Ask HN: What's Your Biggest Regret?

I legitimately do not understand the philosophical exercise of 'free will doesn't exist'.

Yes it does. I could walk into the street right now. I could walk into the office next door and slap a co-worker. I could learn German. I could leave my life and walk to China.

What is your justification that free-will doesn't exist? Other than biological needs like eating and sleeping, I have control over the rest. Or, rather, I have control over how shitty the rest is. I have yet to hear an argument that has swayed me at all.

Working for PagerDuty.

I gave PagerDuty a $100k discount on my market rate in exchange for 2% of stock.

The week I got fired, I had just taken us to AWS Re:Invent and helped sign a lot of business.

During this conference, a gross creeper named Jedidiah Smith (really) from Linode/Foursquare, started sexually harassing and stalking our Office Admin who had come to help with the conference. Our child of a CTO wouldn't do anything about it, so I took matters into my own hands and had him fired, because his boss was a friend and former customer of mine. This made my boss feel impotent, knowing I acted like a man, and he acted like a coward. A man protects his people at all costs. A coward drinks whisky and hobnobs while a potential rapist threatens his people.

( True story, when Moira of the Apache Foundation killed herself, Jed was considered to have shared some of the blame for his constant harassment over her for having been raped, and for being trans. When I still had LinkedIn, he stalked me every 3 days terrified I would do something to him. )

During the conference, AWS us-east-1 went out, and I was blamed for PD's shitty single-AZ, single-region infrastructure, even though 110% of my work had been marketing at that point, and I had not really done anything technical. The founders were to blame for every shitty technical decision they had made, but I was the oldest person in the company, and the easiest scapegoat because I wasn't a young techbro (I was 30, they were 24).

On the flight home to San Francisco my father died. When I arrived at the office that afternoon I was fired. No stock, no severance, just "we locked you out, give us your laptop, fuck you". I was fired and paid a half day's pay for that week.

Working for pagerduty was the worst mistake of my life. I was still idealistic and happy when I first started there. I loved the project. I thought we were going to take over the world. They became billionaires, I became homeless. My stock would be worth like $100m now. For a while I lived on the roof of Pagerduty's office. It's easy to walk by the security guard, the view is stunning, and it's really warm in the loft up above the elevator shaft.

The last picture of my father, he was wearing a PagerDuty shirt he had just received. On the way to bury him, my brother in law and closest friend in this world died of an accidental oxycotin overdose due to a surgery. Boy didn't even take aspirin until his achilles tendon snapped, first week of painkillers he died. Just like that. Poof. Living consciousness to dead meat in a box. My grandfather and mother all died within a year of that.

I fell into a hopeless depression, tried to kill myself several times, spent the next year and a half in a drug-fueled haze.

When I woke up, I was living in a stolen RV, my fiancee had left me, all of my friends had ghosted me, my family had disowned me, I'd been arrested three times and was over $75k in debt. I decided to nullify my life.

Cynicism and nihilism is my life's philosophy. For the past 11 years I have only slept with women I paid, so that I don't need to have any attachment. I have no ties, no responsibilities, no connections.

I lie to people about my name if I socialize so that I never have to engage with the same person more than once. If I do accidentally connect with the same person twice, I decide it's time to move on, which happens every 2-4 months. I've moved about 50 times, if you can call drifting "moving". Digital nomadding, I dunno, whatever.

I own three motorcycles, (all R1250RTs) the one I'm on now, one in London and one in Mexico City I imagine has long-since been stolen. I have a backpack, a hand drum, a laptop, a few burner phones, about 50 sim cards, a wallet, a two pairs of custom hiking shoes, a week's worth of hiking clothes and a couple of Neal Stephenson books. Also, some antacids, i have the worst acid reflux.

I carry my Do Not Resuscitate on me, I have not had a social media account of any type for 10 years. My real identity is long lost, sometimes I refer to myself by one of my fake identities so much I start believing them. My passports and IDs are all fake, and I'm happy being anonymous. I've managed to squirrel away a few hundred thousand dollars in cash and gold in storage lockers in my favorite cities. No crypto, I prefer pure anonymity. Before I die I'll collect it all and give it away to homeless people.

I like sitting with bums, drug-dealers, hookers and junkies. They're honest, they accept me for who I am and never ask me questions I don't want to answer, and I never ask them any either. The closest I come to having friends is knowing drug dealers by name in 20 or so countries. When I come to a new city, I walk around looking for the thugs, make a deal, hand them a beer and talk to them for a bit. I haven't actually done drugs in 5 or 6 years, besides cannabis and acid, I just like talking to real people and there ain't nobody realer than a hustler. My old man was a hell's angel, I prefer lowlifes to the rich.

I left tech for a while, made a pile by selling coke, heroin and mdma to yuppy tech bros, many, many of whom worked for YCombinator companies. Let's just say I know where a lot of bodies are buried. If I wrote a tell-all book, I could run the lives and reputations of at least 20 names you recognize very well. Don't worry, I am an animal with integrity when it comes to secrets.

Within a few years I will be breathing through an oxygen tank because of congenital emphysema, and a few years after that I'll be dead. This is my remaining comfort, this knowledge of my mortality is strangely very comforting.

The series of events which began with PagerDuty nullified my life. I hold only bitterness and hatred for my peers, my colleagues, my employers and my customers, and each and every one of you on this site. To me, you are prey, somebody to rob or jump for fun. Don't worry, if I jump you, I won't keep your wallet, I'll give it to the first bum I see. I'm too old for that now anyways, my lungs are failing.

My last ~20 employers never knew my real name. I have a few people I hire off of UpWork to be my references when I need a new gig.

I have no social media presence, no saved e-mails, no photos, no papers, no property. Just the bare essentials to survive and to keep moving, I'm like a shark, always gotta keep moving.

I don't exist.

For those of you who are familiar with GG Allin, he defined who I became after PagerDuty with more eloquence than I ever could.

"Everybody knows that I'm a scumbag They won't come and see me in this dive Everyone's afraid of what might happen to them Or if they'll even get out of there alive

Some fuckhead in the corner is getting to me Talkin' about the way I look and smell Well I guess he don't know that I'm the Outlaw Scumfuck Someone aughta' warn him before I knock him straight to Hell

Because everybody knows that I'm a scumbag I like sluts and whores and I don't care You can say just what you want to say about me But if I hear you I might just go knock you off your chair'

Cause I like to drink whiskey by the gallon I live on peanut butter sandwiches, I don't care I spent some nights in jail in this old country Everybody hates me and I just don't fucking care"

Fuck y'all, especially you Alex. Fuck you, Alex.

I was in Silicon Valley just before the start of Dot-Com with nearly a decades experience running a couple of software startups (in Texas, not in a high tech city) working at Apple and left to go back home thus missing out on enormous opportunities. I thought Apple would go out of business and figured no point in sticking around. What a doofus... I never looked around and asked, would my experience be useful somewhere?

My career was OK but who knows where I might have wound up.

Trusting my family.

Nothing. In fact, I’ve worked hard to come to accept that of which occurs in my life that is undesired - be it from my actions or actions that are outside my control. Everything that has occurred has happened for me, not to me. I’ve learned a great deal along the way and build my character from all my experiences. And just like everyone in this thread, you wouldn’t be who you are without these “regrets”. Hindsight is one thing, having regrets is another. I don’t like to say I regret anything, I’m just living and learning, accepting and letting the pieces fall into place. Life is too short to live with regrets.