When I was in high school going over college, I decided to go to a school based on its prestige over the school I fitted in. Reasoning that a school with a better name would help me get a better job and impress people when I go to dinner parties.

When I was in college, I decided to chase girls that I can't have and break off with girls who I clicked well with. Reasoning that I should get what I can't have and that most people will judge me better with a good-looking girlfriend.

When I'm working, I chose to work at a well-known Wall St. company over a unknown startup. Reasoning that the compensation and the cocktail impression factor would be better this way.

Like a trader, everyday people make choices. Some people choose to play it safe their whole life, stay, work, marry & die in the same town that they were born in. Some people take incredible unwarranted risks, like dedicating their lives to be a professional athlete/musician/actresses despite overwhelming evidences that they don't have the talent for it. Some people take huge risk by letting themselves emotionally vulnerable when they fall in love. Some people follow the most optimized investment plan, go to the right school/major, work at the right company, choose the right partner, put the right contribution into one's 401(k) plan, have the kids and then retire the right time and finally die the right way.

But the market is simpler than life because in the end, everyone's measuring stick is the same, how much money you made/lost. But in something vague as life, everyone has different measuring stick; what's even more frustrating, your own measure stick is constantly changing; what I thought was important two years ago is completely trivial to me now and vice versa for what I thought was trivial.

And there's no use in predicting what you think would be important to you in the future because you most probably end up being completely off; plus, it'll just leave you frustrated to forgo your present moment to work towards a future that you might discover that you won't want anyways. Attribute that to any philosophy or psychology B.S you want (cognitive dissonance, confirmation bias, existentialism), all I know is that it has happened and will happen again.

The only certain I'm certain about is the present; I'm not talking about being hedonistic, but to take risks for the present and to leave the present moment without any regrets. Kiss the girl, stay up late to finish coding & take the day off just to take a walk.

Life loves to subject us to the useless positional (numbers) measuring sticks that mean nothing in the long term. Case in point: Someone name (off the top of their head) the ten wealthiest men - in the correct order - back in 1970.

This is why it's so important to develop a set of principles that you want to live by, and let those principles be the compass that guides you through life. You'll never know the path that you'll be taking, but at least you know you're headed in the direction that you want.

These principles I'm referring to are things like love, honesty, integrity, etc. For me, I think the example provided by Jesus in the Bible highlights the best example of human principles I've ever seen, so I try my best to follow those.

I will add though, very easy to talk about this concept, extremely hard to do.

Irrelavent. Can anyone name the top 10 wealthiest in the correct order, today? More importantly, why does it matter whether you know or not. What counts is whether they consider to be living the life that makes them feel great. What's wrong with that involving money for some people?

You think money can't bring happiness? Look at the f*ing smile on my face. Ear to ear, baby.

http://www.youtube.com/watch?v=zvICN8DNMpY#t=2m10s

Let me restate the point of it for you, since it clearly went over your head: In life, it's best to have a personal (internal) measuring stick that keeps you grounded regardless of how you choose to play the "numbers" game...

It means a lot to me in the long term that I'm living in a nice big house with a nice big garden for my kids to play in, which is also close to a world class city and world class companies. That's going to be very expensive. Therefore money isn't a useless positional measurement stick that means nothing in the long term to me. It's an incredibly important number that if I attain will mean fulfilling a dream and bringing me and my family much happiness. No internal measurement stick is going to make me happy about being forced to bring up my kids in a trailer park in rural Texas.

Jeff Bezos' Regret Minimization Framework:

"...it really was a decision that I had to make for myself, and the framework I found which made the decision incredibly easy was what I called -- which only a nerd would call -- a "regret minimization framework." So, I wanted to project myself forward to age 80 and say, "Okay, now I'm looking back on my life. I want to have minimized the number of regrets I have." I knew that when I was 80 I was not going to regret having tried this. I was not going to regret trying to participate in this thing called the Internet that I thought was going to be a really big deal. I knew that if I failed I wouldn't regret that, but I knew the one thing I might regret is not ever having tried. I knew that that would haunt me every day, and so, when I thought about it that way it was an incredibly easy decision. And, I think that's very good. If you can project yourself out to age 80 and sort of think, "What will I think at that time?" it gets you away from some of the daily pieces of confusion. You know, I left this Wall Street firm in the middle of the year. When you do that, you walk away from your annual bonus. That's the kind of thing that in the short-term can confuse you, but if you think about the long-term then you can really make good life decisions that you won't regret later."

