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Planning Vs Overplanning

Getting Out of Your Head and Back to Work

Imagine if you lived a life that was completely regimented and meticulously planned. Eating the same meals every day at precisely the same time every day. Adhering to the same exact exercise routine every day with brutal regularity. Keeping a regular social calendar with a select group of associates. Every moment of every day is planned out from when you open your eyes to when you close them. Could you do it? Would it open vast worlds of time and opportunity to you… or would you go mad just from trying? 

An 18th Century philosopher named Immanuel Kant lived precisely this type of life and became one of the most influential (and controversial) thinkers in history. “Tech Bro” CEOs frequently exhibit a “lite” version of this, today, with limited wardrobes, simple footwear, and rigid schedules. This sort of hardened structure is loved by promoters of efficiency, but does it help in a business sense? Where is the line between planning and overplanning? 

Planning Vs Doing

Planning, in life and business, is a universal good. It allows you to think critically about a task, project, or event, and properly prepare so as to prevent poor performance. It is broadly advisable to look before you leap. However, it is possible to wrap up in your own head tight enough that you fail to act or only act after the opportunity has expired. This is the fundamental conflict of planning vs. doing. 

Imagine, for a moment, that a new job posting has come up that you’re interested in. Maybe you think about it for a day or two. Maybe you look up the company and its products. Work up a new resume, type the best cover letter, go back and check to make sure your portfolio and all your socials are up to date. And, maybe all that prep pays off and you land the job. Or, maybe you go back to find the job posting is already closed.

In life, and in business, we can’t afford to let the planning prevent the doing. Yet, it is incredibly easy to overplan. Planning should help make the doing easier, not harder

Make Planning Routines

Let’s take a step back to our example of Immanuel Kant, for a moment. He had the highlights of every day planned out, not because he loved planning, but by planning out a routine he could prevent indecision in his day and save time. Making planning routines eliminates that step from your day, allowing you to react more quickly to changes as they occur. By planning, you enable more doing. 

Plan out the small things in your life and you can optimize your time in your personal life. Plan out the small things in your business life and you can optimize your time there. For instance, should your job involve periodic social media posts, creating a list of topics for a month, six months, or a year in advance can save vast amounts of time when the stress of a deadline approaches. 

Avoid the Planning Doom Spiral

If you have trouble thinking about things from every angle–exhaustively–without ever taking any action, it can be incredibly difficult to pull yourself out of that mindset. Two pieces of advice: start small, and embrace randomization. 

Instead of extensively planning where you’re going for lunch today, take a walk. Try the first place you find. Instead of planning a meet up months in advance, drop a text to a few friends or coworkers and just see if they’re free for a beer (if that’s your thing) or a movie. Repeat tactics like this, gradually, until it becomes easier to make decisions without tons of forethought. 

So, which is worse? To act without planning or to be unable to act without extensive planning? Honestly, both. But, with a few of these tips, you can avoid overplanning and stick to planning. 

planner calendar on desk with laptop and alarm clock


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