Five lessons I’ve learned from five years at a startup.

I've been working at Grammarly for five years, and in this post I share the five most impactful lessons I've learned throughout this time.

Over the last five years, I’ve been working as a product manager at Grammarly, a startup trying to improve people’s communication through AI writing tools. When I started, we were about 100 people and had two offices in San Francisco and Kyiv. Today, there are over 1000 employees remotely distributed across many countries, with hubs where people can gather in person in San Francisco, Vancouver, Seattle, New York, Berlin, and Kyiv.

I wanted to use this post to codify the most important lessons I’ve learned from my last half decade at Grammarly. Some of these lessons may be useful to you, some might be things you already knew, and some might not be relevant at all. That’s okay. My goal in writing them in this blog post is to ensure I have a quick reference guide for myself.

The five lessons I’ve learned are:

1. Invest for success.

2. Boring = successful.

3. People >> work.

4. 10% vs. 10x.

5. Don’t forget about fun.

Invest for success.

I’ve seen many examples of people spreading themselves too thin by simultaneously working on too many things. I frequently made this problem early on in my career, working on my full-time job, this blog, my fitness, one or multiple side projects, and so on. In reality, I was really only making progress on my full-time job and making marginal to negligible progress on everything else. Either that or I was getting only a few hours of sleep every night and would get sick every other week.

And I wasn’t the exception. People tend to set too many goals rather than not enough goals. The issue isn’t a lack of ambition. It’s a lack of focus. Jeff Bezos famously said that leaders don’t need to make hundreds of decisions every day. Instead, they need to make several high-quality decisions every day. I strongly resonate with this idea and believe it applies to tasks and projects I’m working on as well. It’s a question of focus.

But over the last few years, I have found it harder to focus. I read a great book on this topic called Stolen Focus. It aims to explain the seemingly universal feeling we all seem to have that we can’t focus as well as we used to. The author tries to explain whether that feeling we all share is, in fact, the reality (spoiler alert: it is) and, if so, what might be causing this inability to focus. However, I don’t think it has great strategies for how to actually solve the problem of reduced focus, so if you’re looking for actual strategies and tactics, I’d recommend a Huberman podcast or some tried-and-true books (Atomic Habits, Flow).

Anyway, the strange thing about this? Ruthlessly prioritizing what to do and ultimately deciding to do fewer but more impactful things was my job at Grammarly. As a product manager, most of the job is figuring out how to get the most impact for the business with limited resources. Many of the decisions I’d make are to say no to things we could do in favor of something more impactful. It wasn’t just a question of the end result but of the return on investment.

So here’s the lesson I’ve learned: My time and energy are assets I can invest. I can choose to spread that investment across a lot of things (i.e., spread myself too thin), or I can choose to invest in a few very impactful things and be successful.

Boring = successful.

Think about the most impactful product or tool you use daily. Perhaps it’s your phone or car. Now, how well do you actually know how those underlying technologies work?

I don’t really know how computers work. And by extension, I don’t really know how phones work. How do silicon chips come together to make the internet that lets me browse memes on Instagram or FaceTime with my friends and family worldwide?

If you take the time to look at the technology powering phones, it’s absolutely insane. Layers upon layers of complexity are all built on top of each other and incorporate decades of research from the brightest minds we’ve ever seen.

As a user, I see none of this complexity. I just use the magical box in my hand that can call, text, browse, navigate, charge, and even fall without breaking. And trust me, I drop my phone often.

At Grammarly, I noticed an interesting phenomenon that I couldn’t quite explain at first. We spent so much attention and care to what seemed like quite simple and trivial things – should we show this underline on top of the other? Should we stop showing this pop-up after three times or four times? How many milliseconds after the user stops writing do we start giving them suggestions?

At first, these questions seemed trivial and potentially even overkill. But the reality is that getting to that level of optimization and detail takes decades of work. Every small decision made can either improve or degrade the product, and a concatenation of thousands or millions of improving decisions leads to an incredible and successful product.

In fact, to the user, the product should seem boring. If a user considers it boring and commonplace that we can analyze their text using AI in real-time and make suggestions right in the text field on any device or application, that’s a win. Because although I consider my phone boring, I use it every day for multiple hours.

