Seize the Pause: Turn Your Layoff to a Sabbatical

Part-Time Internet Celebrity, Michelle and I are launching Turn Your Layoff to a Sabbatical next month — a live, cohort-based course to help people reframe that negative experience into a wonderful one. 

This course is a natural extension of what Michelle and I have been doing for a while. Both of us worked in tech for 5+ years and left for sabbaticals. Since then, we've spoken and guided scores — more than 100 – across phone calls, panel discussions, Zoom calls with friendly strangers, newsletter essays, Twitter DMs, Tweets — to do the same.  

Both of us know the emotional gauntlet of a sabbatical. We've felt how lonely it gets when you're the only person in your friend group doing something so radical. We know how scary it is to climb a staircase blindfolded without guardrails. You feel dizzy and don't know if you're going up or down. We know how exhausting it is to explain to everyone that you're not ‘chilling’.

We want to build on the conversations we’ve been having with people in this place. There are lots of myths about sabbaticals. ‘No one will hire you again’ is a lie. Many people choose to travel and write on sabbatical, but you don't have to. The goal is to rediscover yourself — to melt and mold your brain back to the plastic, curious form you used to have until the stifling weight of an unfulfilling, 40hr workweek turned it into a rigid rock. 

In this course, we're going to talk about money — the literal cash aspect but also the hidden scripts we hold dear about finances: What do you think you can afford? What's the purpose of money? We'll talk about running creative experiments and navigating the turbulence when things go awry (Spoiler — it's not all cake and roses!) And we'll share our approaches to finding community so you're not all alone on this journey.

Take it from this Josh, someone who took the leap:

Quitting my job sounded TERRIFYING. When I was working, I knew I wanted to be doing something different. But getting serious surfaced all sorts of doubts. Will I have a stain on my resume? Does the grass only seem greener on the other side? Will I be financially safe? It turns out: yes, the grass is greener! You’ll walk away from this course with a plan, confidence, self-awareness, and a few new weird friends.

You can enroll here. Or send me a message with any questions.

OK, now the promo is over, here’s today’s story!

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Layoff to Liftoff

It sucks to lose a job. You feel shocked, ashamed, and maybe even angry. In the zero-interest days, your company called you a part of the family, and now, there's a gross email in sitting in your inbox with some generic, techno-babble blaming "broader cuts due to macroeconomic shifts." It feels sickening. 

The slap to your ego and sudden loss of control throw you into survival mode. You don't want to feel like you're on a rudder-less ship. So you rush into action spraying your resume around in hopes you find something. 

For many people, this is the reasonable approach. You know your circumstances and obligations better than me — how could I tell you otherwise? Your money pipe might require instant patching. Jobs provide purpose, identity, and community too, maybe you need those supply lines restored ASAP. 

I have a message for the people in a different place. 

Sometimes, an unwanted jolt to the system plants the seeds for a necessary transformation. In 2022, I was pretty unhappy in life — genuinely depressed, discontent in various parts of my life, grappling with golden handcuffs, and dealing with several griefs. But I was doing that human thing of huffing and puffing, and falling and failing, and hauling myself to the next day. Waking up, brushing tired teeth, and dragging one heavy, weary, unwilling foot after the other.

I lost a friend suddenly in 2020, someone I'd known for twenty-something years, who I sort of assumed would make it till old age with me. One day she was here with us, the next she wasn't. That grief lay dormant in the back of my mind, silent and well-mannered, till it sprang unannounced and tag-teamed with the latent slew of sorrows within and set me on a chain of existential questioning. 

I realized I was assuming many things about life. I had tacitly agreed to The Deferred Lifeplan — “Do non-fun things for $$$, save and invest, then spend the money on your passions later.” As if I knew for certain I'd be here that long. As if I could sip from the money-teat for two decades and one day, remove my lips and declare myself sober: “Enough goodies for me. I want no more of this sweet drug.”

I was massively undersizing the value of time in its present sense, how I felt each day, and whether I was interested in the problems I was solving. And I was over-inflating the value of money.

Around that time, I read a summary of a piece by a palliative nurse, titled the “The Top Five Regrets of The Dying”. You’ve probably seen it, it floats around social media every now and then. Number one regret on that list: “I wish I'd had the courage to live a life true to myself, not the life others expected of me.”

Death has a way of reminding us what we truly care about. There are no status games in the graveyard. No RSUs, No IPOs, No ROI, No Term Sheets, No Exits — unless you're talking about the final one. But there are rows and rows of deferred dreams, sigh.  

My friend was an incredibly talented artist and eventually, I found solace in the idea: “At least she got to sparkle while she was here.” Thank God she got a chance to make art that hugged other souls. This brought me to the mirror — what was I doing with my time on loan here?

Not the kind of stuff I wanted to do. 

