On Founders, Creators, and Employees 🎭
Thoughts and learnings about the various professional experiences I have had so far.
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Hey everyone — this is a more personal piece than usual, where I reflect on the various professional experiences I have had so far, and the main differences between them.
I am writing it because at various points in my life people were puzzled about what I did for a living, or they thought they understood it while they really didn’t.
There are plenty of myths and misconceptions about the work of founders, creators, and even regular employees. I have friends in all categories, and I found that when people build a strong identity around some role, they tend to become defensive and skeptic of the other ones.
This piece dispels some of such myths, while also shedding light on some parts that I believe we don’t talk enough about.
🙋♂️ About me
My career so far has been made of three main experiences:
I have been co-founder and CTO of Wanderio for 8 years — I raised ~$4M in Italy, grew a 20-ish people team, and served 25M+ customers.
I have been Head of Engineering of Translated for about one year — a larger, 150-people tech company working with AI and translation services.
I am now the creator / writer of Refactoring — the very newsletter you are reading right now.
These experiences were all very different one from another, both in ways I expected, and others that I didn’t. Also, I didn’t plan for things to look like this. They pretty much unfolded in their own way, and I hope I will be able to connect the dots backwards, one day.
I am extremely grateful for having experiences that are so diverse. Today, I feel I am more equipped to make the right calls for my life, and I also have a clearer picture of what I want to achieve and the lifestyle I desire.
The goal of this article is to pass you some of such learnings that have been important and counterintuitive to me.
🍀 The Four Quadrants
There are possibly infinite ways to dissect the differences between jobs.
I have found that a useful one to reflect on what the lifestyle is like and what’s the best for you, is based on two coordinates:
Community: team-based work vs individual work
Autonomy: high autonomy vs low autonomy
This separation is clear to me now. I understand why such qualities matter to me, and why others don’t, but it hasn’t always been like this.
When I was younger, I was obsessed with impact. As a founder, when people asked me what I loved about startups, I always replied: impact!
But what is impact, really?
Impact is our idea of how much our work matters. I argue that in most cases, this idea shouldn’t be trusted.
🔮 Impact is a fallacy
Impact is unreliable for two main reasons: it is hard to measure, and it is subjective.
1) Impact is hard to measure
Our actions have first, second and third order consequences that are hard to fully grasp.
For example, as an entrepreneur, you live in the trenches and you have the opportunity to see the first-order impact of your work. This is enthrilling, but is it the only way to do meaningful work?
In my last years of university, I didn’t even know what a startup was, until I attended a course on entrepreneurship. The course was held by a gifted professor, and it had a decisive influence on me — I went on to found a startup right after my M.Sc.
How should this professor evaluate his own impact? Is it the combined impact of the startups he helped to create? Is it higher or lower than that of the individual entrepreneurs he influenced?
As a writer, I feel that my impact now is higher than ever, because I have the leverage to help thousands of people at the same time. Still, I don’t fully trust this feeling, because 👇
2) Impact is subjective
I know several people who work at Google.
A couple of years ago, I happened to have chats with two of them, within a matter of days. I asked each of them how things were going and if they were happy with their work (they both came from a startup environment).
The first person was very happy. She could see her work being used by billions of people — it was a dramatic shift in scale and perspective from her previous job.
The second person was not happy, because she felt she had become just a small gear in a large machine.
They both described their impact (high vs low) as if it was an objective truth, failing to see how their personal preferences about the environment, culture, and style of work influenced their judgement.
Today, I don’t trust myself to evaluate my own impact, so I ask myself mostly two questions:
Is what I do a net positive to the world? I have found that this is an easier question to answer, and I don’t bother to calculate how much of a net positive it is.
Do I enjoy doing it? This question is more profound than it may seem. Enjoying what you do is a clue for many things, including that your values are aligned with those of that company / activity; that you feel an intrinsic reward for it; that the workload is sustainable, and more.
So, if impact shouldn’t be trusted, what are the defining differences between the various types of work?
When I was a founder, other than impact, I cared a lot about autonomy. That was the crucial difference, to me, with an employee.
I still stand by it, but I also think such a difference might be overplayed sometimes.
When you join a healthy company in a role where you have a good amount of responsibility, you can still experience a good degree of autonomy. Granted, you have more stakeholders and boundaries, but you can still feel the weight of your decisions.
When I joined Translated after my startup, I held a hybrid role as a Head of Engineering who also had product management responsibilities on some internal products. In more ways than not, my daily routine and activities resembled those from my “co-founder & CTO” times.
What I struggled more with, in retrospect, was my sense of identity.
After seeing myself as a founder for 8 years, it was disconcerting to leave that behind. Being a founder is such a radical choice that it easily becomes a big part of your identity and your sense of self-worth. If you let that happen, you may become blind to other opportunities, and to the virtues of different lifestyles. You may also become unhappy with doing anything else — in a way that is totally irrational and self-inflicted.
Paul Graham wrote a wonderful piece about keeping your identity small. I argue that one of the best ways to do so is by trying many different things.
So, my work as an employee turned out to be somewhat close to my founder's one.
As I understood later, a big part of what made the work familiar was the sense of community.
When I left Translated to work on Refactoring, I thought the vibes would be similar to that of my previous startup.
