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Leaving the company I co-founded

NB: Here’s a very brief bit of background: Romy, David and I started Monaru in May of 2019. We were part of the Y Combinator summer 2019 batch (you can read about it here). We pivoted a number of times before raising a seed round in March of 2020 (you can read about that here). This post is about my experience leaving the company in the summer of 2021.

Also important to note: this is all based on my own memory - it's written from my subjective viewpoint.

We make one of our countless private jokes, and I laugh so hard that my stomach hurts. I’m sitting around a table with David and Romy. It’s like old times.

“So it will all be be back to normal?”

“Yeah of course - it’s all good.”

“And like, legally?”

“Ah, I’m sure the lawyers can figure it out”

19th of October 2021 - 96 days since my last day

I’m woken up by a particularly sharp jolt. The snow is pounding the windows of my night train. I'm traveling from Lapland in northern Finland to Helsinki. For a split second, a wash of relief hits me. It’s all going to be back to normal. It’ll be like nothing ever happened. The uncertainty of the last 3 months will vanish and I can slip back into my old life.

When did we say I start back again? I try to remember.

Wait, where did we have that conversation? I try to remember.

I look around the empty carriage and take in my surroundings. It’s an old, but comfortable train car - like the dozen or so others I’ve been in since the start of my Interrail trip a month ago. And then it hits me. My stomach drops. I can feel tears starting to form.

It was just a dream.

I put my head in my hands and I start to cry softly to myself. I don’t make much of a sound, and my quiet sobs are drowned out by my snoring neighbors and the rumble of the train engine.

What have I done.

The [Bridge's model] identifies the three stages an individual experiences during change:

Ending What Currently Is, The Neutral Zone and The New Beginning.

Ending What Currently Is

11th of June 2021 - 42 days until my last day

“I don’t want you to be better for me, I want you to be better for you…”

I look at Romy, utterly confused. What does that mean? We’re walking around the Iveagh gardens in Dublin, having another conversation about how I need to improve in my role. It's a standard Irish summer day - we were hiding from a rain shower a few minutes ago and now I'm worried I might be getting sunburnt.

I might not have Romy's mind-reading superpowers but even I can tell that she's incredibly frustrated. She's trying to stay calm and keep a kind tone to her voice but there's still an edge there.

"Like, sure, I can give you a list of things I think you should do, but unless it comes from you you're never going to actual do it in the long term. We've seen that already. And, like, it's not my job worrying about whether or not you're doing what you're supposed to. It's exhausting having to think about it"

It's hard to pinpoint exactly when it started. It's like asking when did the wooden beams in a house start to rot. The signs aren't clear at first. The change happens on the inside.

After a while, they become more obvious. Maybe someone starts to notice a smell in the air. Maybe a few small cracks appear in the roof. But they can be explained away. They can be covered with a fresh coat of paint.

When things get really bad, when the roof starts to sag and the walls warp, when the structure becomes unstable - it's often already too late.

What does burn-out actually mean? It covers any number of sins; for me - it felt like slowly sinking. Feeling a little bit less competent, a little bit more at sea, slightly more overwhelmed - each day.

Then a deep panic sets in, and all of the worst aspects of your personality are amplified. And this leads to shame, and the cycle continues - each time spinning faster like a negative flywheel.

The signs were subtle at first. I'd take a little bit too long to respond to an email. Or I might forget to respond at all. I'd never actually forget. The unanswered email would constantly be in my thoughts. I'd write 50 different responses in my head.

But how do you respond to an email from a VC firm that you've read more than a handful of books about? How do you seem eager, but aloof? How do you make sure that you don't commit some cardinal sin that writes you off as a possible investment?

And how do you assess a job candidate from just an email and a CV? Your inbox has 100 others just like it. You can't hire them all. You can barely read them all. People have spent hours on their application and you're going to just dismiss them out of hand.

When someone pointed out that I'd been sitting on an email for far too long, I'd nod and say "Oh yeah, thanks for reminding me" as if I'd somehow forgotten that one of my heroes had sent me a cold email.

I'm a big believer in pushing your limits, of pushing yourself out of your comfort zone. But those stints beyond the realm of your ability need to balanced by time spent doing things you're a master of. Otherwise, the constant feeling of uncertainty seeps into your bones and you internalize and essentialize your shortcomings.

