Not Part of the Plan: An Organizer’s Journey to Being Flexible - Craft Your Content

Not Part of the Plan: An Organizer’s Journey to Being Flexible

Since the day my first grade teacher handed me an assignment notebook (analog tablet, for all you teens reading), I’ve been hooked on planning my life.

Carefully penciling in daily activities, to-do lists, and passing thoughts … once I found time management, I never let go. Just ask the teetering pile of journals in my childhood bedroom.

While my nervous, scribbling little self may have been somewhat of a childhood oddity, it turns out my planning habits prepared me for 21st century adult life here in the United States.

You know the one — where we all hack our days, our time, and our sleep, in efforts to make every minute count. Squeeze in, optimize, achieve, repeat.

This mentality seeps into both our daily and professional lives. See: vision boards, multitasking, and hiring virtual assistants to do all the stuff we don’t have the time to do, because we’re so busy trying to do everything else we’re supposed to do.

Never sleeping? A badge of honor.

Hustling? A rally cry.

Having a coffee addiction? Don’t we all?

These go double if you’re an entrepreneur or other creative self-starter.

Technology feeds our time optimization. With planners and organizers and list pads, time tracking add-ons, and tomato-shaped timers, we’ve fast become Pavlovian responders to beeps and pings.

Anyone who doesn’t fall in line is lazy.

For a long time, I never really questioned this. After all, I was good at planning; it helped me feel accomplished, it made me feel in control, and hell — I even liked it. From elementary bell schedules to college class selection to professional Google Calendar invites, I divvied up my days in nice, neat (color-coded, when possible) squares.

Check. Check. Done. Phew. Gotta run. What could ever disrupt my well-oiled system?

Bet you can guess what’s coming.

In 2015, I decided to move south. Way south. To Chile — a country where it appeared, unlike the show-up-10-minutes-early culture into which I was born, people did not worship the almighty clock.

What followed was possibly the most frustrating and best thing that could have happened to me.

It’s Not You, It’s Me


Nothing quite makes you reflect on your upbringing more than a long-term international move will. Every day, new situations confound/surprise/delight/disgust you.

You kiss every new person you meet.

You pick out milk and eggs on unrefrigerated shelves at the store.

You find mouthwateringly fresh-baked bread on every street corner.

You witness people having sex in the park — regularly.

You can’t find bagels anywhere (can you tell my life revolves around bread?).

To name a few. In a word, things are different.

I met any of said changes with a shrug and a “give me all the loaves of marraqueta you have.” No biggie.

One thing proved a challenge, though.

Time. Plans. Order. Gulp.

It took a blunder or 178 for me to understand how much I’d need to bend.

At first, I frequently showed up to classes at least 10 to 15 minutes early. Based on the standards I knew, I thought I was getting there on time, so as to prep and start teaching the moment the clock told me I should. My students’ clocks said otherwise. Was my watch broken?

My friends or their family members would gape at me when I cleared the dishes from the table immediately after eating, or when I asked what time I should be ready to go somewhere. My “See you tomorrow,” was met with, “If God permits us.” Well, that’s spooky.

After a few too many instances of showing up alarmingly early to social gatherings, I started asking Chilean friends, when they invited me to a party that “starts at 9,” when do I actually arrive? I honestly still don’t know.

At some point, I finally realized: the efficiency and timeliness I considered respectful came across as hasty, boorish, or even rude. My “get down to business” attitude seemed cold, unfriendly, and rushed.

World, meet upside down.

My North American obsession with promptness wouldn’t work out in Chile. Arranged times seemed to have the same authority as speed limit signs. That is, not much.

The planner in me couldn’t survive like this. She had to adapt.

Adjusting to Chilean time might not seem like that big of a deal to the average (read: more flexible) person. But do recall — I am Gina, lover of all things organized and neat.

Reluctantly, I put down my planner.

Let’s Take it Slow

Every day presented opportunities for me to test my own waters — to dip my toe outside the plan-obsessed arsenal of commands that each morning’s alarm clock would awaken.

The changes proved small, yet significant. To avoid feeling constantly frustrated, I leaned in to this different way of life.

No more lining up my week with back-to-back Google Calendar events. I added margins.

No more fast-moving lines. I took a number and brought a book.

No more Irish goodbyes at parties. I kissed everyone’s cheeks on the way out (and inevitably stayed at least another hour).

No more expecting people to be “on time” according to my standards. I started defining “gringo time” or “Chilean time” when making plans.

Of course, my plan-oriented sensibilities didn’t simply vanish overnight. Often I felt confused, frustrated, miffed, or any other cocktail of emotions that accompanied the adjustments.

I learned how to be flexible, one painstakingly slow step at a time.

But after months passed, something miraculous started to happen; I started to like this newfound mentality around time.

Once it sunk in that no one was going to shame me for showing up “late,” or if lunch ran over by 15 minutes, or if overbooking dominoed the rest of my day into pushed back engagements, everything was still … okay.

No one thought I was lazy or a hot mess or disorganized. The world kept spinning.

Things not going to plan? Well, that’s to be expected. It’s life, after all. Que será, será.

How had I not landed on that epiphany before?

What initially felt like an exercise in how many deep breaths I could take before I exploded, turned into an understanding that my concept of time was just that — mine. And that maybe there was something to this seemingly nonsensical structure of organically evolving days.

