It’s practically a truism that aspiring product managers should start side projects in order to show some combination of ambition, product sense, grit, technical skills, motivation, and then some. But how do you actually approach working on these projects? To find out, I spoke with Jerry Registre, a former Google APM intern, as well as Diego Granados, who’s quickly establishing himself as one of the preeminent product management YouTuber/LinkedInfluencer/Clubhouse-ers on the internet.
What emerged wasn’t a step-by-step guide detailing which products to build or which tutorials to follow, but rather a mindset and framing that reveals the fundamental value proposition of side projects.
The first notion we need to dispose of is the showmanship that comes with a side project. “A lot of people think that to have a side project, you have to have the CEO title. At the beginning, when I was just starting to be active on LinkedIn, I was reading all of these. There’s the ‘Who saw your profile’ and I suddenly started seeing CEO of whatever company, co-founder and CEO of whatever company, so many of those, I was like, ‘Wow, I’m doing something really great. I’m attracting all these CEOs.’” Diego says about when he first started out on LinkedIn. “Fast forward to today. I know that many of them are side projects, which is awesome. But there’s a misconception that you have to be the CEO, the founder.”
Diego is referring to the fundamental misunderstanding of side projects, that they are first and foremost supposed to succeed externally, a badge to be worn on your profile.
Now there’s nothing wrong with dreaming big. “I like to just imagine all the crazy things that could happen. But at the same time, you don’t want to be attached to some outcome that you haven’t gotten,” says Jerry. Even he entertains the moonshots, the “throwaway what-ifs?” But in the end, he’s “making the videos for me, and I detach myself from the outcome and it’s going to be a successful thing.”
That’s the key. Detaching the process from the outcome. Because the process is really what these projects are about.
As a kid, I wanted to play in the NBA for my hometown Dallas Mavericks. I would spend entire afternoons with the hoop in my backyard, imagining the ball in my hands, the team down 2 points with seconds left to play. In my world, I would always make the game-winning shot.
In middle school, I joined the 6th grade basketball team. I didn’t try very hard in practice, perhaps deluded by all those afternoons of imaginary game winners. I thought I would just be great when the games came around.
I was not, and I quit the team after that year.
It’s perhaps unreasonable to fault a middle-schooler for not having a well-thought-out plan, but let’s just take a look at my approach:
- I had a dream with an end-goal, but no plan to get there
- I assumed repeated attempts at the “real thing” (playing in games) would be enough for me to upskill
- I didn’t take any steps to identify why I sucked in games, and definitely didn’t do anything to fix my shortcomings
It would be ridiculous to imagine a professional athlete succeeding by only playing in games and skipping practice. In fact, almost all of the most revered athletes have work ethics to match.
Building a side project to be its CEO is a product manager’s equivalent of playing in games without practicing. In fact, the whole conception of side projects is backwards. The project isn’t the thing you build — that’s merely an implementation, the exercise you’re doing.
The real project is the skill you’re acquiring.
Explanations of “deliberate practice” are a dime a dozen, but the habits-focused author James Clear extracts the most relevant point here:
Deliberate practice requires focused attention and is conducted with the specific goal of improving performance (source)
Product management cliches tell us to “focus on the problem, not on solutions.” A side project should originate from a skill, something you need to practice in order to become a better product manager.
When it comes to picking side projects, Jerry has a three part formula he considers. He broke it down for me using his YouTube channel as an example:
1. Personal interest
“[YouTube is] something that I think is very cool. I think YouTubers, the whole video scene, are very interesting. I’m personally awed by it.”
Fundamentally, anything we do has to start with an internal motivation. Successful entrepreneurs spend years falling in love with the problem they’re solving, and at a more approachable level, we need to be interested by whatever we’re doing to have any shot at following through with it.
2. Practicality and usefulness of skills
“Video editing, being able to storytell, to craft content, and to share a message in a way that’s quick and to the point while being interesting is quite a fascinating skill. I haven’t gotten to practice it in other mediums. So I see something that’s training me and teaching me those skills as I do it.”
We’re seeing a two-birds-with-one-stone efficiency emerge. Personal interest is what hooks us into a project, but recognizing its underlying first principles is what turns this from a curiosity into a self-improvement exercise.
3. Fitting into a roadmap
“I’m going be a PM and more generally, I’m going to want to build things that solve problems that are worth solving in interesting ways. And I think being able to storytell is super important to influence within a company or inspire people to join your project and work with you in whatever initiative that you want. So [storytelling] has a place within the things that I think I’m going to be doing in the future.”
Tying the skills practiced back to the larger narrative gives this side project a goal-focused orientation. Not only has Jerry found an exercise that successfully hones a skill, and has the interest factor to keep him hooked, he also found a skill that moves him further along his ultimate goal of becoming a more effective PM.
When all three benefits align, from the micro up to the macro, a side project has the necessary ingredients to become multiplier on yourself.
