A (sort of) handbook for anyone who isn't in love with their work. Yet.

On

Apr 29, 2024

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A (sort of) handbook for anyone who isn't in love with their work. Yet.

On

Apr 29, 2024

Share

A (sort of) handbook for anyone who isn't in love with their work. Yet.

On

Apr 29, 2024

On Thursday 21st April 2022, almost two years ago to the day, three things happened:

  1. I joined Planhat (I wrote this about it at the time, and filmed this video that week).

  2. I moved from Jakarta (where I’d been working with Kargo Technologies) to Stockholm

  3. Planhat raised its $50mn Series A

This week, a couple more things happened:

  1. My role changed

  2. I’m leaving Stockholm (to NYC, L1 permitting)

In this time (which I'll lovingly call "The Stockholm Years") I've learnt a lot about finding and leaning into work you enjoy, rather than forcing yourself into certain types of work because its something somehow more credible or noble. Turns out, becoming the thing you need to be has a lot to do with trying to be many of the things you shouldn't be.

Coming from a family of architects, I've always loved telling stories and creating beautiful things. So it turns out I shouldn't be a doctor (as I thought I should be, aged 10); I shouldn't be a banker (as I thought I should be, aged 17); and I shouldn't be a product manager (as I thought I should be, aged 21). I am most myself when I am being a storyteller, so that is what I should be.

Now pause to ask yourself "what am I creating when I am most myself?". If that thing is the thing you do for a living, stop reading this and go do that thing. Sorry, there's nothing for you here.

However, if that thing isn't also the thing you spend most of your days doing, or derive your primary income from, chances are you're not in love with your work, and therefore you're also not in love with your life. To me, that realisation screams "time for change!". So now you owe it to yourself to do two things simultaneously:

  1. change your environment

  2. change your approach

This article is a summary of how I've gone about doing those two things to start making a living doing the things I love, and how you can too.

Disclaimer: this is in no way a definitive guide. What works for me might not work for you. Importantly, I claim in no way to have found some "silver bullet" for loving or mastering your work (especially since I am by no means a master of anything), but I've started to love my work for the first time in my life, and think that's something worth writing about.

TL;DR: If you'd rather not hear about how I ended up here, skip to "A (sort of) handbook".

“I believe everything in life comes from the environment you're in, and more importantly the mindset you have while occupying it.”

On Thursday 21st April 2022, almost two years ago to the day, three things happened:

  1. I joined Planhat (I wrote this about it at the time, and filmed this video that week).

  2. I moved from Jakarta (where I’d been working with Kargo Technologies) to Stockholm

  3. Planhat raised its $50mn Series A

This week, a couple more things happened:

  1. My role changed

  2. I’m leaving Stockholm (to NYC, L1 permitting)

In this time (which I'll lovingly call "The Stockholm Years") I've learnt a lot about finding and leaning into work you enjoy, rather than forcing yourself into certain types of work because its something somehow more credible or noble. Turns out, becoming the thing you need to be has a lot to do with trying to be many of the things you shouldn't be.

Coming from a family of architects, I've always loved telling stories and creating beautiful things. So it turns out I shouldn't be a doctor (as I thought I should be, aged 10); I shouldn't be a banker (as I thought I should be, aged 17); and I shouldn't be a product manager (as I thought I should be, aged 21). I am most myself when I am being a storyteller, so that is what I should be.

Now pause to ask yourself "what am I creating when I am most myself?". If that thing is the thing you do for a living, stop reading this and go do that thing. Sorry, there's nothing for you here.

However, if that thing isn't also the thing you spend most of your days doing, or derive your primary income from, chances are you're not in love with your work, and therefore you're also not in love with your life. To me, that realisation screams "time for change!". So now you owe it to yourself to do two things simultaneously:

  1. change your environment

  2. change your approach

This article is a summary of how I've gone about doing those two things to start making a living doing the things I love, and how you can too.

Disclaimer: this is in no way a definitive guide. What works for me might not work for you. Importantly, I claim in no way to have found some "silver bullet" for loving or mastering your work (especially since I am by no means a master of anything), but I've started to love my work for the first time in my life, and think that's something worth writing about.

TL;DR: If you'd rather not hear about how I ended up here, skip to "A (sort of) handbook".

“I believe everything in life comes from the environment you're in, and more importantly the mindset you have while occupying it.”

On Thursday 21st April 2022, almost two years ago to the day, three things happened:

  1. I joined Planhat (I wrote this about it at the time, and filmed this video that week).

  2. I moved from Jakarta (where I’d been working with Kargo Technologies) to Stockholm

  3. Planhat raised its $50mn Series A

This week, a couple more things happened:

  1. My role changed

  2. I’m leaving Stockholm (to NYC, L1 permitting)

In this time (which I'll lovingly call "The Stockholm Years") I've learnt a lot about finding and leaning into work you enjoy, rather than forcing yourself into certain types of work because its something somehow more credible or noble. Turns out, becoming the thing you need to be has a lot to do with trying to be many of the things you shouldn't be.

Coming from a family of architects, I've always loved telling stories and creating beautiful things. So it turns out I shouldn't be a doctor (as I thought I should be, aged 10); I shouldn't be a banker (as I thought I should be, aged 17); and I shouldn't be a product manager (as I thought I should be, aged 21). I am most myself when I am being a storyteller, so that is what I should be.

Now pause to ask yourself "what am I creating when I am most myself?". If that thing is the thing you do for a living, stop reading this and go do that thing. Sorry, there's nothing for you here.

