How To Make Your Regrets A Source Of Strength

Pick your most painful regret and do this to heal it.

Ever wish you could go back in time and slap yourself?

I can.

In between my first and second year of college, I languished at my mom’s house like a lump of Jell-O that refused to even wiggle.

Three days per week, I lifted weights at a nearby gym. Every evening, I boiled some spaghetti, dumped it on a plate without tomato sauce or cheese, retreated to my older brother’s former bedroom (because it still had a television) and watched a line-up of The Simpsons, Seinfeld, The Tonight Show With Jay Leno, Late Night With Conan O’Brien, and some other shows mixed in between. On weekends, I anguished over what I’d watch without the usual weekday lineup, and usually found some mediocre movie.

Why was I wasting my life?

I told myself I was waiting. My goal was to create how-to products about fitness and weight training. First, I decided, I had to get more muscular, which could take a few years, but I had the time. As I waited for my muscles to grow, I figured I didn’t have anything to do but work out, eat plain spaghetti, and wait.

My pasta routine didn’t produce the glamorous body I was anticipating. Years later, I’d think about the wasted potential — the wasted time — and wish I could go back to slap myself silly and awaken some semblance of sensibility.

For most of my late-twenties, I worked as a sign-spinner and stood on the corner of the street in front of a store, waving a sign to traffic.

Usually, I wore a smock that looked like a big $100 bill. It got so soaked and caked with exhaust fumes, sweat, and grime that it turned grey, peppered with questionable splotches of black. It looked like a billfold that had been shoved through too many vending machines, waved around at too many strip clubs, and rolled into too many straws for snorting coke.

Once, as I waved my sign wearing the nasty smock, a car rolled by and a woman shouted from inside, “You need to clean your uniform!”

I looked down. She was right. During my break, I said we needed a new smock and, the next morning, someone brought over a fresh one. As I pulled it out of the packaging, I marveled at its sheen, the subtle shades of green, and the detail of Ben Franklin’s face.

I strode outside, proud to look like a hundred bucks. The same car rolled by again. The woman looked at me and gave a thumbs-up.

I didn’t always wear the smock. During the holiday season, I wore a Santa Claus outfit.

One day, a woman with a missing tooth walked by and said, “Do you have any idea how many women want to sit on your lap?”

“How many?” I asked.

“A lot!”

Maybe some guys did too. One man in his sixties slinked beside me near the end of my shift and, as he darted glances back and forth, said, “Just about ready to go in?”

“Yup,” I said.

He said, “We’ve, uh, gotten to know each other pretty well, you know?”

We’d had one exchange a few days before.

“Uh I guess so.”

“Can I ask you a personal question?”

“Sure,” I said.

“What do you think of sex?” He gestured his hands out, palms up — the kind of motion someone would say while exclaiming picture this.

I had no idea how to respond so I said, “Could you be more specific?”

“Well…”

Our short conversation ended with him moseying onward up the street.

One more story:

I often did my sign-spinning barefoot (earthing, baby!) with my shoes sitting off to the side. For a few months, around two in the afternoon, a parade of junior high school kids shuffled down the sidewalk. They usually said nothing — thank heaven for small favors — but, one time, a kid grabbed one of my shoes.

I lunged toward him and reached to get it back. “Get the f*** off my shoe, kid!”

Just as I got my hand on my footwear, he pulled it to his face, took a giant whiff and said, “That smells good, man!”

He let my shoe go and walked on.

“Thank you,” I said, slack-jawed, and chuckled for the next hour or so.

More than once, I counted how many weird things happened to me during that job. Maybe two hundred. That’s two hundred stories. I made ten dollars and fifty cents an hour — and that was after two raises. I had a business I was trying to grow on the side. Every week, I managed to scrape together $30 to fund my advertising campaigns. I was also trying — but not particularly hard — to get clients who wanted advertising copy written for their businesses.

Why am I saying all this? Because, just like with my spaghetti-eating phase, I look back on this time and I want to slap myself silly. I was racking up all these stories…why didn’t I write about them?

I never blogged about my stories. It would have been fun, free, and I could have built up an audience. Every story could tie into a lesson about one’s spiritual path, especially the Daoist path (I’m still trying to figure out how to connect that to the retired guy asking me about sex). I could have been writing about my experiences for the past eight years.

Many times, I’ve thought about this and cringed. I regretted the lost opportunity that I just didn’t see.

Ever have regrets about a time when you could have put in just a little extra effort on a project and, as a result, could have transformed the trajectory of your life?