You're not someone who is struggling to hire a candidate - you're someone who is bad at hiring. You're not someone who needs to improve your investor comms, You're someone who is bad at fundraising. And on, and on. Until everywhere you look, there are massive pillars of business building that you've convinced yourself you're just not fit to approach.

And sure - there is something to be said for focusing on what you're amazing at. But when you're starting out in a business - the list of things you need to do competently is still quite long.

I know now with the benefit of hindsight and space that this was not a very effective way to handle the new pressure I was under. I should have done any number of things to get myself in the right headspace.

My Dad is a psychotherapist (as a side job - his main work is in finance. He trained as a psychotherapist in his spare time. He's very cool). He has an image he uses to describe what happens when you get stressed - imagine a bucket that is half full. That's your normal stress level. It's manageable. You can deal with it without things spilling over.

When a novel stress is added - when something new is poured in - it takes up the free space. It might not make a spill at first, but the normal day-to-day things that would usually fit can make your bucket overflow.

When Covid hit, I think my bucket reached the brim overnight. I didn't notice because there was just too much to do - I had to become the family 'Covid expert' to keep the people I love safe. I had to keep the team moving forward. I had to hire amazing people to keep the team growing. I had to find Product Market Fit with our nascent idea. I had to keep positive, and to prepare for when Covid ended, which was going to be any month now. It felt like there was a hundred things I should be doing with every moment of my waking day.

At the same time, my usual outlets silently disappeared. In normal times, I'd to the gym nearly everyday. I would spend about an hour listening to music and thinking. I'd process the events of my day with happy, healthy endorphins flowing around my body. That time was now replaced with compulsively refreshing the Live Covid News feed on the Guardian website.

The slip ups at work went from small and sporadic to frequent and irritating. My inbox went from a few unanswered emails to 300+ and growing every day. I'd start a task, find it impossible to complete, and then just move on to the next thing - leaving a mess of half finished work in my wake.

All the while, the drumbeat of progress was pounding in my head. “You're supposed to be further along by now. Your friends from YC just raised an A. Your other friends just hit $1M in ARR." My internal monologue was getting more and more critical each day.

Along with all this was the feeling that I couldn't really be unhappy because so many others were suffering much worse than me. I had friends working as doctors and nurses and their stories were horrifying. I was living my dream - running my own well funded startup, working safe and sound out of my bedroom. I had nothing to be complaining about. So I didn't. I pushed it all down.

And in the cold and damp, hidden from sunlight, the rot got worse. The structure became unstable. The walls sagged. The roof began to collapse.

"Maybe you should travel a bit, change your environment you know? And take some time off?", Romy offers helpfully.

"Yeah that sounds like a good idea actually"

We finish our coffees and stroll back to our temporary office. Maybe that'll be the silver bullet. A bit of time off. I book my flights that evening.

1st of July 2021 - 22 days until my last day

The final afterglow of the sunset hangs across the horizon, a dark blue fading to purple. The rest of the sky is navy and black. Stars twinkle above us. I feel the coarse sand between my toes.

"Are you ready?"

"One more second"

My tech friend is scribbling furiously on his piece of paper. His cargo shorts are flapping in the warm breeze. The night-time sounds of the small village are starting to build. Latin music from a handful bars and taco stands. Sporadic shouts and laughter from locals and tourists. We're some distance away - alone on the beach.

"Ok, that's me done"

He holds up his work and it wriggles in the wind like it's trying to escape his grasp. My own letter is safe in my pocket. I finished it hours ago. It's been burning a hole in there ever since. I originally planned to do this on my own but he was so enthusiastic about joining in that I couldn't say no. His own startup is going through a transition as well.

We've been staying together here in Sayulita, Mexico, for the last week. Both of us want to visit the US but because of the travel ban, we have to be outside of the EU for at least 2 weeks beforehand. For my first week I worked remotely from Playa Del Carmen, but this week I'm taking some time off. A whole week. Uninterrupted.

It's probably the longest stretch I've taken off since we got on the plane to San Francisco in June of 2019. It's definitely the longest stretch I've gone not speaking to David and Romy since before YC. It feels strange - I'm so used to having them in my thoughts at all times.