However, if that thing isn't also the thing you spend most of your days doing, or derive your primary income from, chances are you're not in love with your work, and therefore you're also not in love with your life. To me, that realisation screams "time for change!". So now you owe it to yourself to do two things simultaneously:

  1. change your environment

  2. change your approach

This article is a summary of how I've gone about doing those two things to start making a living doing the things I love, and how you can too.

Disclaimer: this is in no way a definitive guide. What works for me might not work for you. Importantly, I claim in no way to have found some "silver bullet" for loving or mastering your work (especially since I am by no means a master of anything), but I've started to love my work for the first time in my life, and think that's something worth writing about.

TL;DR: If you'd rather not hear about how I ended up here, skip to "A (sort of) handbook".

“I believe everything in life comes from the environment you're in, and more importantly the mindset you have while occupying it.”

A Case of Mistaken Identity

For a decade, I did things because they’re the things smart people are “meant to do”. I worked obsessively hard from a young age, always got the right grades, did the extracurriculars, and so on. I took subjects because they were credible, not because I liked them. I took the most open-ended degree, PPE (Philosophy, Politics & Economics) because it was known at the time as “The degree that runs Britain”, and was associated with smartness. I interned at hedge funds and an American bank because finance earned clout on campus, not because I enjoyed spending eighteen hours a day in Excel. Then I went to business school and did an MSc in Analytics because applied data science is useful, and difficult, and sexy (this last point is dubious, I know). I then found myself in Product Management because (at least at the time) it was the only other “honourable path” for a driven problem-solver with an aversion to the corporate grind. Despite the fact I was doing things I didn’t love at all, I loved every minute of the journey because I love to do difficult things and - again - because I felt somehow that I was spending my time on the “right things”.

But this also meant that I spent a lot more time being quite good at things I didn’t really enjoy, rather than becoming exceptionally good at the things I love. And over time, that started to wear on me. I think a lot of people feel this way at some point in their lives, and some people feel this way for their entire career.

Why I'm Writing This

In early 2022, I read Mastery by Robert Greene (the first of 4 books I think everyone should read in their twenties, alongside: Sethi's "I Will Teach You To Be Rich"; Perkins' "Die with Zero"; and Attia's "Outlive") and decided I needed to figure out how start a career doing my thing.

Its taken two "Stockholm Years", but I finally feel like I'm starting out on the right path. And I've got here by applying a handful of simple principles gathered from countless writers, friends and mentors along the way. If there's even just one thing someone else can learn from my experience, this article has been worth writing. The handbook below is a summary of the ideas that got me from a classic five-day-sprint, two-day recovery working week (Sunday scaries included), to a seven-day routine blending daily creation and rest in whatever measure is needed to bring the vision to life. For the first time, I am creating things not because they are asked or owed of me, but because I feel a creative duty to bring them into the world. It's still early days, but the difference is monumental.

Why Two Parts?

I believe everything in life comes from the environment you're in, and more importantly the mindset you have while occupying it (I've written a little about this with my company Altere Studios). I don't think any guidance could be complete without accounting for both.

Because of the ideas in 01 (finding the environment you need), I ended up sitting in front of Kaveh Rostampor at Planhat. The interview was dramatically different from any job interview I’d had before, and it says enough that I haven’t even considered taking another since. Planhat was (and largely still is) a relatively unknown company to those outside customer success, but it seemed at least from the outside to be a place with an incredibly high density of smart people doing the things they love. Kaveh promised that Planhat would be the place I’d find my niche doing things I actually loved, provided I went all-in with an open mind. Though I’d forego a well-defined title and role, the company was bootstrapped, profitable and remote-first. I couldn't think of any good objections, so I took my chances. It’s taken two years, but I think we both delivered on our promises, in no small part because of the ideas in 02 (becoming yourself).

In short, the guidelines below - in combination with a bunch of incredible sparring partners at Planhat and Altere Studios - have given me the confidence, focus and freedom I've needed to lean into and succeed in the things I care deeply about (and arguably, I am best at). With Planhat, I'm honoured to be owning the visual identity and voice of a business at this major inflection point (we're soon to launch the next generation of our product and brand - watch this space); and I'm excited to see where we end up with Altere as we take our first product to market this summer (check it out here).

And yet, some small part of me still feels some sort of insecurity over the fact that after years of toiling over the intricacies of econometrics, statistics, game theory, etc. I now spend my entire day playing almost exclusively with colours, shapes and words. I often think "why did I study so hard for this?" - then I remember that the only reason to do anything is to find the thing you love and spend your life doing it.

And in that sense, I guess almost a decade of mistaken identity did the trick.

Below are my notes on how you can cut the prelude and get straight to the good part.

“The more I build and interact with businesses, the more I see them as stages on which we perform to the world: opportunities to get out of our comfort zone and create things at the edge of our capability.”

A Case of Mistaken Identity

For a decade, I did things because they’re the things smart people are “meant to do”. I worked obsessively hard from a young age, always got the right grades, did the extracurriculars, and so on. I took subjects because they were credible, not because I liked them. I took the most open-ended degree, PPE (Philosophy, Politics & Economics) because it was known at the time as “The degree that runs Britain”, and was associated with smartness. I interned at hedge funds and an American bank because finance earned clout on campus, not because I enjoyed spending eighteen hours a day in Excel. Then I went to business school and did an MSc in Analytics because applied data science is useful, and difficult, and sexy (this last point is dubious, I know). I then found myself in Product Management because (at least at the time) it was the only other “honourable path” for a driven problem-solver with an aversion to the corporate grind. Despite the fact I was doing things I didn’t love at all, I loved every minute of the journey because I love to do difficult things and - again - because I felt somehow that I was spending my time on the “right things”.

