I first got a sense for the power of planning as a statistician and programmer working for the TSA. During those five years, I saw very smart analysts (programming “worker bees”) move into management, then fail where they had every right to shine. Additionally, I saw wildly successful managers in every sense struggle with personal relationships despite a genuine concern for their loved ones and a desire to keep bonds strong.
Still a “worker bee” myself at the time, I was watching these managers and executives from the outside. I used to think “if these people aren’t successful in areas where they seemingly have all of the necessary skills, what chance do I have?” Adding to this confusion was something else that I noticed – there were people who I viewed as having below-average technical skills, or were less socially adept, who were thriving at work and at home.
This confusion stuck with me as I moved on to a career in the insurance industry as a rate analyst. The workload in this role was more varied and time-sensitive, and I was sinking underneath the new pace and volume of work. Often I would resort to pulling a string of late nights to catch up only to get behind again. Looking back, I was probably never really “caught up” in the eyes of my manager because I constantly underestimated the importance of some tasks and overvalued others.
The bottom line was that I was failing.
But I wasn’t the only one. Many of my colleagues were struggling too -- spending too much time on unimportant tasks and rushing the critical ones, the ones that had to be error-free. As professionally limiting as this was for them (and me), this way of working was also forcing us to neglect our personal lives more often than should be expected.
This way of working just isn’t sustainable. I knew it wasn't fun, but I didn’t know how to get out of the cycle, or if I should even expect to. Does this imbalance of work and life just come with having a well-paying corporate job?
After about a year of working like this, I knew that regardless of how many people in my field worked this way, it wasn’t going to work for me. I was going to burn out.
Around this time, I was relieve to see that this in fact WASN'T how everyone in my role worked. There were high-performing analysts and managers who seemed to be living a more balanced life, even though at their level they had far more responsibility than I had.
I began asking those analysts, managers, and executives how they were getting everything done without getting overwhelmed. At first, I think people thought that it was a bit strange, but after a while I became known as the guy who wanted insight into everyone’s “process.” And not just the successful people. I asked those who were drowning as well. I wanted to have a thorough and concrete “positives” and “negatives” list of ways to approach our seemingly endless stream of priorities. Should I answer every email as it comes in? How does one decide what’s the “most important task?”
The pattern that became clear was that, for the "drowners", planning was thought of as a luxury that they just didn't have time for, thinking that was time they could be spending on completing a task. And which task should they complete? Whichever task will land them in the hottest water if they don’t finish it that afternoon. Talk about a stressful workday. In contrast, the more relaxed high-performers seemed to always have an appropriate “time cushion” to complete a task, rarely finding themselves in a situation where they have just one afternoon to both start and complete something.
Through these conversations, I began to develop an appreciation for planning as an art. Like some world-famous painters, some of the greatest planners I talked to didn't really know how they arrived at the planning tools in their toolbelt, while others deliberately built their practice as I now have -- through observation, trial and error, and a few painful lessons learned. Savant or not, they all had something to teach me about how planning can change one’s career trajectory and life satisfaction in a very short time.
This is why The Art of Planning exists. I've put a lot of time into cultivating a practice of planning for myself, and now I want to devote my time and energy into sharing what I've learned. I created The Art of Planning 12-Month Daily Planner & Travel Journal to give people something simple that is more a mirror than a guide. For experienced planners, this book will give them the freedom to use it how they see fit. For beginners, there aren’t a barrage of questions that one needs to answer on each page. Many planners require too many pointed questions that beginning planners may find cumbersome and intimidating. It’s not that they aren’t useful questions, but planning is truly effective when there aren’t numerous boxes that one has to “fill in” before calling it a day. Like meditation, planning is most rewarding as a daily practice, so we need to keep it light at first.
On that topic, The Art of Planning is not just this planner. It is an organizations centered around this idea:
A consistent planning practice is one of the best ways to get smarter every day, and to get more of what you want out of life while getting get less of what you don’t. Like any routine, a planning practice is most effective when it’s challenging enough to be rewarding, but not so burdensome that it feels like a chore. It’s at this critical point that planning becomes an art.
While our 12-Month Daily Planner & Travel Journal is minimal and without too much guidance, we will be offering advanced materials in the future. Planning is such a rich and rewarding practice to maintain. It teaches you invaluable lessons about your own values, and in doing so serve as a self-actualization tool, helping you to adjust your focus and get closer to who you want to be.
I look forward to going on that journey with you and hearing about your successes!
Founder, The Art of Planning