Around 10:30 am last Saturday, I walked into my teenage daughter’s bedroom to determine whether she was awake.

Her friend had slept over, and I assumed the two girls had stayed up late, glued to TikTok and Snapchat on their phones.

But much to my surprise, I found evidence of another nocturnal activity: festively decorated lists of the pros and cons of dating various boys. The sight of them induced nostalgia: I had spent years dutifully making pro and con lists, certain that an analytical process would help me get what I wanted in life.

“Hey guys!” I said. “It’s time for breakfast.”

And then, I quietly added, “You know, if you need to make a pro and con list about whether you should date someone, then you probably don’t really like them very much.”

The girls laughed and gathered up their papers. I wanted to say so much more.

Good On Paper

Benjamin Franklin is purported to have invented the pro and con list when he described it as a decision-making process in 1772 in a letter to his friend, Joseph Priestly.

Nearly a century later, in 1838, Charles Darwin famously weighed the pros and cons of marriage to his cousin, Emma Wedgwood.

On the positive side, Darwin listed:1 “Constant companion and friend in old age who will feel interested in one; object to be beloved and played with; better than a dog anyhow; someone to take care of house; Charms of music & female chit-chat; These things good for one’s health. But terrible loss of time.”

On the other hand, Darwin wrote: “Conversation of clever men at clubs; Not forced to visit relatives, and to bend in every trifle; to have the expense & anxiety of children; perhaps quarelling; Loss of time; cannot read in the Evenings; fatness & idleness; Anxiety & responsibility; less money for books etc.; if many children forced to gain one’s bread.”

Darwin married Emma and luckily for them, the marriage was a success, lasting for over 40 years, until Darwin’s death. But I don’t believe the marriage worked because of any great insight gained from his lists.

The bad reputation of the term good on paper is warranted, as anyone who has tried to reason their way into a relationship has learned.

I spent most of my twenties making lists of the pros and cons of each new date, believing that if someone had all the attributes I thought I wanted in a love interest, it would all work out. Several heartbreaks later, I finally learned to stop checking boxes and focus on my feelings.

Technology Upgrade

But I couldn’t entirely give up the lists.

In my thirties, happily married, I turned to the other big question that nagged me: what was my purpose, calling, and mission in life?

I was jealous of successful people who said they just knew at a young age what they were meant to do, and from then on set their course.

My job at a financial services company was financially fulfilling2, but increasingly otherwise not. A discordant tune played faintly in the background of my life; in quiet moments I had the niggling sense that something wasn’t quite right; that my purpose lay elsewhere.

But while I didn’t love my job, I was good at it. And one of the things that made me effective was my lists…and spreadsheets. Accordingly, my pro and con lists graduated from paper to Excel, where creating neat, orderly lines of options gave me a sense of accomplishment.

I listed alternative jobs, graduate school programs, and entrepreneurial ideas, sure that if I could just get all the right pros and cons lined up, I’d know what career I was meant to be in. I read self-help books, skipping the parts about “looking inside your heart” and going straight to the exercises that directed me to list my strengths and weaknesses.

I was inseparably attached to the idea that I could think myself into the right life and career and that my feelings were irrelevant.

What Could A Nun Possibly Know About The Meaning Of Life?

We all start out the same: little humans with big feelings.

But when those feelings don’t fit into our environments or match what is expected from us at school, work, and within our families and cultures, we learn to ignore and distrust our feelings, wants, and yearnings.

In a process that may sound familiar to you, the well-meaning adults in my life had given me advice that resulted in my enduring sense of confusion.

I was told many times, “you can do whatever you want!” And while I knew it was meant as a compliment, this statement was unhelpfully vague and misleading. Because the truth is, each one of us feels a strong urge to create a life doing something quite specific: the things we’re uniquely suited to do.

It also soon became clear that the adults in my life didn’t really believe I could do whatever I wanted, because they had definite ideas about who and what I should be.

In grade school, I said I wanted to be an actress and was told not to waste my brain.

In high school, I said I wanted to be an editor and was told that if I liked reading and writing I should become a lawyer because it was much better paid than publishing.

After dutifully enrolling in Law School, I told an advisor I wanted to work in family law but was directed to choose a field of law that was more challenging and paid better.

And so I found myself at the financial services company, which was both challenging and well paid, where, when I told my superiors that I wanted to work in the human resources department, I was told to forget about it because that function wasn’t valued as highly as the outward-facing parts of the firm.

I came to believe that I should not trust my own feelings when it came to career decisions. Everyone else knew better.

Now, I did receive one piece of conflicting advice when I was in high school. My favorite teacher, who happened to be a nun, said this: “Do what you love. You could be a garbage collector, and if you love your job and are the best in the world at it, you will find a way to be successful and make plenty of money if that’s what is important to you.”

Her comment stayed with me. I turned it over in my head for years, comparing it to what everyone else had said; but I dismissed her advice, thinking, what could a nun possibly know about choosing meaningful work?

All Good Things Must End

My enduring love affair with pro and con lists ended in a therapist’s office in my early 40s when I discovered the meaning of the term: feel your feelings.

I had resorted to the therapist out of desperation because even after leaving the financial services firm to work for charities, hoping that nonprofits would bring me the sense of purpose I wanted, I still felt a lack of meaning and direction.

After spending months patiently allowing me to read aloud to her my many lists of strengths, weaknesses, and career options, my therapist kindly asked me how I felt when I talked about these things.

And then she helped me to understand that over the years, each time I said what I wanted and was told that I shouldn’t want it, I had learned that it was better to say nothing: to keep my pesky feelings and silly ideas to myself. It was my way of avoiding the pain of not getting what I wanted and feeling wrong for wanting it.

From there, I developed the habit of hiding my true feelings and yearnings, even from myself. This is a common reaction. Humans work very hard to avoid feeling pain – even if it ultimately causes us more pain.

Waiting For Lightning To Strike

And so I had it: the key to solving my lifelong quest. I would need to feel – not think - my way toward finding my purpose in life.

Getting in touch with my feelings actually meant getting in touch with how my body felt. And it was subtle. I had assumed that all those successful people who just knew what to do with their lives had been driven by strong, impossible-to-ignore feelings, like a lightning strike accompanied by a drumroll.

But it turns out that the feelings that send us in the direction of our purpose are quiet and small – more like gentle raindrops and fluttering leaves. The feelings that lead to locating mine were more like niggles, slight twinges of curiosity: a tightening in my throat; butterflies in my stomach; tensing in my shoulders; a twitch in my eye; sweaty, shaking hands.

I learned that I had to pay careful attention to the messages from my body, because they were quickly drowned out by the loud voices inside my head, telling me how I should want to be and feel.

So, what are pro and con lists good for?

Use them when deciding between two things of relatively equal weight, like two comparable job offers, or which TV, cellphone, or car to buy.

But when it comes to the truly big decisions in life, go with your heart (and your gut and your throat and your belly) not your head.