First of all, congrats on the nickname. “Rob”—so much better for you than “Robert.” Robert is stuffy, formal. Rob is laid back, cool. Except for that Redford guy. Yeah, he’s so cool he makes Robert work. But you, you’re not that cool. Stick with Rob.

This is me talking (or writing) to you. You’re the younger version of me, the high school kid, the college student–I’m the fully grown married-with-two-kids-and-a-mortgage version of Rob. We learned a lot over the years, but there’s still a ton to go I guess. In several ways, you actually pulled it off, the grandest con of all. You became a professional actor, with dreams and desires that carried you all the way to Broadway. So congrats pal, you weren’t crazy. Well, maybe that’s debatable, but you did the thing “they” said couldn’t be done. Who were “they” again?

You’d think they were your enemies, but in truth they were the people who loved you most. Your parents said don’t do it, don’t go into acting. The life is too hard; it leads to terrible (wonderful) things. Your friends said maybe think about this—are you sure you’re as good as you think you are? Your teachers, who thought you would make a great teacher yourself, were concerned that maybe you lacked the discipline you would need for acting.

But you had to go. YOU HAD TO TRY.

Uh…keep trying kid.

It was far from easy. You struggled to get here, struggled while you were there, and you still face different challenges today. Yes, you learned a lot, more than you ever thought there was to know. But you forgot some things too, so I’m going to remind you of a few of those. And warn you about other things you haven’t even thought of yet.

REMEMBER WHO YOU WERE IN HIGH SCHOOL? I don’t mean the awkward guy who couldn’t really talk to girls (until you could, but that’s another letter), I mean the guy who discovered Drama. The guy who was inspired almost from the minute he walked into class. The guy who only took the class because his best friend did, and he wanted to hang out and get an easy “A.” Then look what happened. You would do anything, ANYTHING to push yourself farther onstage than you had gone before. Try a difficult accent? Piece of cake. Play a gut-wrenching scene? Yes, please. Write your own work, expose your greatest vulnerabilities? Yes, yes, and yes.

But as you got older, you grew fearful. Reserved. Once you started to do theatre that “mattered”, you played it safe. You stopped taking risks, at a time when the risk brought the greatest reward. It’s easy to see why, you were making money with your art. And we need money to survive, so we can keep making art. So you played it safe, didn’t do anything too “out of the box,” just showed ‘em you had skill and technique, that would be enough. WRONG.

I like to tell this joke sometimes: “I wish I was as good an actor now, as I was in high school.” The truth is I am, and so much better. But I stopped being brave. So buddy, do us both a favor, stay brave. BE BOLD, ESPECIALLY WHEN THERE’S SOMETHING AT STAKE.

Maybe not that bold.

While we’re talking about being a student, here’s a pretty new idea: YOU HAVE TO STUDY. You’ve got talent, no doubt, but all that talent can’t be fully displayed without some sort of focus and technique. Raw talent is almost never enough. You need to know what to do when your raw talent isn’t as readily available as you would want. That’s a heady concept, but it happens. What separates the greatest from the great is most often the practice. And little fish, when you get to the big pond, everyone can swim.

I’ve been a little harsh, so let me throw in a compliment: I admire your confidence. You think you’re above the fray, that you’ll be the exception to all the rules. It’s not really true, but you must believe it at least on some level, so congrats. Maybe it’s a little arrogant, but if you don’t believe in yourself no one will, right? Hang on to that.

But back to the tough love: YOU’VE GOT A FUNNY IDEA ABOUT “BACKUP PLANS.” There’s another one you like to tell: “I don’t have a backup plan, because I’m afraid I’ll use it.”

Uh, hello?  MCFLY?!  (Google it kids).

That one is pretty high on the regret-o-meter. You don’t have a whole lot of skills outside the business. Why would you need them? You’re going to act, and sing and danc…uh, act, and sing…for big bucks!

Well…yeah, sometimes you do. Most of the time you don’t. Most of the time it’s barely a livable wage in the greatest city in the world. And jobs don’t last—except for the very, very few and fortunate. But hey, you can wait tables, cater, be a temp in a lousy office, you can make money, right?

If I’m being wholly honest, I think the well-crafted backup plan is an invitation to failure. It means you don’t really have much faith in your ability to DO THE THING YOU DECIDED TO DO. Why choose an insanely hard path, when you’ve got a nice comfortable option just waiting for you to say yes?

I’m not advocating a fallback career, I’m asking you to develop some survival skills. Things you can do to earn a living that are also spiritually rewarding. Instead of hustling from one restaurant to another, wouldn’t it have been more fun and fulfilling to teach piano? Or tutor a kid, or seven? Or be a fitness instructor? Or, I don’t know, ANYTHING but a waiter?! With all due respect to the hard-working men and women in that industry, one I was in for about ten years, sometimes it is just a grind. Even when I liked it, I didn’t like it. DON’T THINK OF IT AS A FALLBACK PLAN, THINK OF IT AS SURVIVAL AND SANITY.

Finally, ’cause this letter could go on for days, YOU’RE A GOOD DUDE. STAY THAT WAY. It’s not that you’ve never crossed anyone, broken the rules, not lived up to a promise (okay you get it), but overall, you do your best. You’re usually pretty nice to people, helpful even. Perhaps without irony, you really would have been a great teacher. But you chose a different path. Kindness goes a long way. So stay kind. The business is full of supreme highs and soul-crushing lows, you ride them out with kindness and grace. When you leave a room, a job, a cast house, make sure you can walk back in that door, and the people there will be happy to see you.

That’s it, kid. I hope this letter finds you well. And don’t worry too much, the truth is this story has a really happy ending. You just can’t see it yet.

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