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> 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

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.

Before buying a coffee shop, work in one. I think it’s pleasant but not everyone does.

how often do coffee shop workers get to interact with customers extensively versus having to solely focus on preparing orders/working?

As one myself, all the time. When it’s busy obviously not, but there is lots of downtime. The reality of the situation though is that if OP were to run a shop he would be very busy with logistics, hiring, keeping up with market changes, coordinating with other owners in the area, keeping the place up to code…

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.

Ah, I’m in this boat. My advice: stop trying to force a job. Explore your interests until you find a spark. Talk to a lot of people about what they’re up to. Maybe you want to go on one of their journeys for a bit.

Best advice.

I agree that this is the best advice.

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.

to be honest i don’t want someone to be on my journey unless they commit to it. i don’t need some guy on my journey who is never going to invest or commit and is just there to pass time.

Well certainly, everything is a negotiation and boundaries are important. Commitment means different things to different people. 50% of first marriages end of divorce. If you’re asking for more commitment then that for these transient/ephemeral experiences, hooboy do I have bad news for you. Take what you can get but hope for the best.

Similar situation. I ended up paying a few bucks for an extension/guest access pass at the local university. I just started auditing lectures in any and all departments, 20+ hrs/week for a few semesters. Eventually I found myself getting really interested in one subject, took all the classes available, and that's what I decided to do for career 2.0

i feel like a 30-50 year old sitting alone in a lecture with mainly 18-20 year olds is… not super well received most of the time?

I seriously doubt any student would care, honestly. When I was a freshman there was an older guy in our courses who was transitioning careers. He was a smoker like half of our group at the time, so we spent a lot of time just shooting the shit with the guy between classes.

Also, if the guy paid for an extension pass and was auditing courses "officially", he's well within his rights.

Not retired but, in 2022 I took four months to hike half the Appalachian Trail after getting inspired by the documentary "It's the People" [1]. After coming back, I wanted more life in my work-life balance, so I started consulting part-time. It is fun and keeps me busy to have little projects going on while paying my bills.

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...

Take the time to build an alternative to something that exists today but is not incentivized to rent seek. Like a social network, an open source EHR system, or just find an open source project and improve its UX so it can compete with commercial solutions, apps and mobile games for kids that aren’t based on micro transactions or ad ridden, etc. that is not to say don’t seek a profit, but build business models that are win-win for both parties. That’s what I’d do if didn’t need the money.

Finding interests seems to be the common issue. Some people "retire" with a ton of interests and wonder where they ever found the time for their previous job. Others not so much. But you do mention a few interests:

- 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...

who goes to a coffee shop to hang out with the owner/employees who are working?

For coffee shops plus a concept, it's pretty common. Coffee shop plus guitar shop, plus maker space, plus plant store, etc.

Funny you say that, I've had this exact experience. I've never socialized much with coffee shop owner or employees but I stopped at a coffee shop plus bike shop and ended up chatting with the owner the entire time.

I am in a similar position to you (though not quite IPO scale exit)!, and I am doing a part-time PhD in work related to what I was doing before so I get to use skills and facts learnt.

I think that I'm doing useful stuff, and the experience is fun!

I've also thought about going back to school. Glad you're enjoying it!

How about starting a charity going into schools and helping people with tech?

At least in the UK a charity is a lot of admin overhead. The volunteer organisation that I spend most of my time with is not even incorporated. I also spent over a decade as a school governor (unpaid!) which I think made a difference, especially to the maths side of things.

I didn’t know that a part-time PhD was possible. How did you end up with that arrangement, if you don’t mind my asking?

I would assume there's a lot of flexibility in non-funded PhDs.

I didn't know that such a thing existed either, in fact I thought that the maximum time you could ever take on one (watching the struggles of an old manager of mine) was less than mine is scheduled to take.

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)...

Trying to earn a living out of building open-source software isn’t the surest business plan. But when you don’t really need the money, it allows you to work only on what you love and you can quit at any time. If you’re unsure where to start, begin by contributing to something you already use.