See: http://www.youtube.com/watch?v=jwG_qR6XmDQ

A big payout is definitely a large factor in jumping ship if you're arrogant enough to believe that you can attain such a thing. If you just want to "work at a startup" without having much of an idea about which startup and no intention of starting one yourself, then frankly in my opinion, jumping ship isn't for you. If you're this concerned about your financial status today, at a company you don't drive the vision for you're going to find it harder to drum up the ambition and drive it takes to get through times where a huge financial payout is not as certain.

I needed to create and to be rewarded for my efforts fully. Everyone I know was against it, wife, family, and friends. Thought I was throwing away something they could only hope for. At the end of the day we live once I'd rather be poor and happy trying something I always wanted than stay in that cube always wondering.

What prompted my move so abruptly was interviewing a guy for a senior position. We asked him what his ideal job would be, and he gave an answer of doing his own business. He excused it as a dream because he has kids, and that's when I realized everyone I worked with had the same reason for not just doing it. That's when it snapped in me.

Week later I put in my notice. No jobs no nets to fall back onto. I actually worked on my own project last week and it was heaven. I have a meeting for a three month contract next week to feed my funds to continue this dream. Brother this has been the best two weeks of my life.

Start something small on the side. Fix your personal finances so you can build up a warchest (it's easy: just live the lifestyle you're considering living as a startup employee). Then, in a couple years, go work for yourself.

Say you are a rock star making $100k/yr. After taxes, in CA, that's ~$60k/yr. If you are single and super-cheap (i.e. celibate), you can live acceptably on about 30k. Thus, you build 30k/yr in capital.

Say you need $3k/mo bare minimum, pre-tax, to retire, and refuse to draw down on capital. At a 5% return you will need $720k. It will take 20+ years to get there, assuming you survive as a corporate cog for that long, which is unlikely, given competition from emerging markets.

Of course, if you ever get married and have a family, this won't work at all. And if Wall St somehow takes 30% of your portfolio one year, you are in serious trouble.

Now, instead, say you quit working for The Man, and build a service priced at $10/mo. You have the tech background already, and work hard to learn the necessary ops, marketing, sales, and other skills. You automate everything. You work from home (saving 1 hr/day commute), have excellent margin, no employees, etc. With a web app, to hit $3k/mo, you probably only need to average 400-500 paying customers.

There are several billion people on the Internet. You just need 500.

Sure, a business producing $3k/mo after expenses is not exactly equal to having $720k in liquid investments. It's much less liquid, requires more of your time, faces competition, etc. But it also has some advantages, such as the potential for very rapid growth.

Most importantly, it scales: you can build more than 1 app. So even though you'll probably fail a lot before success, you're probably still better off.

I wish somebody told me this 10 years ago.

Add on bonuses & that puts smart but not necessarily rock-star kids at close to $100k/yr straight out of school.

I suspect that for most people the calculation comes down to some version of "what's the most interesting work I can do while still having a reasonably comfortable income".

Since this is a financial article, I'll focus on financial stuff.

Its anecdotal but I think the average financial return for doing a startup is slightly better overall, and probably decently better if you are highly intelligent and skilled overall.

If you are not highly intelligent and skilled overall its possible working at a company is a better deal.

Two questions to consider:

Q1: Long term--what will open up more avenues of opportunity for me?

In general I was not a very good corporate climber. Some ppl are. Some ppl aren't. I am not. I dress casually, speak colloquially and comparatively don't care too much about what other ppl think and don't like 9-5.

Given I already have startup success, it was easy for me to decide startups are financially more lucrative for me.

Why didn't I stay and wait for all my earnings to pay out?

1. I got most of it already

2. I'm not getting any younger

3. I found a great team that I wanted to start a company with.

4. The remaining cash would not change my life significantly.

Given all of that, I decided I'd rather leave.

Q2: Having been in your position when I was a bit younger and first starting out (relatively high paying job...didn't love it but i wasn't going to shoot myself), I'd ask myself the "bezos/jobs question" : When you are 80 and on your deathbed, your life flashing before you in your last days, will you look back and regret the decision you took to jump ship and do a startup?

Imagine all sorts of realistic worst case scenarios....completely flops, you go bankrupt, waste 3 years of your life, gf leaves, mess up your health for a while...whatever is really bad but realistic.

Does the 80 yr old regret the decision of doing the startup? If so, then thats fine. Don't do it. I think I would have balked if I had a mortgage, kids and no savings.

However, in general people regret things they haven't done more than things that they did.

The team is definitely the most important. I've been looking for the last year. The advice has been oft repeated but here is my top criteria:

- Get people who can, at the end of the day, do everything.

- Get people who are better than you at something or multiple things (for example, coding, sales)

- Get people who are awesome at as many things as possible.

