Right now, I’m thinking of smoking a cigarette. I have a chronic sore throat, which is probably from sinusitis, hopefully not cancer. It doesn’t always hurt, but I need to drink something every time I smoke. That means I also want a drink. That drink could be whiskey, but then I’ll think about smoking again.

Smoking for me is more than a chemical thing. It’s a relationship. Probably the steadiest relationship in my life. Smokes have been there for me during every mandatory 15 minute break, every drug experience, every late night conversation, every all-night programming binge. They’ve been there sharing the best conversations with the best friends of my life for 90% of the last 17 years. There isn’t an important day of my life, that there wasn’t a cigarette to share it with me.

Smoke, stoge, butt, fag, stick, bomb, Camel, Dunhill, Marlboro, Wills, Gold Flake, Drum, Three Castles, Davidoff, Shermans, Chesterfield. The best is Dunhill. It always has been since I could get packs for $2 in Berkeley from the liquor shop on 51st and college which served anyone (sorry dude, everyone knows anyway…). The first I ever smoked was one of my dad’s unfiltered Pall Malls. It wasn’t his usual brand (Chesterfield), which is why it was probably sitting around forgotten in a basket on his bed stand. It made my throat so sore I cried. I came back to light it again 20 minutes later.

2nd was a Camel. 98c from the 76 on Solano Ave in Albany. That will be the equivalent of your grandfather’s 5c candy bar — remembering when cigarettes were a dollar a pack. I smoked it with Asher on the way to our jobs — I worked at a candy store and he at a cafe up on College. It is harsh, but the smoke is interesting now and the headrush is scary and wonderful.

Now I’m 17. I joined a pilgrimage and I walk 15–30 miles every day. Every hour we walk three miles and take a 15 minute break. I smoke 2 cigarettes with Kazu. We end up smoking 20 Winstons a day for months as we walk. It all balances out I guess. We’re fit little bastards — we have no idea how privileged we are to have late model bodies.

Every break, every breakup, every breakdown, every cup of coffee, every beer, every car trip, you’ve been there for me. I haven’t lived a life I’m particularly proud of. I’ve accomplished less than I’d hoped for, I made decisions based on fear and rationalization over passion and courage. Smokes have always been there to even me out, to keep from going full mid-life crisis, to keep the emotional mind in check. I’m only 32 / already 32 (depending on my mood) — there is still time to change.

So I’ve quit.

It’s not the first time I’ve quit. But I have a feeling this is it. Cliched as it may be, I’m not living for myself anymore. Zoya turned Three this past week and I just can’t keep hiding it from her. As much as I may be ashamed of myself for things I’ve done or haven’t done, it’s not fair to her to be ashamed of her papa. I don’t have to be perfect, but I will strive to not be a hypocrite.

That’s me, crossing the fence I never wanted to be on the other side of. The goody-goody, the person who fakes a pretentious cough when walking by us, the slowly suicidal. The one who stays in the bar while the bad kids make friends, laugh, and share the tobacco bond. I’m really going to miss that. I wish I could control it, but after 4 attempts at stopping, I know that I can’t.

Originally published at on March 22, 2013.

Jacob Singh
CTO in residence at Sequoia Capital. Independent product and Engineering Coach Mediocre guitarist, singer, rock climber, point guard and baker Dedicated dad. American in New Delhi.
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