It's also the first time in a long time that I'm just me. Not startup co-founder. Not tech person. Not CEO. Just me. And I feel different.

I reach into my pocket and unfold the crumpled sheet. It feels heavy in my hand.

"How are we gonna do this?", he asks eagerly. "Like should we burn it in the middle, or should we burn it from the side? Or maybe we should just burn it in lots of places at once. This is such a good idea man, such a good idea. I'm so glad you said it to me. I really like the symbolism of...."

He's talking a mile a minute. It's his default in conversation - almost like he can't speak fast enough for the stream of thoughts running through his head. I zone out a little though. I'm thinking about what I have written on the scrap in my hand.

I can't remember the exact detail of what was written on it now but it was some mixture of the idealized qualities I had pictured for myself and the startup. I had such a rose tinted view of what the startup was supposed to be - the vehicle to actualize all of my dreams. Me, David, and Romy were the perfect founding team. We were best friends, our skills complimented each other. David and Romy were the smartest people I knew.

And whenever I felt like the startup wasn't working, when we hit roadblocks, when we were "failing" - I felt like I was failing at life. I thought that in order to be successful, I had to be all in - that I had to completely fuse my own life with that of the company. This meant that the stakes were so much higher. When things weren't working - I would fixate on it, pick at it like a scab.

The point of this exercise was to loosen my grip on this idealized reality and accept things for how they were, warts and all.

I do remember the last line I had written down. It was probably the largest single idea I had to let go of. It was just 4 simple words.

Being the perfect CEO

That obsession with being perfect was really an obsession with comparison. I needed to be perfect, as defined by the caricature I had of Patrick Collison or Brian Chesky in my head. Whenever I inevitably missed this imaginary, unattainable bar, I would feel ashamed and try to hide it from myself and others. This meant it was impossible for me to receive feedback or even see the areas I needed to improve for what they were. Instead they remained frozen in place.

"I don't think it matters too much - the book just said that creating some sort of ritual around the transition is what is important"

I'm referring to the book that was the inspiration for this makeshift ceremony. Unsurprisingly called "Transitions" by William Bridges. It's what I've been reading on my week off. My Dad (the part time psychotherapist) recommended it to me when I spoke with him about what was going on. He looked at me knowingly, and with his usual slow and soft voice said "can I share a book with you?"

400 pages later and I'm standing here in the dark, about to set fire to a scrap of paper to symbolize the transition I'm going through. From naive, unrealistic startup founder to mature and balanced company builder. I hope. I'm slightly cynical about the whole thing but at this stage I'm desperate.

It takes a few seconds to light the paper, but soon the fire is curling and distorting the writing. Slowly at first, and then all at once, the words disappear. And then they're gone.

I feel lighter. The wind blowing in my face feels fresh. It feels like change.

Then an idea hits me. Something I never allowed myself to think before. The ultimate heresy.

It's time to move on.

Over the next couple of weeks, that idea grows roots. When I push it away, it reappears. Stronger each time. My inner monologue was pleading with me.

“You’re really not happy.”

“Something isn’t working, it hasn’t been working for a while”.

“Why are you forcing this - you’re making David and Romy incredibly stressed too.”

“Just let go.”

The one relenting voice pushed back with a defiance.

“I’m not a quitter...”

I went to a 4th of July party when I arrived in LA. It was with a group of start-up founders. There was one guy there who had left his own start-up a few months before. I asked him how he knew it was time to leave. He looked at me with a knowing stare. There was a quiet intensity behind his eyes.

“Listen dude, if you’re asking that question - you probably already know the answer....”

9th of July 2021 - 14 days until my last day

"Wow, ok...ok...yeah, thats...thats...."

David's struggling to find the next words. Our Zoom connection isn't great but I can see his face is gripped by emotion. He forces a smile.

"...that sounds like it was a really tough decision. When did you make the call?"

"Over the last couple of weeks"

We talk for about half an hour. David is genuinely curious about my thought process and we can speak candidly about the challenges of the last few months. It's cathartic, but also scary. I know there's no going back after this conversation.