My shift even went from functional to emotional.

I noticed changes within myself: I felt less stressed, less rushed, less concerned about what time it was or if I was responding promptly enough to text messages.

Things started to slow down all around, and damn … it felt good.

People Don’t Change … or Do They?


As I puttered along in Chile, I noticed how certain cultural idiosyncrasies worked their way into my life, much like the places I had lived before it.

Since graduating from college, I’ve called South Florida, Boston, and Santiago, Chile home — with visits to my hometown in rural Ohio in between. People live differently, and their attitudes, values, and ideas vary.

Floridians donning jackets in 60-degree weather. Bostonians saying “Do I know you?” when I asked them for the time. Ohioans paying for the coffee of the person behind them in line (I’m from here, I’m biased to show how awesome we are). Santiaguinos incessantly honking while driving.

What flies one place is rude elsewhere. People in one place might treat divergent ideas with skepticism while others embrace them with curiosity. In some places, a plan is a necessary answer, to be pulled from your back pocket at a moment’s notice, and in others, a hilarious practice in futility.

As a product of dedicated, rule-following, Midwest, middle class folks, I learned early on about the importance of timeliness. Being on time indicated that you had a host of other good qualities.

It’s a fine lesson to learn, but not the only one. And context is key.

Moving abroad made me reexamine those lessons. The stark contrast of my closely held values against those of another culture called my planning and organizing habits into question.

You might wonder –– has this experience completely upended my personality? Have I, as New Girl’s lovable, yet tightly wound character Schmidt, shifted from a rigid, anxiety-driven mom-figure to a bongo drum-playing, free spirit drifter?

So far, can’t say that I have.

But I have learned to unlearn some things — to challenge the organizer within and see what happens. Perhaps even find a happier medium.

But I Could Never Do That

“Great — so the only way I can stop stressing out is by moving to South America.”

Hold on there, drama queen. You may not need something so drastic.

My changes in perspective about time, yes, can be chalked up to my moving abroad. But what it really boils down to?

Comfort zones restrain growth.

Luckily, pushing your limits doesn’t require a passport, an adrenaline addiction, or a death wish.

I’ve found it most when I allow myself to look stupid or foolish for a second, or risk failing hard and publicly. For me, moving to an entirely new culture where I often felt vulnerable, confused, or frustrated (amongst many other more positive emotions, of course) forced my organizing self to take a backseat for a second and allow my spontaneous side (yes, she exists!) to drive.

In doing so, I discovered that most of the time nothing bad happens when things don’t go as planned. Actually, it can be a lot more fun.

Going against your natural inclinations, be they to (never) plan, to (never) play it safe, to (never) go with the flow? That experience shows you how different life or work could look.

“That’s great for them, but I could never be like that.”

Y tho?

You actually could push your limits.

Make a point to note when you make excuses for not doing things that you may secretly want to do, whether it’s ziplining, knitting, learning another language, flipping a house, starting your own business, publishing a book, or the like.

Those excuses are your comfort zone talking. You can either listen to it, or choose to buck it.

A little secret — anyone who does those things you wanna do doesn’t have some magical X factor making them better at life, more daring, more interesting, or more [whatever] than you. Unless they are a trust fund baby or other such lucky duck, it’s not all about money, either.

At some point, they chose to get uncomfortable, and take a risk outside of their comfort zone. Why can’t you?

If you’ve wondered about “how other people do it” — ask yourself: what is one step you could take today to come closer to doing what they do? Just focus on the first step — nothing else.

Maybe you take a deep breath and — attend a meetup group, subscribe to a website, borrow a book from the library, email an expert, or sign up for a class.

Who knows, one thing might lead to another.

I’m not going to tell you how to live your life. But I did learn that shaking up my perspective produced unexpected and wonderful results in mine.

I didn’t discover a great secret to balanced living, or the ultimate life hack.

I just chose discomfort, change, and yes … uncertainty.

While You Were Planning


As a young professional with big, entrepreneurial dreams, I am not immune to the allure of the #hustle culture, worship of the almighty god Busy, or desires of a fully-lived life.

You can bet your ass I still make lots of plans. As I write, I can see at least two to-do lists, a calendar, and a notebook with Planea Nuevas Aventuras (Plan New Adventures) written on the front.

Planning still helps me take some of the cacophony inside my brain and turn it into manageable chunks. It’s not all bad or futile.

In fact, I think the best planning should be the kind that makes us less stressed, not more, that makes us appreciate each block of time in our lives, instead of hurrying through it to get to the next one.

Some days I clutch my lists and plans to my chest, and other days I’d like to set fire to them all.

So no, I haven’t let my planning self go. But she’s getting better at understanding that things rarely turn out the way they’re written down.

I’m gonna have it both ways, thank you very much.

Most of the time, despite my organizational intentions, my life feels like a beautiful, crazy, messy disaster.

Better write it down.

About the Author Gina Edwards

Gina Edwards is an unapologetically snarky blogger with a love of parentheses (but who isn't?) and beer with funny names. She's currently be-bopping around Santiago, Chile on her bike, teaching her native language to fancy people. Her skills include making hilarious puns, no-bake cookies, and mountains out of molehills.

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