But this also meant that I spent a lot more time being quite good at things I didn’t really enjoy, rather than becoming exceptionally good at the things I love. And over time, that started to wear on me. I think a lot of people feel this way at some point in their lives, and some people feel this way for their entire career.

Why I'm Writing This

In early 2022, I read Mastery by Robert Greene (the first of 4 books I think everyone should read in their twenties, alongside: Sethi's "I Will Teach You To Be Rich"; Perkins' "Die with Zero"; and Attia's "Outlive") and decided I needed to figure out how start a career doing my thing.

Its taken two "Stockholm Years", but I finally feel like I'm starting out on the right path. And I've got here by applying a handful of simple principles gathered from countless writers, friends and mentors along the way. If there's even just one thing someone else can learn from my experience, this article has been worth writing. The handbook below is a summary of the ideas that got me from a classic five-day-sprint, two-day recovery working week (Sunday scaries included), to a seven-day routine blending daily creation and rest in whatever measure is needed to bring the vision to life. For the first time, I am creating things not because they are asked or owed of me, but because I feel a creative duty to bring them into the world. It's still early days, but the difference is monumental.

Why Two Parts?

I believe everything in life comes from the environment you're in, and more importantly the mindset you have while occupying it (I've written a little about this with my company Altere Studios). I don't think any guidance could be complete without accounting for both.

Because of the ideas in 01 (finding the environment you need), I ended up sitting in front of Kaveh Rostampor at Planhat. The interview was dramatically different from any job interview I’d had before, and it says enough that I haven’t even considered taking another since. Planhat was (and largely still is) a relatively unknown company to those outside customer success, but it seemed at least from the outside to be a place with an incredibly high density of smart people doing the things they love. Kaveh promised that Planhat would be the place I’d find my niche doing things I actually loved, provided I went all-in with an open mind. Though I’d forego a well-defined title and role, the company was bootstrapped, profitable and remote-first. I couldn't think of any good objections, so I took my chances. It’s taken two years, but I think we both delivered on our promises, in no small part because of the ideas in 02 (becoming yourself).

In short, the guidelines below - in combination with a bunch of incredible sparring partners at Planhat and Altere Studios - have given me the confidence, focus and freedom I've needed to lean into and succeed in the things I care deeply about (and arguably, I am best at). With Planhat, I'm honoured to be owning the visual identity and voice of a business at this major inflection point (we're soon to launch the next generation of our product and brand - watch this space); and I'm excited to see where we end up with Altere as we take our first product to market this summer (check it out here).

And yet, some small part of me still feels some sort of insecurity over the fact that after years of toiling over the intricacies of econometrics, statistics, game theory, etc. I now spend my entire day playing almost exclusively with colours, shapes and words. I often think "why did I study so hard for this?" - then I remember that the only reason to do anything is to find the thing you love and spend your life doing it.

And in that sense, I guess almost a decade of mistaken identity did the trick.

Below are my notes on how you can cut the prelude and get straight to the good part.

“The more I build and interact with businesses, the more I see them as stages on which we perform to the world: opportunities to get out of our comfort zone and create things at the edge of our capability.”

A Case of Mistaken Identity

For a decade, I did things because they’re the things smart people are “meant to do”. I worked obsessively hard from a young age, always got the right grades, did the extracurriculars, and so on. I took subjects because they were credible, not because I liked them. I took the most open-ended degree, PPE (Philosophy, Politics & Economics) because it was known at the time as “The degree that runs Britain”, and was associated with smartness. I interned at hedge funds and an American bank because finance earned clout on campus, not because I enjoyed spending eighteen hours a day in Excel. Then I went to business school and did an MSc in Analytics because applied data science is useful, and difficult, and sexy (this last point is dubious, I know). I then found myself in Product Management because (at least at the time) it was the only other “honourable path” for a driven problem-solver with an aversion to the corporate grind. Despite the fact I was doing things I didn’t love at all, I loved every minute of the journey because I love to do difficult things and - again - because I felt somehow that I was spending my time on the “right things”.

But this also meant that I spent a lot more time being quite good at things I didn’t really enjoy, rather than becoming exceptionally good at the things I love. And over time, that started to wear on me. I think a lot of people feel this way at some point in their lives, and some people feel this way for their entire career.

Why I'm Writing This

In early 2022, I read Mastery by Robert Greene (the first of 4 books I think everyone should read in their twenties, alongside: Sethi's "I Will Teach You To Be Rich"; Perkins' "Die with Zero"; and Attia's "Outlive") and decided I needed to figure out how start a career doing my thing.

Its taken two "Stockholm Years", but I finally feel like I'm starting out on the right path. And I've got here by applying a handful of simple principles gathered from countless writers, friends and mentors along the way. If there's even just one thing someone else can learn from my experience, this article has been worth writing. The handbook below is a summary of the ideas that got me from a classic five-day-sprint, two-day recovery working week (Sunday scaries included), to a seven-day routine blending daily creation and rest in whatever measure is needed to bring the vision to life. For the first time, I am creating things not because they are asked or owed of me, but because I feel a creative duty to bring them into the world. It's still early days, but the difference is monumental.

Why Two Parts?

I believe everything in life comes from the environment you're in, and more importantly the mindset you have while occupying it (I've written a little about this with my company Altere Studios). I don't think any guidance could be complete without accounting for both.

