A number of you have flattered my ego by asking for regular updates on my personal journey. Going forward, I’ll dedicate a post or two each month to tell you where I am, what questions I’m toiling with and where I am in my journey.

A wild Tobias in natural habitat. 📸: Megan F.

San Francisco / who turned on the lights?
I’m nearly a month into my career break. And my oh my, it’s been a mental hurricane. I stepped onto this canoe knowing that the winds and waves ahead would be unpredictable. And the sea has delivered as much. So much is uncertain - where I’ll be, where I’ll go, what I’ll do, who I’ll meet, and how I’ll introduce myself.

Once the adrenaline and confetti washed away, I was forced to contend with myself. So much of our days are spent in relation to work - preparing for it, recovering from it, crushing it, pretending to do it, evangelising it, drinking to escape it. So when you’re not working, you are exposed to your raw subconscious in a special way: Who are you without work? What do you feel compelled to do? What do you miss? What don’t you miss? How will you deal with the uncomfortable realisations that you will find on your journey?

I’m learning to detach from the need to be immediately productive. The achiever voice in my head keeps mumbling: “okay, so what’s the next thing?”. Generative AI is incredibly hot now, maybe I could build something with GPT-3? Maybe I should partner with my other wandering friend to start a company. Maybe I should reply one of the recruiters in my DMs. Hmm maybe not. We have a tendency to fill time when we’re trying to escape uncomfortable conversations with others and ourselves. We hop from job to job, partner to partner, place to place, without giving the space to authentically audit our souls. I get it, it’s often unbearable to be so vulnerable even with yourself. You have to skip the performative nonsense. You have to unmask and reacquaint yourself with your true, unadulterated self. Not the you that you want to be, but the true you. The person underneath all that bullshit protective, plastic casing.

People would rather be electrocuted than spend fifteen minutes with their thoughts. What does this say about ourselves? What are we hiding from? We have these big beautiful brains that can create fantasies, recall memories and ponder endlessly yet we seem to run away from introspection. We employ justification gymnastics to convince ourselves that we want certain things. But we don’t know for sure. How can we know unless we create the environment to probe and find out?

I remember when I realised that I didn’t want a promotion at work. It was deeply unsettling. I looked around my team and I did not envy anyone - not my manager nor tech lead or anyone around frankly. I existed in this local maximum where I was “winning” by external factors but dying internally. A high-status, well-paying job at a brand name company is rightfully the envy of many, but it was a source of pain for me. The money from a promotion would’ve been nice for my ego. It would have felt good and novel for a little while until it became my new normal and then I’d just want more. Ultimately, it would have distracted me from asking the deeper, more existential questions. I was already questioning the familiar stories of work in tech - of building these startups, of selling more ads, of hustle culture, of trying to gatecrash an IPO, of resting and vesting, of getting counter offers to get more money, of spending your finite days in pursuit of “an exit”.

In the religion of work, admitting a lack of corporate ambition is tantamount to heresy. I may as well have signed my name off to be chucked into the river as deadweight: a solemn sacrifice by the success cult in the temple of tech. I didn’t exactly broadcast this realisation. So you do what others before you do - you play the game, you try to thread the needle and manage appearances. Some of you reading this right now are doing this very thing. I know the pain you feel. The invisible weight you carry that others can’t understand. Once your soul has begun to ask existential questions, it’s almost impossible to focus on the mundane minutiae of daily work and life. It’s a blessing and a curse. I hope you find the courage and wherewithal to break out of this prison.

Our culture isn’t built for introspection. At work, you’re supposed to stay focused enough to achieve outcomes for the business. When you’re not at work, you’re likely taking care of responsibilities or entertaining yourself. Let’s lie to ourselves and say you spend only one hour a day on your phone - whatever your favourite drug might be - TikTok, YouTube, Twitter, Netflix etc. However long you spend there is likely to increase over time as these companies hire more soldiers to invade your leisure time. As we continue to run away from boredom, we run away from ourselves. How can you wander the halls of your own mind if you’re constantly entertained?

With all this “free” time, I’ve been able to reminisce on the great times I had at work. When my manager surprised me with champagne to tell me I’d been promoted. All the happy tears I laugh-cried during the happy hours. All the genuine friendships I made that will carry over into my next lives. When I co-presented a gameshow and gave out prizes like Oprah. When I taught college kids how to negotiate for more money. When I started partying at 5:30am on IPO day. All the times I did engineering stuff that I initially had no idea how to do. These memories will live on with me.

I also reflected on the unpleasant times. At its worst, my weeks were full of dark, meaningless days that never seemed to end. I vividly remember feeling nothing - the apathy and numbness were loud and clear. My palette was dull and grey, devoid of colour, pattern, taste, sound or anything substantial. My mind, slowly dulled and lulled into a rigid, cement brick. I couldn’t write. My body was present, but my mind was far distant. Focus was remote. I stayed indoors too often. All of this negatively affected other parts of my life - my wellbeing, my relationship (at the time) and my perspective. Depression is a word that gets bandied around like candy but it definitely described my ordeal. I found temporary escapes that never lasted. Thankfully, I’m better now but these memories also persist.

So what do I do these days?

I wake up lighter and limber in a way no vacation could permit. It’s like someone turned on the lights and there’s all this new possibility. I go on walks through different neighbourhoods. I adopted a local cafe. I took a short course on learning how to build a portfolio of small bets that suit and fund your lifestyle. I find my thumbs checking for Slack messages. I’ve thrown a few mini dinner parties. I’m trying to replace my Twitter addiction with Duolingo. I’m constantly drafting essays. Colour is finally returning to my vision.

There will be a time to return to work. It is not here yet, and I’m thankful for that. Most people never get a chance to take a career break. Mortgages, kids and partners don’t take too kindly to “pauses” and as I have none of those, I felt I needed to do this. I remember a coworker’s face when I told them I was doing this sabbatical. He begged me to do it. He would love to do something similar but is tied up for the next twelve years wishes until his kid finishes college. I feel immensely lucky to have this opportunity.

So here I am dipping my toes into the pool, hoping the waters not too cold and the pool’s not too deep so I can swim off to a better place.

Oh, I booked a few flights. I’ll be in Barcelona in late January. Then Madrid and Portugal. Please send me your recommendations if you have any!

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Wandering the Grey

🌴🏖 sober sabbatical: scene one, take one