What a Tech Founder's $60M Crisis Can Teach Us About Career Changes
"I am rich and have no idea what to do with my life" - Vinay Hiremath
I’ve been reading about Vinay Hiremath. After Atlassian acquired his video messaging company Loom for $975 million in October 2023, founder Vinay found himself at a crossroads. He's just shared a raw account of walking away from a $60M retention package, offering a rare glimpse into the psychological challenges of success. While most of us aren't facing that exact decision, his story reveals universal truths about career transitions that my podcast co-host Jamal and I see every day.
The Golden Handcuffs Are Real (At Every Level)
When Vinay, Loom's founder, describes struggling to walk away from his $60M package, he captures something we see constantly: the paralyzing grip of "golden handcuffs." While the numbers in his case are exceptional, the underlying dynamic is the same whether you're walking away from $60K or $60M – it's about the gap between financial security and personal fulfillment.
"Your mind does funny things when you start to consider numbers like this," he writes. Sound familiar? We've all been there, staring at our compensation packages, benefits, and stock options, trying to rationalize staying in roles that aren’t right any longer.
The Pressure to Have It All Figured Out
One of the most striking parts of Vinay's story is his admission:
"I had no idea. But I was hell bent on making sure everyone knew I had it all figured out. Out of ego. Out of fear of wading into the unknown."
This resonates deeply with my own experience. After selling my last company and facing my share of turbulence, I felt afraid of being honest and vulnerable. There's an immense pressure to have the next step perfectly planned before making a move. But here's the truth: career transitions are messy. They're supposed to be. The need to project certainty is often what keeps us stuck. Plus, after reading the excellent Working Identity by Herminia Ibarra I see the fallacy of the “one perfect idea”. As comforting as the idea of having a perfect role for me, that’s not how things work, I’m afraid.
The "Trying to Be Someone Else" Phase
Vinay's "trying to be Elon" phase – diving into robotics because it seemed impressive rather than authentic – is a common pattern. We often see professionals initially pivot toward what they think they should want rather than what truly calls them. Indeed Ibarra identifies a pattern in her own research:
The list [of possible identities/career options'] often starts with what gets framed as the “reasonable option” - one that exploits the past but in a new context or job” - Ibarra
This is why we always encourage our listeners to start with honest self-reflection rather and then experiment with a range of options. The goal isn't to copy someone else's path or to be someone else’s version of who you are, but to find your own.
The Role of External Validation
Something subtle but important emerges in Vinay's story: how external expectations shape our career decisions. He writes about how "growing expectations" from others affected his sense of self. This is particularly relevant for successful professionals – the more you achieve, the more others expect from your next move. Isn’t it time you let go of others’ desires for you?
What This Means for Your Career Change
If you're contemplating a career transition, here are the key takeaways from Vinay's journey:
Permission to Not Know: You don't need to have it all figured out. In fact, accepting uncertainty is often the first step toward authentic change.
Question Your "Should's": Are you moving toward something because it genuinely interests you, or because it sounds impressive at dinner parties?
Redefine Success: Success in a career transition isn't always about maintaining or exceeding your current status. Sometimes it's about taking a step that aligns more closely with who you are.
Embrace the Process: Career transitions are rarely linear. Vinay's journey took him from tech to almost-robotics to government work to studying physics in Hawaii. Your path might be equally full of twists and turns.
The Most Important Lesson
Perhaps the most powerful insight from Vinay's story is this question he poses: "Why couldn't I just leave Loom and say 'I don't know what I want to do next'?"
In our work with career changers, this is often the hardest but most liberating realization: it's okay to be in progress. It's okay to be figuring it out. It's okay to take time to rediscover what matters to you.
The pressure to have an impressive next chapter lined up often keeps us trapped in roles that no longer serve us. Sometimes the bravest career move is admitting you don't know what's next – and being okay with that.
If you're feeling stuck in your career and looking for guidance on making a change without breaking the bank, check out our podcast "Stuck" where we tackle these challenges head-on with expert guests and real stories of successful transitions.