What you find when you stop looking
/alt title: what happened when I stopped trying to sprint-plan my life
I left my job as a software engineer 6 months ago.
It marked a hard-stop to 5 years of working in high pressure environments with people trained to problem-solve for a living. It was fast-paced. It was intellectually challenging. It was also really, really inefficient at times.
Taming the Boogeyman
Part of being a software engineer is trying to put a lid on chaos. We are the technical experts that provide reality checks. A big part of our job is giving point blank estimations and elaborate blueprints for future plans on almost zero information. It’s like being asked to make a police sketch of the Boogeyman based on a crying child’s description of its nightmares.
To do this, we create frameworks to contain the chaos (or sometimes, just to cover our asses if things don’t go according to plan. Which is often.) People create project management r̶e̶l̶i̶g̶i̶o̶n̶s̶ ideologies like agile, spread by devoted followers called scrum masters who enforce the holy word in bi-weekly rituals (no joke — we actually call them rituals). Tools like the Atlassian, Asana, and monday.com are multi-billion dollar empires used by virtually every technology company. Engineering managers devour book after book on how to make their teams happier and more productive. Often, we work on the way we work more than we actually just…work.
I’m not being mindlessly critical here. Most of the time the overhead is necessary. When software gets to a certain size or complexity, you need more than one person working on it. Getting a group of people scattered around different locations and time-zones to come together to build something remotely good under short timelines needs structure. The alternative would be giving everyone free reign to interpret the brief however they like, step over each others toes, and try and piece together something cohesive that comes out from the scraps like a git supported Frankenstein. You’re never going to make anything of scale like that.
And so, we plan.
The general logic is
- We can build anything — but we should build something that has impact
- Impact is either Money, Time saved (which is also money, cause we can use that saved time to build other money making things), or Happier people (which is also money cause happier people work better, and we don’t have to keep replacing unhappy people who leave for different companies!)
- But it takes time to build something. How do we guess what will be the most impactful in 6, 12, or 24 months time? We’ll have to make an informed guess and call it a vision
- Yeah but the word vision is too wishy washy and hard to get people to rally behind. So let’s break it down into deliverables and KPIs to hyper-fixate on for better or for worse
Seems like a sensible plan, right?
When things go right it works pretty well. But when things don’t (like when the entire world goes into a recession, VC funding dries up, and every tech company in the world makes crazy redundancies), it’s painful to watch companies drown in bureaucracy quicksand. Reality is painful. You can’t plan your way out of a sinking ship.
And yet, it’s hard to stop drinking the kool-aid when software engineers need to report to project managers, who need to respond to sales people, who need to respond to a CEO. And so, the ever chugging corporate machine continues to spit out developer velocity metrics and GANT charts while the engineers sit around twiddling their thumbs.
When I said goodbye to work, I took one big lesson from it:
Planning only works when the world around you is in relative equilibrium and the assumptions you make aren’t thrown out the window every five minutes.
Road to nowhere
Most people who have known me in my adulthood would classify me as Type-A . Organised, motivated by anxiety, endearingly neurotic (emphasis mine). The ultimate mom friend. Great to have when planning a trip. Less fun when she’s reminding you that you only have 15 minutes allocated for “chill-time” before you have to get your ass moving.
There were times when I’ve treated my entire life like an agile project. We’re talking short and long-term goals with measurable KPIs to chart progress. Setting R-A-G statuses for personal projects. Relationship kanban boards for date ideas and chores to-do. The works.
I don’t think there is anything fundamentally wrong with proactively setting goals for your life (having said that, I’m also organising a powerpoint party for my birthday so take everything I say with a pinch of nerd-flavoured salt). The issue is when the organisation become a coping mechanism or a band aid for something darker lurking underneath.
The software project management tools I mentioned before provide high-level metrics to measure success and performance of an individual (number of task tickets completed, how many lines of code written, number of pull requests made). This sort of big brother monitoring markets itself as “data driven insights”, but is grounded fundamentally in a distrust of workers. Most people with a bit of sense understand that these metrics are red-herrings and completely ignore it, but it’s an easy (and lazy) fallback when you don’t have any other means of telling if someone is doing well.