- Make sure your values and your expectations are in alignment about the endeavor. If one person expects VC funding and good pay to support a family and the other wants to go into ramen profitable mode it'll be tough.

- Make sure they are not pansies. Some people who have succeeded all their lives will give up at the first sign of trouble for 'easier pastures'. As best you can, try to find people who have grit and determination.

- If you're not sure, pass. Its alot cheaper to make the right decision than to have to divorce later.

Leaving the high-paying job was the best decision I ever made. I make far less money now than I used to, and even less than almost all of my friends; but I work on what I want, when I want, and at my own pace, and I can take as many days off as I want. (Yesterday I spent the entire day exploring Waterloo in the sunshine, because I felt like it. Next week I go to Oktoberfest in Munich).

Basically, I went from rich and dangerously depressed to comparatively poor yet happier and more satisfied with my life. As long as you have enough cash flow to keep a roof over your head and some healthy food on the table, that's all you need.

Your risk is lower but so is your upside.

And that is one thing that entrepreneurship/startups offers - the chance at building something and being rewarded big (albeit generally at insanely high risk)

So I was making $85K a year as a project manager/developer. I went to work in a contract period for a startup who, if I had gone full time, would have offered around $65K to me as well as much worse benefits.

That would have included a certain number of shares. The founder gave me his expectation as to what would be a low, medium or high exit. Based on that I would have made between a couple thousand dollars and, at most, $100K. Now, I would have to work at the startup for 4 years to fully vest, meaning I would have lost $20K per year in salary. This means even if had a large exit and I made $100K, it would still just be a little over what I had lost in salary.

After a couple of months there, I went to work at another "regular job" and made $100K per year, which means it would have been a loss no matter what. Now I still work making good money and am working on my startup on the side. Since the startup-people were expected to put in significantly more than 40 hours a week anyways, I'm probably just working about the same amount of time and making way more money AND controlling my own destiny with a startup I am personally passionate about.

This is a business; don't get too romantic about it.

You say there are a lot of risks associated with a startup. As part of my decision process, I realized I had to consider the long-term risk of being unfulfilled at your job, not developing your skills and talents the way you expect. This is a bigger risk IMO.

1. Had a solid financial cushion via savings to really give myself enough runway to do the startup thing sincerely and whole-heartedly

2. Knew that if even things blow up, I'd always be employable

3. Very few folks become really wealthy working for someone else

The upside monetarily is a motivator, but the bigger thing I've realized after jumping to startup-ville is that my worst day in my startup is honestly better than my best day in corporate America. There are immense non-monetary benefits (and a whole lot more stress as well)

Had my job offered to double my salary or something rediculous like that I probably still would have left, but coming from a middle-class family where having a high paying job was a major motivator (for the stability, not the luxury), it would have been a very painful thing to do.

18 months ago I was at a "high paying job" by most standards. I worked 45 hours a week, had great coworkers, and even generally enjoyed my work.

I left because a regular job gets in the way doing other things that are important to me: enjoying the sun in the middle of the day, not working on tuesday if i don't feel like it, traveling for 3 weeks at a time, etc.

Being incredibly rich or owning shiny toys isn't nearly as important to me as scheduling freedom (and hopefully eventually location independence), so it wasn't for me.

Sure, it'd be great if I somehow had a big payout for doing what I'm doing now, but its not even in the top 5 factors for why I chose to pursue "the startup route".

No amount of encouragement or advice from others who have left their jobs will help you decide if its the right choice for you. You have to dig deep, figure out what you ACTUALLY want, then you can decide if leaving the day job is right for you.

I realized the the upside really exists for the founders...so that's what I'm doing.

"...and the framework I found which made the decision incredibly easy was what I called -- which only a nerd would call -- a "regret minimization framework." So, I wanted to project myself forward to age 80 and say, "Okay, now I'm looking back on my life. I want to have minimized the number of regrets I have." I knew that when I was 80 I was not going to regret having tried this..."

- quoted from http://www.achievement.org/autodoc/page/bez0int-3

Your comment also implies that people should only base their career decisions on what non-outlier (average) people have done. That sounds like a recipe for mediocrity.

"A reasonable man adapts himself to his environment. An unreasonable man persists in attempting to adapt his environment to suit himself. Therefore, all progress depends on the unreasonable man." - George Bernard Shaw

If salary is important to you, I'd recommend a later stage startup. It will likely be the happy median between an early stage startup and BigCo.

You'd be working mainly because a) it isn't a BigCo and b) the startup culture is still apparent.

Sadly both of those things are only going to get less and less true as time goes on if the company is successful.

I took a 50% paycut to work at a company that was "re-inventing" itself and starting up a technology organization. I switched jobs, because my current job at the time was moving from building new stuff to maintaining old stuff, and the new job was all about building from the ground up and learning new skills.

