Five Financial Do Overs

Can I have a do over? Ever asked yourself that question? Have you ever looked back and said, "If only I....?" I would certainly be better positioned financially if I had taken these five simple steps early in life, and if only I had five do-overs I would:

1) Finish college. I didn't go to college right out of high school. I worked at a department store for a year as a stockboy, housekeeper, maintenance assistant and receiver. I developed a strong work ethic that was reinforced by my time in the U.S. Air Force. My time in the service was a valuable resource that has served me well throughout my life, but, oh if I had it to do over again, I would take advantage of the educational opportunities available to me while in uniform. Opportunities that I let slip through my fingers in search of other recreational adventures.

After my time in the service, I worked full time in a warehouse before entering college and earning my Associate degree. And then I stopped. If I had it to do over again, I would have used the full extent of my G.I. Bill benefits to complete my Bachelor's degree. Instead, I traveled to Hawaii; but, you know what? There are universities in Hawaii, too.

If I had it to do over again, I would:

2) Get and maintain productive employment. Oh, I've been employed. I've had steady employment; at least as steady as I wanted it to be. I've made decent enough money, although at the lower percentile range of my age group. I haven't, however, had steady employment with an employer that offers a full spectrum of benefits, and the opportunity for wage growth. I've worked for tips most of my adult life. My hourly wage when I stopped working behind the bar was only two dollars an hour more than it was when I first tended bar 22 years earlier. Trust me, tips did not make up the difference. Had I stayed at my warehouse job after the Air Force, my wages would have easily outpaced my earnings as a bartender. I also would have had life, health, disability, and dental insurance, along with a 401K and a profit sharing plan. Hell, as a bartender with 22 years experience, the last 12 with the same employer, I didn't even get a paid vacation. No paid time off for any reason. But, I made my own bed. If I had it to do over again I would:

3) Save. I would save with a passion. I would save and I would not stop saving. See, I was always good about socking money away in savings accounts. Then, I would take a sabbatical. And I would spend all of the money in my savings account. Dumb. Really dumb. With a do-over, I would plop most of my money into stocks and bonds. That way, I could take a sabbatical, a shorter one, and still have my money working hard for me, growing from a young age to support me in my older age, which is rapidly approaching. Some of my money would be in:

4) Real estate. Not all of it. Not even most of it. But, if I had it to do over again, I would buy and hold on to a piece or two of real estate. That way, I would have an anchor, a place to call my own no matter where my travels take me. Had I bought way back when, I would have a house that was fully paid up. I wouldn't worry about price spikes or price collapses because I would look at a house as a place to live. Trust me, it would cost a lot more to buy it today than it did 25 years ago, even on an adjusted basis. It's security, just like:

5) Insurance. If I had to do it over again, I would get and maintain health and disability insurance. Yes, it's expensive. The alternatives are all far more expensive and no fun when you have to dig your way out from under a pile of medical bills with no income. If only.....