This is just the product management framing of his channel. What he didn’t even mention is that the channel is entirely in Spanish, and its conceit is that it’s a Spanish-lesson-slash-journal. We could run through these three steps again, with “becoming fluent in Spanish” as the motivating skill here, and the project would stand up just as well.
Notice though, all of his motivations and explanations derive from the skills he’s building. He’s not aiming to go viral, or to snag a DuoLingo sponsorship.
Diego has a similar skill-based orientation around what side projects to take on. He says “When you’re starting, before jumping into any project, you need to figure out ‘What are the skills that I need to learn?’ If it’s a technical role that I want, then figure out what side project can give you that. If it’s more a PM thing, where it’s more on the soft skills, then what kind of side project is going to help you with communication, where you need to write a lot of emails, write a lot of documents. It’s figuring out the skills.”
Once you embrace the notion that side projects are skill-focused rather than product focused, you can start to see many different variations of side projects all around you.
For starters, and even though it’s obvious by now, I asked Diego if he considered his channel to be a side project even though it didn’t involve coding. “100%!” he said. “This is a side project that I’m adding on my resume. A side project doesn’t have to be an app or a website.” He mentions storytelling, conciseness, and literally producing videos among the skills he’s been honing throughout this process.
A YouTube channel still has an immediate, identifiable output though, but even that is not strictly necessary to achieve the benefits of side projects.
“Academically different disciplines allow you to think about a problem in different ways” Jerry says. He’s studied stem cell biology alongside computer science in school, and his internship career started in consulting before moving to product management. “So think, studying computer science, while I’m in the lab. I’m going through gene sequencing. I’m curious as to ‘How could I build something that processes all these gene sequences and create primers for me using computer science?’ or ‘Artistically, why is it that cells are shaped this way?’ These disciplines have a funny way of interacting with each other.”
Exposure to different fields is an immense advantage to product managers, even if that work and knowledge doesn’t immediately manifest as something tangible.
There’s a famous story Steve Jobs told in his 2005 Stanford Commencement:
Reed College at that time offered perhaps the best calligraphy instruction in the country. Throughout the campus every poster, every label on every drawer, was beautifully hand calligraphed. Because I had dropped out and didn’t have to take the normal classes, I decided to take a calligraphy class to learn how to do this. I learned about serif and sans serif typefaces, about varying the amount of space between different letter combinations, about what makes great typography great. It was beautiful, historical, artistically subtle in a way that science can’t capture, and I found it fascinating.
None of this had even a hope of any practical application in my life. But 10 years later, when we were designing the first Macintosh computer, it all came back to me. And we designed it all into the Mac. It was the first computer with beautiful typography. If I had never dropped in on that single course in college, the Mac would have never had multiple typefaces or proportionally spaced fonts.
His knowledge about fonts never had “a hope of any practical application in [his] life” at the time he took the classes, but it eventually made its way into one of the defining characteristics of the Mac, and Apple’s design culture as a whole. Jerry elaborates on that process: “Most things, whether they have a direct or an indirect connection, gaining context and different disciplines, different interests, both academically, but also just like dancing, art, music, sports, are all just data points on life. They can collect. And then when it comes time for you to do things, whether they’re professional or personal, it allows you to draw from all these different areas of life to build these unique situations and unique solutions and unique perspectives. Or at least be able to know that there’s other ways of doing things.”
Side projects don’t have to be groundbreaking. They don’t have to produce a net-new product into the world. They don’t have to produce anything. As long as the knowledge they provide accrues in your head, you’ll have had a productive, valuable side project.
By now it should be clear that my interpretation of “side project” is not any specific product you build, but rather a framework. It’s a framework for practicing, and for approaching a self-focused iteration cycle.
Let’s get really meta: Diego has a full time job at Microsoft, a family, and is working towards his second Master’s Degree at Georgia Tech in addition to producing videos for his YouTube channel. When I asked him how he has time for all of this, he reached all the way back and told me that he had to make sure his life was in order before he could make time for something new. Starting with sleep and establishing a routine of getting 8 hours every night, knowing that rest and health was the foundation of his ability to do anything. Identifying other unhealthy habits to eliminate from his routine to make time to work on the channel. In other words, his first side project was “tweaks and bugs fixes to his daily life.” Really, anything can be a side project.
It’s the same work that product managers do day in and day out: prioritize features, invest in the foundations. It’s the skills that Diego developed at work that are powering these improvements to his life, it’s these improvements to his life that enable his side projects, and it’s these side projects that feed back into his work and enable to perform even better as a product manager. It’s a virtuous cycle.
So take that as your motivation for side projects. Don’t worry about picking the latest tech stack, the best tutorials, or the flashiest business model. Turn your focus inwards, reflect on the skills you want to develop, and leverage your energy to build a side project that lets you practice them.
After all, as a product manager, your first and best product should be yourself.
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