[Q4273j3b]

If I read all that right:

- you are making $60k/year post-tax off non-angel investments

- your yearly expenditures are about $2.5k * 12 = $60k

- you are about to quit your job (or already have) and anticipate an even lower expenditure next year (<$60k)

Dude/dudette, forget switching careers---if this is really and truly your financial situation (no debt, etc.), you could just go ahead and retire. You don't have to go back to your old job that you hated. You don't have to go back to any job. You are pressure- and fancy-free.

If web development is what you want to do in your first year of retirement, well, go for it. Financially speaking, you have nothing to lose. You could just as easily become a fly fisherman in Montana.

High five yourself! And go read http://www.mrmoneymustache.com/.

[beginagain]

Well I think your math is off there, more like 30k, or closer to 35 actually per year for expenditures.

I want to have a lot more money though. I want to be one of those guys with 100 million. So I don't like the idea of not working anymore. Plus, I want to work on something I am passionate about. I have had enough relaxation and vacation to last me a lifetime. I am sick of it. I want to find meaningful work.

I feel guilty right now that I'm not producing anything, and ashamed. [There are people a lot less intelligent than me with a lot more money than me. What is wrong with me? Why can't I be one of those people?] is the recurring thought in my head. But I think it's more about finding meaningful work than it is the money. Easy example, but if I was Anthony Bourdain, Paul Graham, Carl Icahn, Steve Jobs, I would be more than happy doing their work even without making the insane amounts of money that they obviously do. Because their work is meaningful.

I worked hard and made some money, but I am 31 and this is all I have to show for it http://i.imgur.com/ACsNRpi.png. I mean, I was paid by an employer and the market for that money. I want to create my own way, not crutch someone else's way. I must figure it out somehow. Just stuck and scared right now. I'm just not sure what to do. I need to push myself more I think.

[avenger123]

First of all good job on being where you are at.

You said, "I feel guilty right now that I'm not producing anything, and ashamed. [There are people a lot less intelligent than me with a lot more money than me. What is wrong with me? Why can't I be one of those people?]"

This is a very dangerous attitude and will lead to great disappointment in your life.

On the spectrum of why anyone is more or less successful than someone else, the notion of where you are born, who your parents are, what school you went to, how rich your family is, when you are born, what race you are, etc. all play a large factor. Don't also forget luck.

The American dream is very nice and all and it emphasizes the "you could do anything you want" mantra but for most people its a nice bowl of bullsh*t soup.

My recommendation would be to take a couple of weeks and figure out what you really want out of life. Why do you want the 100 million? Why are you so driven by this desire? What void are you trying to fill? We all struggle with these questions but it takes a certain kind of person to actually take the time and try to fully understand one self.

You are already 10 miles ahead from most people. Please don't equate meaning with your life with making lots of money. Find the most needy organizations in your city and go devote your time to helping them. These organizations need people's time as much as they need the money. You may already be doing this but if not, seriously think about doing it. Also, do some travelling around the world. Travel to Europe on the cheap, visit the Middle East, visit South America. These are good uses of your money not bad.

Also, relax, you are still a spring chicken and you have accomplished already what most Americans will not. Understand that your questions of finding meaning are not unique and we all go through it at some point. For some of us, our life circumstances resolve us to certain goals (and no, no amount of Anthony Robbins "go do it" message can change things). I would recommend looking at this mind map to provide some kind of framework for your thinking: http://www.biggerplate.com/mindmaps/g304883/life-planning

We are creatures of change. We change, the environment around us changes. Find what makes the most sense to you knowing that you will likely change to something different in a few months, or years. We operate on feedback. Give yourself feedback so that the loop can be complete. Doing different activities, volunteering, traveling, etc. All these are giving you feedback. You have the privilege of having the luxury to try out many things to see what fits.

Don't chase software development as a way to make lots of money. A lot of it depends on where you are and your unique skill set. If you do want to go down this road, pick a project you want to do and use the technologies that are the most in demand in your area and will pay the most. Start learning and stick with it for a few weeks. If you can't stick with it then its not for you. Sure, learning to develop is worthwhile but it doesn't stop you from building a software business, you can always hire developers (especially someone in your situation).

[Q4273j3b]

Whoops, you're absolutely right about the 30k. I'm leaving my poor arithmetic up there for posterity.

So. So so so. First of all, I gotta say, you are very good at writing how you feel. Which is quite the nontrivial thing. People are gonna jump all over you for your very admirable tour de honesty. Don't let the turkeys get ya down (as my mom always said).

Second of all. It sounds like you are in a bona fide self-loathing free-floating ambition doom spiral. (I am no stranger to them myself.) And as though your usual way of caring for your soul in pain is to sit on it firmly until it stops screaming. So, speaking of souls, & their care and keeping, I think you should get a book called _Care Of The Soul_ by Thomas Moore and read chapters 3 and 9 in particular. Also if you can get your hands on _The Power Of Myth_by Joseph Campbell, that one's not bad one either.

Hang in there, unknown internet buddy. I believe you when you say it's not about the money. But---if you'll allow me to be a little crude, here---greatness is not some constipated stool than we can anger-push out of us. First we gotta linger for a little bit with the Dulcolax of philosophy.

[cprncus]

> "Just stuck and scared right now."

This just says something about human psychology, that someone can be a wee bit past late adolescence, be making $60k clear for doing nothing, and yet feel "stuck and scared." Thankfully, most of the people in, say, Bolivia or Sierra Leone are unable to easily read Ask Hacker News. Ahh, humanity, you're a gas!

[mswen]

In many ways you are in an enviable position. You can take pride in the fact that you worked hard (at something you apparently didn't like)but you worked hard enough and competently enough that you got paid really well. Second you can take a healthy pride in the fact that you were wise enough that you lived on less than you were making and built up investments such that you could retire on a modest income at 31. Relatively few people achieve that level of income and even fewer exercise that kind of discipline.

But you now desire significance and the potential for even greater financial success. Great, get started and quit worrying about whether you will succeed. As others have pointed out if History or English majors can teach themselves the skills needed to succeed in web or mobile development there is no reason to imagine that you will fail to acquire the skills that you need.

Quit worrying about competing for a "job" and use your investment income as an extended start-up runway.

As you start developing an idea, go learn the specific technology needed to develop that prototype. If it starts to get traction great, you might have a hit on your hands and retain all the equity. If it doesn't get traction, at least you learned a new technology. Rinse and repeat. Since you have basic income covered, I would focus on the significance side of the equation. Do projects that you care about.

If you eventually tire of trying to build your own ideas, find a non-profit whose mission you believe in. Use your newly developed skills to work for them and help make something good happen in the world. They probably won't be able to pay you all that well, but you have basic income covered.

[CyberFonic]

Please read some of Paul Graham's articles. The key is to create VALUE that people will pay money for. So look for a $1000m problem that get's you excited/passionate. Chip away at it. At 10% you've got your $100m.