Dear person who keeps choosing both,
The month after I launched my business, I accepted another full-time job.
Not because I was afraid of the leap — because I genuinely didn't know if I had what entrepreneurship actually requires. The discipline. The tolerance for the specific loneliness that comes with building something from nothing. And I wasn't ready to give up what I had. I led partnerships at a crypto startup, which meant my calendar was full of founders building things that were genuinely changing how money moved, and in a year I was in Singapore, in Paris, in Brussels, at F1 races, at conferences where the after-party mattered as much as the panels. If you know anything about crypto, that's exactly how it works — and I was doing all of it. I was good at it. That, it turned out, was the problem.
So I gave myself a year. I managed both — a second phone on every offsite, building publicly on social while my corporate calendar stayed full, goals up 15-20% every quarter, every number hit. From the outside, I was doing it all. From the inside, my body and my attention were quietly paying for both, in ways I wasn't ready to name out loud. The job felt too good to leave. And the life felt too good to walk away from.
What I wasn't ready to lose wasn't just the job. It was what the job let me say about myself — being someone doing both, running at full capacity in two directions at once. There's a specific kind of confidence attached to that. I wasn't ready to put it down. That's not noble. It's ego. And ego is rarely the thing we lead with when we explain our decisions.
Then someone filed a complaint. They found me on Instagram, followed the thread to my LinkedIn, found the company I worked for, and submitted three paragraphs through the website contact form — conflict of interest, unfair to my employer — and it went into Slack and up the chain.
My manager raised it in our weekly sync a couple weeks later, casually, because we were close and the whole team already knew about the business. He wasn't asking me to choose. He was telling me that if my performance slipped, it would have to be addressed — and my performance hadn't slipped, it had grown every single quarter. But once the alarm is pulled, the conversation has to happen.
I put in my resignation before anyone asked me to. I was the most senior person managing that role alone, responsible for 25% of the company's pipeline, and I had no interest in leaving under circumstances that weren't mine. I negotiated the transition — find my replacement, train them, then leave — and walked out at the year mark with every relationship intact.
The person who filed that complaint probably thought they were doing damage. What they actually did was hand me the permission I hadn't realized I was waiting for. I was already leaving revenue on the table by splitting my attention, and I already knew the golden handcuffs were going to keep getting heavier — comfortable enough that I might stay through a pregnancy, and then through early motherhood, and then quietly never leave at all. The complaint didn't change the math. It just made me stop pretending I hadn't already done it.
I thought I'd have years before starting a family. Life surprised me six months after I left — in the best possible way. But here's what I know: if I'd still been in that job when I found out I was pregnant, with a salary and benefits and a title that felt safe, I would have stayed. I know this about myself. The golden handcuffs don't get lighter. They get heavier in exact proportion to how much you have to lose.
Everyone who makes this move talks about the courage it took. I don't think it was courage. I think it was math. The math said I was leaving more behind by staying than I was by going. I just needed someone to force me to look at it.
Quitting your job is the headline. Timing it right is the actual skill.
Sincerely,
Shreya
The longer version of this — the part I hadn't figured out how to say yet — is on Substack.