Career regrets: 10 tech workers share what they wish they’d done differently

Ask a tech worker about their biggest career regret, and they might have a hard time picking just one.

In a fast-changing, highly competitive industry, it’s easy to second-guess career decisions — and wonder whether another path might have been the better one.

In interviews with Business Insider, tech professionals from companies including Amazon, Google, and Meta reflected on the career decisions they wish they’d handled differently. Some regretted not leaning into AI sooner, while others mentioned turning down a job offer, staying too long at one company, or waiting too long to build a professional reputation in the broader tech industry.

Here’s what 10 tech workers said they regret most. (Their responses have been edited for length and clarity.)

I learned the hard way that loyalty wasn’t a two-way street

Mike Kostersitz is a senior director, product management at Nike. He worked at Microsoft for 31 years before being laid off last year. He’s in his early 60s and lives in Oregon.

My biggest career regret is not moving on more decisively before I got laid off.

I stayed loyal to a company that had been great to me since I started back in the ’90s, even as the job market and the industry itself changed dramatically around me. I kept believing loyalty was a two-way street, that sticking it out would be reciprocated.

In the end I learned the hard way that it wasn’t; the market shift hit me anyway, loyalty or not. If I could do it over, I’d have started testing the market well before the business yanked the carpet out under me.

I walked away from machine learning before it took off

This tech worker is a software engineer at Meta.

My biggest regret is not sticking with machine learning when I had the chance.

In 2019 and 2020 I was building machine learning models at an edtech startup; things like dropout prediction and engagement scoring. Even back then, the direction the field was heading felt pretty clear, even though the models were limited.

But when I went to graduate school I made a deliberate choice to focus on systems and infrastructure instead. It felt like the safer, more rigorous path at the time. Looking back, if I had stayed on the machine learning side, I would have been years into it by the time the field took off. I don’t regret the systems background, since that’s what makes me valuable now, but it’s hard not to wonder what that other path would have looked like.

I waited too long to build a reputation outside my company

Nikhil Singh is a data scientist at Amazon. He’s in his 30s and lives in Seattle.

If I had to pick one thing, my biggest regret is probably waiting too long to share what I had learned publicly.

I spent over a decade building products, solving problems, and watching the field of data science evolve from early analytics to today’s AI-driven landscape, but very little time writing, speaking, or contributing to the broader conversation around technology and decision-making.

What I didn’t appreciate early enough was that professional growth also happens outside the walls of your company. Within an organization, people may know the ideas you developed and the problems you helped solve. But outside it, you can easily be seen as simply another person with a title on LinkedIn rather than someone with meaningful expertise or a distinct point of view.

Had I started writing, speaking, and exchanging ideas with others sooner, I would have built not only a stronger body of public work, but also a broader professional identity beyond the companies where I worked.

I wish I’d handled some moments differently

This tech worker is a software engineer at a startup. She’s in her 20s and lives in the Northeast.

I honestly don’t have any major career regrets. Even the experiences that weren’t pleasant taught me something valuable about myself or about how organizations work.

There are smaller moments I wish I’d handled differently. Early in my career, there were a few difficult meetings where I became emotional, and with more experience I know I would handle those situations differently today.

I also worked in an environment where I felt concerns about a manager’s inappropriate behavior toward female colleagues weren’t addressed effectively. Looking back, I wish I had documented what I observed more thoroughly. That experience reinforced how important good documentation can be when raising serious workplace issues.

I underestimated how much location would matter

Sachin Jain is a data analyst at Google. He earned a master’s degree in business analytics and data science in 2025 from the University of Texas at Dallas. He’s 26 and lives in the San Francisco Bay area.

My biggest career regret was probably the timing and location of my master’s degree. As an international student, I came to the US during a period of significant policy shifts and one of the toughest tech hiring markets in years.

In hindsight, I also wish I’d chosen a university that’s more embedded in a major tech ecosystem like Silicon Valley. Being closer to where the industry is concentrated creates more opportunities for networking, internships, and serendipitous conversations that can make a real difference.

That said, I don’t regret pursuing the degree itself. The experience taught me resilience, forced me to adapt, and ultimately helped me land a role I’m proud of. If anything, the experience reinforced how much environment and timing matter alongside individual effort.

I wish I’d immersed myself in AI sooner

Sneja Shah is a senior technical program manager at the software company Red Hat. She’s in her 30s and lives in California.

I don’t have a major career regret, but if I could change one thing, I would have immersed myself in AI even earlier. My career began in data analytics, where I built a strong foundation in data engineering, business intelligence, and product analytics. Looking back, I wish I had started working directly on AI strategy and generative AI sooner.

That said, those years in analytics gave me the skills to understand business problems, measure impact, and make data-driven decisions. Those experiences have been invaluable in my transition into AI strategy, where I now focus on helping organizations adopt AI in ways that create measurable business value.

I learned that internal reputation doesn’t travel

Abhinav Bohra is a senior applied scientist at Amazon. He’s in his 30s and lives in Seattle.

My biggest career regret is that for most of my career, everything I built lived and died inside Amazon. People outside were publishing on the exact problems I was solving, and I never joined the conversation. I kept telling myself the work was proprietary. Honestly, the data was proprietary. The ideas never were. Some of them would have made decent papers.

Lately I’ve flipped that. I’ve started speaking at industry events, reviewing papers, and have become more involved at conferences.

If I’d started this sooner, I’d be a few years further along. Internal reputation doesn’t travel. Inside Amazon plenty of people knew what I’d built, but outside the building none of it existed.

I turned down a great job offer

This tech worker is a tech lead at a company in the insurance industry. He’s 41 and lives in Atlanta.

My biggest career regret is turning down a great job offer from my former boss, who was a vice president at my previous company.

I declined the offer because I had made a commitment to a client and wanted to see it through. But five months later, I was reassigned to a different client anyway.

In the end, I wasn’t able to fulfill the commitment that led me to stay, and I also missed the opportunity to work for a leader who knew my strengths. Looking back, as he’s built a large portfolio of business, I think I could have grown alongside him had I accepted the offer.

I sometimes wonder what a different career path would’ve looked like

Aimen Moten is a software engineer at Google. She’s in her 20s and lives in the San Francisco Bay Area.

For my biggest career regret, it would definitely be not exploring more of the career paths available in tech. I focused so heavily on software engineering that I never really explored roles like product management, solutions engineering, or cybersecurity.

When I talk to people in those roles, I sometimes wonder what my career would have looked like if I’d taken a different path.

I focused too much on execution — and not enough on impact

This tech worker is an engineer at Amazon. She’s in her 30s and lives in Virginia.

My biggest career regret was focusing too much on execution early in my career. I spent a lot of time making sure I built things well, but not enough time stepping back and asking what customer problem I was actually solving, why it mattered, or what impact it would have. Over time, I’ve realized that’s what separates a good engineer from someone who builds products people truly value.

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