Because of the ideas in 01 (finding the environment you need), I ended up sitting in front of Kaveh Rostampor at Planhat. The interview was dramatically different from any job interview I’d had before, and it says enough that I haven’t even considered taking another since. Planhat was (and largely still is) a relatively unknown company to those outside customer success, but it seemed at least from the outside to be a place with an incredibly high density of smart people doing the things they love. Kaveh promised that Planhat would be the place I’d find my niche doing things I actually loved, provided I went all-in with an open mind. Though I’d forego a well-defined title and role, the company was bootstrapped, profitable and remote-first. I couldn't think of any good objections, so I took my chances. It’s taken two years, but I think we both delivered on our promises, in no small part because of the ideas in 02 (becoming yourself).

In short, the guidelines below - in combination with a bunch of incredible sparring partners at Planhat and Altere Studios - have given me the confidence, focus and freedom I've needed to lean into and succeed in the things I care deeply about (and arguably, I am best at). With Planhat, I'm honoured to be owning the visual identity and voice of a business at this major inflection point (we're soon to launch the next generation of our product and brand - watch this space); and I'm excited to see where we end up with Altere as we take our first product to market this summer (check it out here).

And yet, some small part of me still feels some sort of insecurity over the fact that after years of toiling over the intricacies of econometrics, statistics, game theory, etc. I now spend my entire day playing almost exclusively with colours, shapes and words. I often think "why did I study so hard for this?" - then I remember that the only reason to do anything is to find the thing you love and spend your life doing it.

And in that sense, I guess almost a decade of mistaken identity did the trick.

Below are my notes on how you can cut the prelude and get straight to the good part.

“The more I build and interact with businesses, the more I see them as stages on which we perform to the world: opportunities to get out of our comfort zone and create things at the edge of our capability.”

A (sort of) handbook

If you've gotten this far, you know its time for a change and all you need to know is how. Here's my two cents. Again, what works for me might not work for you, but it's a start.

01 The Stage: Finding the Environment You Need

The more I build and interact with businesses, the more I see them as stages on which we perform to the world: opportunities to get out of our comfort zone and create things at the edge of our capability. They perform this function because, among other things, they:

  • pool resources (which allow us to "play bigger" - compete at a higher level);

  • bring people together (which enable us us to focus and specialise); and

  • apply pressure (which force us to make things happen)

These things rarely exist in the same way if you start a business yourself, so the easiest way to be in the right environment is to find a well-established company and work for someone else (I found Planhat, which might also work for you). Starting your own thing comes on the side (mine are Cipity Holdings and Altere Studios ), or later altogether. So here's how I'd go about finding the right company for you.

01.1 Find a Fitting Business

There's lots of things that make businesses good or bad, and despite my time in equity research, I don't claim to know much about it. What I do know is this:

  • profitable businesses give you more time to do things right, which matters a lot when you're learning to do your life's work.


  • medium size businesses (50-200 people) give you more flexibility and visibility than big businesses (200+ people) and more resources and impact than small businesses (<50 people). They let you become "the go-to person" for the thing you love and build a personal brand (more on this below).


  • scalable businesses are on the up, globally speaking. If I'm looking for a sound business that'll become the Stage I need to do what I love, I might go with Uber (ride-hailing software) but I'd never consider ABC Taxis (your local taxi dispatcher). Taxi dispatchers might exist for the next 100 years, but there's no scale advantage to be had, at least not in the same way as Uber. Which might explain why old school cab drivers are always so grumpy.

01.2 Screen Your Manager

Let's say you've found three great companies you're excited to join. Now its time to make sure the person you're working for is going to allow you (read: propel you) to get where you need to be. Here's a series of questions I always asked in my interviews (this is why it's important you're interviewed by someone you'll actually work for/with). If the answer to any of these questions is "no" then one of the other answers would have to be extremely compelling for me to take the job. I've never personally experienced this: normally a "no" means you should terminate the application and find an employer that's worth your time.

  1. mentorship: "have these people mastered their craft?". They don't need to be a master in your craft. The thing with mastery is its an approach - not a skillset: constantly turning up, failing, trying again, failing bigger, etc. So even if your manager is not the best at the thing you want to be doing, as long as they are the best at the thing they do, they have the potential to be a sounding board and mentor. If they are - great, you might get some very targeted coaching. If they're not - potentially better, you'll get fresh perspectives and interdisciplinary inspiration from a true master.


  2. visibility: "when I do things in this role, can I actually see the result or outcome?". Its impossible to get better at hitting your target if you can't see the target. You'll never be able to know the link between the thing you're doing and the outcome, which means you can't calibrate yourself or refine your own practice. So you need to be able to see the result of the thing you did. There are roles that have visible, tangible outcomes like that, and roles that don't. If you want to become exceptional, you yourself need to see the result so you're not relying on others to subjectively calibrate and coach you. Why? Because only you can be pushing yourself all day everyday, testing something and seeing its impact, tweaking it and trying again. The moment you delegate your feedback to someone else, you'll never be able to improve fast enough to become exceptional.


  3. ownership: "in this role, do I own an entire cycle from idea to execution?". There are roles that involve very small repeatable tasks in a given value chain. The entire value chain might appeal to you greatly (say you love cooking and are considering joining a Three Michelin kitchen), but your small part in it (chopping onions) probably won't do it for you after a couple of months. Of course it's fine not to own it all from day 1, but you need to know that you can already own even a very small cycle (say, making the French Onion Soup). While chopping onions is a cog in the machine, owning the French Onion Soup is an entire gear train: you can take feedback from patrons and tweak the recipe infinitely. If it becomes the most loved menu item, you might put the Head Chef out of a job. There is nothing more rewarding than taking an idea (no matter how small) through to execution.