In my first conversation with a coach in sabbatical life, she mentioned how I always used pragmatic language to describe my career and school choices, and very few words with feelings. It was always “Well, I was good at sciences, so I did engineering.” or “I loved economics but I had to drop it for physics.” As a writer who is perceptive about emotions, this is a bit bizarre. The Figma File for my life had all these pixels defined about what I had to do….but it overlooked the day-to-day experience — that's how I ended up working as lab researcher in 2016 even though I hated pipetting!

In the fourteen months since I left tech, I've had dozens and dozens of conversations with current tech employees, friends, and strangers who wish to do something similar. “You're so brave, man. I wish I could do something like that.” 

And I'm like “You know, you could do this too, right?” The response usually touches on fears around money or time. I get it. I was there too. It's scary to veer left when there's a steaming hot pile of gold in front of you. Or a road that feels secure and stable. But there's a bit of a misconception here. 

Sabbaticals come in different sizes. You don't need to quit your job and travel to Bali like I did. It's much more a mindset. You could take one month, or a single afternoon even — wander without explicit direction, pickup a lost hobby your inner child loved, see if you can differentiate between your wants and what's expected of you (even by yourself). 

Paul Millerd ‘s framing helped me here — if you're going to work a typical career, about 500 months, can you spend 3 months — less than one percent on true self-discovery?

What you want to do is get really clear about the games you're playing and whether you want to win them. Consider the career path you're on and extrapolate that graph. Be generous in your imagination. Be painfully honest and think about the total package if you win that game. By package, I mean consider all the important intangibles from your workday. People always count the money and benefits but forget the daily stuff.

Do you have autonomy in your work? What about time freedom? Do you get to be creative? Is the problem space meaningful to you? Are you making progress on it? Do you get to use your gifts? Are you intrinsically motivated to do this work? If you're not, have you counted the cost? The cost exists whether you count them or not. For me, it was the dimming of my light and the narrowing of my vision — I made too much money to consider others that could've been more fulfilling.

A lot of this will feel foreign because we are conditioned to consider work something we 'endure'. Like a crazed obstacle course with lava dripping from the ceiling and grenades hiding in the ground. Look at the vocabulary we use to describe work — The Sunday Scaries, Monday Blues, Thank God It's Friday, Hump Day, The Rat Race. Doesn't that tell you something?

You might do these reflection exercises and recommit to the game you're playing. The goal of a sabbatical is not to make you un-employable. The ‘win’ is to play a game with eyes wide open and value alignment. That game looks different for everyone because each of us has a unique regret that will chew and gnaw at us if we never try — maybe it's writing a book, or living abroad, or completely ripping up the playbook and leaving tech to pursue visual art and bodywork like my friend did Caryn did.

Failure, in this world looks like blindly sitting on a train that takes you to a place you don't want to go to. And then wondering how you got there….as you stare back at the destination written in black paint on a white background. It was always there.

So if you've been laid off and you can afford it, the decision to leave has been made for you, and while that sting hurts today, you have been given a rare gift. I know that sounds crazy, but the hardest bit is often the first step. The chance to rediscover and reinvent yourself is massive. Plus, the silent truth is that stability is a myth and many jobs aren't as future-proof as we'd like to think.

Right now, we're in the first innings of a watershed moment. Artificial Intelligence (AI) is blossoming from promise to real-life superpower. Twelve days ago, OpenAI announced this crazy thing: 

a tool that creates ultra-realistic 60-second videos from text. Usually product demos are cute but nobody reallllllly takes them seriously. Not here though — Tyler Perry, the famous filmmaker took one look at SORA, saw its cinematic potential, and pumped the brakes on a proposed $800 million expansion of his film studio. 

SORA is the latest in the long list of AI tools released in the last six months. People are using AI tools to create high fidelity movies, completely new songs, complex videos with tricky camera motion, videos with characters where the audio is lip-synced, incredible images, art, basic websites, apps – you get the idea. Most of these tools only require text as input. 

Intelligence is becoming rentable. We’re moving to a world where if you can imagine it and describe it in words, you’ll be able to make it. Without needing to spend ages to master tricky tools like PhotoShop, Final Cut Pro, Logic Pro, GarageBand — non-technical people will be able to make impressive first drafts and prototypes.

I’ve been using ChatGPT nearly everyday as a muse and assistant — to prepare for a rent negotiation (I got the money!), review personal journal entries to look for hidden patterns, get ready for client meetings, review code snippets, pretend to be an editor for my contract work, learn random technical things, and debate philosophical ideas

So if you've been laid off and have the time, you could start playing with AI today. If you're a designer, you could explore the latest AI design tools like MidJourney, Runway, Pika. Copywriters could work with Copy.Ai or Jasper. Or completely ignore AI — your sabbatical is yours to define! This is a golden chance to rest, unplug, and explore new skills. 

On the other side, there will be lots of us — Michelle Elisabeth Varghese , Paul Millerd , Cécile Marion , Cissy Hu , Matt Yao , Vinamrata Singal , Simone Stolzoff , Caryn — cheering you on, showing you can live a life more aligned with your values.

If you're curious about the course, check it out here , message me, or comment below.