This was the relationship I held with myself for years: simultaneously distrustful manager and micro-managed worker. Fuelled by a complete lack of trust. I feared that if I stopped governing myself, I would completely steer off course and be sucked into the gravitational pull of laziness and failure. I shoved disappointing numbers underlined in red in my own face, trying to scare myself into performing better for the biggest stakeholder of them all — my bruised ego.
Underneath all this manic organisation, there was a lot of anxiety and self-doubt about my professional life. I really loved being a software engineer, but was never able to shake the doubt that it wasn’t the perfect career choice for me. This doubt permeated everything, I struggled to feel fulfilled by my professional work; personal projects never went anywhere; I projected my disappointment in myself onto loved ones; every passing year brought with it increasingly intense self-criticism and a deepening sense of feeling stuck. Despite my best intentions/neurosis, whatever the hell I was doing really was not working for me.
Pumping the brakes
After 5 years of work, I found myself in a position where everything my life pointed to taking a career break. I decided that I would quit my job with no future prospects set up and backpack across Latin America for 3 months. My parents were obviously overjoyed at the prospect. It took me a long time to come to the decision. But one thought kept echoing in the back of my mind:
“The pain of change is nothing compared to the pain of standing still” — some linkedin person, probably.
So, I gave in my notice. People congratulated me, but they also asked me why on earth I was doing it. I would give one of the three following answers:
- I have a completely selfish existence with no dependents, so I want to fully explore that before my circumstances change.
- I would like to become less uptight and better at handling stress and uncertainty. A backpacking trip with with minimal planning will really challenge me to think on my feet.
- I’m generally really happy with my life. But I also want to see what happens if I throw a spanner in the works (I would come to refer to this as a conscious perturbation from the equilibrium. Heavily inspired by our glorious leader, Gwyneth Paltrow)
The second point was the biggest challenge. I couldn’t imagine myself as a wild and free-spirited backpacker, but I wanted to meet her.
As the days went by, I felt that familiar fear of failure creeping into my psyche. In this case failure looked being a loser: making no friends, paying inflated gringo prices, making inefficient travel plans, and the worst case scenario of all: coming back as the same person I was when I left.
As a result, the first two weeks of the trip were planned to the hour. Every hostel and restaurant booked, every connecting bus and “insider tip” bookmarked, every detail documented in a shared document where me and my friends would leave comments like “should we take the full-day tour with Company A, or ride a chicken bus ourselves?”. For every activity, I mentally assigned the OKR it would contribute towards (e.g. drinking local Peruvian cactus juice with friends on a torturous 6-hour hike → 10% increase in spirituality, 5% increase in connection to nature, 100% increased awareness of what your friends sound like throwing up in a beautiful glade).
We showed up in Lima with bright eyed and grand plans in hand. In a massive up yours move by life, we were immediately thrown a curve-ball: our bags were left behind in Paris. The plans which made sense in our heads lost their confidence when exposed to the real world. Whether it was standing on a curb for 25 minutes waiting for a bus that never showed up (“yo tengo una boleto de autobus, comprar en linea” was met with confused faces) or realising that every vendor on the street was selling identical tours that cost 30–40% less than what we paid for on an online english travel site. All that planning actually cost us more time and money than if we just went up to people in the street and asked them what to do.
We’d packed our days so full that even when we met cool people, we’d have to tear ourselves away too early to catch a bus the next morning. I found myself re-learning the same lesson I first encountered in quarterly planning sessions.
Planning only works when the world around you is in relative equilibrium and the assumptions you make aren’t thrown out the window every five minutes.
Letting go
When my friends flew home, I boarded a bus that brought me across the Peru-Bolivia border. I was nursing a bad bout of food-poisoning from eating river reeds on the lake (our host Luis told us it was like their local bananas. I didn’t know bananas in Lake Titicaca were pure evil). The driver told me that I was the only person on the bus who needed a visa, and that I had 15 minutes to get it otherwise they would leave my bags by the road.