My lesson learned here: strive to build something that abstracts away the complexity of the underlying technology and instead create something that seems so simple people find it boring.

People >> work.

The third lesson I learned was about the importance of the people you’re working with over the work you’re doing.

First, a caveat – the work you do does matter. Everyone’s preferences are different, and some people may care more or less about the actual role or the field they’re working in. My point here isn’t that you should do any job you’re offered as long as the people are cool. Rather, I’m trying to capture the relative importance.

So why are the people more important than the work itself? Because what you’re working on can radically change day-to-day or quarter-to-quarter, but the people you work with and the meaningful relationships you make will follow you through as friends, mentors, investors, and advocates. Even if you’re no longer working with them.

As part of a project at Grammarly, I interviewed dozens of People and HR executives at companies ranging from newly IPOed startups to Fortune 500 companies. I asked them two simple questions.

First, I asked, “What is the top reason employees at your company quit?” The #1 response? A bad manager. Then, I asked, “What is the top reason employees choose to stay?” The #1 response? Close friends at work. Both of those responses have nothing to do with the work itself but rather the people you’re working with.

The lesson I learned here: Think of my professional growth as a series of mentorships and chances to work with talented, driven, and experienced people across the company.

10% vs 10x.

Something that seems obvious in retrospect but was difficult to grasp at the time was the difference between a 10% change and a 10x change. Let me explain what I mean.

When building a product, you’re constantly looking for ways to improve it. In software, those improvements are usually realized through features.

Most of the changes will lead to small, incremental improvements in the product, on the order of a few percentage points. Those are the 10% features. They take less time and effort to build and are less risky because you can A/B test them to measure the improvement and undo the change if there’s no positive impact.

Other features are risky, big, and difficult to A/B test, but they also lead to huge improvements in the product if they’re successful. They’re high-risk, high-reward. Those are the 10x features. Some famous examples are Microsoft switching Office from a pay-once to a subscription model or Amazon deciding to launch 2-day shipping. It’s a high cost and hard to test, but if it pays off, it can reshape the company.

But these two different features require very different levels of investment and different levels of conviction, skillsets, and feedback loops. You might need a team that’s very good at execution for the 10% features but a chaotic and creative team for the 10x features.

How does this relate to my life outside of Grammarly and the software world? This metaphor of 10% vs. 10x improvements applies to almost every goal you can have in life.

Say you want to become more healthy and fit. Well, what kind of improvement are you actually looking for? If you want to be slightly healthier and lose a few pounds, that sounds like a 10% improvement. You can probably accomplish it by going to the gym more often and skipping the pastry or bagel with your morning coffee.

But if your definition of becoming more healthy and fit is to run a marathon, having never run one before, that starts to look like a 10x change. And that 10x change requires a mentality shift and lots of daily training. You need to radically alter your day-to-day habits to achieve that goal.

The lesson here is to be honest about what type of return I’m looking for with every goal and ensure I’m properly investing to achieve that return. A 10% goal is very different from a 10x goal.

Don’t forget about fun.

The final lesson is probably the most important. On paper, my journey at Grammarly over the past five years looks intense. I started when there were 100 people across two offices. I worked on various teams and complex projects, and the company today has over 1000 people and is one of the biggest unicorns in the world. When I tell people how long I’ve been there, I often hear, “That must have been an intense few years.”

There were certainly times when it felt intense, but it never felt unsustainably intense because of how much fun I had every day. And I don’t just mean the classic corporate sense of fun. Don’t get me wrong, I did enjoy almost every project I worked on – they were challenging, interesting, impactful, and taught me a ton. As someone who loves challenges and personal growth, that is fun.

But I also had fun in the general sense of the word. I traveled to cities like Vancouver, Berlin, and Kyiv and met incredible people with incredible life stories and experiences. I also took advantage of the remote-first lifestyle and lived in places like Hawaii for several months, and surfed every day with incredible coworkers I consider some of my closest friends.

These are experiences I wouldn’t have if I didn’t consciously try to balance working hard and enjoying my life alongside work. Had I not done this, I probably would’ve found the past five years unsustainably intense.

The lesson learned here, despite its apparent cliché, is to not forget about enjoying life alongside your work.