  4. suffering: "when I fail in this role, do I feel pain?". This is perhaps the most important of all. Pain is the greatest teacher. If you mess up, but you don't feel anything because of it, you'll probably just mess up again and again. But if it really hurts, you'll do everything in your power never to mess that thing up again. I never forget to ask "what does failure look like in this role?" and "how will I feel that failure?". In the case of product, failure means your feature didn't solve the pain point it was designed for. Worse, it probably created some confusion that harmed usage of some other suite of features. Your product becomes less loveable. In the case of storytelling, failure means the thing you made didn't resonate with the audience. So if you fail, you get humiliated. You were off the mark. You didn't get it. Your assumptions were wrong and you ran with a delusion. That's painful. You feel like you misunderstood the assignment. So you pay closer attention to the nuances next time.

02 The Performer: Becoming Yourself

You can get started with (02) even if you haven't yet nailed down (01). Here are the key behaviours that I've found to be catalysts when it comes to building a life doing work that you love (and doing it well).

  1. association: figure out a way to describe the thing you identify with, and make sure people know it. I consider myself a storyteller, so I use that word to describe myself. When people need a story told, they think "storyteller" and then they think "Alberto". Yes, it is that simple. You'll become the go-to person for the thing, which gives you an infinite excuse to do what you love.


  2. no ego: no matter how good you are at the thing, there's a million people better than you, and there's also a million different ways someone else can make you better. If you produce a piece of work, no matter how much you love it, it is only genuinely good if it fulfils the purpose it was made for. If I write something and it doesn't resonate, no matter how long it took me, I scrap it and start again. You'll learn to master your craft and your audience and you'll become creatively free because you're unattached to your work.


  3. listen to everyone: it doesn't matter if the person speaking doesn't know the first thing about what you do, how it works, etc. - everyone has different life experiences and skills to you, and therefore everyone has something to contribute to your work. It's your job to filter input for relevance, and assuming the input is relevant, it is your responsibility to rebut it. If you cannot rebut a point someone is making about your work, then you should seriously consider revising your work in light of the rebuttal. This requires you to be extremely meritocratic in the way you work. It doesn't matter where the input comes from: if it is good input, you would be a fool not to act on it. Importantly, always credit good input that shaped your work for the better: whoever gave it will be inclined to give more of it in future. You'll get to know your audience intimately and be able to design your work more consciously around their varying needs.


  4. do the different thing: there are people who are already decades ahead of where you are in doing the thing you love. That means they have a lot of experience. But it also means they've learnt their "way of doing things", and that often makes them closed off to potential sources of innovation and disruption. Humans are creatures of habit. Once we find something that works, we do it again and again both because we consider it to be good enough, and because it becomes comfortable second nature. The greatest creators (the ones that come to my mind immediately are people like Grant Achatz, Virgil Abloh, etc.) force themselves to reinvent their work and throw out old assumptions ritualistically. Learn from them in two ways: 1) look to the unexpected place (e.g., I'm rebuilding Planhat's B2B brand not by looking at other B2B giants, but learning from the world of B2C, luxury goods and old school adverts from the "Mad Men" golden era; 2) force yourself to throw out your existing assumptions and just do something different. Not because you think it will work, but because you think it's going to be fun to do, it doesn't carry any big downsides, and because if it works it might just be the thing that makes a name for you. You'll feel out the boundaries of your craft and eliminate the risk of falling out of love with it by punctuating obsession with playfulness.


  5. steal what's good: at school, copying people is considered to be bad and inauthentic. In real life, every single thing (even the most authentic thing) is a remix of other things. There is nothing truly, completely original (which is why the last point was all about sources of inspiration): originality is just a recombination of ingredients other people already executed exceptionally. When you start out, you should focus on finding the people who do the best work in your space and copying their work 1:1. If you can copy the masters, then you can outdo the masters, too. What you'll find is that there's no such thing as a 1:1 copy if you're actually doing the thing you love. You'll inevitably add a creative flourish, a touch of you, a hint of other inspirations from your lived experience. You just won't be able to help yourself. And then, you'll start to create your original. Your original twist - style - approach. Whatever it is: pick the best, copy them, remix them. I'm too early in the journey to know, but from what I'm told, Mastery comes as a side-effect. You'll find your style at the intersection of the imaginative, diverse approaches you love and wish you had created yourself.

I hope this article has been in some way useful to you. If it has been, reach out and let me know. And of course, Planhat is always looking for curious, daring minds across all functions. So if you're ready to start doing your thing, drop us a line.

Meantime, back to work.

A (sort of) handbook

If you've gotten this far, you know its time for a change and all you need to know is how. Here's my two cents. Again, what works for me might not work for you, but it's a start.

01 The Stage: Finding the Environment You Need

The more I build and interact with businesses, the more I see them as stages on which we perform to the world: opportunities to get out of our comfort zone and create things at the edge of our capability. They perform this function because, among other things, they:

  • pool resources (which allow us to "play bigger" - compete at a higher level);

  • bring people together (which enable us us to focus and specialise); and

  • apply pressure (which force us to make things happen)

These things rarely exist in the same way if you start a business yourself, so the easiest way to be in the right environment is to find a well-established company and work for someone else (I found Planhat, which might also work for you). Starting your own thing comes on the side (mine are Cipity Holdings and Altere Studios ), or later altogether. So here's how I'd go about finding the right company for you.

