You know when someone casually mentions they’ve been working for 20 years, and you think, “Wow, that’s a long time” only to realize…wait, you’re that person? Yep, that’s me. This year marks 20 years in software, and it feels surreal.
In 2004, I started as a fresh graduate at McKinsey & Company. I was excited, nervous, clueless, and had no idea where this path would lead me. Two decades later, I’ve worked with some of the best teams at McKinsey, Microsoft, Target, and, yes, Microsoft again—because sometimes you come full circle.
So, here’s my look back at 20 years in software—20 moments, lessons, and memories that shaped this journey:
1. I started at McKinsey straight out of college.
I didn’t really know what McKinsey did—or what “consulting” even meant. My first role: IT Analyst. I showed up fresh out of college, clueless about the industry and without a proper business suit. But I was eager to learn, and that’s what set everything in motion.
2. Microsoft was next—my tech playground.
At McKinsey, I worked on internal apps and slowly got into relational databases, learning everything from scratch. That gave me the fuel—and just enough confidence—to apply to Microsoft. I joined as a Product Support Engineer, where I spent my days solving all kinds of tech puzzles. And I loved every minute of it.
3. My first “aha!” moment about communication.
A thing I learned early was that tech skills are only half the battle. The real test is explaining a deep technical concept so clearly that even a middle schooler could get it. That’s when it clicked—clear, simple, and consistent communication isn’t just nice to have; it’s everything.
4. Target was where I truly grew up.
When I joined Target, I went from fixing systems to building systems for a multi-billion-dollar retail business selling everything from toilet paper to TVs. It was my first time on the other side of the fence—where even a few hours of downtime could mean millions in lost sales. Let’s just say, I learned real quick how important keeping things running was!
5. Open-Source software (PostgreSQL and Linux) became my best friends.
During my Target years, I discovered the power of open-source software, and let’s just say I’ve been a PostgreSQL nerd ever since. There’s a certain joy in tweaking pg_hba.conf or scripting a perfect grep | awk pipeline to save the day—it’s the stuff geek dreams are made of.
6. Microsoft called me back in 2022.
Like a boomerang, I found myself back at Microsoft in 2022—but this time as a Product Manager. Same company, completely different role. Now I wasn’t just fixing products; I was actually building them. It’s like going from patching the boat to designing the ship—hope it floats!
7. Good product design is about solving the right problems.
As a Product Manager, I’ve learned that building great products isn’t just about adding features. It’s about understanding what people really need—even when they can’t explain it—and creating something so simple and useful that it feels like it’s always been there. The best designs don’t scream for attention; they just work, quietly making life better. That’s what I aim for.
8. Empathy is a superpower.
Understanding a customer’s goals, frustrations, and perspective has been the key to building products that actually matter. Once, I had to deal with a customer who renewed their enterprise license, carefully stored the new key in their office safe—but forgot to actually update it in the system. This caused production downtime, and they were understandably frustrated. The only way to solve this was by listening with empathy, acknowledging their stress, and working with my team to create a solution—like enabling auto-renewals. (Also, thanks to cloud subscriptions, we don’t run into these kinds of issues anymore!)
9. I once spent 14 hrs. troubleshooting code… only to find out it was a missing semicolon.
Ah, the joys of tech. The logs didn’t help, and nothing made sense. After hours of debugging, I found the issue—a single missing semicolon. I fixed it in two seconds and just sat there, wondering why I didn’t see it sooner.
10. Seeing my team’s work in action is the best feeling.
When customers use the features we build and share real-time feedback, it’s a great feeling—but it’s so much more than that. They’re not just using our product; they’re trusting us to run their million-dollar businesses. It’s immensely scary, humbling, and empowering all at once. Knowing that our work keeps their operations running smoothly—and sometimes even saves the day—reminds me why I love what I do. It’s a responsibility we don’t take lightly.
11. Sharing knowledge makes the whole team stronger.
Whether it’s writing blogs, mentoring, or speaking at conferences—we grow by learning from each other.
12. Patience is a skill.
Building great products takes time. So does solving tricky bugs. I’ve learned to push forward but also know when to wait.
13. I’ve presented in boardrooms, at conferences, and… once to an audience of two.
It turned out to be one of the best conversations I’ve had. So sometimes you crush it, other times you learn. Either way, you keep going.
14. High availability, low stress? Not always.
I’ve seen systems fail, recover, and bounce back stronger. Tech has its challenges, but resilience is part of the fun.
15. Life-Runs-On-Code—literally (also my Facebook username).
Millions of users. Billions of transactions. And it all comes down to the lines of code we write. It’s amazing—and a little terrifying—to think that so much of the world relies on the systems we build. But that’s also what makes it so exciting.
16. High-Touch complements High-Tech.
Users love technology that works, but they remember the people who make it feel effortless. High-tech solutions solve problems, but high-touch moments—listening, understanding, and empathizing—build trust. That’s how great experiences are made. iPhones, anyone?
17. I’m grateful for the mentors who guided me.
From McKinsey to Microsoft and Target, I’ve been lucky to learn from the best.
18. Work-life balance is a moving target.
Some days I nailed it. Other days, not so much. And that’s okay.
19. I’ve written countless lines of SQL, and I still think PostgreSQL is magic.
Just putting it out there 😊
20. Finally, two rules I’ve learned along the way.
- The climb is the fun part.
- The person who has the most fun wins.
Looking back, I’m proud of the journey—starting at McKinsey, growing with Microsoft, scaling at Target, and returning to Microsoft for innovation. Looking forward, I’m more excited than ever for what’s next.
On to the next 20. 🚀
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As a friend, it’s inspiring to see your incredible 20-year journey in software—filled with passion, growth, and lessons that make me proud and genuinely happy for all you’ve achieved.
Thanks Samik! Glad you found this inspiring ❤️