It was happening. The solo travelling. The chaos. The thinking on your feet. The vomiting. I was well and truly locked-in.
That stressful border crossing was the first of many misadventures. But it reset something in my brain. Sure, I could have avoided this if I had thought to apply for a Bolivian visa online. But then, I wouldn’t have learnt that I possessed the charm to convince that same bus driver to pay for printing my documents as I had no Bolivianos on me. All while managing to not vomit on him.
Instead of wounding myself even tighter with anxiety when things went wrong — I started to trust myself more. As my self-confidence grew, my grip loosened.
I noticed my planning horizon begin to shrink. What started as 2 weeks of back to back plans turned to 1 week of hostels booked ahead, became knowing what town I would be in in 3 days, to waking up in the morning and deciding where I wanted to fall asleep that evening.
When I landed in Mexico in the final month of my travels, I arrived to the overwhelming bustle of CDMX at 10pm sleep deprived, without the faintest idea of how or where I was going to spend the next month. That flexibility meant that I was able to pack up and join new friends on their next adventure with barely any notice. A trip to a Hello Kitty market with a stranger resulted in a 3 day detour to Mexico’s only nude beach. A chance friendship in a hostel led to eating lunch with their family in their hometown 2 weeks later, in the beautiful city of Merida that I’d never heard of beforehand.
I would stay in a place for as long as it felt right. It started to bother me less if I missed out on an event, or didn’t get through my wish-list. Slowly but surely, it became more fun to listen to my heart and my body about where it wanted to be and who it wanted to be with. FOMO, the ever-lurking demon in my life, had started to ebb away. In it’s place, I felt an old feeling resurface. It had been estranged for so long that I didn’t recognise it at first: the feeling of listening to my own gut.
Things didn’t fall apart when I stopped trying to keep it all in place. It gave life space to breath and to grow organically. And it was kind of magical.
The wrap-up
I know that these revelations are kind of basic. Yes, travel is fun! Going with the flow and being spontaneous is good! Only fucking psychopaths use JIRA to plan dates you freak. Yeah, duh.
I also know that it’s cliched to come back from travelling preaching new life philosophies. Good news for every one. I have none! In fact, I’m convinced that it would be pretty awful to constantly live like a backpacker. Perpetual change of environment is exhausting. Prioritising absolute freedom is lonely because you can’t make long-term plans or build long-term friendships. I’m also OK with never sleeping in a jungle hostel in 40°C heat ever again. I don’t even think that I’ll always travel like this. If I show up for a 3-day weekend trip with zero plans, it’ll be over by the time I realise that that hike I saw on instagram is actually a 5 hour bus ride away.
It’s all about context. Structure and planning works wonders when there are constraints and clarity. However, in times of great uncertainty or information deficit, that effort you put into planning gives you nothing but the illusion of control. It’s effectively procrastination. Instead, lean into the uncertainty. Expand your solution space. Whether you’re a company that needs to pivot to save the business or a woman in your late-twenties contemplating a career change, heed the wise words of our elders that echo throughout the ages: fuck about and find out.
At the end of the day, that’s exactly what I’ve come back with: a lived experience on how functional and safe it can be to stop looking so hard. It’s taught me how to meet uncertainty with adventure instead of fear. In fact, it’s torn my entire relationship with fear apart. The years I spent being controlled by fear was so much like being in a toxic relationship: I thought it was the only thing keeping me afloat, but it was actually the exact thing that was keeping my head below water.
My gut and I are still talking to each other every day. In fact, we’ve had a discussion and decided that it’s going to take on some of anxiety’s workload. A shift from planning to just being. Though, nowadays, it’s looks a little bit less like mountain biking down death road, and more like finally starting that blog I’ve always wanted to, even if I’m not 100% convinced that anything I have to say is worth the read. Here’s me doing it anyway.