I thought about such regrets this morning while standing in the backyard of an Airbnb in Seaside, California, doing my daily routine of Daoist meditation. My wife and I had just attended a friend’s wedding.

As I trained, another thought popped into my head.

Would I regret not writing stories as a small child, when I was still learning how to draw the letters A, B, and C?

No.

Why not?

Because I couldn’t write stories. Scrawling out A, B, C was the best I could do. I was learning and working on the perfect things to master at that perfect moment, on a longer journey.

Was my time as a sign-spinner any different? Sure, I could berate myself with a big list of things I should have done. I could mentally roll the list into a tube and smack myself as if it were a newspaper and I’d just piddled on the carpet. But what if my time as a sign-spinner was another A, B, C time of growth?

I could hate myself for the years I spent watching hours of television every day.

I wasted time, my youth, and my health. But I learned to value time and train my body in a way that preserves my feeling of youth and health.

So, what’s the proper way to judge my past? Where are the cosmic compasses I can jab into my decision points, twist to draw circles, and measure my life’s worth? Where’s the AI-driven data-aggregator I can feed my moments of arrogance, awkwardness, and dereliction of duty, so it can produce a report of how I can best disparage myself and measure my worth. Is the AI still in development? Has the start-up behind it gone public? Maybe I can invest.

Until the tech is available as an app, I’ll stick to something provocative.

What if I thought of my life’s trajectory as perfect? What if I thought that, like a cocooned caterpillar, I was developing perfectly for my next stage?

As I stood barefoot in the backyard of my Airbnb, bits of mulch poking between my toes and sun shining on my face and chest, I thought about timing. If I hadn’t done everything just as I had, what breakthroughs would I have later missed?

I continued my morning practice, rhythmically moving my body and feeling energy go through certain organs in my body. I thought about the three things I cherish today — my wife, the Daoist training I practice, and my (now-published and available here) book that I had been putting the finishing touches on.

What if I hadn’t gone through that multi-year rut as a sign spinner? What if I hadn’t screwed up my life before and, as a result, never needed to take that goofy job? What if I hadn’t cocooned myself in front of the television?

Maybe I wouldn’t have met my wife. Maybe I wouldn’t have met my current teachers. Maybe my book, something I’ve nurtured for the past three years, wouldn’t exist.

Now, my time parked in front of a television set didn’t seem so bad.

What if my biggest regrets today were how I avoided being alone? How I avoided getting lost on my spiritual path? What if they were how I avoided getting stuck with a career or business that drained the life out of me? What if going back and “doing things better” would be my undoing?

As I thought about this, I finished my morning practice, stood still for a minute, then stepped through the mulch to the back door. After I settled in the dining room, I wrote this article.

Think of a regret you have — a big, juicy one that makes you shake your head from the anguish you feel.

Now picture yourself as a child, giggling and drooling as you push one of your arms forward, drag a leg behind you, and make little thumps on the floor as you learn to crawl.

Would you yell at that child for not running full speed? Would you be that cruel? No? Then, why do you punish yourself for what you did — or what you didn’t do — when you were still learning and growing?

You still are learning and growing, by the way.

Now think of three things you cherish in your life, right now.

What if your deepest regrets actually helped you create what you now cherish? Let’s say you could wave a magic wand, re-write the past, and remove your regret. What if that also removed that you cherish? Would you really want to mess with your past, Marty McFly-style? Maybe the result wouldn’t be as dramatic as making you and your siblings disappear but you might be surprised by what you’d lose.

Maybe this isn’t logical. Because of the way life’s actions ripple and crash into each other, splintering possibilities beyond what we can consciously perceive, we can never know what was best for us. Then again, is it logical to steep yourself in regret? Sure, it’s good to learn from mistakes but when we’re feeling crushed by what could have been, are we in learning mode?

When you’re not chained by regret, it’s like finally being able to push your head above the water’s surface, breathe, and see. You’re more likely to make decisions you’ll be proud of. Regret begets more regret, but gratitude also begets more gratitude. Even about our regrets.

After dropping out of college, Nate Rifkin had dedicated himself to self-help and pursuing his entrepreneurial dreams. Yet he failed to achieve any of his goals. Worse, he spiraled into debt, drank every morning, felt lonely, lost, and hated himself.

A few years later – after a brutal bankruptcy and a stint spinning signs on a street corner – Nate Rifkin had quadrupled his income, married the woman of his dreams, and found happiness and contentment. He's published a book on how he did it, titled The Standing Meditation. It's now available here.