I am a certified overthinker. Most of the energy I get from food doesn’t go into movement; it goes into thought. My mind is constantly running mental simulations, analyzing, computing, and re-evaluating endless variations of whatever situation I’m currently facing. More often than not, the majority of these imagined scenarios never come to life. But sometimes, they do.
You’d think that all this thinking would make me a great forecaster. Ironically, it does the opposite. When I try to predict outcomes, I get lost in the vast number of variables I’ve put into the mixer. In the end, I’ve opened so many lines of thought that my ability to forecast gets affected. Overthinking alone can be misleading at times.
Still, as much as overthinking can feel like a curse—it puts you in a state of permanent daydreaming—I’ve never tried to fight it. I’ve never tried to “think less”. I can’t. This is who I am. I’m a chronic, shameless overthinker, and I will likely die that way, as long as my brain is capable of firing any synapse.
Overthinking doesn’t paralyze me. I don’t live in constant “analysis paralysis”. Sure, I dip into it now and then, but for the most part, I keep moving forward as my mind keeps computing the state of affairs.
Naturally, I overthink every aspect of my life: as a parent, a partner, and a citizen. So it should be no surprise that I bring this same overthinking to my work. Earlier in my career, when I wasn’t leading organizations, my overthinking stayed mostly in the technical domain, questioning my decisions, checking and re-checking documentation, and evaluating implementation paths. However, as I transitioned into more managerial and decision-making roles, this tendency expanded to an organizational, systemic level. Suddenly, I wasn’t just thinking about my tasks—I was thinking about the business.
And I don’t think that’s a bad thing. Otherwise, who is thinking the business?
Organizations operate in incredibly complex environments. They're embedded within economic, political, social, and technological systems, all of which are constantly shifting. A business must be prepared for a multitude of potential futures, even the unlikely ones. That requires deep, deliberate, and constant thinking.
Interestingly, I’ve often found myself in contexts where the business was not, in my opinion, thought enough.
I’ve attended meetings—management meetings—where there was barely anything to discuss. Where the conversation stayed at the surface level, as if everything was already sorted. Startups, by nature, are constantly threatened by the conjuncture and by their own internal challenges. Everything is in motion, everything changes, time and money are constantly running out. So when there’s nothing to talk about, nothing to challenge or to analyze, I always have this strange, uncomfortable feeling: surely we are missing something. In several cases, time has validated my suspicions.
As an organizational obsessive-compulsive thinker, I’ve come to firmly believe that someone must always be “thinking the business”. Not just reviewing numbers in a spreadsheet or ticking tasks off a list, but truly analyzing the organization. Taking a full-body X-ray. Every day. Businesses need constant scanning, and constant questioning of assumptions, structures, and trajectories. A healthy suspicion that surely we are missing something.
And no, I’m not talking about creating anodyne “processes”, writing endless manuals or elaborate flowcharts where people are expected to behave like tokens in a Petri net. I’m talking about cultivating a collective awareness of the landscape the org is in. About regularly analyzing scenarios, including corner cases, and having a degree of preparedness; not necessarily a full-blown plan, but at least a shared understanding of what could unfold, so no one is surprised should that scenario finally materialize1.
This kind of thinking shouldn’t rest on one overthinker’s shoulders. Left unchecked, it can create an echo chamber. That’s why organizations need to institutionalize overthinking in a constructive way. They need to build think tanks within the company; diverse groups of overthinkers with critical minds who come together regularly to dissect the business inside and out.
Needless to say, these think tanks shouldn’t be homogenous. In fact, they must be composed of people with differing perspectives, even with healthy degrees of disagreement. As I said before, friction is a feature, not a bug. It sharpens the conversation and helps uncover blind spots. I’ve worked in companies where there was little to no debate; no arguments, no counterpoints, no analysis, just constant status-checking. And those organizations are often the first to falter when change inevitably comes.
Businesses must embrace overthinking as a discipline. This even means performing regular “wargaming” of threat scenarios, with a proper assessment of consumer, geopolitical and economic changes, and thoughtful evaluation of internal dynamics like key departures or organizational shifts.
So, if you think you're thinking about your business: think again. Real thinking goes beyond gut checks and robotic status updates. It means stepping back, zooming out, and assembling a team that isn’t afraid to obsessively dig deep, challenge the status quo, and feel comfortable with uncertainty.
Like an elephant storming into your peanut factory; you gotta be ready when that happens: