Looks like Thief’s thieving has landed her in the slammer. Good thing our sticky-fingered tiefling has friends on the outside willing to come up with a brilliant escape plan. If it were me though, she might not be so lucky.

This might not be a popular opinion, but I don’t care for in-depth heist-style Oceans Eleven planning. Not on the tabletop anyway. Murphy’s Law is in effect every time your party puts a complex scheme into motion, meaning you’re going to wind up improvising around unforeseen obstacles anyway. To my way of thinking, that makes anything more than a broad-strokes “here’s their security system, here’s how we’re going to work around it” overkill. It’s a GM’s job to put complications in your way after all. That’s why I appreciate the flashback mechanics in Blades in the Dark, Honey Heist, or (to a lesser extent) the brilliant planner feat. These mechanics simulate uncanny criminal foresight without demanding that players actually go full-on Xanatos Gambit.

A lot of my thinking on the subject came from my group’s first Shadowrun campaign. We’d come over from our various dungeon-crawl games, and were ready for a change in setting. We got excited. We made deckers and riggers and adepts. I was a “cajun combat troll,” and my accent was full-on ridiculous. (Beauregard Saucier Dupré remains my all-time favorite PC). In short, the mix of archetypes and personalities was amazing, our GM was enthusiastic, and everyone was on board for some Leverage–style shenanigans. Unfortunately however, there were nine PCs.

“What’s your plan?” said our GM. “How will you intercept the van en route to its destination?”

“Drones! We’ll laser-cut through the roof! We go through the sewers! We hack the local traffic grid! Come up from a manhole cover! Fake a heart attack in the crosswalk! Come out guns blazing! Ride up alongside on mopeds Mad Max style! Attack the van while it’s still at its base!”

“Ok… Those are all ideas that could work. Which ones would you like to do?”

I shit you not, it was two full four-hour sessions of arguing. Every time we settled on a plan, someone would come up with another contingency that had to be addressed. The municipal traffic system might be too powerful to hack. The drones would be spotted. Attacking the base would draw too much heat from the gang of genetically engineered drug runners we were trying to rob. My troll would not fit on a moped.

Eventually we settled on the traffic / manhole cover plan. I believe we had to call a vote to make that happen. We wound up sticking the van at a never-ending red light, cut a hole through its undercarriage, and got the goods without triggering any alarms. Unfortunately, by that time everyone was thoroughly sick of heists. Our gang of shadowrunners were successful, but it wound up feeling like an anticlimax after all the bickering.

Now obviously there were too many cooks in that cyberpunk kitchen, so let’s not waste time agreeing that 9 PCs is too many. Instead, I’d like to focus our collective attention on the notion that overthinking really and truly is the trap (NSFW). Executing a clever plan is a lot of fun, but not 10 IRL hours later and at the expense of your sanity. So for today’s discussion question, let’s figure out how to find a better balance. How much planning is too much? Tell us all about a time when you executed a complex heist-style plan. How did you cover all the contingencies without driving yourself nuts? Sound off in the comments with all your best machinations and schemes.

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