I loved the new job, but then due to severe fiscal mismanagement multiple rounds of layoffs came about and the remaining people got their salaries cut by 20%. I went from cashflow positive to cashflow negative. With a mortgage to pay, I went back to a job with a high salary (and more boring actual work).

Without the salary cuts, I would still be at the job. Too bad, I really liked it. However, the family's well being comes first.

the whole 'fun' thing has two aspects.

There's the practicality aspect i.e. business in general and startups in particular are painfully difficult and you can't really win if you don't like (or ideally love) what you jump in to.

If you can work only 8 hrs a day but your opponent loves his work and words 14 hours a day you're screwed.

There's also the reality aspect. NO ONE ever does a start-up without motivations like money and pleasure and importance.

If your prime modality is making money and comfort then a start-up isn't right for you at all.

Also, all your reasons for wanting to do a start-up are meaningless. stepping stone to other opportunities?

if you're taking such a big risk fucking do something that is the ultimate opportunity.

Post-acquisition, the salary was good, the bonuses amazing, but the company was dumb as a bag of hammers, and the job became soul-crushing. Dilbert bosses, communication by powerpoint, pointless projects. It got to a point where I just had to get back to a startup. All but one of the really early employees left for similar reasons, and also to join startups again.

That said, I'm not sure I'd make quite the same decision if I couldn't get in very early to a startup that I thought had a really good chance of succeeding.

I've since left and joined a startup, I'm making slightly less and with less benefits but I'm definitely having more fun and learning 10x as much working in a small very early stage startup versus a corporate 100+ year old company.

if (there is a very promising good startup offer): take it else: work on your side project until it takes off as a real startup

My thought process was pretty simple: at the time, I was more or less independent, and living /very/ frugally, which made the decision easy. I do know this: if my financial needs were different, I wouldn't have moved.

I am also in India. I am interested to know more about your story.

This is the kind of startup that doesn't figure all that much on HN, since it's in a rather specialized niche of a specialized industry to begin with. I'm not a founder, but one of the early employees.

Actually I wish our profession wasn't just 0 or big chance payout but had some in between too.

It's not. I mean, if you don't take on investors or debit, it's pretty easy to setup a sub-minimum wage business for yourself. I've set up more of those than I care to remember.

Now, getting yourself up to ramen profitable from that is a little more work, (I can live on $15/hr, but not on $5/hr) and getting yourself to opportunity cost profitable is a lot more work. But if you are bootstrapping, there is a whole continuum between zero and 'big payout'

P.S: he also wrote a book on Xen which is in my ToRead list.

I have a double Masters in Business Administration and the "traditional" way for students like me is to start as a consultant (McKinsey and the gang), investment banker or whatever. In Switzerland that meant a starting salary of at least six figures but money was not really a factor in my decision it was mostly based on the fact that I wanted to do what I liked.

In the year between my Bachelors and Masters degree I interned 6 months for a Swiss web/technology consulting company and 3 months for Accenture. Both experiences bored me to a degree I had not thought possible. It wasn't that I had no responsibility - which I had - or that the tasks were repetitive - they were only slightly - but I just wasn't faced with the challenges I was looking for. From quite early on I loved to create my own things and I realized that just was not possible in a corporate environment and I had to do something about it. My first plan - following conventions - was to be a part-time entrepreneur. I wanted to work at one of those strategy consulting companies and have my own thing on the side. When I look back that idea seems crazy but at that time I was convinced I could do both. But in March I talked to a successful Swiss Entrepreneur and he convinced me that this is an all or nothing game. Either I went all-in or I had to fold. I decided to go for it and haven't looked back.

As I said before money wasn't really a factor in this decision and that is for a few reasons:

1. I have a safety net through my parents. This obviously is a very comfortable situation that not everybody has.

2. I looked at my potential salary as opportunity costs and decided that it was worth the costs that I could do what I wanted.

3. If I need to I can still go work for those companies I decided to forgo now or another company. I have an excellent education and I see my entrepreneurial endeavors as an extension on that. Obviously after having been an entrepreneur for several years I probably won't fit into the mindset that Strategy consulting companies look for but there will be plenty of opportunities if need be.

4. I never had massive amount of money available to me. I always lived comfortably and still do but I was never a big earner and therefore don't have an expensive lifestyle to support. Also at the moment I don't have any responsibilities, no family, no children to support.

On a side note: The consequences of my decision to start my own business have not always been easy. One of the harshest things is that many of my friends now almost can swim in money but once I talk to them about their Job I am convinced to have made the right decision.