Three Decades Down

Turning 30 with Reflection, Perspective, and Gratitude

Jay Kapoor
Jay Kapoor
7 min readOct 28, 2019

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2009. 2014. 2019.

Turning 30 is really bittersweet.

It’s the first birthday I’ve ever had without a hug, phone call, or 12:01am text from my Mom and, understandably, I’m missing her a lot. When I tried to reflect on the positive things from just the past year, being honest with myself here, I came up pretty empty. A year ago, I had incredibly high expectations for the last year of my 20s but instead, I spent most of it in mourning, grief, doubt, and depressive moods. I did my best to hide it, to look alright, to do my best impression of the “old me”. But some part of me always knew that the day my Mom passed, that old me left with her.

But I guess it’s all about perspective. Trite as it sounds, the old adage that “People overestimate what they can do in one year and underestimate what they can do in ten” has real truth to it. So this year, as the clock struck midnight and I turned the page on my 20s, I looked past one tortured year to think about the most important experiences and learnings from this whole last decade, for which I am truly and honestly, so grateful.

Graduated from Carnegie Mellon (despite my own best efforts)

One person in this picture did all the project work but I’m not saying who ;)

With my incessant diatribes against higher education, this might sound like a weird thing to be proud of, but I am really proud of it! Going to Carnegie Mellon was one of the best decisions of my life.

To be clear, I’m still not sure I learned much in my classes (sorry Dr. C!) but surrounded by the most talented, diligent, unstoppable classmates and future colleagues I found “my tribe” — we Tartans, we will never have things handed to us easy. If we want something, we fight for it. From the first class to the last you’re reminded that life is full of brick walls, but the brick walls are meant to be there for you to prove how badly you really want it. The brick walls are there to keep out those that don’t want it enough. It’s taken me many years since graduation to fully appreciate that lesson but I’m grateful for the constant challenges and failures Carnegie Mellon afforded me to learn that.

Recorded an Award-Winning Album (that debuted on Spotify)

Wanna really feel old? Go back and see your college a cappella group 8 years later…

Founding and running Deewane remains the best thing I did in college, not least of which because I made so many lifelong friends along the way. We went from 7 strangers practicing in a hallway to a formidable mainstay of the collegiate a cappella circuit, in just four short years. Over a decade later, it’s amazing to have built something that not only outlived my college tenure but also outshone my wildest expectations.

Founding Deewane was also a constantly humbling experience. Leadership is really, really hard. When you convince people to build something that has never been, you are asking them to put an incredible amount of faith in the fact that you know what you’re doing (even when you usually won’t). Deewane taught me that this trust must be treated with respect. That solving problems together is more important than solving them your way. That the culture you build as a leader from the very first day reverberates long after you’ve left the room.

Along the way, I even recorded a professional EP with Deewane called Kal in the same studio where John Legend did his first album in Philadelphia! These award-winning tracks spent several years on Spotify — until Coldplay’s lawyers filed a C&D and the whole album got taken down. Effing Coldplay…

Built a Career For Myself That Finally Gave Me Purpose

If there is one thing my winding, circuitous career path has reinforced to me, it’s that plans are utterly worthless, even if planning itself is invaluable. Coming to New York, I had set out a narrative for my career, and by my own definition, I had attained real success in it by working for some of the most enviable and unattainable companies. So why wasn’t I happy? Why wasn’t I fulfilled?

It took me until a few years ago to recognize that I was, in fact, living according to the wrong plan and a distorted definition of success. So the healthiest thing I’ve tried and done for my career is to be comfortable not having long-term plans. Instead, I constantly ask myself if I am doing something that most excites me, challenges me, teaches me and makes me of service to others.

In conversation with a mentor recently, I told her that the closest thing I had found to “my purpose” was seeking out passionate, talented people and clearing a path for them to find success. The more I say it out loud, the more right it feels to me. No matter where I end up in my career, I’m comfortable knowing that this purpose can be my North Star. It was only when I stopped having plans, that I started finding purpose.

Trained for and Finished 5 Half Marathons

It’s very rare to find a race day picture where I’m smiling… unless it's at the finish line.

I hate running. There. I said it. I love all the positive things that come from running, sure. But in the act and in that moment, I’d rather be anywhere else. In fact, most of the time on long runs I try to think about anything but running. Thankfully, the faster I go, the sooner the misery stops. Just like that, over the last decade, I logged over 1,000 miles, completing numerous 5Ks, 10Ks, 10-milers, and even 5 Half-Marathons (Manhattan, Brooklyn, Staten Island, Pittsburgh, & San Francisco) — running my fastest in 2h22m58s

Then somehow, in the last two years, I forgot what an important part of my life running really was. Now, being older, heavier, and out of running form as I train for my 6th half-marathon… is scary. Reflecting this weekend I was reminded of the most important lesson that running had taught me: Anything worth doing is hard, requires discipline, requires sacrifice, and yeah, sometimes requires pain. I love running.

Got to be near to and to be able to care for my Mom

Family is everything to me. It’s no secret that I’ve stayed in the same city for over 8 years now to be near them. Despite the west coast calling many times with increasingly lucrative job offers, I held firm on the decision to stay close to home so I could support my sister and Dad, and be there for my Mom, especially as she fought valiantly through illnesses. Then, she left us last November, and I found it really fucking hard to find any gratitude for the worst, most unfair, thing that has ever happened.

“It is a gift to exist. With existence comes suffering. There’s no escaping that… If you’re grateful for your life, you have to be grateful for all of it”

Ever since I watched this exchange, I’ve been meditating on this idea a lot. Without fully acknowledging the many sufferings in life, those of others and of ourselves, I don’t think we can truly know what it is to be grateful. None of us are exempt from loss. Only by letting ourselves feel loss, can we appreciate what we have gained, and respect what we have yet to attain. Because I am grateful for the good things in my life, I have to be grateful for even the worst things too.

My Mom was the most important person in my life and she taught me through her ceaseless examples, what it means to live a good life. Despite the sorrow I feel daily, I am at least grateful that I could be near her to give her some modicum of joy, support, and comfort in her toughest times. Her final lesson was to teach me that life can be unfair, cruel, and random but that doesn’t mean you let it change who you are. I am grateful to her for this too.

I don’t know what the next decade holds. At 30, I’ve learned enough to not even try and guess. All I can promise is that wherever I am, whatever I’m doing, I will do it the best that I can. I will try many new things, and likely fail at some of them, so I will not fear failure. Ten years from now, all I hope I can do is look back at my thirties and proudly say that I lived them boldly, and with purpose.

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Jay Kapoor
Jay Kapoor

Seed & Early Stage VC investor | I read and write about Tech, Media, SaaS, & Investing | Don’t be afraid of failure. Be afraid of being ordinary.