01.1 Find a Fitting Business

There's lots of things that make businesses good or bad, and despite my time in equity research, I don't claim to know much about it. What I do know is this:

  • profitable businesses give you more time to do things right, which matters a lot when you're learning to do your life's work.


  • medium size businesses (50-200 people) give you more flexibility and visibility than big businesses (200+ people) and more resources and impact than small businesses (<50 people). They let you become "the go-to person" for the thing you love and build a personal brand (more on this below).


  • scalable businesses are on the up, globally speaking. If I'm looking for a sound business that'll become the Stage I need to do what I love, I might go with Uber (ride-hailing software) but I'd never consider ABC Taxis (your local taxi dispatcher). Taxi dispatchers might exist for the next 100 years, but there's no scale advantage to be had, at least not in the same way as Uber. Which might explain why old school cab drivers are always so grumpy.

01.2 Screen Your Manager

Let's say you've found three great companies you're excited to join. Now its time to make sure the person you're working for is going to allow you (read: propel you) to get where you need to be. Here's a series of questions I always asked in my interviews (this is why it's important you're interviewed by someone you'll actually work for/with). If the answer to any of these questions is "no" then one of the other answers would have to be extremely compelling for me to take the job. I've never personally experienced this: normally a "no" means you should terminate the application and find an employer that's worth your time.

  1. mentorship: "have these people mastered their craft?". They don't need to be a master in your craft. The thing with mastery is its an approach - not a skillset: constantly turning up, failing, trying again, failing bigger, etc. So even if your manager is not the best at the thing you want to be doing, as long as they are the best at the thing they do, they have the potential to be a sounding board and mentor. If they are - great, you might get some very targeted coaching. If they're not - potentially better, you'll get fresh perspectives and interdisciplinary inspiration from a true master.


  2. visibility: "when I do things in this role, can I actually see the result or outcome?". Its impossible to get better at hitting your target if you can't see the target. You'll never be able to know the link between the thing you're doing and the outcome, which means you can't calibrate yourself or refine your own practice. So you need to be able to see the result of the thing you did. There are roles that have visible, tangible outcomes like that, and roles that don't. If you want to become exceptional, you yourself need to see the result so you're not relying on others to subjectively calibrate and coach you. Why? Because only you can be pushing yourself all day everyday, testing something and seeing its impact, tweaking it and trying again. The moment you delegate your feedback to someone else, you'll never be able to improve fast enough to become exceptional.


  3. ownership: "in this role, do I own an entire cycle from idea to execution?". There are roles that involve very small repeatable tasks in a given value chain. The entire value chain might appeal to you greatly (say you love cooking and are considering joining a Three Michelin kitchen), but your small part in it (chopping onions) probably won't do it for you after a couple of months. Of course it's fine not to own it all from day 1, but you need to know that you can already own even a very small cycle (say, making the French Onion Soup). While chopping onions is a cog in the machine, owning the French Onion Soup is an entire gear train: you can take feedback from patrons and tweak the recipe infinitely. If it becomes the most loved menu item, you might put the Head Chef out of a job. There is nothing more rewarding than taking an idea (no matter how small) through to execution.


  4. suffering: "when I fail in this role, do I feel pain?". This is perhaps the most important of all. Pain is the greatest teacher. If you mess up, but you don't feel anything because of it, you'll probably just mess up again and again. But if it really hurts, you'll do everything in your power never to mess that thing up again. I never forget to ask "what does failure look like in this role?" and "how will I feel that failure?". In the case of product, failure means your feature didn't solve the pain point it was designed for. Worse, it probably created some confusion that harmed usage of some other suite of features. Your product becomes less loveable. In the case of storytelling, failure means the thing you made didn't resonate with the audience. So if you fail, you get humiliated. You were off the mark. You didn't get it. Your assumptions were wrong and you ran with a delusion. That's painful. You feel like you misunderstood the assignment. So you pay closer attention to the nuances next time.

02 The Performer: Becoming Yourself

You can get started with (02) even if you haven't yet nailed down (01). Here are the key behaviours that I've found to be catalysts when it comes to building a life doing work that you love (and doing it well).

  1. association: figure out a way to describe the thing you identify with, and make sure people know it. I consider myself a storyteller, so I use that word to describe myself. When people need a story told, they think "storyteller" and then they think "Alberto". Yes, it is that simple. You'll become the go-to person for the thing, which gives you an infinite excuse to do what you love.


  2. no ego: no matter how good you are at the thing, there's a million people better than you, and there's also a million different ways someone else can make you better. If you produce a piece of work, no matter how much you love it, it is only genuinely good if it fulfils the purpose it was made for. If I write something and it doesn't resonate, no matter how long it took me, I scrap it and start again. You'll learn to master your craft and your audience and you'll become creatively free because you're unattached to your work.


  3. listen to everyone: it doesn't matter if the person speaking doesn't know the first thing about what you do, how it works, etc. - everyone has different life experiences and skills to you, and therefore everyone has something to contribute to your work. It's your job to filter input for relevance, and assuming the input is relevant, it is your responsibility to rebut it. If you cannot rebut a point someone is making about your work, then you should seriously consider revising your work in light of the rebuttal. This requires you to be extremely meritocratic in the way you work. It doesn't matter where the input comes from: if it is good input, you would be a fool not to act on it. Importantly, always credit good input that shaped your work for the better: whoever gave it will be inclined to give more of it in future. You'll get to know your audience intimately and be able to design your work more consciously around their varying needs.


