Ask HN: Buying Yourself a Job
I got lucky some time back and got an IPO exit that means I don't really have to work any more, or at least can make a lot less in exchange for doing something I love. I've tried starting a couple companies, but finding PMF is hard and my experience has always been more scale-up. I've done a bit of consulting, but it's a lot of work and not necessarily what I'm best at to find and maintain customers. I've considered buying a coffee shop or maker space or something and just hanging out with my customers for a living, which sounds nice in theory, but a lot of people will say dont do this because you're just buying yourself a job, and I can see that. Ive also tried to work jobs at smaller companies where I'm significantly underpaid, in theory in exchange for a little more freedom and more ability to make a difference, bit eventually that gets a bit boring.
My question basically boils down to, for those who don't have to work but enjoy working, what have you found to do that worked out that felt like it gave you some rewarding purpose, and maybe let you earn enough to break even until actual retirement age?
52 comments
[ 4.6 ms ] story [ 105 ms ] threadI think that I'm doing useful stuff, and the experience is fun!
I am self-funded.
Part-time means that I can take up interesting opportunities (eg a new start-up) on the side. And I can keep some IP from being tangled up with the university, in case anything very interesting turns up (eg a new start-up)...
What I realized with these experiments that I like working as part of a team so last year I decided to do freelance development. Main criteria for me is the Team culture. If I don’t like the team or people or org or product, I leave within 3-4 months, I don’t do work for free (too many freeloaders) and expect market rate.
Is that a bad thing? Can you afford to buy something? Can you afford the case of a total loss in value of the thing you buy?
Steve Ballmer is in a similar situation as you. He used excess money to buy a sports team. It's dumb to me and many other people. But he can afford it and may get enjoyment out of his ownership duties.
I spoke with Steve shortly after he bought the Clippers and he told me…
1. He’s a sports fan
2. The asset value of major market teams along with the accompanying real estate generally increases. Provided that you do not run a significant deficit, it’s a profitable endeavor once sold.
Several of his players were represented by CAA located in Beverly Hills which I worked with.
I’ve also met and talked to many other famous business elite. At private events, there’s usually only 50-200 people in a room so the famous mill around with everyone else without security. It’s pretty easy to get a conversation started as they are all regular people. Some people are assholes usually entertainers but most of the businesspeople are pretty approachable.
Be aware that you will have to kiss a lot of frogs.
It sounds to me like you would prefer to go ahead with the coffee shop / maker space thing, but you kinda feel like you "shouldn't" do it because people have told you not to - but you still kinda want to.
My general experience is that when I have a peaceful preference towards something, especially when it's something other people have told me I shouldn't, and especially when it's been true for months (not just a fleeting one week idea), then when I end up doing it, I feel particularly glad that I did. And when I don't follow my peaceful preference / my gut and go with it, I tend to lastingly regret not doing so. (So, perhaps consider some meditation i.e. sitting with eyes closed and kinda talking to yourself to get clearer on your intuitions - what do you feel you "should"/"shouldn't" do, what do you have impulses to do/avoid, and what do you overall peacefully prefer?)
My suggestion would be to trust your gut! Consider trying the coffee shop / maker space thing, in a small way. But if you still wanna just go big and buy one, then do that.
But you could try it out by renting a temporary space for a week or a month, and creating a pop up cafe or maker space. Could work especially well during holidays or alongside any special events.
I think owning a coffee shop for the community is a much more achievable and realistic goal than moving to the country to farm, but it smells of the same kind of “grass is greener” energy.
I was really worried about what I would do AFTER so I just kept working a day job even after I made FU money.
The difference was that I started working for different reasons which was meeting people and learning about the problems they faced.
Meeting new people and deepening relationships with people I already knew has been great for my mental health too.
It’s given me cool things to work on as well.
Also, if the guy paid for an extension pass and was auditing courses "officially", he's well within his rights.
I have some online businesses and I've considered buying some more (eg. on acquire.com) which would be buying a job.
I would definitely do it but people overvalue they're business so much it's ridiculous. I think they're using some startup multiplier and apply it to their tiny projects. So I always ended up building a competitor instead.
If you want to specifically buy a cafe I would do it only if it makes business sense.
Eg. I would not buy a cafe in a country with high tax, high bureaucracy with all the young people leaving for better places.
Worst idea ever and I’m not comfortable expanding here. But the dynamics are just too problematic.
Here is my suggestion to you:
1. Go ahead and open the coffeeshop but a really small one with a small office for yourself. You don’t mention where you live and if you are open to move to other places. To make sure you are running a small operation, you should have only one employee (excluding cleaning which you can outsource)
2. Work on an open source project. Find what most interest you and the stack that will make work a delight. Do you want to create a bitcoin node with Rust? Go ahead and do that!
The morning you’ll go to the coffeeshop, you can brew your own coffee and maybe service customers if you feel like it. Or not. You can work from the small office when you need peace or hang at your own coffeeshop to maybe socialize with fellow customers.
- scale-up
- coffee shop or maker space [etc] hanging out with my customers
- more freedom and more ability to make a difference [for a little while at a time]
- rewarding purpose
You could dig in that direction: identify what's underdone or missing in your field or city or tribe and put some energy into that. Don't worry about "buying yourself a job": as part of the scale-up, install an on-the-ground manager there - since after all it won't matter too much if you are paying yourself or making a profit.
There is one thing you don't mention and that's paying attention to your investments. This is where your living and retirement and (now expensive) hobby money all come from - and so that should actually occupy a decent fraction of your time...
Help friends with what they're doing. My friend opened a bistro and hired her two fresh outta college cousins to help out (her cousins are in the rich part of their family and don't need money). If they didn't have that financial safety net then they wouldn't have been able to create amazing memories for the 2 years that they spent there.
It's just about enjoying life. Join people on their journeys. Your friend wants to walk across the USA? Join them for the 6 month trip. Go join remote year and meet nomads. Follow some tribes. Try leaning into your hobbies and going to the best place for them (if you're into hiking, then you can go to Everest. You can just hang out at basecamp and make friends, you don't need to summit.).
Maybe try being a personal assistant for someone interesting? My friend is an influencer and her assistants are usually fresh out of college and don't mind being paid a terrible salary in exchange for meeting cool people and attending events. You could join an NGO that shares your vision and make a difference (or as much of a difference that a normal person can make).
Do you have enough to invest money? I'm sure some startups would love both investment money and someone who is willing to tinker with some of the less glamorous but still somewhat interesting tech work, or fill in gaps or whatnot.
With my free time, I spend a few hours a week teaching people how to code for free. I became a volunteer firefighter and started working at the academy as a helper. I joined a local sailboat racing team. Between all that and running, I feel like I've got a full enriching life. Mix in some video games with friends, some Great British Bake Off, and my leisure time is set.
Even still, there are moments where I want to go back out on trail, and each day get closer to putting on my pack and heading into the woods.
[1] https://www.youtube.com/watch?v=hiVbB7Pf2lY&t=3s&pp=ygUNZWxp...
A while back, I took a leave of absence from the tech industry to work on climate change issues, and was amazed at what it felt like to work on issues that really seemed important.
Of course, it doesn’t have to be climate change, but if you are interested in that, you might have a look at: https://airminers.org/