After three long years of service, my iPhone has finally fizzled out.

It’s been on its last leg for a while, crashing dozens of times a day without warning and leaving me in all sorts of pickles. Despite its unreliability, I coddled it, refusing to upgrade until timing deemed it absolutely necessary.

I’ve swung back and forth on the technology pendulum for as long as I can remember. Generally speaking, my ebbs and flows with connectivity have mirrored the ups and downs of my career.

When my days have consisted of juggling projects and back-to-back meetings, I’ve fully depended on iCal appointments and Siri reminders to keep me on track.

During times I’ve aimlessly floated from place to place, only vaguely aware of the season and usually unsure of the day, I’ve gotten by with flip phones and sticky notes–usually without complaint.

At 23, I was a front runner of the no-contract movement before it was a movement, and instead a necessity.

After Verizon sent me to collections over months of unpaid phone bills, I used a prepaid Walmart debit card to buy a prepaid T-Mobile phone kit and got my first no-contract plan. I was off the grid and off the hook!

(Naturally, this was back before the Credit Karma app told me actually how ON the hook I was… but I digress.)

I liked the phone-in-a-box burner life, but thanks to male roommates who demanded cable to watch sports, I soon discovered a life I liked even more: the landline. It came as a Comcast bundle, and while the roomies scoffed at the cordless phone we pulled from the box on installation day, I was delighted by it. In fact, I liked it so much that I soon stopped re-upping my mobile minutes and relied entirely on the landline to let me call out to the world.

(See how the pendulum swings?)

I was in this dial-up state of being the night I met my best friend in Seattle. “I want to hang out with you,” she told me, “but I have no idea how to get in touch with you. How can I even reach you?”

“Oh! Just call my landline,” I said. This was 2012.

The next five years brought a number of changes: namely, stability in my employment and a crystal-clear career path.

As I blossomed from a young, misguided tumbleweed into something of a career woman, my cell phone habits also changed.

I upgraded my devices a handful of times before landing on the iPhone, which felt like the holy grail of professional status. It was a symbol that I’d made it–that my T-9 burner and cordless days were truly behind me, along with the “wherever the wind will blow, I’ll go” antics. I paid extra for insurance and encased it with an Otterbox, vowing to treat it right for the rest of our time together.

Almost overnight, I was constantly connected; able to reply to emails or respond to meeting invites at any hour with the quick tippity-tap of my thumbs. I downloaded apps like Mint to track my spending, Fitbit to track my sleep, and Starbucks to put in mobile orders which I’d pick up in the lobby of my downtown high-rise office. I set appointments. I set reminders. I set alarms! I was a woman connected.

A woman transformed.

But alas, the pendulum swings.

Flash forward to now. Mark had his job offer pulled. I gave notice at my job (but agreed to work remotely). We moved out of our rent-controlled apartment—two wandering souls and a pup, all packed up and no where to be.

We’ve been on the road for going on 10 days, staying everywhere from charming coastal cottages to seedy, meth-riddled motels. My most muttered phrases tend to be related to the quality of the mattress, the pressure of the shower, or the metallic quality of the water in whatever place we’re laying our head down each night.

This transient state brings back vivid memories of yesteryear, when I had no direction and craved no connection.

The irony of my phone deciding to break today, the literal day before I’m scheduled to begin my fully remote working life, is not lost on me. It’s the pendulum drawing me in, telling me to hop on board and say sayanara to the grind; to the man; to the golden handcuffs.

“Can’t be truly happy if you’re still connected!” it taunts. “Why not call it quits all together?!”

Career vs. happiness has always felt like a black-or-white decision that I could never quite settle on, so I’ve spent the greater part of a decade bouncing between both.

Earning an income while maintaining my freedom had been a pipe dream that I was convinced could never be realized.

It’s been all job/no job; phone/no phone up until now.

But, for the first time ever, I’m realizing that just because the pendulum is swinging by doesn’t mean I have to ride it all the way to the other side. I can hang out right here in the middle.

What I mean to say is that just because I’m living out of a suitcase doesn’t mean I can’t also crank out some work to earn a paycheck. Just because I’m still working doesn’t mean I can’t take a beat, go outside, and soak up some new surroundings. And just because my phone happened to break at a very poetic time doesn’t mean I get to interpret it as a sign to ditch my responsibilities, live in a camper off the 101 and learn to surf. (But my GOD! Doesn’t that sound nice?)

It’s all about balance, man. At least that’s what the bumper sticker on the back of an Airstream in Big Sur said.

So yeah, I’m drifting. Again.

And anyway you slice it, this era definitely bears a resemblance to the cordless phone days. But I like to think of this round as drifting with a purpose–Tumbleweeding 2.0–with a salary, a story, and beginning tomorrow…a new phone.