These are things I've learned from chances I should have taken, but didn't AND from correct decisions I made:

- If you're going to start a business, start one before you have kids or when they're very young. It's infinitely harder to take the leap when you have a mortgage, kids in sports and activities, etc. etc.

- You'll have to jump from company-to-company to make substantially more money (in many/most careers). Staying somewhere for more than 3-5 years is simply not rewarded very often in today's world. Sometimes it is. But usually it isn't. But often you'll get, at best, a 2% raise per year and that's it, if you stay somewhere. Whereas, if you switch you'll get big bumps.

- Don't be afraid to ask for a raise--even a big one. It's FAR more expensive and is far more hassle for your boss to go hire someone new than it is to pay you A LOT more.

- If you're in tech, focus on the equity. It'll change your life...or at least change the trajectory of your retirement, buying a car, or finishing your basement, instantly.

- Know how to negotiate equity. Too many people get screwed on vesting, equity, etc. because they simply don't spend 20 minutes Googling some of the basics needed to get more stock, have it vest immediately upon a 'Change in Control', etc. etc. Too many people rant and rave that they got screwed on equity, when in reality they just didn't know what they were doing when they were offered equity.

- Make decisions about where to work based on the management team and the company's growth NOT on your day-to-day job description

- Don't make decisions based on $3K more in salary or whatever. Make leaps of $20K - $25K in salary. Small leaps often aren't worth the hassle.

- After you've been at a place for some period of time (1-2 years in tech, likely longer in other industries), start at least occasionally taking a recruiter call or listening. Why? Because the worst time to look for a job is when you're trying to find one. And the best way to negotiate with your current job is when you have a new one (and btw, they don't need to know you found a new one...you can just really really push for a big raise without fear of them saying 'no'...because if they say 'no' you can leave).

- Remember that you work primarily to make money...of course your mind will go to the exception---people who truly love their job, find purpose in it, etc. etc. etc.--but the vast vast majority of people work because they need to work to pay the bills, go to dinner, go on vacations, etc....and because you work to make money, don't be afraid to ask for more money or leave a job when you're not getting enough money.

- 95% of companies will not be loyal to you if it's inconvenient/not profitable to be loyal to you...so there is no need to be overly loyal to them. Don't stay at a company for emotional reasons or because you 'love your co-workers'. Guess what? At your new job you'll likely love your co-workers too.

- How do you know it's time to leave? If you start to feel that Sunday afternoon/evening feeling of dread...go find a new job.

- Personally, I've never regretted leaving a job, however, I've deeply regretted staying too long on two occasions.