
Most articles about starting a business cover planning. Creating your business plan. Creating your marketing plan. Creating page upon page of plans, plans with great intentions and perhaps excellent potential for success. There’s nothing wrong with planning itself; if there was, I’m sure we wouldn’t see such an emphasis on it in business literature.
But not so often mentioned is the dark side of planning, and it’s the dark side that captures many a bright and hopeful entrepreneur into its trap ensuring that their great ideas never see the light of day: overplanning.
I’m sure most of us have known, worked with, or even been the person who falls victim to overplanning. It’s no surprise as the planning phase is a tempting comfort zone; the idea is that the more there is planned, the more that is lined up in a perfect row and ready to go for launch, the better things will work. Things rarely work out this way. Businesses tend to grow organically, despite the best-laid plans, and when they explode with popularity from the very beginning it’s often plain luck. They may have had a good plan to help them on their way, but so did a slew of viable business ideas that didn’t succeed.
What’s important to note is that people who get stuck in the planning phase and never move on to execution are often stuck in planning because they are scared. They’re afraid of how their idea will be received, whether it’ll succeed or fail, and scared that if it does fail it’ll reflect on their abilities.
Execution of plans is an art, because few people can draw on the courage to make things happen.
Two Alternatives to Overplanning

So what can you do to avoid the trap of overplanning? There are two approaches that might work for you:
Ready, Fire, Aim: I’m not sure who first coined this phase that describes a particular way of operating, but the first place I read about it was in this article a few years ago. The premise is that you dive straight in and start executing based on whatever plans you had to start with — in other words, acting on your idea as a plan in itself — and making adjustments as you go along. This way you’re organically growing your business as you plan its future, making sure you don’t get stuck in an unprofitable no-action phase. It’s a good concept and can be applied to plenty of businesses, especially fairly basic ones that involve providing a service as a freelancer or selling a digital product.
Plan Deadlines First: Another way to try and dodge planning paralysis is to make the first act of planning the deadlines for implementation. You might stipulate that you should be advertising and working with your first client by the 1st of the next month, or your information product will be edited and ready for digital distribution within three months on a specific day.
The hard part about making this concept stick is that you might just change the deadlines. Do what you can to make yourself accountable. Many people suggest telling a family member or friend about your self-imposed deadline but I don’t think this works effectively. It’s better to book an ad with a non-refundable deposit or make some other sort of business arrangement for that date so you’re forced to be ready!
The first objection to that method of keeping yourself accountable is that you’re screwed if things go wrong and you simply can’t get ready by the deadline. I think it’s a fair risk to take and losing a deposit is much better than getting stuck in the planning phase!
Lastly, I want to say that there are certain projects and endeavors that do take extensive periods of time to put together and coordinate before they can be launched. These are rare, few and far between and incredibly difficult to get off the ground, but they do exist. Chances you’re first business will be one of these? Well, I wouldn’t say it’s out of the question, but it’s also not too likely, so don’t use it as an excuse!
















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This is a great post. Want something overthought? Call me.
Overthinking comes from fear I think. Fear of making a mistake, or not doing a perfect job. Nothing is perfect. Just do it now!!! Thanks
Interesting,funny
Ocassionally I’ll overplan something, and other times I’ll just take the Ready, Fire, Aim approach. I have to say, the latter approach makes things easier.
When you overplan any problems you think of appear bigger than they actually are. If you just dive right the problems may still pop up, but they’ll seem less burdensome.
You hit the nail on the head here! Inertia is a very powerful force, especially in business.
You are better off moving forward and making adjustments as time passes. After all, things are likely to change the moment your long thought out plans are in writing anyway.
-Di
I lived 40 years by the planning method. On my 40th birthday, I got a sledgehammer and busted through that wall that held me back for so long. Now I also often tell people, stop talking/thinking/planning/mulling/pondering/fretting and just start already! Thanks for the backup!
Great insight. planning and execution are both equally important. Fortune often favores the brave and unique ideas!
Ahmed
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