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Overthinking: How To Defeat The Silent Killer of Financial Freedom

Diarmaid McMenamin
6 min readSep 30, 2024

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Ever find yourself lying awake at night, replaying every decision you’ve made during the day, wondering if you did the right thing? That voice in your head keeps whispering, “What if that wasn’t the right move?” or “What if I could have done better?” Before you know it, the sun’s coming up, and you’re left with no new insights and another day where you’re stuck in the same cycle. This is overthinking at its finest.

Overthinking — we’ve all done it. Some of us are practically professionals at it. And while it might feel like you’re being responsible by weighing every option a hundred times, the truth is, it’s holding you back.

If you’re trying to build a life of time and financial freedom, overthinking is one of your biggest obstacles. But don’t worry — this isn’t the part where I tell you to “stop overthinking” (as if it were that easy). Instead, let’s look at why overthinking happens, how it’s sabotaging your path to freedom, and, more importantly, how to overcome it.

The Paradox of Overthinking

Understanding the paradox of overthinking can be a revelation. The more you do it, the less you actually do. Overthinking doesn’t lead to better decisions; it leads to no decisions. You might feel like you’re being thorough by examining every…

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Diarmaid McMenamin
Diarmaid McMenamin

Written by Diarmaid McMenamin

Helping busy, time-poor professionals build a life of time and financial freedom by improving financial education and investing in property.

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