It reminds me of a similar call that happened nearly 3 years before. That time it was David telling me that he was leaving our team at Intercom in Dublin to move to the London office. That lead to a couple months of us not working together every day - the only significant gap in the last 4ish years. Hour for hour, David was by far the person I'd spent the most time with since March of 2018. And that was about to end.

I still feel unsure but there's really no other option. I can't go on the way I am. It feels like less of a decision and more like an acknowledgment of the inevitable.

And now the wheels are set in motion.

Once I shared that I wanted to leave, Romy and David were extremely supportive. We quickly worked through the logistics and spoke with the other stakeholders in the business.

As the company itself was going through a transition, we decided it was best for me to move on as quickly as possible.

My last day was the 19th of July, 2021.

My overwhelming feeling for the first few weeks afterwards was relief. And then complete fatigue. I spent about a month doing nothing. I could hardly concentrate long enough to watch a tv show or read a book. I didn't realize how stressed I was until it was over.

After that initial wave, I was incredibly confused. So much of my self identity had been wrapped up with the company - I didn't have a clear sense of who I was without it.

I was also shell shocked by it all. What the fuck had just happened. I didn't really understand what had gone wrong. When the stress receded - a deep feeling of regret filled the space. Why didn't I just try a bit harder? Or work more efficiently? Or be a bit more disciplined? How did I let the opportunity slip through my fingers?

The Neutral Zone (aka - the messy middle)

30th of August, 2021 - 44 days since my last day

"Oh yaah, that is goood"

I say this in my best mock Swedish accent. I'm exaggerating the slight lilt in the otherwise flawless English of our Swedish friend. Me, David, and the potential ABBA member are sitting in a recently opened pub in Galway. It's the first time I've seen David since leaving. And things are going well. We're having fun. And we're religiously sticking to the agreement that we would not talk about work. So far, so good.

Our friend smiles and clears her throat - she's ready to tease us back (for context - this is how Irish people show their affection).

"So much better is the company now that Patrick has left?"

It takes me a half second to register what she said before a wall of emotion floors me. My throat closes over. My eyes water. My face is hot.

David says nothing. I'm unable to speak. Our friend looks worried - she quickly realizes that she misread the room. Finally David manages to stumble through a sentence.

"I's a bit...too early for those kinds of jokes...."

I'm staring at my feet. We don't say anything for a few seconds. I mumble an excuse and run to the bathroom. I grab the nearest stall and close the door behind me. And then I cry - big hacking coughs. It sounds a little bit like I'm getting sick.

It feels like grief. The only time I've experienced anything like it was after the death of a loved one. It's a deep feeling of loss. I've lost the imaginary future I had built in my head. But that future felt real. And now it was gone.

The hardest part was that the answer was undoubtably yes.

The company was better without me.

After the first month of lethargy, I hit a pocket of mania. I mentally cycled through everything that I couldn't do while working on the startup. All of the options that were previously closed off to me were now on the table. Each day I would become obsessed with some new alternative path.

One morning I woke up convinced that I was going to go back to college and study an arts subject (maybe philosophy). That lasted 2 days. Then I was captured by the idea of moving to Canada after seeing a friend post some cool photos on social media. That lasted about a week. I was gonna write a book. Then learn Spanish and move to Mexico. Then work for a dating app. Then maybe a VC?

I threw myself into some new projects. I swam in every county in Ireland, documenting the journey online. I did start to learn a little Spanish. I read voraciously - and started writing short stories again. I played piano. I made small web apps. I hung out with my family.

But I didn't really dwell on what had happened. I didn't sit with my thoughts. I didn't try to put together the pieces. I wasn't ready for that yet. I filled my days with constant noise, and during any empty moments I always had a podcast or some music playing in my ears.

I knew I wasn’t ready to dive into something new. I didn’t want to fudge this and have unresolved issues follow me to my next thing. But I also needed to keep busy. I needed a project to sink my teeth into.

About the same time, the first solid improvement in the Covid situation was breaking across Europe. The vaccination drive had been successful. The EU covid pass was promising somewhat normal travel across the continent. Things were definitely not perfect but they were a lot better than they had been. I’m not exactly sure where the idea for interrailing came from but it quickly became the prevailing one. It felt like a cross between a holiday and a challenge.

