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.

academia, goals, grit, happiness, perseverance, real world, success

The Problem with Confusing Ambition and Happiness

It’s Saturday afternoon and you really want to be doing something relaxing. As you think about lazy activities, you are slowly reminded of all the loose ends you left at work on Friday evening. I really should just work you tell yourself as you open your laptop. And well, that’s the excuse you’d use if a friend called. But the crazy thing is you kind of do want to work because you like what you do. You’re pretty happy with it. It’s not what you tell your friends though. They’re so set on starting companies and moving mountains that it would just feel awkward to admit your current happiness.

Especially if you’re on your second or third post-college job, the above scenario may especially resonate. You’ve been on the project that you hated, you’ve been at the company that felt stepping-stoney, and now, you are where you are and you’re generally content. But is that allowed? Are you still the “rockstar” that you once were in your eager beaver days?

We’ll get there, but first some important anecdotes:

During my childhood, the drive home from any family outing – a birthday party, dinner at a friend’s house, a play date, a day trip, a sporting event – would be spent by listening to my brother, despite everything that we did get to do, complain about what we didn’t.

“It’s not fair. Why didn’t we go on that one ride?”

“Why did I have to leave earlier than Nathaniel?”

“I didn’t get my second turn on the Nintendo 64.”

My parents would listen silently while my brother whined, until finally, one would say in a disappointed sing-song, “You’re nev-er hap-py,” as if that made it all better. It kind of did, too, because it provided no conversation around the matter. Nothing on which my brother could linger.

As he left behind his childhood, my brother also left behind his annoying obsession with identifying the negatives in a generally positive situation.

What he didn’t lose, however, was his unbeatable threshold for personal satisfaction. He holds himself to the highest standard, only briefly celebrating his successes before turning more attention to the fine hairs that were out of place. He is smart, but more importantly, he is focused.

This likely explains how my brother continually achieved academic success at the concrete tasks he tackled. He wasn’t happy until he could achieve that “little bit more.” Tangible (albeit controversial) proof includes a near straight-A (or above) record from kindergarten through his graduation from Yale.

Nine months ago, I started tutoring a high school senior in English. She moved to America from China two years ago, and belongs to a family who is still disappointed by her gender (they wanted a boy) and repeatedly told her she would not get into college. They were also unwilling (one parent) and incapable (the other parent) to pay for it.

Over the course of our time together, I watched as my tutee wrote and rewrote tens of essays and researched college upon college not just for its prestige or programs, but also for its commitment to ESL students, women, scholarships, and post-graduate opportunities in pursuit of her goal to be the first female in her family to attend college. “I will be so happy if that happens,” she said to me once.

This fall, my tutee will not only be attending one of her top choice colleges, but also with a fully funded scholarship for her first year. With no more essays to write (Praise the Lord!), we now go for weekly walks practicing conversational English. Last week, I stopped us midway and turned to her.

“How happy do you feel? You got into your top choice school! And with full scholarship!” She looked back at me unmoved.

“It’s my second choice school.”

“Right, but still…”

In 2007, psychologists Duckworth and Peterson set out to understand personal indicators of professional success above and beyond intellect. In their research, they found that one specific non-cognitive factor called “grit,” defined as perseverance and passion for long-term goals, accounted for a significant 4% variance in attaining success. They concluded that in addition to talent, success relied on focused and sustained talent over long periods of time.

Grit helps us reach goals. Grit is what my brother has. My tutee has grit.

While part of me wonders if I am being the “I’ll be proud of you no matter what” parent/guardian type, the other part of me remembers that I too experienced similar disappointment to my tutee when, eight years ago, my dad wrote a check for my deposit to UPenn. Despite having achieved my general goal to attend college on the East Coast, I wasn’t completely happy about it. “But maybe I’ll come off the waitlist at Columbia,” I told him while thinking, “If only I had gotten into Yale.” (I know, I know.)
To anyone who is past the stage of pre-professional academia, the cases of my brother, my tutee, and me might be worrisome. Is it unhealthy that ambitious individuals are unable to be happy?

Considering the somewhat healthy outcomes of this reluctance to be completely happy with the status quo (self-motivation, hard work, personal goal-setting), I would argue that it actually isn’t a problem during the phase of formal education. Goals are so concrete, landmarks so predictable (the next exam or class project), external validation so clear-cut (a grade), and paths mostly linear (semester after semester). For example, a student might peg happiness on receiving a good grade on her AP US History final project. The ambition is concrete because getting some grade on the assignment is inevitable. Upon receiving a B+, she will likely be unhappy, but the unhappiness won’t linger long because the project itself will never show itself again, and there will be future final projects for which she can strive to perform even better.

The problem comes after school.

Every year around this time, tens of thousands of black-gown-clad college graduates hear some version of the advice to “follow your passions” to “find happiness.”

The advice reiterates what they have learned to be true for most of school: Ambition is conflated with happiness.

While mostly harmless during childhood, this conflation erupts in a post-academic world where paths are meandering or worse nonexistent: When is it okay to say you are happy? If you say you are happy, are you void of ambition? Can you only be perfectly happy once you attain your goals?

This brings us back to the weekend work scenario.

I know a lot of twenty-somethings with big goals. They want to start companies. They want to go to top business schools. They want to travel extensively and exotically. They want to be doctors. They want to get books published (I know this twenty-something particularly well). They want to find soul mates.

But achieving some of these goals is kind of far away. They aren’t like grades that can be earned and improved within weeks of one another. They aren’t really sure-things either. Long-term goals assume many unknowns and are not guaranteed to pan out the way we might anticipate.

If, like in school, we plant our happiness on some far off planet that houses our goals, we start to deny everyday joys and successes. A good streak at work is clouded by the fact that we are not yet working our dream job (how much do you love to hate “#ilovemyjob” instagrams?). A restorative road trip pales in comparison to the desired years-long escapade through Asia. A self-published book is nothing like a Times bestseller. Attending a top business school is yet another sign of being lost. A good boyfriend is “probably not” the one.

This is a problem because these everyday joys and successes are the ones that fill the majority of our lives.

As a follow-up to the Duckworth et al. findings on grit, Singh and Duggal Jha probed further to understand if and how grit is related to happiness. The study demonstrated a significant positive correlation (+26%) between happiness and grit.

Correlation does not prove causation, which in this case helps to prove my point. Grit does not cause happiness, but instead the two are intertwined and positive influence one another. Increased happiness suggests increased grit on the meandering path toward self-identified success.

Happiness cannot be the destination.

Rather than ignoring happiness or worse, convincing ourselves that we cannot be happy yet, we in the real world should be identifying what in our lives makes us happy today. Be okay with admitting it. Bring it with you wherever you go. Because you know what? Happiness is what’s going to get you wherever you need to go. It will motivate you to work harder and embrace what you have in the process.

Happiness is not the lack, but a driver of ambition.