Minimizing campaign regrets

When Jeff Bezos was deciding whether or not to start Amazon or not, he had a conundrum. He had a good idea (selling books online) he wanted to pursue. But he also had a great job that paid well.

He had to decide what to do. He gave himself 48 hours to make a decision. And so he picked a framework to use in making that decision – a regret minimization framework.

He himself asked a simple question: In the future, will I regret not starting Amazon? If the answer was yes, he should start Amazon. If the answer was No, he would keep his current job.

The answer, obviously, was yes. He imagined his future self at 80 years old and looking back on his life. If he didn't try to pursue Amazon, he felt this future self would regret it.

In campaigns, we rely on intuition, logic, and data as much as we can. But we can't know the right answer to every question. We can't always know if we are making the right strategic choice or not.

It's in these moments where utilizing this framework can be helpful. It may or may not give us the right answer. But we probably won't ever know what the right answer was. And that's sort of the point of the framework.

In the absence of knowing whether or not a strategic choice is the "correct" one – because some things are unknowable – the next best alternative is to make the decision that will generate the least future regret. Because after the campaign is over and if it ends in a loss, the candidate will be looking back and wondering what they could have done differently – and for the sake making sure they feel good about the effort put forth, you don't want to have any regrets.

This is all pretty conceptual, so let's walk through a couple scenarios.

Let's say a candidate is $1,000 short of their budget. They have confidence in the budget, and they feel as though if it gets funded, they'll have a good shot of winning.

But the donations aren't coming through any more and the campaign is running out of time. Should the candidate simply donate $1,000 of his own money to the campaign?

We don't know for sure if the $1,000 will get them a victory. But it certainly won't hurt. There isn't a clear answer.

So the alternate question: "After the campaign is over, and if the candidate has lost by only a few votes, will they regret having not donated the $1,000?"

The answer depends on the candidate. To a millionaire, the answer will be "yes." To the candidate with more modest means – where that $1,000 may be more important than winning that particular election – it might be "No."

And it also depends on how important winning really was. Some candidates run strong campaigns but view elected office as an interesting but non-imperative activity. Others see it as their future life's work.

Another scenario:

You're running your campaign. In the same geography, one of your political allies is running as well. You want them to win, because you're friends, or because you hate their opponent, or because you know they'll help you implement your agenda.

While your race isn't a slam dunk, you feel like things are going your way. Your ally, on the other hand, is in a tight race.

You have funding to get out one final piece of mail. Should you send it out with just your name and message on it, or should you be generous and use some of the mailer's real estate to advocate for your ally. Again, there is no clear cut answer. You're diluting your message, but it may not matter a whole lot. And it will help your ally, but maybe not enough to put them over the top.

If you end up losing, will you regret doing that? If your ally loses, would you regret not doing it?

Again, it all depends on the candidate. How important is it to them that their ally wins? Is it the end of the world that they will lose?

This framework probably won't help you win your election. But that's not the point. It's to make you feel better about your election. If you win, you likely throw any regrets out the window. If you lose – especially if you lose narrowly – you might be spending the a chunk of your life regretting the choice you made.

And that can be a higher price than many candidates want to pay. And if you're that type of candidate, I hope you consider this framework.