Five years ago today, I smoked my last cigarette. Previously, I smoked a pack a day for ten years. Time for a bit of reflection on that. I always enjoyed this quote from Choire Sicha on his article about stopping smoking:

It’s like KonMari, except easy, because the only things you throw out are your cigarettes and your entire sense of self.

Starting Smoking

Like most, I started smoking as a teenager out of curiousity. My dad smoked his entire life, and I think his smoking habit was a big contributor to that curiosity. I remember buying my first pack of cigarettes, Marlboro Reds (like dad), and smoking them with a friend saying, “Help me finish this pack of cigarettes so I can be done with them.” I was fourteen.

That pack wasn’t the last, and it was the start of a long journey with cigarettes. I found a place in town that would sell me cigarettes despite being clearly underage, and I’d smoke 2-3 cigarettes a day at regular intervals (lunch and after school).

I didn’t try hiding it from my parents. I remember telling my mom, “I’m not sure if you know, but I started smoking. I’m going to go out and have a cigarette now.” My parents had both been smokers, but my mom stopped during her pregnancy and never picked it back up. Neither were thrilled about it, but I wasn’t admonished either.

Over time my boundaries with cigarettes slowly eroded. The idea of a morning cigarette seemed disgusting to me initially, but very quickly became part of the morning routine with coffee. I was caddying in the summers and a normal routine might look like a cigarette on the way to work, two cigarettes while waiting for a group of golfers, three cigarettes on the golf course, and one after the round ended. That’s 7 before noon. Pretty quickly, my casual 2-3 cigarettes a day became a pack a day.


When I was 19, I visited my father who had developed a bad cough. Not like the normal smoking bad cough, I’m talking about a deep, audible gurgle. We sat on the front porch and he rolled a cigarette from his Bugler pouch. My father was trying to save money rolling his own cigarettes, smoking them unfiltered, and coughing with that deep gurgle along the way. I joined him with a cigarette fom my pack told him he needed to see the doctor, he replied that he made an appointment for the following morning.

The doctor had my father hospitalized immediately, where he was diagnosed with pneumonia and intubated. After several weeks of intubation without improvement, I received a call from the doctor asking my approval to install a tracheal tube on my father, which is essentially a catheter that goes through the neck and directly into the trachea. This would allow him to stay on oxygen while mitigating the risk of infection from prolonged intubation. The doctor assured me this was reversible and would only be needed until he recovered. I visited my father after the operation, smoking cigarettes on the way there and after leaving.

The tracheal tube was never removed. My father was diagnosed with emphysema, a condition caused by damage done to alveoli in the lungs which makes it difficult take in oxygen normally. He was placed into assisted living where he lived with supplemental oxygen for two years before he died of respiratory failure in 2011. I was twenty-two.


A few months after my father’s death, I was working at a small startup building wireless networking software. The founder, my boss, was French and also a smoker. We planned a business trip to Paris to demonstrate the technology with a few French companies that were interested in piloting it. Before the trip, my boss asked what I planned to do about the flight and not being able to smoke. I told him I planned to just not smoke, but my boss told me he had an extra electronic cigarette to give me.

These e-cigarettes were not your modern JUUL. They were three-part devices with a long body for the battery, a middle portion with a cotton-piece where you would drop liquid containing nicotine, and a mouthpiece. Periodically, you would take this thing a part, drop your liquid nicotine in, and put it back together for the next fix.

At this time, e-cigarettes were not well known or popular. The question about smoking them on airplanes also fell into a gray-area where you probably knew it wasn’t “allowed”, but it wasn’t expressly forbidden either. While the e-cigarette eased the nicotine withdrawal on the cross-Atlantic flight, I have to say I’m embarrassed that I smoked e-cigarettes on an airplane.

During the trip I converted entirely to the e-cigarettes, finding that they satisfied my needs, and switched to them exclusively afterward. After a few months, I ran out of liquid nicotine, and stopped smoking altogether.


After eight years of smoking, I stopped smoking for 18 months. At the time, I credited e-cigarettes for weaning me off cigarettes.

