High-flying, risk-taking women

I have a secret, and it's time I came clean.

This will shock absolutely no one who reads my blog regularly, but growing up, I was a cheerleader. From fifth grade all the way through my senior year of high school, pleated skirts, pom-poms, glitter and spirit sticks ruled my life. Oh, sure, I considered myself an atypical cheerleader, or Sprit Leader, if you must. Coming from an inner-city Jesuit high school best known for academics, where our post-game-loss chant was "That's allright, that's OK, we have higher GPA's!" you can't really take yourself too seriously. But still, that was me. And I'm OK with it. And I thought you should know.

Why am I talking cheerleading? Because as all former cheerleaders know, there's huge risk involved in the sport. Have you ever watched a group of 90-lb girls attempt to learn a basket toss, a three-person climb or a head stand-spin move that ends in a split? I have, and if the number of female investors out there are any indication, many of those daring, awe-inspiring, high-flying risk takers grow up to totally avoid the element of risk that is investing. It's amazing to me.

So grab your pom-poms, ladies, we're going to reminisce for a while and figure out how to recapture our youthful risk-taking tendencies and bring them back into our adult lives.

Let's start by going way back... to grade school. Aside from learning super-awesome cheers composed by my fifth grade squad ("The Cats are hip, we're happenin', the top's where we belong!"), the team had the unique ability to get a group of girls to take big physical and mental risks, like convincing flyers to be tossed into the air or climbing up to the top of a pyramid for a stunt. Back in the early 90's, we trained on these tiny mats in my church basement, so looking back maybe those risks weren't terribly smart. But we took them. I'm guessing it was the support of the group, real or perceived, that allowed us to believe that even if we fell down or got hurt, the other girls and our coaches would help us back up, and that we would get up and move on.

The concept of a support group is a lesson women seem to forget when we talk about finances. We so often think we have to go it alone, that it's just us and a piece of paper or a Web site asking us to part with our hard-earned cash. In my case, I usually sit around pondering what I should do for so long that I eventually just give up. Staring at the Vanguard Web site isn't going to tell me whether investing in a mutual fund is a good idea or not, and it would be too painful to make a wrong decision that results in a loss. So I generally do nothing.

But there are women out there changing this trend. Jean Chatzky is a big believer in financial support groups for women. WIFE.org sponsors Money Clubs all across the country. And don't forget the power of your own social networks. It's OK to talk to your friends about money, about their goals and how they save or invest. And if you're friends aren't good with money, look to all the personal finance bloggers and Web sites that exist out there for women and get inspired. Because as we learned in grade school, you can't perfect your technique without a few drops, scrapes and bruises. Having the right people to help you pick yourself back up is key to ensuring that you try new things.

Another behavior my squads employed to encourage risk taking was letting the creative process flow. In high school, I remember spending hours on choreography. During practice, after practice, before class... you name it. I was always challenging myself to come up with new routines, new ways of looking at the same problems. And I had a coach who was incredibly receptive to our ideas, skilled at fostering talent and encouraging of any ideas we threw his way. So rather than sit by idly and take direction, we were always pushing ourselves to try new moves, take on new challenges. Sometimes it worked, sometimes not, but once we got it in our mind to try something new, we tried it and never looked back. (OK, sidenote... my freshman year of high school we had this CRAZY coach who took our money to buy new uniforms and then RAN OFF WITH IT, true story!)

So if you're worried about the risk involved in investing, see what you can do to spark your creativity and come up with solutions to the issues that are bothering you. If you're worried that investing in your own future will put your kids' college funds at risk, it's clearly a legitimate concern. But what are some ways to get around it? Don't just do a Google search and be done with the question. Internalize the matter and find a solution that works for you and your family. Let the creative juices flow!

Alternatively, you can also use creativity to figure out how to get the best deal in a negotiation. For your next salary discussion, brainstorm three or four additional "nice-to-haves" that would turn a so-so raise into a great raise. More vacation days? A work-from-home day once per month? More responsibility? More support? Use your creativity to come up with other "wins" that you can use during a negotiation or payroll discussion. Then, when your boss lowballs you on that big raise he's been promising, your creative solutions will encourage you to ask for other concessions on your company's part. (The worst they can say is no, so you might as well ask.)

One more way the squad encouraged people to take risks was through competition. Did you guys watch Diddy's "Making the Band" when they were making Danity Kane and the girls had dance-offs in the dance studio? We totally had to do that in high school! I remember there were times when I was too scared to try something new, or just thought I couldn't do it, but I knew that if I didn't try it, the spot on the floor went to someone else, or I got put in the back of the formation. I'm not sure what the real-world equivalent of that would be. Maybe you could challenge all your friends to do some investing and if you don't do it, you get some sort of (non-financial) penalty? It's not fully baked yet, but you get the idea. Competition is good for risk-taking. (Then again, maybe I can't think of any equivalent because we're not yet using the concept of dance-offs to fire up our financial brainpower. A girl can only hope. Sigh.)

I know it's a bit far-fetched, but I think there's something to be said for cheerleading teams in that they create very positive environments that spur women to take risks that they ordinarily wouldn't. (Can you imagine any other situation where you'd be willing to be thrown high into the air, only to caught by a group of teenagers with a tumbling mat for a safety net?) I'm postulating that some of the ways teams do this is by offering a trustworthy support network, fostering creativity and encouraging competition. I'm sure there's more to it, but I believe these are all concepts that can be applied to help women get more comfortable with finances, negotiations and investing.**

It's worth noting that I also, at varying points in my youth, was on softball, track and volleyball teams, and participated in a variety of student leadership organizations, and none of them even came close to getting me to step outside my comfort zone and take risks like my cheerleading squads did.

If you were a cheerleader, I'd love to know your thoughts on how your team environment fostered risk-taking among the girls. Are there any special techniques I'm missing?


**Disclaimer... clearly not ALL women are uncomfortable with investing.