I was in a similar position in 2010. I really liked teaching but didn’t want to go through the education and credentialing process. I went to work part-time at an Apple Store as a Creative teaching folks how to use hardware & software. That six month experiment turned into seven rewarding years and many dozens of good friendships. I followed that with five years in Peace Corps (4 as a volunteer and one year working at HQ). If you’re interested in owning and operating a coffee shop, go work at one for a while to see if it’s all you expected. Good luck and congratulations on your success!

So, I have been in your situation for last 10 years. I tried lot of different things but nothing panned out. But most of the things were solo activities that I thought I will build upon and May be find my own group of like minded people.

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.

I've long dreamed of FIRE but haven't reached it yet, but here are my thoughts. A lot of us are lucky enough that work is enjoyable. It sounds crazy to the layman but I genuinely enjoy turning figma designs into react components. But work can just be anything that's "productive" and I love work (a lot of people would just want to watch tv and order uber eats every day if they RE'd)

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).

Unfortunately not in your position, but know some people who are. They have found it rewarding to do angle investing. There are some really interesting start ups out there and you can pick choose to find the ones that have PMF and are about to start to scale up - which is where you can probably add the most value from your own experience.

Be aware that you will have to kiss a lot of frogs.

> 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.

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.

> you're just buying yourself a job

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.

Buying a NBA team isn’t like a buying a boat.

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.

lol you're friends with steve balmer or casually run into him at gatherings???

I’m not a friend with Steve Ballmer but often ran into him at private dinners and other social events in the LA area after he purchased the Clippers.

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.

Boy was he right

Why don't you just find a maker space, become a regular there, and help people with their projects? You get all the benefits of owning one without any of the downsides.

Work on open source projects that encroach on the space of FAANG products. Examples: it is nowadays possible to write a version of client-first web based Google Docs using CRDT libraries like y.js and freely available WebRTC signal servers. It would be obviously more limited than Docs, but it would be "good enough" for 80% of the average user, that needs to work on a shared presentation, update their calendar or edit their CV on their phone and print it with their desktop machine. Nobody packaged this hypothetical "app" into a javascript static file yet because it's hard work, but if this project was willed into existence for free it would be good to see how it fared against Workspaces or Office365.

Another example: a kit to write your own specialized (scalable but not planet-scale) search engine. An user-friendly free ⁸executable app that runs a commercial-grade large language model on your Mac, with automatic configuration and updates. A music player app that uses your S3 / D3 storage for songs and manages tagging (with Musicbrainz?) and uploads / CD ripping for you. I'm sure all these things exist already, but they're not finished as a commercial product is, because it's hard work.

Have you considered working at FAANG? Plenty of chill teams where you don't have to work too hard but can get intellectual stimulation.

Not anymore not in this economy I'm afraid

Have you considered teaching and/or mentoring? I’m sure you have a lot to offer to students and people who are early in their career.

I’ve struggled with a similar idea. One thing you have going for you is that you don’t actually have to make money. You can buy your retail location with cash and just cover the daily expenses without covering real estate costs which are a major piece. The problem with these businesses is that you actually have to be there at the times it’s open which can cut into your other life stuff unnecessarily. One way you can compensate is to overstuff and pay above market for talent but still you will occasionally have to deal with issues like staff quitting during a vacation or some other major life disruption annoyance that small businesses have to live with.

I’m surprised that no one has suggested: pick something that you actually care about, which may not be a lucrative job opportunity, but gives you the opportunity to “make a difference“. Most nonprofits desperately need help with their tech.

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/

Well, I like to create digital products, always have, always will.

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.

>but finding PMF is hard and my experience has always been more scale-up.

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.

If you have the funds, why not invest in a number of startups that interest you?

Why don’t you treat learning to enjoy something other than working as your job?

Buy a small company on flippa or similiar.. 1000-5000 and scale up.

try consulting with the folks on /r/fatFIRE on reddit (if you're okay with that). many folks on there in your position, i'd assume.

Do you have hobbies? Maybe go travel for a year or two.

Ask HN: Buying Yourself a Job