How overthinking can fail you as a leader

Last evening I decided to journal my thoughts in long-hand. It’s something I used to do every day but haven’t been lately. I remember the last time I did this — December 2018. Exactly a year ago. And boy, did I not accomplish most things I thought I would. Except, of course, a few exceptions which I should’ve been okay with but I wasn’t. 

And mind you, I’m not an overachiever. It’s just that the things that didn’t get done were basically put off because I didn’t prioritise them well enough. Creating two new keynote speeches on leadership and team management had been one of my big priorities earlier this year but things fell through the cracks. I haven’t done anything about it and the year’s come to an end. 

How could I have let that happen? Simple, I let my thinking ruin it for me. Each time I would sit down to work on my speech, instead of just writing out the whole draft, I would try an apply a keynote framework that I know works well for creating speeches. I know because I created it to polish and finalize some of the speeches I’d delivered a few years back. While the system works best to create a keynote from the scratch, I believe it’s more powerful when used to refine an existing speech. Particularly for (selectively) perfectionists like me. 

Think about it — if I can show up to write every day. What do you think is getting in the way to write out a mere draft? Nothing at all except that I’ve been using the system as a crutch to ship out a perfect speech that doesn’t exist. Yes, the purpose is for high-stakes presentations that offer value to prospects and clients alike but I let the scope and application of the purpose take me away from getting this done. 

Of course, now that I’m hyper-aware of what’s going I’ll figure out a way to get this done before the year runs out (by simply sitting my butt down in the chair). The point is that I shouldn’t have let my thoughts distract me away from the goal in the first place. And weirdly enough, this is akin to situations that leaders often face in their day-to-day businesses. When they overthink and overanalyse their way out of a problem that should’ve been addressed months back when it was fresh or the time was appropriate. 

We know why that would happen. Right? Because they wanted to deal with it when they were fresh or the situation was just right, which basically never happens in a leader’s life. Why even bother waiting? Some times the best solution is to simply roll up the sleeves and get the work done. Yes the outcome wouldn’t be perfect but you would still have something concrete to work off of, to make it better, or keep iterating. 

This is common sense but we know that ain’t common practice. Even the best among us, leaders or not, fall in this trap. The key is to recognise it as soon as you can and start working on shipping it. The sooner you do better the chances that you’re going to ship out something that’ll turn into something meaningful. Just the way you’d originally intended. But start. Right now. 

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