Got my founder hat once again, guys, let’s sail ARRR 🏴☠️
— more or less what I told everybody at that time
Now, while I found the same, intoxicating degree of autonomy that I enjoyed in my startup, I also found myself in a largely different routine: I had to work completely by myself.
Regular work in a company, whether you are a founder or an employee, provides you with a place in the world where you belong. This is stronger, of course, if you work in an office, but it doesn’t really go away even if you work remotely.
A big part of it is about being part of a community where you feel useful and you work with others towards a goal. It is very powerful.
Conversely, when the work becomes completely centered on yourself, many things change, for the better or worse.
Here are the biggest changes that I noticed:
1) Self-reflection & motivation 🧘
I am now more acutely aware of my own state all the time. I understand my motivation, productivity, and even physical wellbeing, better than ever before.
This was a necessity.
When you work by yourself, nothing gets done if it’s not you doing it. It might seem trivial, but think about it: in a company, you can have a slow day and still get a bunch of things done: meetings, a chat with a colleague about a design problem, 1:1s, pair programming, and more. The flow of things happening around you carries you forward and reduces the fatigue of deciding to do anything.
When you work alone, instead, every bit of work that you do is intentional. This is empowering, but it also means that you are spending decision energy on literally everything.
As a creator, you have less friction if you want to take a day off. But this also means you have more friction to do a normal day of work.
To fight this, I do two things:
📣 Commit publicly — to friends, to my readers, to people on Twitter, on the things that I will do. This creates accountability and makes it easier for me to get anything done.
🔄 Create processes — I organize my time carefully, create recurring activities, block time on my calendar, and more. Feeling that I am part of a larger process helps me get going and get into a state of flow. I wrote more about how I manage my time here 👇
2) Social isolation 🏔️
Working by yourself can not only affect your motivation, but also loosen your ties with peers and colleagues. Think of it as similar to the shift to remote work, but 10x.
For most people, in fact, the company they work for contributes to a big chunk of their professional network. Without that, you need intentional work to nurture these relationships.
And I don’t think there is any need to say this, but I will say it anyway: good professional relationships are incredibly important. In my case, here are some of the things they helped me with:
Getting out of my head / echo chamber
Getting validation (or invalidation!) for what I am doing
Finding professional opportunities
Staying in touch with industry trends
Just human connection
To break isolation and nurture my network, here is what I do:
💬 Hang out in internet communities — I am active in various communities, including, of course, the Refactoring one. This is the base layer of my network.
🍻 Touch base with my work friends — I built a small CRM on Notion to keep track of the people I want to stay in touch with (more on that in an upcoming article!) and reach out to them frequently.
💂♀️ Personal board of directors — following Gibson Biddle’s advice, I built a close circle of friends that I consider my “personal board of directors”. I reach out to them for advice about the various areas of my life, and I also give it back whenever I can.
💼 Consulting — I spend 10-20% of my time doing some consulting on the topics I cover on Refactoring. This helps me stay grounded, have work interactions with people, and it mitigates the risk of eventually turning into an “ivory tower writer”.
📌 Closing notes — what should you choose?
When I was a founder, my friends who were employees looked at me suspiciously. Then, my founder friends gave me the same looks when I joined a larger company as an employee myself. Today, almost everybody is puzzled by what I do with Refactoring.
Ultimately, whatever other people do, it’s on you to figure out what your journey should be. Or, more simply, what the next step should be.
This article has no pretense of being exhaustive. I definitely haven’t seen it all — I never worked in a FAANG, never worked in a web agency, never grew a 100 or 1000-people company as a founder, and more. So this is more of an arbitrary slice about the things that mattered the most to me, and that I learned along the way.
If I had to start fresh, here are some things that would help me decide what to do with my life:
🎯 Ask yourself what you can do that is a net positive to the world and you would probably enjoy — trust your gut on this. It’s totally ok to be wrong; you will learn and adjust. Also, what you enjoy will likely change over time.
🎒 Ask yourself what degree of autonomy you like — if you don’t know, look for clues: do you enjoy making decisions? Do you seek hobbies where you experience such freedom? Are you bored by open-world games? (less stupid question than it seems).
🤗 Figure out how much community matters to you — are you energized by the idea of working daily on a great team? Or, do you envision getting up every morning and calmly going through your tasks by yourself?
🤹 Try things as side projects — you won’t be able to understand many of these things unless you try them (yes, this article won’t help). That includes both things about the world and yourself. So, try them! Refactoring started as a 1-hour-a-day side-gig. I only went full-time when I was confident that 1) I liked it, and 2) I could turn it into a business.
🍻 Talk with people — reach out to those you admire and whose careers you would like to mimic. What is it like to be a founder? Or a VP of Engineering? Ask them what it’s all about, and, eventually, get advice on how to get there!
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This hits the nail on the head! I've had kind of a similar path, minus the shift to creator. Started as co-founder & CTO right after my masters, shift to employee in a large enterprise, then switch back to co-founder & CTO.
In the first instance the team was too small, I at most had 1 or 2 colleagues at times, and most of it I was the only technical person. As a result, the part I struggle with the most is the network. Not easy forming one when your job doesn't provide at least a way in.