  4. do the different thing: there are people who are already decades ahead of where you are in doing the thing you love. That means they have a lot of experience. But it also means they've learnt their "way of doing things", and that often makes them closed off to potential sources of innovation and disruption. Humans are creatures of habit. Once we find something that works, we do it again and again both because we consider it to be good enough, and because it becomes comfortable second nature. The greatest creators (the ones that come to my mind immediately are people like Grant Achatz, Virgil Abloh, etc.) force themselves to reinvent their work and throw out old assumptions ritualistically. Learn from them in two ways: 1) look to the unexpected place (e.g., I'm rebuilding Planhat's B2B brand not by looking at other B2B giants, but learning from the world of B2C, luxury goods and old school adverts from the "Mad Men" golden era; 2) force yourself to throw out your existing assumptions and just do something different. Not because you think it will work, but because you think it's going to be fun to do, it doesn't carry any big downsides, and because if it works it might just be the thing that makes a name for you. You'll feel out the boundaries of your craft and eliminate the risk of falling out of love with it by punctuating obsession with playfulness.


  5. steal what's good: at school, copying people is considered to be bad and inauthentic. In real life, every single thing (even the most authentic thing) is a remix of other things. There is nothing truly, completely original (which is why the last point was all about sources of inspiration): originality is just a recombination of ingredients other people already executed exceptionally. When you start out, you should focus on finding the people who do the best work in your space and copying their work 1:1. If you can copy the masters, then you can outdo the masters, too. What you'll find is that there's no such thing as a 1:1 copy if you're actually doing the thing you love. You'll inevitably add a creative flourish, a touch of you, a hint of other inspirations from your lived experience. You just won't be able to help yourself. And then, you'll start to create your original. Your original twist - style - approach. Whatever it is: pick the best, copy them, remix them. I'm too early in the journey to know, but from what I'm told, Mastery comes as a side-effect. You'll find your style at the intersection of the imaginative, diverse approaches you love and wish you had created yourself.

I hope this article has been in some way useful to you. If it has been, reach out and let me know. And of course, Planhat is always looking for curious, daring minds across all functions. So if you're ready to start doing your thing, drop us a line.

Meantime, back to work.

A (sort of) handbook

If you've gotten this far, you know its time for a change and all you need to know is how. Here's my two cents. Again, what works for me might not work for you, but it's a start.

01 The Stage: Finding the Environment You Need

The more I build and interact with businesses, the more I see them as stages on which we perform to the world: opportunities to get out of our comfort zone and create things at the edge of our capability. They perform this function because, among other things, they:

  • pool resources (which allow us to "play bigger" - compete at a higher level);

  • bring people together (which enable us us to focus and specialise); and

  • apply pressure (which force us to make things happen)

These things rarely exist in the same way if you start a business yourself, so the easiest way to be in the right environment is to find a well-established company and work for someone else (I found Planhat, which might also work for you). Starting your own thing comes on the side (mine are Cipity Holdings and Altere Studios ), or later altogether. So here's how I'd go about finding the right company for you.

01.1 Find a Fitting Business

There's lots of things that make businesses good or bad, and despite my time in equity research, I don't claim to know much about it. What I do know is this:

  • profitable businesses give you more time to do things right, which matters a lot when you're learning to do your life's work.


  • medium size businesses (50-200 people) give you more flexibility and visibility than big businesses (200+ people) and more resources and impact than small businesses (<50 people). They let you become "the go-to person" for the thing you love and build a personal brand (more on this below).


  • scalable businesses are on the up, globally speaking. If I'm looking for a sound business that'll become the Stage I need to do what I love, I might go with Uber (ride-hailing software) but I'd never consider ABC Taxis (your local taxi dispatcher). Taxi dispatchers might exist for the next 100 years, but there's no scale advantage to be had, at least not in the same way as Uber. Which might explain why old school cab drivers are always so grumpy.

01.2 Screen Your Manager

Let's say you've found three great companies you're excited to join. Now its time to make sure the person you're working for is going to allow you (read: propel you) to get where you need to be. Here's a series of questions I always asked in my interviews (this is why it's important you're interviewed by someone you'll actually work for/with). If the answer to any of these questions is "no" then one of the other answers would have to be extremely compelling for me to take the job. I've never personally experienced this: normally a "no" means you should terminate the application and find an employer that's worth your time.

  1. mentorship: "have these people mastered their craft?". They don't need to be a master in your craft. The thing with mastery is its an approach - not a skillset: constantly turning up, failing, trying again, failing bigger, etc. So even if your manager is not the best at the thing you want to be doing, as long as they are the best at the thing they do, they have the potential to be a sounding board and mentor. If they are - great, you might get some very targeted coaching. If they're not - potentially better, you'll get fresh perspectives and interdisciplinary inspiration from a true master.


  2. visibility: "when I do things in this role, can I actually see the result or outcome?". Its impossible to get better at hitting your target if you can't see the target. You'll never be able to know the link between the thing you're doing and the outcome, which means you can't calibrate yourself or refine your own practice. So you need to be able to see the result of the thing you did. There are roles that have visible, tangible outcomes like that, and roles that don't. If you want to become exceptional, you yourself need to see the result so you're not relying on others to subjectively calibrate and coach you. Why? Because only you can be pushing yourself all day everyday, testing something and seeing its impact, tweaking it and trying again. The moment you delegate your feedback to someone else, you'll never be able to improve fast enough to become exceptional.


