0 to 100, real quick

Dileepan Siva
4 min readOct 19, 2016

--

My best friend Sandeep’s grandfather turned 100 earlier this month. I’d love to see him write a post on what he’d tell his 40 year old self. I turned 40 today and believe you me, I’m hard pressed to know what I’d tell my 20 or 30 year self. Are there really points at which I can look back and remark on what I wish I had known back then? Maybe. The more honest answer is that I knew what I knew then and that I made the choices I made without regret.

It’d be a blessing to live till 100 because I’ll settle with 80. Eighty has always stuck in my mind as a milestone for two reasons. In my parents’ culture — one has not only lived to see 1000 full moons but it’s also marked as the point at which commitments or duties to family, friends, society writ large…you name it, fade away. And it’s the time at which one begins to contemplate liberation from the cycle of birth, death and rebirth. At the risk of sounding morbid, seeing my parents age has undoubtedly made this more real as each year has gone by.

With an average life expectancy of just shy of 80, I’ve got another 40 years left on this Earth (or if I’m lucky enough, Mars with Elon). Put another way, that’s about 15,000 days to play with. That’s a whopping big number. What an amazing gift to be able to experience–and reflect on–these bountiful days and remind myself that how I spend that time is really all that matters. And when I think about time, I keep coming back to a few days I spent in Big Bear just before going off to college. More than any book I’ve read or talk I’ve attended, that experience still grips me.

Hard to remember exactly how I stumbled into this but I got clued into a weekend spiritual retreat in the Big Bear Mountains from family friends. Think meditation redux sans smartphones (it was 1994 mind you) let alone apps in a stunningly beautiful part of Southern California not far from where I went to high school. A bit of context, I grew up going to temple every now and then but never really saw the purpose–meditation on the other hand seemed like the core essence stripped of any fixins. And getting out of the house for the weekend to the coolness of Big Bear was hard to beat.

Huddled up in the lodge, we’d meditate off and on for what seemed like forever. The stillness in the air was palpable–my mind on the other hand was running a mile a minute. The raw food diet didn’t help and In-N-Out Burger was miles away. As evening approached on the second night, younger ones like myself were paired with older folks to chat about what came up while sitting to meditate. I got paired with a father whose sons I actually knew of growing up. He started to talk about his practice sessions…and before I knew it, tears were streaming down his face.

In between uncontrollable sobs, he muttered that he had sacrificed time with his family to provide for them. He worked well more than the 40 hours a week he had to to provide them with the creature comforts of shelter, sustenance and everything in between. But I could tell he was looking back on this decision with regret–and his tears were proof. And I’m remembering this experience today because when I heard that story at the ripe old age of 16, he was 40. Forty. Years. Old. I don’t have kids yet but I’m blessed to still have and be connected to my parents, brother, sister and countless friends here in the Bay Area and spread across the globe.

And to be honest, I do regret not spending enough time with family and friends. As a third culture kid, it was much easier to seek out new experiences. Jet-setting around the globe for work and play was exhilarating. Living in one place for more than two years was not. I’ve got stories galore but after the 100th telling, it’s become hard to separate fact from fiction–especially for the more dramatic ones. The story that does stand out from all these years is the one from Big Bear and that one’s more than twenty years old.

It’s a constant reminder that what’s important is not just spending enough time with loved ones but how I spend that time. How can I best spend the next 40 years with family and friends? This may sound counterintuitive but I don’t know of a more effective way to understand how to better spend time in life–and with those you care for–that spending more time in solitude, meditating. More than any other routine, meditating has helped me understand my emotions, why I feel those emotions and ever so slowly begin to see what values underlie those emotions.

Values determine the nature of our problems and the nature of our problems determines the quality of our lives. That’s where the real work lies. And if a weekend spiritual retreat can uncover this for a regretful yet loving father, here’s to 40 more years of sitting still…in meditation.

--

--

Dileepan Siva

Former founder and executive turned coach who scaled 3 venture-backed startups (all acquired) and led business units at 2 public tech companies.