Hillenmeyer's Retirement Playbook: Work With What You've Got

This column comes to you live from our annual NFL players' union meeting in Maui. Each team has one union "rep," as the lingo goes, who serves as a liaison between the NFLPA and each individual roster. Each rep comes down here once a year to gather all the key directives that we then disseminate to our teammates back home. The trip, in reality, is one part business, one part education, and, yes, one part leisure. At the beach, leisure for me usually involves some golf and a pina colada. Right now, it involves sitting on my porch and checking in with my buddies at the TheStreet.com.

Being that market hours start here at 3:30 AM, I am going to use this week to talk about my investments in a more general sense than in my previous columns. This is only my second year representing the Bears as the union rep. In both years, I have found myself reflecting on my career to this point. I came into the NFL just hoping to make a roster. Getting cut from the Green Bay Packers in my first year probably meant that a long career was not in the cards. Yet, here I am heading into my sixth year and sitting on the porch in beautiful Maui on a "work" trip with some of the best and brightest across the league.

When I first got to Chicago, I found myself third on the depth chart at middle linebacker. The starter at that spot was Brian Urlacher, the best linebacker in the NFL. Knowing that earning that job was too tall a task for me, I had to figure out what I was best at and how to get the most out of what I had. I think the lesson I learned can aptly be applied to investing as well. Trying to be Brian Urlacher would put me on a short path to nowhere, but focusing on my own unique strengths could, at the very least, improve my chances of success. Likewise for many of us independent investors out there, trying to invest like a multimillionaire with what's saved up in the piggy bank might be a recipe for disaster.

Don't get me wrong; most people with all those zeros in their bank account clearly have an insight or two we could benefit from. You have heard me sing the praises of Berkshire Hathaway's BRK.A Warren Buffett. In the same vein, I would have been a fool not to learn everything I could in playing with a future Hall-of-Fame linebacker. But the point is: I will never weigh 260 lbs or run a 4.5 second 40-yard dash. I had to hone my knowledge of the game, focus on being a great tackler, and continually work to perfect my technique to evolve into an NFL starter. Likewise, investors with different paychecks, risk preferences, liquidity needs, or even amounts of free time will find that a unique approach may be best for them.

In my situation, I have allocated my income with a strategy that works for me. My personality has always been an aggressive one. I am risk taker, in spite of myself. Knowing the secure financial future that lies ahead if I protect the income I earn during my playing days, I have the lion's share of my money conservatively invested with my primary financial adviser.