Why I’m Changing The Way I Think About My Plans–Both Big And Small

Recently, I attended a wedding in Fort Myers. Yes, this Fort Myers, the one that Irma visited just weeks prior to that. On the phone with the bride two weeks before the wedding, I asked her how she was feeling. Having been hit hard by the hurricane, the wedding venue was closed down for repairs. Recognizing the first-world-problem-ness of my question, I assumed my friend was struggling with the reality that her meticulously planned weekend would almost certainly not go according to plan. And when you (ideally) only have one wedding, that’s a difficult reality to accept. “The only person that should be freaking out is me, and I’m not. What can I do?” She responded. “Bring your swimsuit,” she joked. “In the best case we’ll hang at the pool, and in the worst, the whole wedding will be under water.”

My friend wasn’t just playing it cool. She is genuinely cool about riding life’s waves, even, as I’ve learned, when they come in the form of a hurricane. Now, she could only try her best to put the pieces back together.

I am the opposite of cool when it comes to these types of situations.

For as long as I can remember, I have struggled when my plans, both big and small, have fallen through, even when (and this is most frequently the case), the outcome was not fully in my control. The thrill that some seek in spontaneity, I seek in a good plan well-executed. So when things don’t go according to plan, my heart becomes heavy with disappointment. I analyze how I might have behaved differently in order to have achieved the desired outcome. For me, a fallen plan is the mark of a failed planner—a failed me. This misconceived schema is largely driven by my “do or do not, there is no try,” upbringing. Growing up, my plans were smaller, and most of the time, I did have complete control over them. Performing poorly on an exam meant I hadn’t planned enough time to study. Failing a piano lesson (and my piano teacher was very generous in handing out failing grades) meant I hadn’t planned enough time to practice.

I started reading Hillary Clinton’s What Happened shortly before my trip to Florida. I haven’t yet finished it, but talk about things not going according to plan. The memoir starts with Hillary at President Trump’s inauguration, and the introduction explains her rationale for writing the book—to share candidly with the world why, in her opinion (and as the title suggests), what happened happened. After believing she would win—planning to win—she now has explanations, confessions, reflections, and realizations (and sass). She wants to discuss the mistakes and misfortunes.

At first, the book was painful for me to read. Painful for obvious reasons, but painful also because it is one big debrief on a plan that went awry. Despite years of planning, years of preparation, years of explicitly and implicitly pursuing activities that qualified her for the job, she didn’t get it. It’s painful to know that nobody is superhuman enough to kill the Wrench that kills plans. It’s painful to be reminded of life’s massive unpredictability.

But as I got further into the book, I started to settle in. In a chapter about why she ran, Hillary cites lines from T.S. Eliot’s East Coker, a poem she has loved since her teenage years:

There is only the fight to recover what has been lost

And found and lost again and again: and now, under conditions

That seem unpropitious. But perhaps neither gain nor loss.

For us, there is only the trying. The rest is not our business.

She writes, “In the nearly fifty years since, it’s become a mantra for me and our family that, win or lose, it’s important to ‘get caught trying.’ Whether you’re trying to win an election or pass a piece of legislation that will help millions of people, build a friendship or save a marriage, you’re never guaranteed success. But you are bound to try. Again and again and again.”*

I appreciated her inclusion of both personal and professional instances of trying.

Since reading the passage, I’ve pushed myself to think beyond my academic notion of failed plans to what I rationally know to be true: If most of life’s outcomes are indeed uncontrollable, I shouldn’t be celebrating wins and cushioning losses as if I had any control. Success is in the intent. And failure is not in the plan or in the planner, but in the lack of trying to achieve.

In the twisted complexity of our modern world, “try” is more of an option, and often, the best option.

One thing we can all learn from Hillary, whether we supported her or not, is how to push forward past the plan when it doesn’t come to fruition. How to look back critically, but without self-blame. How to cope with the fact that the plan was just a plan.

Because Hillary, like my friend, knows better than to be married to a plan.



*Clinton, Hillary Rodham. What Happened, Simon & Schuster, 2017, pp. 57.

Related posts

Leave a Comment