24 November 2012

On knowing when you're finished.

I wrote a post for the UC blog this week about something that I've been mulling over for a while. Fenske told us once in grad school that knowing when our work was done was as valuable a skill as the specialized crafts we were learning over those sixty weeks. This wisdom popped into my head a few months ago, when I was up late working on my first proposal and was plagued by self doubt. Instead of continuing to stay up all night, tweaking and re-reading and comparing it to past proposals written by the peers that I look up to so much, I made a decision that it was ready to send in its current form, and went to sleep. So here it is on the site, and cross-posted below.

I recently co-ran workshops at a couple of graduate schools in Stockholm. At the end of one of the sessions, a series of questions from the students evolved into one of the themes of the day: Knowing when your work is finished is one of the most valuable skills.

This was very helpful wisdom to hear as a student several years ago, and it’s important for everyone in the strategy world to take to heart. Because intellectual labor is intangible and expansive – and strategy is about making things without a defined “right answer” – we can get trapped in a cycle of perfectionism and hesitancy. Knowing and deciding when your work is ready is a powerful way to avoid being paralyzed by ideas staying in our heads for too long.

Opbeat’s much-shared F**k It, Ship It image encourages the same behavior – stop worrying about failure and learn to love the Launch button – but comes from a different place. Deciding and trusting when something is ready, rather than resigning yourself to the fact that there are dozens of additional things you could add to your work, is a powerful choice that requires skill, understanding of your own mastery of the subject matter, and an ability to pull yourself out of the storm of self-doubt that can prevent you from seeing the work from a higher, objective level. Deciding when your work is done isn’t easy, so here are four ways to help frame things.

1. Know your skill level, and tweak your judgment accordingly.
I wrote my first ever strategy document in 2004. I rewrote it 15 times before it was finished. There is a starting point in any craft in which you’re learning, and it’s sometimes necessary to do things many times to grok the craft and learn how you do your best work. The more mastery you have over the thing you’re making, the easier it is to pull yourself out of the weeds and realize when you’ve got it. But even if you don’t have the sufficient hours behind you, you can use your understanding of the context, time constraints (more on this next), and audience to make decisions within the parameters you are given.

2. Use your time wisely.
However much time you have to do something, it will take that much time. Because project scopes vary greatly and you don’t always get to choose how long you spend on certain things, you have to let your skills in the subject matter inform the intensity you put into the work, based on how much time you actually have. Let’s use the example of audience research. Over the past year, we have worked on projects with three-week research work streams (the most fun), and ones with three-day research work streams. With only three days to learn about a group of people on the Internet, you don’t have the luxury of getting lost down a bunch of rabbit holes. So, you force yourself to see behavioral patterns, motivations, and archetypes more quickly, and decide when you have an intuitive grasp of that group online – supplemented with all of your existing knowledge, of course. The result will be something that is appropriate for that project.

3. Resist the paint war.
A high school art teacher once described a dangerous tipping point in paint mixing. When you keep adding more and more of each color to get the perfect shade, eventually you end up with a muddy brown-gray mess – and you’ve wasted a whole lot of paint. When you stay up all night pushing pixels around until 4AM, or trying to cram every interesting link and quote you found in your research into a deck, you can get into a never-ending cycle that increasingly binds you to the work itself rather than your mastery of the material. When you have sufficient comfort with your process and your craft, eventually you recognize the point at which you’re good to go – you have made yourself a miniature expert in that one area and can riff on it freely. Conan O’Brien put this advice perfectly in his Guide To Creativity in Fast Company last year:

My formula has always been I’m big on preparing. Prepare like crazy. But then just as you’re heading out, half an hour beforehand, forget all of it. It’s there. It’s in your reptile brain. Go out but feel loose enough to grab opportunities as they come up.

4. Remind yourself that the Internet is never finished.
Like a city, the Internet is a dynamic and ever-evolving place that is forever being built upon and modified – there will always be things you can do to improve something. The Internet as a whole has gotten more keen on this reality, which is why we don’t use “Under Construction” banners on our sites anymore. Similarly, with strategy we don’t ever want our work to be the last thing, but rather a contributing factor along the way – a starting point rather than end point, to frame and begin conversations. Keeping this in mind will make it easier to put a stake in the ground about what the end of this project looks like, and in turn where to start the next iteration.

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