When is the last time you tried something new?  Was it scary or exhilarating?  Or a little of both?

It’s one thing to try a new dish or a new route home.  But what about trying a new line of work?  My mother likes to remind me that near the top of the list of things “people dread most” are moving and starting a new job – and that I do both on a fairly regular basis.

This is typical among Renaissance Souls – those of us that have interests in too many things to pick just one.  In fact, in the past 10 years I have had at least seven jobs that many choose as their life careers. And they weren’t all exactly related.  What do a park ranger, a math tutor, a physical therapist and an anatomy instructor all have in common?  Me.

You’d think that I’d eventually get over the fear of trying something new.  Unfortunately, that’s not the case.  Will Keim, in his book “The Education of Character,” reminds us that “Everyone is a Freshman at something,” but I wonder: does it get any easier with the wisdom of age?

Today, as I made some concrete moves to add a new interest to my repertoire, I asked myself what knowledge I had gained in all of my “freshman” attempts.  The answer I kept returning to: role-playing.  I know – not what you were thinking.  But hear me out.

Though talking about ideas to friends helps, role-playing the actual conversation is where I really start to build confidence.  Let me give some examples.

When I wanted to start tutoring math, my biggest fear was calling a high school guidance office to tell them about my services only to stumble over my words or not know what to say at all.  As I fretted over this, one friend said to me, “Okay – so I’ll be the Guidance Counselor – let’s go.  Ring, ring.  Good morning, high school guidance office, can I help you?”  And with that, I had my first role-playing conversation.  Yes, I stumbled over the words.  But I got to do it over, and after a couple tries I had down what I was going to say.  I made the first real call, was successful, and then the rest were a piece of cake.

When I decided to go back to work as a physical therapist after being out of the field for 10 years, I worried that no one would want me.  After all, I’d left the field only three months after getting my degree in it.  This time, I didn’t need a friend to play the role of potential employer.  As I drove in my car one day, I played both roles.  I practiced until I had it down – until I could clearly answer the inevitable question of why I left and why I wanted to return.  Then I made the call.  Then another.  A week later, I had a job.

So take some time and think about some of your recent “freshman” experiences and what wisdom you’ve gained from your attempts.  And if you haven’t had any “freshman” experiences lately, I think it’s time:)