As you know, I have nothing but regrets.
I’m reaching that age where some of my superiors are younger than me. I don’t begrudge them. They all deserves their spots. Some older guys I work with don’t appreciate that they got passed over, but I think it’s our responsibility…as the “elders”…to bestow upon the younger generation what wisdom we have learned (in my case, what little wisdoms I have learned).
I don’t know if this is a regret I have, it’s more like a big “what if”. I spent some time in the military. Even did three years of ROTC in college. It’s laughable to think I could have been an officer now, but it almost happened (before I realized that I loved drinking WAY more than I loved the military). Despite the abysmal failure of that endeavor, a few lessons stuck with me.
“Just make a decision,” I’d always hear, “don’t worry about if it’s the correct one.” I thought that was stupid advice at the time, especially in a military situation where people’s lives might depend on it. But it seems to make a little more sense now.
Who are the three greatest military commanders of all time? It’s obvious: Captain Kirk, Captain Picard, and Captain Sisko.

“But they aren’t real,” you might say.
So? Real life isn’t real.
I remember Mike Stoklasa praising Bill Shatner’s acting capabilities (in a video discussing Shatner’s hatred of Mike Stoklasa). You can laugh all you want, but it’s true: Shatner is an extraordinarily effective actor. And, for better or worse, Captain Kirk is Bill Shatner and Bill Shatner is Captain Kirk.
Kirk understands that he is playing a part as Captain of the Enterprise. He has to project confidence as its leader because the survival of his ship might depend on it. Shatner, I think, understands that Kirk himself is playing a part, which might explain some of the strange speech patterns he exhibits throughout the series and films.
That’s why I think it’s great that the handlers of Star Trek (at least back then) cast classically trained thespians for the role of the Captain. Just the ability to “play the role” is necessary for the crew to rally behind, even when the leader isn’t completely confident in his (or her) decisions.
Obviously Picard is the superior Captain. No disrespect to Shatner, but Patrick Stewart knows when to dial up the acting and when to hold back (even if, in my belief, Stewart didn’t completely understand the appeal of his character or Star Trek). But what Picard does better than anyone is embrace his mission: “explore strange new worlds”. He seeks out moral quandaries and mysteries because he understands that these hold the secrets of the universe. He’s an explorer but not in the usual sense of the term.
I think to be a leader, one has to be open to that sort of exploration.
Of course, Sisko was far more grounded than either Kirk or Picard. He had a life outside of Starfleet and his job was to navigate the political complexities of a particular section of the galaxy. While Kirk and Picard were explorers, Sisko’s mission was different: he was an ambassador attempting to bring together warring factions. But just like everyone else, he had to “play the part.”
“But those were actors that had scripts,” you might say. “Real life doesn’t have a script.”
True that, but if you understand the more technical aspects of your work, in a sense you kinda already do have a script. You can’t just willy nilly your way through a job, you are confined and in many aspects you have direction. It’s just making the best decision with the options you have.
So I think it’s interesting that the three best Captains in Star Trek history each explore the three most important aspects of leadership: confidence (or the projection of), eagerness to accept challenges, and being the middle man between conflicting parties. But most importantly, “just play the part.”