Ask HN: At what company were you happiest and why?

My first real job at an ecommerce company in Sri Lanka. It had a trifecta of awesomeness. A team that cared. A company that at least at the start had a cohesive mission and till my final day there I had a 95% autonomous role. Obviously there were certain overrides but I never felt rank was pulled on me except by 1 person in that entire time. Funnily enough that 1 person was largely responsible for the downfall of the company culture, something that he too admitted.

Regardless, that was easily the most creative period of my life. I would work on one project after another, investing into productivity tools. The company was at the time doing daily deals. I wrote a suite of tools that would take a word doc which was the terms of agreement with the merchant, and convert it to the relevant HTML blocks to be pasted into our ecommerce CMS. After that was done it would cross-check the site against the doc to see if everything was pasted in correctly, and then use a set of defined resources to generate newsletters.

I passed that autonomy down to the rest of my team and it resulted in people tweaking workflows to be more efficient and learning things and taking on other jobs around the company without having to consult me.

Easily the best work of my life for now. By far.

At every single company! But that lasts for about 1 week to 12 months. Then everything is automated or routine and becomes boring really fast.

You make 200k as a developer?

The outfitter that I used to work for. I taught whitewater kayaking. Great people, play outside all day, interesting clientele, sense of accomplishment at the end of the day. It never once felt like work. The pay was not good by software industry standards, but it ticked every other box you could imagine for a great place to work.

I've been at Segment for 2.5 years, and it's been pretty amazing. The founders have done a good job of establishing a solid, but not cultish, culture. Karma is a value, and it's pretty well expressed. Yes, there's plenty of room for improvement, but it's been a terrific ride, and I'm excited for more. #datkoolaid

Secondarily, every time I've volunteered my hard skills, it's been a lot of fun (and oftentimes has a positive payoff down the road). Eg back in Atlanta, I volunteered at a local private school for a couple of months which turned into a $50/hr * 20hrs/week gig.

When I first moved to the Bay Area, I met with a friend of a friend, and when he said he had kids, I casually mentioned that I'd be happy to tutor them if they ever needed any help. This blossomed into a great relationship, and this person is now a good friend and mentor that I've kept up with for the past 6 years.

I suspect one reason that volunteering is so fun is because it's low stress because you can't really get fired, and if you do, it doesn't matter because it's not your primary livelihood. I might sort of say the same thing about some second jobs (in that it doesn't really matter if you lose the second job); however, if the second jobs pays really well (or you really need it), then that stress of keeping the job can creep in.

Driving for Lyft was also a lot of fun. I only did it part time for a few months, but it was great meeting people and exploring the city. The limited-time casual conversations are very interesting because people are more willing to overshare because chances are you'll never see each other again. Back when I drove, it wasn't as mainstream, so the clientele was mostly tech-savvy early adopters, so most conversations were very interesting. I wish I had done it for longer so as to better learn the city's nooks and crannies and also to meet and chat with more people.