When Too Much Planning Can Kill Your Business

I don’t know about you, but I’m a chronic overthinker. I can analyze the you know what out of just about anything. In fact, I’m pretty sure I start analyzing my day before I even wake up, because by the time my eyes flutter open I’m already mid-thought. I think that creative types tend to be this way. 

We also have a tendency to plan everything at least a decade in advance. Whether this means wondering if so-and-so is good father material when you’ve only just shook hands, or worrying about whether or not you put too much cream in your coffee, option weighing is all but an art form for us. 

Planning is, overall, a good thing. So is drinking water. And eating. 

Do anything too much, though, and suddenly things fall apart. 

When it comes to planning, you need to know what to plan and what to leave. Unless you happen to know exactly what’s going to happen every minute for the rest of your life, there are some things you simply can’t plan. And when you try to plan everything, something is bound to get messed up or sidelined in that plan. And when that happens, you tend to have an extremely unproductive day. 

Ask me how I know. 

It takes a lot of restraint for me to plan my day responsibly. But I had to learn how to do it after I spent a full week planning the crap out of my business, only to do…well…roughly nothing by the end of the week. I planned and re-planned and planned how I was going to do the next plan. But all I did was plan. 

If you haven’t experienced this, thank your good fortune and let this be a lesson for you. If you know this all too well, here’s how to stop it. 

Think simply. 

I know, I know, it’s hard. But all those 204 things you just put on your to-do list, I promise, funnel down to about three. I used to plan out every query I was going to write, every corporate proposal I was going to send, exactly how many Constant Content submissions I was going to write and exactly what they’d be about. And then I’d wake up, realize that I didn’t like such and such query idea, look at my overwhelming list of things to do, and go get another cup of coffee. Or check the garden. Again. 

Simplify, simplify, simplify. The beauty of owning your own business and freelancing is that you don’t have to have a gigantic list of things to do that are so specific you think engineers have it easy. If you come from a corporate job, though, it’s completely understandable to think that somehow you have to have a demanding quota, or list of things to do, or specific itinerary for your day. 

But you don’t. 

These days? I just make sure I cover my bases. Those bases are querying magazines, pitching corporate clients, and writing for the Kindle and Constant Content. I’ve pretty much let everything else go. Yes, I have my longer ongoing projects like my novel and I do things like blog – clearly – but those are things that are already routine for me. I never really over-plan them. The business side of my life is what I tended to over-plan the most. 

Instead of reworking your plan, just jot down the areas you want to cover. By having less written on my to-do list I get more done, and I feel more accomplished. I also am much freer to do what I want to do and follow leads where they take me. If you have a list of certain clients to pitch and you learn about someone you think is a better fit in the morning, what happens to your plan? You already feel behind, even though that plan was a creation of your own mind. 

In order to really hit my income goals, make a comfortable living, and be where I want to be financially I know I need to go catch the bigger fish, write the higher paying things, and let the little ones go. I know that I need to make querying and prospecting an absolute priority, so they’re at the top of my list. Instead of tracking what I need to do, I track what I’ve actually done. 

If you’re not marketing, submitting, or putting words on a page you’re not earning a dime. So keep planning short, don’t get too specific, and only worry about the basics. 

I know what I need to earn per word, minimum, how much I need to write at a few different pay rates to hit my goal, and where I can get the best paying work. That led to my knowing the top three or four areas I need to market in. Bam. 

Everything else is a day to day thing. And that’s really the best way to have it. One lead can take you to another which can guide you to a story that would be perfect for XYZ Magazine and suddenly you’ve landed a $1,000 writing gig you never had on that list. 

So if you find yourself broke, not where you want to be, and can’t figure out how that happened, start keeping track of the actual marketing and writing you do. If it’s not the majority of your day, there’s your answer. 

Do you have a story of when over-planning cost you cash? Tell us in the comments. 


3 Comments Add yours

  1. JInmanmarket says:

    Reblogged this on jinmanmarket.

  2. nakularora says:

    Haha… I can so connect with this article. For me, over-planning didn’t cost me cash, it cost me 1 wasted year. I had made such elaborate, detailed plans in my head that i didn’t realize as and when i diverted from it being about where i had to go to it being about simply following the plan no matter what.. It became more of a task to me than a means to an end… Learnt that lesson the hard way.. 🙂

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