For the past few years the one thought that has never been far from mind is my “could vs should” debate. Essentially, I think we’ve become a society that has stopped asking if we “should” do something and instead default to if we “could” do it. “Can we get away with it?” has become our guiding imperative. In fact, asking if we should actually do something, when we’re able to do it, will probably cause people to wonder if you’re nuts.

Think about this example. It’s imperfect but might work: You’ve worked for years and are fortunate to make enough money to build some savings. Now, say bad times hit and you get laid off, but you have your savings to fall back on for now. Do you collect unemployment insurance? Of course, you could collect it. One on hand, this is what you’re supposed to do (it’s expected, right?). You and your employer have paid into the fund. On the other hand, should you? You know that lots of people are losing their jobs, and the state really doesn’t have enough money for everyone in the end. You have your savings, so you don’t really need it. But is that fair you might ask? The reason the guy down the street who lost his job doesn’t have any savings is because he spent all his money on a BMW and a flat-screen while you saved. So should you? Based on my small sample of friends, it’s an insane question to even ask.

I’ll note that the question of how to think about could vs should is something I’ve been chewing on since college, but really only hit close to home in the past few years. I found The Apprentice to be the ultimate personal experience with could vs should. Why? Because the whole experience is sort of like life on steroids. It’s so much of our everyday just compressed into a finite time period. The goal was clear, last each “week” until you get “hired” as “The Apprentice.” With this goal in mind, everyone did everything they possibly *could* to win. This included undermining one another, lying, ganging up, sabotage, and whatever else you can think of. In fact, this is what got under my skin during filming. The entire time we were taping I was practically a monk in my calm. My fellow contestants were always remarking at how quiet and even keeled I was. That is except after episode five when almost everyone around me decided to forget what actually happened and said whatever they thought would give them the advantage. I was livid (though, in retrospect, how naive was I to expect any different?). I got back after the boardroom and tore into my “teammates” asking them to not lie, and reminding them that they all had jobs, family, friends to go back to after the show was over and that they should remember that as they lived in this little lord of the flies fairytale world. Anyway, before going on the show, I thought long and hard about could vs should and did my best to only act in ways that I thought I should. Could I get away with a lot more? Oh, yeah. But I knew I shouldn’t and I let that guide me.

Bringing this home, I find that this problem starts not just with individuals but the institutions around us. We’re not asked to do the right thing. To sacrifice. To really, truly help each other. To ask ourselves if we should be doing something. Instead we’re told to always act in our own best self interest. That this is what a great American capitalist would do. That in doing this, and taking it to its extreme, we maximize all of our mutual self-interest and outcomes. Perfection ensues. I think this is a load of horseshit. As I look around me and a horribly battered world economy, I can’t help but conclude that this is the result of these ideas to their natural conclusion.

Of course that mortgage broker didn’t ask if he *should* be trying to approve the guy who’s making minimum wage for his $500K mortgage. The broker just asked if the guy *could* be approved. I mean everyone was doing it. Why wouldn’t it be OK? How about a level above him, the investment bankers who were chopping up these securities into tranches and selling them off to whoever. Should it make sense that you could make risk completely disappear from subprime mortgages? Not really, but who cares? The market said you could do it. Could the US as a whole continue to consume waaay more than we produced? Why were we or our government not asking if we should be? The list is endless.

I was reminded of this simple debate in my head as Barry Schwartz spoke at TED on our loss of wisdom. And that’s really what this is, isn’t it? Asking “should” is really using wisdom instead of defaulting to arbitrary limits.

As one thinks about could/should, you are naturally led to decisions. When you ask should, you’re really making yourself think hard about countless decisions that you might otherwise default to whether or not you’re allowed to/what everyone else is doing. And that brings me to the conclusion. Some thoughts on how I make decisions.

In my first position at P&G the head of our group, would always boil decisions down to principles. She’d ask what’s our principle here? If we had a principle in place, than we’d reason through it that way. If we didn’t, we’d find our way towards creating a new one. Making our decisions based on principles was a great way to do the right thing and not get caught up in the BS. Is it common sense? You bet. But since then, I’ve been lucky enough to observe literally thousands of people and business situations. And in 99% of them expedience (the “could”) dictates what gets done. Virginia, in her graceful way, always strove to avoid could and instead ask the should question. So that’s one of my decision criteria: What’s the principle here?

I’ve made really bad decisions in my investments. I’ve invested in the stock market since like 11th grade, and I think I’ve lost money almost every year. Just terrible timing and decisions. But out of these bad decisions came a pretty good principle for decision-making. When deciding whether or not to sell a stock, I found the most effective guide was asking myself “what would I regret more a year from now?” If I found that I’d regret not selling at a profit because I was greedy for more, than I’d sell. If instead, I found that I’d regret more missing out on a stock that could go through the roof, than I wouldn’t sell. Putting myself in my future shoes, and picturing which would cause more regret made my decisions so much easier.

My last big decision making tool is my newest. And, I guess, it’s not even really a decision tool. Basically when I’m stressed about a decision, or when I’m in a really, really bad situation, I ask myself a really simple question. “5 years from now, when I look back on this moment, how do I want to remember handling it? What will I be proud of myself for?” Usually a pretty clear image of what I’d actually be proud of comes to mind, and then I try to focus on acting in that way. A whole bunch of decisions automatically get made and I get to work. I think it’s my version of Jack (LOST reference!) letting the panic overtake him for 5 seconds, counting it down, and then purging it from his mind.

This was a long, meandering post that I’m sure no one made it to the bottom of. But as I look around at the world around me, I can’t help but think we’d be in a far better place if, as a society, we valued decision making more. If we valued the long term, and the collective best interest. And to me, all of these things come back to “could” vs “should.”

Oh. And maybe this is burying the lead. But it’s not lost on me that this was the year of “Yes we can!” Ironically, I think it should be “Should we?”