Confessions of an Anti-Planner

I would like to keep it my dirty little secret, but everyone knows. Every personality quiz/culture index/strength assessment I’ve ever taken has said I’m not detail oriented. My college roommates could concur, so don’t put me in charge of planning and organizing (you’ve been warned).
Let’s be clear: this isn’t my pride and joy. It’s something I’m working on – it’s right at the heart of my personal and professional growth, you could say.
Of course, this has had an impact on my job searches and career choices, and if my career choice is any measure of how it’s working (hey, I helped start a company), I think I’ve figured out a thing or two about not dotting every “i” or crossing every “t.”
And so I’ve started to think, what if — in the areas that allow for it — I let go of my anti-planning guilt? Because, know your strengths, right? Feel personally patriotic about who you are. Own it! What could this acceptance possibly look like, you ask? How could I laugh in the face of expandable folders, label-makers, and color-coded post-it’s, when the calculating corporate world values such discipline and structure?

Embrace the flexibility, my friends! Be the person who can go with the flow; roll with the punches, and be ready to pivot to that new thing that suddenly needs to get done. The flexible person is often a critical teammate because they can shift gears when that new need emerges out of thin air and let’s be honest, things come up every day (at least they do at a start up).

I know there are tips and tricks that would move me into the fast lane of planning and productivity. Most of those tips center around the idea that if I just scheduled my day well enough, I would be more productive. But I’ve tried this and know that I only use that tip to procrastinate from actually completing anything on my to-do list. But I have begun to make, shall we say, accommodations.
To live in a planner’s world, I make lists. I make a to-do list of the things I need to do, and then I allow myself to jump from item to item on the list. This way I don’t feel too confined with the structure, but I still know what needs to get done and by when.
I also set goals. I’ve found it’s much more effective for me to figure out what I want the result to be, rather than planning all the detailed steps to get there. The structure and planning of the process makes doing the work all that much harder for me, which is why I feel much more effective when I can just show myself that I am moving in the right direction.
As I’ve been writing this, I started to think about why it is I feel like planning doesn’t work for me. I think the biggest reason is that even when you plan, and you put everything into place, you can’t really control for all of the things that might change. I might even harbor a wish that things might change unexpectedly.
You can’t plan for every version of what life throws at you (especially at work), and for me having a concrete plan makes it harder to be flexible (are you getting that I love to be flexible?). While the opposite is true for many people, not over-structuring my work allows me to feel more comfortable going into any given situation because I know I have options.
That leads me to my favorite anti-planner way of working: trial and error.
One of my biggest issues after college was not knowing what I wanted to do. I liked writing, working with people, strategy, magazines, the food industry, PR, the outdoors (and that’s not all). Trial and error and staying flexible allowed me to try a lot of my interests as jobs — some simultaneously — to move from city to mountain to another city and figure out what would best fit with my interests and strengths.
This meant I got to work in PR, write for a magazine or two getting paid to try new restaurants and cafes, live in Boulder, be a friendly hostess at a dynamite sushi restaurant. Not having a plan meant that when a writing and marketing role at a start-up popped up, I was game to drop the other things to jump at the chance. Who knew that the novelty and lack of predictability of a start-up would suit my personality so well?
If you’re like me, you might feel like you never know what’s really going to work until you get out there and try, so just start. Working this way gives me the flexibility that makes me feel more secure than a structured plan. If something isn’t working, I can always change it. Similar to agile design, I prefer to start and make small or large adjustments as I go so I can continue to be productive without having to stop and plan and start over again.
Planning is useful for many things, but sometimes, it’s better to set your general direction, stay focused on what you want to get done, and be open to the great opportunities that you could never plan for.