  3. ownership: "in this role, do I own an entire cycle from idea to execution?". There are roles that involve very small repeatable tasks in a given value chain. The entire value chain might appeal to you greatly (say you love cooking and are considering joining a Three Michelin kitchen), but your small part in it (chopping onions) probably won't do it for you after a couple of months. Of course it's fine not to own it all from day 1, but you need to know that you can already own even a very small cycle (say, making the French Onion Soup). While chopping onions is a cog in the machine, owning the French Onion Soup is an entire gear train: you can take feedback from patrons and tweak the recipe infinitely. If it becomes the most loved menu item, you might put the Head Chef out of a job. There is nothing more rewarding than taking an idea (no matter how small) through to execution.


  4. suffering: "when I fail in this role, do I feel pain?". This is perhaps the most important of all. Pain is the greatest teacher. If you mess up, but you don't feel anything because of it, you'll probably just mess up again and again. But if it really hurts, you'll do everything in your power never to mess that thing up again. I never forget to ask "what does failure look like in this role?" and "how will I feel that failure?". In the case of product, failure means your feature didn't solve the pain point it was designed for. Worse, it probably created some confusion that harmed usage of some other suite of features. Your product becomes less loveable. In the case of storytelling, failure means the thing you made didn't resonate with the audience. So if you fail, you get humiliated. You were off the mark. You didn't get it. Your assumptions were wrong and you ran with a delusion. That's painful. You feel like you misunderstood the assignment. So you pay closer attention to the nuances next time.

02 The Performer: Becoming Yourself

You can get started with (02) even if you haven't yet nailed down (01). Here are the key behaviours that I've found to be catalysts when it comes to building a life doing work that you love (and doing it well).

  1. association: figure out a way to describe the thing you identify with, and make sure people know it. I consider myself a storyteller, so I use that word to describe myself. When people need a story told, they think "storyteller" and then they think "Alberto". Yes, it is that simple. You'll become the go-to person for the thing, which gives you an infinite excuse to do what you love.


  2. no ego: no matter how good you are at the thing, there's a million people better than you, and there's also a million different ways someone else can make you better. If you produce a piece of work, no matter how much you love it, it is only genuinely good if it fulfils the purpose it was made for. If I write something and it doesn't resonate, no matter how long it took me, I scrap it and start again. You'll learn to master your craft and your audience and you'll become creatively free because you're unattached to your work.


  3. listen to everyone: it doesn't matter if the person speaking doesn't know the first thing about what you do, how it works, etc. - everyone has different life experiences and skills to you, and therefore everyone has something to contribute to your work. It's your job to filter input for relevance, and assuming the input is relevant, it is your responsibility to rebut it. If you cannot rebut a point someone is making about your work, then you should seriously consider revising your work in light of the rebuttal. This requires you to be extremely meritocratic in the way you work. It doesn't matter where the input comes from: if it is good input, you would be a fool not to act on it. Importantly, always credit good input that shaped your work for the better: whoever gave it will be inclined to give more of it in future. You'll get to know your audience intimately and be able to design your work more consciously around their varying needs.


  4. do the different thing: there are people who are already decades ahead of where you are in doing the thing you love. That means they have a lot of experience. But it also means they've learnt their "way of doing things", and that often makes them closed off to potential sources of innovation and disruption. Humans are creatures of habit. Once we find something that works, we do it again and again both because we consider it to be good enough, and because it becomes comfortable second nature. The greatest creators (the ones that come to my mind immediately are people like Grant Achatz, Virgil Abloh, etc.) force themselves to reinvent their work and throw out old assumptions ritualistically. Learn from them in two ways: 1) look to the unexpected place (e.g., I'm rebuilding Planhat's B2B brand not by looking at other B2B giants, but learning from the world of B2C, luxury goods and old school adverts from the "Mad Men" golden era; 2) force yourself to throw out your existing assumptions and just do something different. Not because you think it will work, but because you think it's going to be fun to do, it doesn't carry any big downsides, and because if it works it might just be the thing that makes a name for you. You'll feel out the boundaries of your craft and eliminate the risk of falling out of love with it by punctuating obsession with playfulness.


  5. steal what's good: at school, copying people is considered to be bad and inauthentic. In real life, every single thing (even the most authentic thing) is a remix of other things. There is nothing truly, completely original (which is why the last point was all about sources of inspiration): originality is just a recombination of ingredients other people already executed exceptionally. When you start out, you should focus on finding the people who do the best work in your space and copying their work 1:1. If you can copy the masters, then you can outdo the masters, too. What you'll find is that there's no such thing as a 1:1 copy if you're actually doing the thing you love. You'll inevitably add a creative flourish, a touch of you, a hint of other inspirations from your lived experience. You just won't be able to help yourself. And then, you'll start to create your original. Your original twist - style - approach. Whatever it is: pick the best, copy them, remix them. I'm too early in the journey to know, but from what I'm told, Mastery comes as a side-effect. You'll find your style at the intersection of the imaginative, diverse approaches you love and wish you had created yourself.

I hope this article has been in some way useful to you. If it has been, reach out and let me know. And of course, Planhat is always looking for curious, daring minds across all functions. So if you're ready to start doing your thing, drop us a line.

Meantime, back to work.

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An abstract render of a Planhat customer profile, including timeseries data and interaction records from Jira and Salesforce.

Thought-leading customer-centric content, direct to your inbox every month.

Thought-leading customer-centric content, direct to your inbox every month.

Thought-leading customer-centric content, direct to your inbox every month.