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You've got plenty of money, you're living on 1% of your savings, which is great - controlling expenses is significant.

You should be able to invest the money with the goal of beating inflation and grow your pile. There's people who retire with a lot less. There's tools to help, where you can play with the numbers, investment returns, inflation rates, etc.

It's difficult to predict the future. You might wish you had more money a couple of decades from now, or you might get hit by a bus next year and wish you had lived it up more when you had the chance. Eventually the stress of your current job is likely to affect your health. It takes a while to get over being burnt out.

The safest option might be to look at your money as a wonderful cushion, giving you options that others only dream of. You can find a different job that you like, even a lower paying job preserves a lot of your savings. You can take time off, maybe doing something along the way that looks good on your resume. You can work on and off. You can change careers. Maybe figure out what you'd want to do if money were not the object. You are way ahead of the game. The world is your oyster!

It can take a while to figure these things out. Best of luck!

I'm still thinking about this comment 2 hours later, so I thought I would chime in. If you and your friends/family think $5.5M liquid is not enough to retire, I just want you to know, that you are in a very very elite and strange SV bubble. I don't live in SV, but I too know people with your net worth in SV, and they all act like they are poor and what they have is never enough.

For this alone, I'd urge you to expand your horizons, maybe when you retire move out of SV or just spend time with people outside your circle.

Have you done the math on this? At your current expenses, you can live indefinitely on the proceeds of pretty safe investments of the 5.5mm, and still hit 10+mm by the time you are “regular” retirement age…

It’s probably too early for you to decide that you are done forever, but you could be if you want to.

You could take a break of 1-2 years and see how that goes. Call it a sabbatical on your resume if you want to go back to work after.

This sounds like classic burnout. You just need to take a break from work, try 3 months or so.

Yeah, grandparent post should just take a year long sabbatical and come back when they’re feeling it.

What is the reason to suggest that a break from work, as opposed to a retirement (more similar to the author’s path), is more appropriate for my situation? Is it a concern about financials/age?

After reading several people describing their experience (even in this thread) as “once you taste the freedom of not working, you will never be able to go back”, I can totally identify myself in that, so I like to think that the decision of “just take a 3 months break” would become a much more serious one.

I am pretty young, so take this with a grain of salt, but the motivation seems simple to me: If it is burnout, then a short break might put things into perspective, and help him decide whether to retire, switch jobs, do something on his own etc.

I'll give you my perspective having gone through something similar. I was in a pretty similar pit, hit rock bottom, and only then did every high achiever in my life open up to me that taking a sabbatical was the best thing they had done for themselves.

Your original comment especially about not enjoying things, not knowing what your hobbies are, etc, are indicating that you've just lost yourself a little bit. I was in very much the same place. It takes some time away from what occupies most of your thoughts/attention (work) to re-learn who you were and who you are now.

For me, I took 3 months away from work. For the first 2-3 weeks I basically did "nothing." And it was only after that initial period did I start to remember things I enjoyed to do and felt motivation to go do them. After that, the remainder of my sabbatical was spent finding every minute I could spend with friends and family that I could.

I came out of that sabbatical with a, still fuzzy but a bit clearer, understanding of what I wanted but I was still the same ambitious person I was before. Chances are, you would still be too. If you're going to do it, think of it less like a 3 month break and instead as giving yourself 3 months of room to think and experience and re-introduce yourself to yourself.

As an aside - if you're feeling and thinking these things, your partner likely notices too. I have no idea what your relationship is like but can guarantee that all this definitely has an affect on y'all and you won't see what it truly is without said room to think and contemplate.

If you don't mind leaving the US, there are lots of places around the world that will make that 5.5m go way further. Keep a very modest/middle-class lifestyle. Never upgrade and you'll have ultimate peace of mind.

> I just dream of spending a life of slow breakfasts, hiking on Monday mornings to celebrate a new week, reading books, slow traveling, and spending more time close to my aging parents.

That sounds like a lot to retire to if you ask me. And $5.5M seems like quite a lot to me. Probably especially if you move back to your home country or almost anywhere else in the world outside Silicon Valley.

Myself, I do have some hobbies but I'd probably go nuts without the structure of having a formal job. If I were you, I'd try and find work that I actually enjoy and find meaningful; you probably don't need to worry about money so much, but if you had a job that covered your expenses, you could let the principle you've already accumulated grow.

> If I were you, I'd try and find work that I actually enjoy and find meaningful

Thanks. That’s easier said than done.

A big reason why (but not the only one) work is so depressing is because, in every single job I had (consulting included), I ended up pretty quickly despising and being highly resentful of my managers, I just don’t like being told what to do, “being coached”, “given feedback”, “pressured”, and oh God those 1:1, I hated every single 1:1 I ever had throughout my career.

Naturally I always put up the right facade to allow me to perform, but good luck finding a job without a manager.

I realize this says more about me than my managers, but this is still the reality.

FWIW, when I’m not working or depressed about the thought of work, I’m actually a pretty happy person.

I think you should try a hand at running your own business, being your own boss. You seem to have enough money and the industry experience to take a shot at it.