It represented the anathema to some of the hustle porn I had internalized while working on the start up. There was nothing efficient about traveling vast distances by train through Europe. I’d spent so much mental energy thinking about optimizing my productivity over the last couple of years that deliberately choosing the slower mode of transport felt a little subversive.

Finally, a long solo trip represented something else. Independence. I wanted to prove to myself that I was self sufficient - that I could do something on my own.

So interrailing it was. I planned a massive route - 24 different countries, thousands of kilometers on trains. Mostly places in Eastern and Central Europe that I’ve never visited before. Icy Lapland, the beautiful baltics, and mighty Istanbul to finish.

I picked a date to leave. I found an Osprey backpack on Amazon. I watched countless youtube videos filled with tips. And I bought my ticket.

15th of September, 2021 - 60 days since my last day

"Ok, I guess that's it then. That's the last of it."

David walks into the kitchen with a duffel bag over one shoulder and a wheeled suitcase in the other hand. I'm lying on the couch of our apartment, eating ice cream out of a Ben and Jerry's tub. The place looks bare - all of the things that made it feel like home for the last year are packed up.

"Do you need a hand taking it all downstairs"

"Nah, I'll be alright"

"Right, wow, guess it's goodbye so...."

We hug. We chat a bit about his journey home. We hug again. And then he's gone. He's the first one to move out. I'm leaving on Thursday. Our friend James will be the last to go - he's handing back the keys on Sunday morning.

After David leaves - I look into his empty room. It seems smaller now. The whole place seems sterile. It's hard to imagine how this felt like home.

In hindsight, living together during a pandemic while co-founding a startup possibly wasn't the best idea. The line between my life and startup-life became entirely blurred. The problem is that when we moved in, we thought that the pandemic was ending. It was during the first "false spring" in July of 2020.

We'd be on a plane to SF before you knew it. Maybe we'd travel over together in October, after setting up a new office in Dublin. You know, after Ireland left phase 5 of the first "emerging from covid" government plan sometime in early September 2020. The 5 strange and stressful pandemic months would be a weird blip. I'd be back on track in no time.

That was how I coped with Covid initially. Think of something fun to look forward to, a trip or a milestone, something that couldn't happen now but could happen when it all ended. Then use it as a motivator when I was finding things tough. Just a few months of this drudgery and you'll be hanging out with your YC friends in New York. Or running hackathons in a swanky office off Fitzwilliam Square in Dublin. Or heading somewhere cool for an offsite. Just a little while longer. Any week now.

They're the kind of mental tricks I've always used to get through hard situations. A lot of my 'mental toughness' comes from my time playing rugby. Often I'd need to push myself through situations of discomfort. I'd always try and chunk the pain into manageable levels.

A grueling fitness session of 6 runs was "Just 3 more pairs of sprints...halfway there...just 2 more left...last one".

A rough, physical match had "just 10 more minutes till halftime, then 10 minutes to catch my breath, then 4 sets of 10 minutes." If I was really struggling, I'd convince myself that I was about to be replaced by a sub. "They see how tired you are, just one more minute and you'll be taken off." And then one more. And another. Until I played another 20 minutes at full pace.

The problem with the pandemic was that the clock just kept running. The horizon was receding in front of me. And I was so focused on it that I didn't put any intention into making my day to day bearable. I created the perfect storm for increasing anxiety levels - I made my personal happiness entirely contingent on factors outside my control. It made me hyper sensitive to any new covid news that could effect these imaginary plans.

I head into my room and continue with my own packing. I've picked up so much stuff in the last 12 months, especially during the lockdowns. I was a frequent patient at the retail therapy clinic known as I'm going to be using my parents garden shed as a dedicated storage locker and my mum has made it very clear that she won't be accepting "a pile of shite you'll never look at again".

The last thing I do is take down the photographs I stuck up on my bedroom wall. Some are from before YC but many are from after. The 3 of us hanging out in our brand-new Monaru t-shirts. Our extended friend group on a hike near the Golden Gate bridge. Celebrating on the day we closed our seed round.

I love creating stories, cosmic narratives where everything was 'meant to be'. All of these moments fitted into the narrative of us IPO'ing in 10 years time. They were the stepping stones along the way. One day they'd be hung up next to the pictures of baby faced Sam Altman, the Collison brothers, and the Twitch co-founders at the YC headquarters in Palo Alto.