In 2013, I took a trip to Fort Lauderdale to visit a friend. At the time, Fort Lauderdale had not adopted the same type of non-smoking policies that were enforced throughout the New York/New Jersey area, and people were smoking freely on the beach and in the bars.

By late afternoon, we were buzzed in a bar, and I asked my friend for a cigarette. He said, “you don’t want to do that dude”, and I told him I just wanted one for old time’s sake. I smoked two more cigarettes with him that weekend before flying back to NYC.

The next weekend, I was hanging out with some of my friends and had a few cigarettes with them. The same thing happened the weekend after, and on the weekend after that I was out drinking without my smoking buddies and bought a pack of cigarettes. Within a month, I slid back from total abstinence to a full blown pack a day smoker.

Thank Genius its Friday

In 2015, I was working with Rap Genius on integrating Instapaper Notes as a launch partner for their web annotations API. and I got invited to their “Thank Genius Its Friday” happy hour. At the time, Rap Genius’ offices were leased apartments at a waterfront building in Williamsburg. The party was held in one of the penthouse units with a large deck overlooking the East River. They had a good vibe going on, good rap music, drinks, and blunts in the apartment.

I was smoking a cigarette on the deck and chatting with one of the engineers I was working closely with on the API integration. I wish I remembered his name because he drastically changed my life. He told me he’d recently stopped smoking after reading this book, and that he’d give me his copy if I promised to read it. I wasn’t really interested in stopping smoking at this point, but told him I’d give the book a read. He went into his office, a bedroom in one of the other apartments in the building, came back, and handed me the book.

The Book

The book was The Easy Way to Stop Smoking by Allen Carr, and I smoked my last cigarette on May 15th 2015 while reading the last page of the book (as instructed). When I tell people that I stopped smoking after reading a book, the first question is always about how a book could help you stop smoking. The book does work and it’s not easy to explain, but part of the reason I started writing this post was to articulate how.

Firstly, the book’s focus is on changing the way you think about cigarettes and your relationship with cigarettes. Most people, myself included, tell themselves they smoke because its relaxing, but its really that the withdrawal from the previous cigarette creates anxiety which is then only satisfied by the next cigarette. This sounds painfully obvious, but viewing cigarettes as the source of the anxiety instead of the source of the relaxation is a fundamental mindset shift for a smoker.

Secondly, the only two instructions you’re given are 1) continue smoking while you read the book and 2) complete the book. This vastly lowers the barrier to start reading, since you’re not asked to make some big leap into a huge lifestyle change, you’re just reading a book. It also forces you to examine your smoking behavior and think critically about it. For anyone who has smoked for more than a few years, it’s not something you think critically about, the same way you don’t think critically about drinking water or reading, it’s just something you do.

Lastly, the book talks about cigarettes and addiction in a guilt-free way. Unlike a lot of other smoking deterrent media, it isn’t about stinky clothes, pictures of damaged lungs, or the dangers of second-half smoke. It’s about changing the way you view your interactions with cigarettes, which is a much more powerful way to convince someone to see cigarettes for what they are: a burden.

I’ve bought the book for several friends since finishing it and they also all stopped smoking, except for one who relapsed more recently.

The Easy Way to Stop Smoking talks about stopping with the use of nicotine alternatives like the patch and e-cigarettes, noting that the methods largely don’t work, and that people who think they quit using those methods usually quit for some other reason. It wasn’t until I read that paragraph that I was able to connect my father’s death to my first attempt at stopping smoking, I didn’t realize I’d been lying to myself and falsely attributing e-cigarettes as the reason I stopped the first time.


After stopping, I kept having a recurring dream where I come across a beautiful woman, she pulls out a pack of cigarettes and asks me if I’d like one. I accept, light the cigarette, and take a deep inhale. In the dream I can actually feel the sensation of inhaling the smoke, it feels real and familiar, but those feelings are quickly replaced with deep regret. In the dream, I tell myself, “I made so much progress and ruined it all by smoking a cigarette,” and I wake up in a complete panic. The feelings are so real in the dream that I need to convince myself it didn’t actually happen.

In my fifth year without cigarettes, those dreams are largely gone, but I know that I’m one cigarette away from devolving to a pack-a-day smoker.