I am inclined to agree with your parents/friends, you still have a lot of human capital (read: your youth) to build financial capital with today so you can have an even more fulfilling life tomorrow when you no longer have all that human capital (read: old age).

This isn't to say you shouldn't life your life now, of course. I wrote in another comment here that living today and not tomorrow is imperative[1]. But to refuse to make money during your prime money making years is also folly, because that money today will save your time tomorrow.

[1]: https://news.ycombinator.com/item?id=41757791

It’s not folly if you have enough to manage your current and future needs. At some point doubling your wealth won’t even move the needle on fulfillment - for almost all people. The point is of course for everyone. And in the other direction deferring fulfillment later for money now absolutely is folly when done for too long, none of us know how long we have.

I am an europoor from Italy but 5.5 millions.. I think I could retire for a few centuries

Yeah, no kidding. Thank you, @madmask, for the comic relief. Can you imagine how nice a life you could have living in a small city/village in the south of Italy with 5.5M USD stashed away? Heaven on Earth!

Damn, I had exactly the same thought. Europoor from Milan here, I'm probably forced to work until 70, so man...

It sounds to me like you hate work more than it’s warranted in normal circumstances. Work-life balance aside, there might be something else in there.

Yeah it’s probably true. I explored this during a therapy session but nothing particularly insightful came up.

I grew up in a family of entrepreneurs (extremely small scale brick-and-mortar solo businesses in my home country, barely making ends meet) and I clearly remember my father and uncles in my childhood being very proud about “not having to work for someone else”, probably something subconsciously stuck.

To be clear, those same people are the ones who are now telling me to absolutely not quit my corporate march due to my demonstrated earning power, and to toughen up and suppress my feelings of unhappiness for as long as this money train can continue. My mother is a bit more romantic and she’s telling me to set a deadline in my 40s, which is still way, way too far.

Dear struggling Internet person: I hate to give a diagnosis over the Internet, but you are either depressed or burned-out. I recommend to take a year off from work. If you are good/valuable enough, your employer might let you take it unpaid. You can probably find some blogs or books about people like you who have done the same. If you are only 38 and worth 5.5M USD, then you are likely very highly skilled. You can easily get another tech job after you take a year off. And, if anyone asks why you took a year off, just tell them you had a sick family member that needed your care. (That makes them shut-up real quick!)

Lastly: About therapy: One thing I tell people: If you believe in it, it will work. (Conversely: If you don't believe in it, then don't waste your time and money.) So, if you do believe that therapy can work for you, try a different therapist -- couples or single. Example: Choose a therapist with a different gender. It will help to open your eyes to a new way of thinking.

> You can easily get another tech job after you take a year off.

Thank you for your comment. It is missing a critical point.

I know that it’s likely I could get another job if I wanted to, after a year self-funded sabbatical (which, btw, wouldn’t be with my current employer, after having been with the company just a few months, remember the “3 companies in the past 4 years” part, I’ve really been on a wild job hopping ride caused by how much I hate working).

What I also know is that I have this strong inner feeling that, if I took one year off work, I would never, ever, want to go back to work, because working after experiencing such freedom would feel even more torturous than it is today. So, I see this strictly as a one-way only, and I would like for any commenter to treat this feeling at face value.

This is, in a way (modulo the entrepreneurship part, for which I don’t think I’m cut), similar to what my dad told me once: “in my early 30s, after I quit my job to embark in my solo entrepreneurship adventures, I knew that, no matter how bad it would get, I would never get another job, the feeling of being in control of your day was way too powerful once tasted”.

    > I see this strictly as a one-way only, and I would like for any commenter to treat this feeling at face value.

Sure, I believe what you say. And still, you have 5.5M USD stashed away. You will be fine financially. After you return from your Eat/Pray/Love-styled adventure, buy some middle class rental property (2-3M USD worth), and you can live forever on the cashflow. Also, move to a cheaper place -- I assume that you live in a very high cost of living place now.

At the risk of overstepping my bounds: I do think that you are underestimating how much a year away from work will rewire your brain. Even 10 days away from the office has a distinct effect upon mine. New possibilities will emerge once your brain is much less stressed for a long period.

> Even 10 days away from the office has a distinct effect upon mine.

Thank you for your kind message. So far, every single time I’ve taken a 1-2 week vacation, it’s been an extremely positive experience, I truly felt alive during the time off, and even my partner routinely comments how I am a brand new person on vacation.

But, coming back to work after such vacations has always been a gut wrenching experience and I felt much, much more depressed than normal for several weeks until reverting to the “baseline” depressed state, to the point where I even seriously considered not going on vacations anymore until I quit for good. For this reason I never related to people saying “a vacation recharges one person for new work challenges”. I can just speculate how the idea of coming back to work after one year off would feel.

> I just dream of spending a life of slow breakfasts, hiking on Monday mornings to celebrate a new week, reading books, slow traveling, and spending more time close to my aging parents.

What is really stopping you from leaving the US and go back to your country? Is it your girlfriend? Is that it's hard to leave Silicon Valley and its tech-scene (i.e., FOMO)?

The money would probably be more than enough in your parents' country. And eventually, you could probably get bored and would find hobbies or passions to entertain yourself..