One of my big fears about leaving was that it would diminish these memories somehow. If I left, or if the company folded, would these moments matter? Would they mean anything?

I stop and hold one in particular. We're standing in front of the YC sign at Demo day. I'm looking sideways and laughing. Romy is smiling at the camera. David is recoiling in horror - I think we were trying to make him join us for a hug. We were tired and stressed at the end of Demo day, for sure. But we were also relieved. And giddy. And excited.

It's not going to be printed in the newspaper. It wont appear in a history book somewhere as an example of the team before we'd made it big. It doesn't have any great significance. It's just a snapshot of a happy memory.

I'm hit by a realization - that's all it ever actually was.

I spend the next few days sorting out all of the little life details that need to be packed away too. On Thursday, I have a last coffee on the roof of our apartment building, drop the last bag at my parents house and then get on the last train from Dublin to Rosslare for a ferry to France. My Interrail odyssey begins.

I'm not exactly sure if I'm running away from my old life or running towards something new. It's probably a mixture of both.

18th of October, 2021 - 93 days since my last day

"Yeah, look, you don't have to say that again...just what do you think?"

I'm sitting in the common room of a hostel in Stockholm. The internet is spotty and I'm trying to Zoom with one of my friends working at an early stage startup. They're looking for advice on building their product. Before sharing my experience, I started with my usual caveats. "Listen, I've never successfully reached Product Market fit so take my advice with a pinch of salt." He dismisses this with a wave of his hand.

"I'm talking to you for a reason like...."

I pause, then start where I'm most sure that they're doing the wrong thing.

"Ok, well, first off - I don't think it should take 6 weeks to decide on a tech stack. You're building a fairly straightforward web app so the engineering team should really just pick something simple and get started straight away. That whole thing about the Database really doesn't matter at this stage...."

I start off with the basics, things that I think are obvious. The more we go on, the more I realize that some of this stuff is very nuanced. For each question he asks, I can think of like 5 different examples where I learned the hard way what the right(ish) answer is.

Don't scope too much, but also don't ship something shit or you wont get feedback. Make sure you know who your first customer is going to be, but don't believe that they'll actually use your product until they actually use it. Work hard to try and hire the best people you know, but also don't put all your eggs in one basket - more often than not you'll be disappointed.

It's like trying to explain to someone how you ride a bike. A lot of it sounds obvious or trivial. Balance while pedaling. Don’t fall over. Pull the brakes when you want to stop. But actually doing it - actually putting all of the pieces together is something that you just have to feel your way through.

For most of my time as CEO of the startup, I felt like an imposter accidentally elevated above my station. I was the hotshot cofounder of a company valued in the millions , with newspaper articles written about me and my team. It felt like people were hailing me as a tour de france hopeful, while deep down I knew that I could barely balance while pedaling. Externally I looked like I was killing it. Internally I felt lost.

Now the opposite was true. To all the world, I'm an unemployed, soon to be broke 20 something. But internally I feel more solid. The trial and error of the last few years has left me with actual experience. It feels like I have a concrete foundation where previously there was just loose sand.

We start to finish up. The session turned into a brain dump. I think I tried to cover too much and got a little lost in the detail.

“Wow ok, lot’s to think about so...”

“Yeah, I mean if it was easy I would have done it...hah” I make a joke but it falls flat.

Over the next few weeks I have a few more calls like this, with him and other startup friends. As the dust starts to settle, I can see that there is something left over. Something useful. Valuable even. The overriding feelings of shame and heartbreak aren’t quite so overriding anymore. Talking about what I learnt isn’t as emotionally charged as it was.

I still avoid talking about how it all ended though. That’s still too close. I try to put it down in words, to start writing this piece, but I get nowhere. Just one or two sad paragraphs are as far as I manage before my mind goes blank.

And by extension, thinking about what’s next feels wrong too. It feels final. I can’t face it. So I just keep floating. In my free time I keep the music and podcasts playing in my ears. I keep reading pop romance fiction books. I keep watching episodes of the peep show. I’m in a holding pattern. The neutral zone is living up to it’s name.

