One thing I always want to try to avoid in these closing thoughts is offering up oversimplified advice or trite answers to life’s big questions. Granted, oversimplifying is hard to avoid when you only have three minutes to say something but one of the ways I try to avoid it is by talking honestly about myself more than sermonizing at you. By the way, I am certain I have failed at that. I apologize. I am trying.

Oversimplified advice is perhaps more dangerous than no advice at all. Like when you’re considering taking a risk or leaping out into the unknown it seems there’s always somebody in your ear saying,“you better know what you’re doing.” I’ve never understood why someone would say that. When you’re brand new at a thing you literally don’t know what you’re doing, so how can you know what you’re doing? Almost six years ago, I had to make a decision about doing less design work in order to carve out time to be on the radio. “You better know what you’re doing,” said the voices. “I don’t! I absolutely don’t,” said I in response. “What are you talking about? I’ve never done this before! Of course I don’t know what I’m doing!” The fact is, it took nearly three of the last six years for me to even begin feeling like I know what I’m doing. Some of you are saying right now, “Dean, clearly you still don’t know what you’re doing.” Probably very true!

The point is, some advice is better left not given, or perhaps more importantly, not listened to. Would I like to know what I don’t know when I really need to know it? Uhh … yeah … but I am well over halfway through this life and it hasn’t happened so far. Wouldn’t it be cool if somebody who absolutely knows every detail about your future kept showing up at critical moments in order to advise you? That’s why I suspect we’re not going to discover how to time travel before I die. Because if I could travel back in time I know for a fact that older me would be right here, right now, helping this me avoid my next blunder. I’d be my own guardian angel. Not only would I have shown up pretty early on with some key financial investment advice, but I’d have a thing or two to say about how to handle certain pains and wounds and trauma because, lemme tell you, that kid did not know what he was doing.

I suppose everybody with regret longs to go back and fix things. And yes, I know, the paradox is that it’s always the healthier, stronger, wiser me who’s wants to help my younger self avoid pain when, in fact, it was working through those pains that got me to my wiser, stronger self.

So what have we learned from all this? Well, probably very little. Except that life is tricky, none of us know the future, and when it comes to your next big adventure, maybe don’t allow the “you better know what you’re doing” voices to shame you. Because when it comes to your next big adventure, of course you don’t know what you’re doing. As for me, I’ve resolved myself to follow some advice from Teddy Roosevelt. It’s, in my opinion, really good advice. Not because he knew something about the future, but because he understood something about the soul:

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood, who strives valiantly; who errs and comes short again and again; because there is not effort without error and shortcomings; but who does actually strive to do the deed; who knows the great enthusiasm, the great devotion, who spends himself in a worthy cause, who at the best knows in the end the triumph of high achievement and who at the worst, if he fails, at least he fails while daring greatly. So that his place shall never be with those cold and timid souls who know neither victory nor defeat.”

“You better know what you’re doing” … nah …of course I...