The work is hard enough without added difficulties, and yet we never seem to be short of roadblocks thrown up in front of us. They come from everywhere, often without malice intended, but obstacles nonetheless. And yet for all of those challenges, the ones that hamstring us the most are the ones we construct ourselves. 

Mature businessman examining documents at desk in office


While some of us are blessed with an uncluttered clarity of thought, many of us are burdened with what could be called overthinking. Anyone who falls into this category would tell you that it’s a blessing and a curse, preventing you from making stupid decisions or dumb mistakes but also often stopping you from making any decision or taking any action at times. It becomes easy to get “wrapped around the axle” as the saying goes, thinking through every difficult decision and possible consequence until you’ve convinced yourself that there’s really no right answer.

And it’s not just decisions that keep you up at night. Every interaction is a potential new source of anxiety, wondering if you’ve said the right thing or done something to ruin that person’s impression. Every meeting can feel like a job interview and every malapropism is bound to pop in your mind for the next few months at least. And those are worries separate and apart from the current crisis we’re all facing where anxieties are rightly high and concern over every aspect of our lives, big and small, feels pretty well justified to even for the most easygoing. 

These thoughts are amplified when it comes to your business, where decisions and interactions can have a more profound consequence or impact than in your personal life. The pressure to get things right is that much greater, so the impulse to spend even more time thinking on it is concordantly stronger. And it makes sense, at least to our way of thinking; enough time spend on a decision means that we’ll crack it eventually. 

But what if more thinking isn’t the answer? Thoughtful decisions are of course good and necessary, but at what point does too much tough become a problem? It’s hard to pinpoint exactly when thinking becomes overthinking, but once you’ve reached the point where you start to second-guess those second-guesses, you’ve probably gone too far. Considering the possibility of being wrong and doing due diligence on decisions is a necessary quality for any leader, but at some point, a choice must be made and action has to be taken. 

Overthinking isn’t something that anyone chooses and, despite its occasional benefits, most afflicted would likely choose to be more in line with the decisive types that are heralded in the business press. But it’s a hard habit to break and a trait to suppress. How do we start to change our thinking?

You might not be able to stop overthinking entirely, but you can mitigate the consequences of that anxiety and indecision with willful practice in simply moving forward and not allowing those thoughts to gain purchase in your mind. We all have doubts, but the people who are able to do and to act, for better or worse, are the ones who make their decisions based upon the information they have, letting the mistakes or bad interactions roll off them, leaving them in the past where they rightly belong. We have to learn from our mistakes, definitely, but beyond that lesson, they serve no purpose other than to breed doubts. Every wrong decision is a ghost haunting future choices, reminding us that we could screw up this decision just as badly. And having that added pressure on every decision only reinforces the negative cycle on the occasions that you’re wrong, as we all are more often than we’d like.

We all have our flaws and weaknesses, but the key is to not let those weaknesses govern us or our actions. We’re going to have decisions that go awry or conversations that don’t unfold as we want them to, and the easiest thing to do, especially for an overthinker, would be to beat yourself up and spend hours replaying things in your head, wishing they’d gone differently. That’s time better spent preparing for the next decision or the next conversation, both of which provide a new opportunity to get things right. 

Perhaps the greatest lesson to be learned is that any decision or any action, even those that don’t go as you want, are better than no decision or action. We can only think up to a certain point before we have to do, or not do, and if we’re not ready for that moment, we’re in the wrong line of work. #onwards.