3rd of November, 2021 - 109 days since my last day

I'm the bustling common area of Greg and Toms party hostel in Krakow, Poland. The crowd is a mixture of teenagers on a gap year, early 20s college grads and 20-something career-breakers. And me.

"Ah nice, what was your job?"

We're finishing off a round of introductions and I've given my usual spiel - "I'm a Software Engineer from Ireland - I quit my job in August to travel for a few months." Usually, when people ask me what the job was I tell a half truth and describe my old job at Intercom. I tell myself it's simpler, but in reality I just can’t face talking about what happened. I’m not sure I can get through an explanation without hitting a wall of emotion.

But this time, this time I feel different. I start answering his question, hesitantly at first but soon I pick up steam. Each word comes out a little faster than the one before.

" was my own company...that I quit. I started it with a few friends and was working there for a couple of years...but over the last while I was super stressed and stopped enjoying it. I also wasn't doing a great job if I'm honest. So I decided to leave..."

I feel like I've just admitted that I'm on parole after being convicted of murder. I half expect someone to wince or make a face. I look around. Everyone is nodding passively. There's a few mumbles of "cool" and "nice" but in reality, no one really cares. It's just as interesting or uninteresting as anyone else's story.

"That sounds like such a fascinating experience. What age did you say you are again? And when did you start it?". The English woman on my left is politely curious.

"26, and the end of May in 2019. A bit over 2 years ago now."

"Wow, that'd be like me starting a company next month. Mental..."

She asks me more questions about the mechanics of starting a company, what it was like trying to recruit people, how I dealt with all of the new responsibilities.

“How did you know how what to do with the money and who to hire and all that kinda stuff?”

“Eh yeah, I suppose I didn’t really. You just kind of try your best...”

When the conversation reaches a natural end, she says sort of breathlessly, “That sounds like such an amazing experience though. Such an amazing experience.”

I’ve tried to tell myself that on multiple occasions, and many of my close family and friends have said something similar to me in the last couple of months. About how I would look back on it all as a great experience.

But haven’t quite internalized it yet. Until now. For some reason, hearing it from a complete stranger makes it feel true.

“So what kind of trip are you doing?”

“Well it’s a little bit heavy to be honest...”

She tells me about her own journey and the significance of her trip. How she was brought up Christian (Church of England) but that her family converted from Judaism after escaping from Poland during WW2. How she is retracing the steps of her grandfather. How she feels strangely disconnected from her heritage because of the difference in faith.

My perspective shifts. I realize how incredibly self centered I’ve been. How irrational it is to be worrying about how everyone else perceives my decisions and apparent failures. In what universe would my story be more than a passing curiosity to her. Or anyone in this room. She has her own journey to think about.

I eat a little more of the bland communal dinner (pasta, apparently without any sauce). I finish my drink. I say my goodbyes, and then I head to bed. I leave behind a mental weight I’ve been carrying around with me through the cities of Europe.

Over the next few weeks I tell the story so often it becomes routine. The sting is completely gone. It’s just another chapter in my life, with ups and downs like any other. It mixes in with all of the other stories in the hostel common room. No more or less interesting. No more or less remarkable. No more or less impressive or embarrassing. It’s just another thread in the rich tapestry that is spun each evening.

It no longer feels like a cosmic mistake. I feel smaller, less consequential. And I feel lighter.

28th of November, 2021 - 134 days since my last day

The sun is setting over Istanbul. I'm standing at a viewpoint overlooking the city. The grey minarets and blue domes of countless mosques stand out against the red and orange after-burn on the horizon. The city is charged with energy - a hum of vendors selling Gucci belts and roasted corn, everyday residents chatting over steaming cups outside of small tea rooms, honking taxi drivers stuck in glacial traffic.

This is it. This is the last stop on my initial route - the plan for my big trip. I did it. I got here in one piece. I’m a mixture of proud and relieved. And excited. In the last few weeks, as this final stop approached, I felt a groundswell of energy and enthusiasm build. Thinking about what’s next went from scary and uncomfortable to an obsession. My new favorite topic. And I started writing again - any chance I got I would open my laptop, my hands would float across the keyboard, and this post started writing itself.

