It was super hard for me to find a job straight out of college—the places where I wanted to work weren't hiring and many of the other jobs didn’t seem right for me. After months of searching and waiting by the phone, I decided to take the plunge. I had done some freelancing throughout high school and college and decided I would trek back home and freelance full time. I had a strategy and I had it all planned out. I really did. It didn’t matter, though. The work I was doing in an attempt to get noticed (and paid) was getting absolutely no attention. I mean, I purchased a website and got little to no views for weeks. I was trying my hardest, and I think on my best day I got maybe 150 views, and maybe 20 folks on my e-mail list. My strategy just was not working. The bright side, however, was that the work I was doing for fun got a lot more recognition than I thought it would and it eventually turned into some decent money. Who would've thought?

Why be strategic?

Having something organized and planned out works for some people. It’s what the experts tell us to do. I hate surprises so I liked the idea of having something to look forward to rather than feeling like I was taking a walk in the dark. Besides, it’s a lot easier to tell people you’re working on your web design business than it is to tell them you have no clue what you’re doing, but you hope it works. Creating a strategy helps you to be prepared. You don’t want to just let yourself loose and hope something happens or catches on. Even when I was doing my primarily creative/fun stuff, I still planned it out. Think about it like this—how often can you open Photoshop (or the program of your choice) with no plan or idea of what to do and then end up creating something spectacular? I know I can’t. Web designers, print designers, architects, painters, and other creatives all have some sort of plan or some sort of sketch before they get into the development stage. Strategy is what some people believe pays the bills. Now, I’ll say that’s up to personal interpretation, but if you have a plan and it makes sense, well then you’re far ahead of someone who has no clue what they are doing. Some folks come along and decide they want to create a blog packed with design inspiration and other creative articles or they want to create branded packages for small businesses. These are great ideas that have to have a strategy behind them…or do they?

Why be creative?

While I absolutely hate surprises, I had no idea how to create a good strategy. Mine were entirely too strict and didn’t give me a chance to totally be creative. If I look back at what I was doing, I was strategizing things down to the very bone—my goal wasn’t to get more Twitter followers, but it was to have 100 new followers a week. My goal wasn’t to just create a website, but it was to create three types of freebies a week and get a certain amount of folks to download them. Thinking like that didn’t leave room for error, which I liked, but it also didn’t leave room for opportunity. If the results weren’t as I expected, then it was wrong. Now if we recall, I said the things I did to have a bit of fun and be creative were getting noticed much more. I have two theories for that:

1. While I still had a strategy, I was being creative. I strategized by saying, "Hey, I see people asking how to make this kind of effect in Photoshop, let me make a screencast video and put it online." That was it. Nothing else, really. I didn’t even write a transcript (which I would do in the future). The idea here is that I gave my "product" time to sit and breathe and be itself. Perhaps with my other idea, I was too involved. Over-strategizing can be the death of any strategy. You’ve got to give your idea time to stretch out and grow and figure out what else it NEEDS to be. You can’t create something and immediately expect it to be something more. Especially when it was as generic as my over-strategized idea.There is an issue with trying to be too involved.
2. People like creativity. Doing something new, or seemingly new, is smiled upon. I think there are a ton of psychological things we can explore here, but basically the idea is that folks are attracted to things that are new, that are different, that are unique. Think about the designers that stand out to you the most or the musicians and companies that are up and coming. Don’t they all have something new or unique to offer? Most times they do, and most times they start by serving a small niche, who were immediately attracted to it. Then as they got older, and got some more feedback, they figured out how to make it a monster—think of Macintosh back when they first started. Some of the greatest sites, products, musicians, etc. came about pretty much by accident (with little to no strategic backing).

The winner is...

I’m not saying that it’s bad to have a strategy but I am saying it is terrible to over-think some things. It’s also hard to put a strategy behind a purely creative idea. Strategies are extremely important to products or services that come about strictly to solve a problem. Most app and program developers have found a problem and developed some app to try and help out. For example, with these high gas prices I was wondering (and hoping) there was an app out there that could tell me how close the cheapest gas was. I had a problem and needed a solution. Now that deserves a strategy for sure—how to get it in front of people who would use it and how much they might be willing to pay for something like that. The thing to be careful of is trying to create a problem for our creativity to solve. For one, you’re probably boxing your creativity up. My bright idea straight out of college was to create affordable everything design for small businesses—I had ads up, I had made connections, but I was putting my creativity in one lane—small businesses. I was only following small businesses on Twitter and my portfolio only had stuff up for small businesses. It sounded right, but I kind of made that strategic decision without letting my creativity find its own way. Secondly, being creative is a very sensitive thing—you can’t just push it on everyone and expect them to like it. Sometimes it’s best to just put your best foot forward and see what you get and go from there. I know this is going against everything everyone else has taught you. Hell, it’s going against everything I was taught, but sometimes we’ve got to take risks and find out what ends up working for us. Take the feedback, cultivate it, and make something great. Do you feel like this theory about creativity is true? What are your results when it comes to strategy vs. creativity?