Taking Time Off to Take Time (Head) On

Tips for how to take time off without becoming aimless or sacrificing your mental health

Hey friend,

As some of you know, I quit my job designing Vouch at the very end of last year. Building that startup from its first days was an incredible four-year learning experience, and leaving felt like a graduation and a breakup all rolled into one. Many teammates asked, “What will you do next?” and I saw that to some degree, my answer stumped them.

I’d say something like, “Over the last 4 years, any time I had a distracting idea or project I’d like to try, I wrote it down in a note in my phone called “The Whims List.” It helped me stay focused on my time at Vouch and the many opportunities and responsibilities that group of people afforded me, but these days I can’t keep the whims at bay. They’re like a cloud of gnats around my face, and they need addressing.”

I’d see folks light up when I provided examples of some of my whims, but many would then conclude our conversation with “Well, I hope you enjoy your time off!”

And to be honest, it didn’t sit right with me.

Time off?

I do not doubt that they were well intentioned in their wishes, but I like to think of myself as productive person, and the implication that I needed “time off” ran against my grain. For one, Vouch did not work me to exhaustion. And none of my whims were about sneaking off to Tulum to rest on a beach. But also - a full-time job provides a pattern to life and a daily script that puts a person on autopilot.

By quitting my job, I felt much more like I was “taking time on,” not off.

It feels rotten to even imply that “time off” isn’t always a relaxing stretch of agency and bliss. But in my experience, it’s not so easy. Staring across the many hours of a week without 40 or more dedicated to one, structured pursuit can be daunting. It takes discipline to wrestle with the hourly ”now what?” and keep coping mechanisms at bay.

So instead of sharing an update on what I’ve done this year, I thought it would be more useful to share how I’m doing it - how I’m “taking time on” and avoiding the many negative feelings it can create while aiming toward the positive outcomes I seek.

Five Tips for Taking Time On

1. Start a “whims list” in a notes app on your phone.

These can be business ideas, people to reconnect with, visions of yourself, vague curiosities, and more. It’s a private place to start many sentences, “You know, I’d like to X someday” without rational thought dragging your dreams to the ground. I chose the word “whim” intentionally, because I do not believe these should be thought of as items to complete or achieve. Whims are not goals, and it’s certainly not a “bucket list.”  It’s just place to acknowledge, collect, and rest your more wishful thoughts.

I suggest creating a whims list in the notes app of your phone even if you have no plans or ability to take time between jobs. My list became a regular reminder of how I’d really like to spend my time and filled me with a stronger sense of self. When a weekend started to tip toward the “same old, same old,” I’d pull a whim to give it a jolt of creative momentum and fun. My friends would get a text like “Welp. I’m sanding little pieces of driftwood into lumpy birds over here for God knows what reason. Minding my whims!” Or “Finally making those tiny mouse mailboxes.” “Finished the secret society branding for the secret society I don’t have. 🤷🏻‍♀️”

Trusting those whims, even when they don’t make sense, is the same as trusting myself. Not to mention it feels incredible to do something with no why. Give it a try!

2. Begin your mornings by “idea gardening”

A friend of a friend at Coda suggested they call brainstorming “idea gardening” instead, because ideas take time to nurture into something interesting or find the right season to grow.

At the beginning of January, I pulled my Whims List note into Trello, a simple task and productivity app, and labeled each whim with it’s recurring themes. With the Trello app on my iPhone, I now start each morning by scrolling through my whims instead of a jumbled newsfeed of articles and junk. Something about that morning brain-state makes it effortless to add small notes and make new connections. It also becomes surprisingly easy to sense what my gut wants to do that day.

3. Think with your brain, feed your gut.
Think with your gut, feed your brain.

As a designer at a startup, my days were filled with making decisions, explaining those decisions, and executing those decisions while shoving the occasional snack in my mouth (Zoom camera off, of course). While taking time on, I flipped that script; let your gut feelings do the guiding and deciding for a time, and feed your brain books, art, new environments and activities, healthier food - whatever gives your mind something to chew on while your stomach takes over its executive function.

4. On days that feel directionless, write a “to-did list.”

Letting your gut make decisions can sometimes yield days that feel wandering and aimless. On those days, I start a notecard where I write not what I plan to do, but what I did. It’s a weird practice, but it makes me feel calmer to read all of the small things I’ve done when all that doing didn’t add up to any one, substantial thing.

5. Keep a list of in-progress projects.

Notice I don’t say “enforce a maximum number” or feel shame for leaving certain work incomplete. I am big damn fan of letting work rest until your interest returns. But reading your list of in-progress projects will naturally draw your attention to items you want to complete, increase continuity, and give you space to prune items back into the whims list for later.

Looking forward

With these practices, I find myself looking back on the “to-did’ list from 2023 proud of my progress and work. Most days began with idea gardening until I have a clear sense of what I feel like doing, and then have me looking up around 2:00pm wondering where the last 5 hours have gone. (Like…with this post for example. 🤯)

For those also staring into an endless stretch of hours, let me know if you have other tactics or tips for approaching the time. Also - I’m a designer, not an experienced writer. If you made it this far, thank you. And if you have feedback on my writing, please don’t hesitate to share it my way!