2017, grit, plans, winning

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.

change, plans, visions

I Knew the Pathway Like the Back of My Hand

About three months into my four-month summer, I became restless. In search of change. I knew it was coming, since for the past four years, I have split my time between San Francisco and Philadelphia. The travel either way always came at the right time. You’d be surprised what a five-hour flight can do to break the monotony. With a flight to Philly off the table, I was forced to be a little more creative, which I took quite literally. On a whim, I decided to remodel my entire room. And it wasn’t just a little feng shui moving around of furniture. A wall was extended. Despite the spontaneity of my decision, I had (and still have, the project is yet to be completed) a general idea of where I was going. A “vision” as a real decorator would say.

Things were going well. I had successfully removed the wallpaper and primed the walls. I woke up in high spirits the Friday morning I had designated to ceiling-painting. Before I could even complete the first paint streak, paint was dripping onto my face. By the second streak, I had a kink in my neck. And by the third, my ceiling looked bigger than ever. I felt sucked in by the white space. Like I was drowning in an ocean but upside down. I can’t do this. I seriously can’t do this. My memory is a little hazy, but I wouldn’t put it past myself to have screamed out loud in frustration. It was at this point that I kicked myself (figuratively). The room wasn’t that bad to begin with. Was this revamp at all necessary?

By streak thirteen, I was completely covered in paint. An additional drop would not phase me. Would not intensify my emotion. Kind of like the all-or-none principle for action potentials. Or like diminishing marginal utility in economics. In fact, being completely covered in paint was symbolic of the fact that I was so deeply entrenched in the project that the only way out was completion. I pulled myself together. I reminded myself of the big picture, the end goal. I proceeded logistically, approaching one small rectangle at a time.

A couple weeks ago, the Senior Vice President of my division spoke to me and my colleagues about what lies ahead. She is one of the most driven and passionate people I have heard in a while. In explaining how she became a senior executive by the age of 33, she advised, “Have a plan. Verbalize what exactly you want to do. Where you want to be. And if it needs tweaking, someone will help you. But pick something. That’s the only way to move up.” And then it struck me. For the first time in my life, I don’t have a solid plan. I have immediate interests. Ambitions. Idealizations. A maybe-too-vague vision. But no plan. And part of it stems from a fear of pigeon-holing myself. Deciding before having fully explored. Being scared of being “wrong.” But she’s so right. It’s better to have an imperfect plan than no plan at all. With no plan, we lose ourselves in the endless possibilities and risk losing momentum. Sometimes, we just have to pick something and go with it until we prove ourselves wrong. Until we reach that threshold where the only thing left to do is tear the wallpaper off and start all over.

I completed the paint job late last month. I’ve selected some furniture and am still on the lookout for accent pieces. Not everything is finalized, but I have a plan. And each day, the vision comes closer and closer to fruition.