Summer of George Tips

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One month ago today I quit my job of over 4 years and embarked on my Summer of George. I consider my first month to be a success, but not a total success. My mistakes were minor, but I figured I should discuss them for those of you that I might inspire to quit your jobs.

Health Insurance

The mistake I made was assuming that I could get health insurance as fast as one could get auto insurance. It took a full month to get insurance and my health card still hasn’t arrived in the mail.

Lesson: Buy your health insurance at least one month before leaving your job. If you work in a small crap company like I did, you may even find a cheaper plan than your employer offers.

Gear Up First

When I was a working guy I had a closet full of golf shirts and tan pants. Now that I’m hiking and biking, my needs are different. During my first month I spent way too time gearing up. I spent a week researching GPS units, only to buy one and learn that it isn’t supported on the 64 bit version of Windows XP. Had I wasted that time back at the office while I was getting paid it wouldn’t have been an issue.

Lesson: Buy all your clothes and toys before quitting your job.

Move Money First

Back in my office days, I’d buy and sell stocks while I was on the clock. I’d read financial articles and check stock tickers throughout the day. Now that I’m playing all day, I don’t want to be glued to CNBC and Ameritrade. The reality is my money is being actively managed by me, so I have to. Buy and hold only works in a secular bull market, which ended in 2000. This leaves the investor with 2 choices: do more homework or find some mutual funds that share your financial values. It took me way too long to figure this one out. Last week I started selling my stocks and soon will be set up in a few mutual funds. Of course I will always have a cash position ready to jump in after a huge sell-off or the perfect penny stock.

Lesson: If you plan to play during your time off, have your investments settled before you quit your job. This was my worst mistake.