The other day I had a dream. One of my older friends, a scientist had figured out how to soup up a DeLorean. It was the mechanics for street racing or anything like that… but when it reached 88mph the car had the ability to go back in time! I know it sounds crazy, but go with me on this one. I thought about what I might tell Lazy Man back in high school and came up with the following:

15. Learn about Compounding Interest – There’s a reason why Einstein called compound interest “the most powerful force in the universe.” (In reality my high school math teacher pushed this on our class, so I did know this in high school.)

14. There’s a young woman who lives less than 8 miles from your home. You’ll end up marrying her, so perhaps you should get started now before she moves 200 miles away and ten years pass.

13. I know it seems like you are saving a lot of money now. You are really doing a good job, but expenses will arise soon.

12. The Internet company that gave you a raise to 90K at age 24, will end up laying off the entire department with in a year…

11. …so you probably shouldn’t buy that new sports car convertible – even if it is under 30K. Plus it won’t impress that girl nearly as much as you thought it might.

10. However, don’t give up that summer in Newport, RI. You’ll have so many memories that will last a lifetime.

9. You won’t end up associating with any of the friends you have now.

8. Day-trading Internet stocks (you’ll understand what an Internet stock is later) is fun – like gambling… because that’s what it will be. You’ll end up losing… Plus… doing your taxes will be a pain as well.

7. Stay away from girls from Maine or named Shannon. You’ll meet quite a few of each and neither will be good for you.

6. The Computer Science degree is great, but really look into getting a MBA.

5. Look into gathering domain names of generic items and concepts as soon as possible.

4. Avoid buying 250-300 CDs, you’ll have better things for money such as…

3. … buying real estate. Seriously look into a home as early as possible. Mom will help you if necessary.

2. You were far ahead of your time with that purchase of Founder’s Growth in high school. Excellent plan to put $50 a month in there. You’ll be even smarter by betting on Bill Miller in two years and getting 10 years of S&P 500 beating performance… just stick with it and don’t cash it all out.

1. Put some time into learning how to read quickly (without compromising comprehension) and write effectively. You are going to have a series of horrendous English teachers that will make you read books like Ethan Frome. You are going to doubt that there’s really anything of any practical use. Dig deep into what they are saying or learn on your own, because it will be more important than programming language you’ll ever learn.

Here are some things that others would say to themselves in high school:

• Rich Minx – agrees with the CD savings. Don’t tell Lazy Man and Health, but spending all your money on alcohol sounds link fun.
• Susanna in the comments says “don’t let your fiance run up his credit card balance.”
• Brip Blap regrets doing vodka shots with Russian Mafiosos. Yes, you read that right.
• Blunt Money sounds like she would tell herself to be more confident.
• Cannibal Crowley wish he tried out for the football team. I wish I did as well, not because I’m athletic, but because I love the game and would like to be closer to it.
• Smith’s Trading Posts had some great thoughts about high school.
• Hockey Mom seems to have remained friends with all her high school friends. That’s the exact opposite of me. Then again that comes as no surprise, since I’m about as far as a Hockey Mom as you can be.

What would you tell your high school self? If you write about it and drop me an e-mail or a comment I’ll highlight your story above.

I’ve been thinking about my Alternative Income Streams recently. I’m trying to put them in context with the earnings from my day job. I’m at a bit of crossroads where I’m not sure what to make of this income stream.

A large number of you leave comments about how well I’m doing each month as I review these income streams. It’s very uplifting to me. However, I wonder if it’s really a lot of money.

The definition of a lot of money was discussed at The Simple Dollar (TSD). The conclusion that TSD came to was that a lot of money in terms of salary was 50% more than what he currently makes. As he makes more money, his definition of “a lot” changes. This makes sense to me, but I have to say that my income streams is nowhere close to being 50% of my salary.

My alternative income is a source of excitement for me. It seems a little odd to me, but sometimes I feel like I’d be willing to trade $10 from my day job for $1 of money from blogging. I was very confused by these feelings until I read this tremendous article from the Washington Post (if you click on any link to leave this site, make it that one). It would take too many words to give context to that article, but here is the key quote:

“At a music hall, I’ll get upset if someone coughs or if someone’s cellphone goes off. But here, my expectations quickly diminished. I started to appreciate any acknowledgment, even a slight glance up. I was oddly grateful when someone threw in a dollar instead of change.” This is from a man whose talents can command $1,000 a minute.

I don’t have that kind of talent at my day job, but I’ve become conditioned to a fairly high salary.  In contrast, in the world of blogging and alternative income, I’ve been conditioned to earning very, very little.   I find that life’s experiences are in relation to the surrounding context – this is another case of that.

I’m terrible at a lot of things. Everyone who has witnessed me try to ski has had a belly full of laughs. There’s one thing that I’m typically really good at – finding the inefficiencies of systems. Sometimes I’m able to use them to my gain and other times, I’m just too Lazy to implement the idea.

Since I started Lazy Man and Money, the premise behind it would be that I’d figure out smart places to put my money and with minimal effort, it would grow. After all, it is an information age and it seems much more money is made through thoughts and ideas than physical work. The problem is that I simply can’t figure out where these places are.

I’ve figured out the problem though. It’s just that the markets are too efficient now. Let’s take the housing market, for example. During my parents’ generation (baby boomers) and even through the early 90’s it seemed as though it was possible to buy a property and rent it for a profit. While real estate is dropping, I haven’t seen such a property in years. Maybe with up-coming foreclosures there’s an opportunity there, but you can imagine that there are millions of people having the same idea.

In trying to think of other ways to make money, the stock market comes to mind. However, the market is so efficient that monkeys throwing darts tend to do as well as the professionals. The only money to be made there seems to be by buying and holding securities with as low expenses as possible. It’s possible that you can time the market and play longer term trends. I’ve looked into this through some sector plays, but it’s still just an educated hunch.

What does this leave me with? It leaves me looking for new markets. By being an early adopter, I like to get in before the market matures and becomes too efficient. This means that I also face increased risk. The best example of this is Prosper.com, an auction house for loans. I see some inefficiency while the membership is small. However, if everyone was a member, lending and borrowing money, I wouldn’t be able to take advantage of these inefficiencies.

Have you found any market inefficiencies? If so, how did they work out for you? Do the inefficiencies still exist?

Even though I’m in California now, I’m still a big Red Sox fan. When news came out that David Ortiz is auctioning off his 50th home run ball for charity, I was very disappointed that I haven’t made my millions so that I could buy it. It comes with a pre-game ceremony where Mr. Ortiz will present the ball himself.

So what would I do if I won the auction? I would show up at the ceremony, accept the ball, and hand it back to him and thank him for the memories. Wouldn’t that be really classy? I hope the person that wins the auction reads this and considers doing just that.