I climb a few more steps and see a whole new vista. The gleaming white evening tour boats are launching from the jetties down below. I take a picture of the view with my phone, then mindlessly open twitter and refresh my feed. I see an update from my ex-teammates. They're posting about a new feature they've built for a beta they just launched. It looks so clean and polished. And useful. I can see the amazing design work. The attention to detail. The craftsmanship.

I wait for the pang of jealously to hit me, the stomach drop, the Fomo.

But it doesn't arrive. In its place is something else - a sense of pride. I feel so proud of them for what they're doing. Proud that I helped to put the team together. Proud that I got to work with them for a moment in time.

It's like noticing that a broken bone, something that's been tender and painful for months, has finally healed. I put my full weight on it. It feels solid. Dense. Stronger than before.

I laugh out loud. Some locals are looking at me but I couldn't care. I smile from ear to ear. It's happened. I made it to the other side. I'm free.

I've moved on.

19th of July 2021 - My last day

"Are there any final things you'd like to say to each other before we wrap up? If there's anything you'd like to say for closure - now's the time..."

I'm sitting awkwardly with my laptop propped up on the dressing table in my hotel room. I'm isolating after catching covid. I haven't spoken to anyone in person in 10 days. My sense of smell has just gone.

And this is my last day at the company. The company I started with my best friends in my parents kitchen. The company I helped shape out of nothing into something. The company I've spent nearly every waking hour thinking about, talking about, worrying about, hoping about. The company I poured over 2 years of my life into.

My journey ends here. 10 minutes after I noticed that my mint shower gel no longer smells of anything. This feels like rock bottom.

We're finishing up a session with a coach who is helping us navigate the logistics of me leaving. It's extremely jarring to suddenly be on the outside - even though things are amicable there is no getting around the fact that I'm no longer on the team.

There are a few seconds of hesitation after his open-ended question. There's so much to be said. How do you say goodbye after over 2 years of highs and lows. And everything in between. How do you summarize the enormity of that?

"I'd like to say something..." Romy breaks the silence. She's a little uncertain at first but then gains confidence. This is something she has already thought about.

"I just want to say that...even though you made things very stressful at times, especially since were the one who started us on this journey and we wouldn't be here without you. So thank you for that."

I feel my heart melt in that moment. I'm stunned. It is so generous, so loving, so kind, that it catches me off-guard. Any anger or bitterness I feel dissipates. It cuts through the wall of shame I have built up around myself. It's exactly what I needed to hear to let the healing start.

I'm chocked up but manage a meek "Thank you for saying that...". I try to say something more but I trail off. Our coach starts to wrap things up. We say our goodbyes. The zoom call ends. I stare at my reflection in the blank screen. I just sit there for a while.

One of the scariest things about starting a business with other people is that you're locked into such a massive commitment with them. Y Combinator describes it as the biggest commitment you can make aside from marriage.

It's impossible not to wonder if you made the right choice. When things are tough, when stuff isn't working well, you think maybe the problem is with the partners you picked. There's always a sliver of doubt.

In that moment, the moment when it all ended, I knew that I had done at least one thing right.

I knew that I picked the best.


I finish this blog post and hit live. Almost immediately, I get an email from one of our investors.

"Just read your post - I'm guessing that means no one is looking after the app. It just went down."

I open my laptop and...oh god...all the tables in the database are empty. All the customer data is gone. I start frantically debugging. I message David. He doesn't answer. No one is answering. And the app is down....

I wake up with a start. My first impulse is to check if David has messaged me back yet. I reach for my phone and then start to realize where I am. I'm in a hotel room in Vigo, Spain. On the way to meet my family for Christmas in Portugal. I don't work at the company anymore. There is no app. It was just a dream.

I let out a soft laugh, then open the notes app in my phone, tapping on the note where I write down any dreams I remember. I scroll down to the bottom and type just 2 words.

"Same again"

Then I drift back asleep.

I think this is the only lasting damage from my startup adventure. My "I didn't study for the exam" dreams have been replaced by "the app is down and no one is responding".

If you're a founder interested in chatting about burnout, I'm always happy to share my experience. My DM's are open on twitter.

If you interested in helping me find out what's next - check out my hire me page for more info.