazon, I get it. Day One thinking means not leaning on yesterday’s wins. You act like you’re just starting — ambitious, focused, and willing to take action so you don’t miss opportunities or let the competition beat you.
This applies everywhere: your job, your relationships, your startup, your investments. Think about the future as if the past doesn’t exist. Avoid “analysis paralysis.” Treat yourself like a startup that needs to win, not like a comfortable legacy business.
You Have to Unlearn to Learn
Very few things stay true forever — not at work, not in life.
What worked 20 years ago may not work today. Sometimes, success in a new role means unlearning what made you good in the old one. A program manager thinks differently from a product manager, a finance manager, or a software manager. The skills don’t always translate.
One book that explores this idea in detail is What Got You Here Won’t Get You There. The behaviors that fuel early success can become obstacles later — especially in leadership.
Build Your Own Path
There’s no single “right” career path. Success isn’t about picking the perfect role — it’s about making the role work for you.
I know people thriving in NGOs, despite low pay. Others can’t stand big companies and live for building startups. Some treat work as a paycheck; others as an identity. All of them can be “successful” on their own terms.
Hard work plus some luck can make even an unpopular, risky choice turn out brilliantly.
Work With Intentions
I almost wrote “define your own success” — but that’s easy to say, hard to do.
What counts as success changes over time: As a fresh grad, it’s getting that first job. A few years in, maybe it’s a promotion or a big project. Later, maybe it’s starting your own thing, or just having work-life balance.
The trick is knowing why you’re doing things. As a friend once told me: always write your objectives before starting anything new. For example, if you get an offer from a FAANG company — is it the brand name you want? The pay? The learning? The scale? Same with a startup — is it the thrill? The equity? The autonomy? Without clarity, you won’t know what to maximize for. Don’t overcomplicate it, but try to understand your “why” even in hindsight. It helps you understand your own behavior.
Work-Life Balance Is More Complex Than We Think
The traditional 9-to-5, never-think-about-work approach sounds nice, but it doesn’t match reality for ambitious careers.
Work and life influence each other. Great opportunities don’t arrive on schedule. Sometimes you need extra effort for critical projects or learning. Other times, you need to step back completely.
The key isn’t rigid boundaries — it’s being intentional. Ask yourself: Is this extra effort strategic, or am I just being busy? Am I working late because it’s necessary, or because I can’t say no?
Sustainable performance requires both intense focus and real rest. Be strategic about when to push and when to pull back.
Save Money
If you read any personal finance book, you’ll get the standard advice: save three to six months of salary for a rainy day. I’d go further — save at least a year’s worth.
Not just as a safety net, but as a freedom ticket. Enough to let you take bold moves: join a risky startup, take a long sabbatical, accept that international role. Money doesn’t just protect you; it gives you options.
Play for Big Success, Not Just to Play Safe
I still remember this line from The Ride of a Lifetime by Bob Iger, Disney’s CEO: “Don’t be in the business of playing it safe. Be in the business of creating possibilities of greatness.”
When I first read it, it was eye-opening. Most of the time, I was following the playbook — focusing on what the business needed, but not making truly bold moves (other than changing companies). When I started shifting my perspective, everything changed. You do things for the possibilities, for getting it right — not for the fear of losing.
If I could sum all of this up, it’s this: nobody knows the “right” way. You have to build your own career, one day at a time. Not only expect change — seek it, and be ready for it.