I had hit rock bottom. Purple V and I were on the terrace of his farmhouse, where I was venting for the first time in my life about everything that had gone wrong in the past six months. I was in shambles, trying to second-guess every decision I had made to be at that place, at that moment. He told me, “Dude, you can’t have those ‘what ifs’ hanging over your head. It’ll drive you nuts. Let it go.” I took those words seriously, and it only took me ten years to be at a place where I can safely say I’ve let a lot of things go. But sometimes I wonder if we truly ever let things go. I know I still wonder about the ‘what ifs’ sometimes. So these are some of the what ifs of my life:
What if your dad wasn’t so hard on you? You were an obedient child who was good at school. You stood first in class every time, but your dad wasn’t happy that you made mistakes. He expected perfection. It wasn’t about being the best among your peers; it was about not making mistakes. You’ve carried that throughout your life, being so hard on yourself every time you weren’t anything short of perfect. You were a perfectionist for most of your life. I’m glad you’ve given up on that perfectionism and started treating yourself kindly.
What if your dad hadn’t passed away when you were 7 years old? And what if his brother didn’t tell you, “You’re the man of the house now; you need to be responsible”? You carried that all your life. You screwed up every now and then—you were a child, after all. But you never made mistakes that would affect anything substantial. Remember how you’d shared with Red D about not just having Plan Bs but Plan Cs and Ds and so on, and she called you crazy? You needed to be that responsible. You weren’t so privileged that you couldn’t have a backup plan. You planned for the worst-case scenario. You learned every step of the way to protect yourself so you wouldn’t hit rock bottom. Ever.
What if your mom hadn’t said, “Don’t worry about getting into an engineering college now, just focus on your next exam,” after you screwed up your chemistry exam in high school? You might have gone to journalism school or art school. But you didn’t give up on your dream. You loved computers. You worked hard on your CET and scored well enough to get into a top university in Bangalore. You have proof now that you are meant to be in technology, and it didn’t matter which college you got into. This was your path. Just look back at all your wins. Was it when you painted something or when you solved a bug? Painting was easy. The problems you want to solve are hard. Look at the state of journalism now. Would you have wanted to be among those peers?
What if you hadn’t chosen a startup for your first job and instead followed the crowd? You didn’t listen to the advice from The Elders. You followed the path you thought was right for you. You knew better. You wouldn’t have realized how much you liked the hustle, the camaraderie of working in a small team making millions of dollars in impact. You now know how boring it is to work in Big Tech. You now have proof that you could hold your own among the best of the best.
What if you hadn’t gone to do your masters in the US? You wouldn’t have been in debt for half a decade. You wouldn’t have felt like you were wearing golden handcuffs for two years. You probably would’ve followed a path of entrepreneurship, surely. You also would’ve missed out on the best two years of your life. You would’ve missed out on the environment you so crave and thrive in. You would’ve missed out on all the friends you made. You would’ve missed out on studying AI, something your gut said you had to learn, 12 years before it was relevant. This thing has kept you excited for more than a decade now. Can you put a price on that?
What if your thesis advisor hadn’t told you your idea was too ambitious for a year-long time-frame? You wouldn’t have had the drive to actually prove him wrong later in life. He had bigger plans for you. He called you an astute observer. He wanted you to work on a bigger problem, an open problem that one of the smartest scientists couldn’t solve but thought you could make “good progress.” You didn’t see it then. But maybe he was just that confident. Your heart was in a different place, though. It wasn’t your calling.
What if you hadn’t landed a job in your first year there? You probably would’ve worked a lot harder in your second year to land a job rather than experiencing all that the university offered. Remember you were having the time of your life?
What if you actually enjoyed the job you landed in Madison? You probably would’ve stayed there a few more years until you paid off your debts, but you would’ve gotten disillusioned with the place eventually and left anyway. That place and the people were dull. It just wasn’t home. It also wasn’t your dream job.
What if you had tried and landed that dream job? But remember what Blue M told you? He said it isn’t all that it’s cracked up to be, and he was bored. This is the smartest person you knew, and he wasn’t making any impact in that company, and things were tied up in red tape all the time. You don’t like slow, remember? You like movement. You thrive on momentum.
What if events between you and Yellow J transpired differently? You probably would’ve had all the support system you needed to land your dream job. But she had dreams too, which were the exact opposite of yours. You would’ve had a lot more ‘what ifs’ if things had actually worked out with her.
What if after moving back to India, you didn’t take that risk with two first-time founders? You spoke to them for an hour, and you were willing to take a shot at being employee number 3. You were going to build what you’ve always dreamed of building since the 8th Grade. You were going to make your childhood dreams come true. Your advisor said you couldn’t do it in a year, but you did it in a month. All your childhood dreams came true, but you didn’t have anyone to share it with. So it hasn’t felt like a victory yet. But it fucking was. And you needed no cheerleader to do it.
What if you didn’t decide to move on and join Company Z for 3 months? You probably wouldn’t have met White M and landed your next job. That job taught you how to be an empathetic leader. You weren’t one previously. You had no patience with incompetence. But you learned to give people a chance to redeem themselves. This has paid off dividends you can’t even count.
What if you had chosen to work for that US startup for better pay and equity than the quick commerce startup you ended up choosing? You burnt a bridge there, and you didn’t keep your word. And I know you feel bad about it. But sometimes you need to do what’s right for yourself and follow your conviction when it is fucking screaming at you. You did well. That was the right call. And it looks like the bridge wasn’t permanently burnt after all. How much more serendipity do you need?
What if you hadn’t taken that sabbatical earlier this year? You would’ve probably killed yourself by working too hard. You would’ve ignored your gut telling you need to do something different. You would have regretted not doing this ten years from now. Your gut is screaming again. For fuck's sake, just listen to it. Sure you would’ve accrued some more equity and built a longer runway. Maybe even retire in a few years. But you needed none of those.
What if you’d not come to attend the writelight circle that one Friday? You wouldn’t have given writing a shot at all. This year you were going to improve your storytelling skills. Just look back on the comments you’ve received so far. You’re getting there. Keep at it. This was the last skill you need proof of before embarking on to bigger things.
What if you just looked back at your life and looked at all the good decisions you’ve made instead of harping about not being perfect? What if you look at the universe lining up to make your dreams come true? What if you just connected the dots for once instead of assuming it’s all random or just lucky coincidences? What if you look at all the proof you’ve accumulated over the years?
What if you dream just a little bigger this time?
What if all those dreams come true?
Just, what if.
