What I learned from working in 5 startups right after graduation

In Range: Why Generalists Triumph in a Specialized World, the best way to figure out your career is through quick sampling — trying many new things to expand your horizons. Sampling period starts with no knowledge, testing various paths to gather information quickly, then refines decisions and narrows focus over time. It’s about asking smaller, testable questions like, Which of my possible selves should I explore now? This approach focuses on a test-and-learn mindset, not planning everything in advance, and avoids premature optimization.

After I graduated in May 2023, as I was trying to figure out my career, some founders also told me the similar concept, “If I were you, I’d try working in different companies and functions through short internships. I regret wasting time doing a slow transition.” Back then, I wondered, “Why would anyone allow me to try that? I don’t have the skills!” Looking back, I realized that I did try five startups in the year before settling down. It was a chaotic time, but it helped shape how I now view “work” as an inexperienced new grad.

What does “work” mean, and what is it for?

Is it just for survival? Fancy lunches at big tech companies? Work-life balance to pursue more hobbies? Exploration of a new field that humans haven’t charted? Establishing good relationships to grow with your colleagues?

Here’s what I do and what I’ve learned:

What I do:

• Startup 1: AI engineering in EdTech
• Startup 2: Technical writing in LLM observability
• Startup 3: Built a startup with a mentor (software engineering) in EdTech
• Startup 4: Prompt tuning in EdTech
• Startup 5: Software engineering in EdTech

Work is about survival. A wide professional network is key to survival.

Of course, work is about survival until you reach financial freedom. Getting a job nowadays feels much easier than it did when I was in Startup 1, thanks to the chaos. It’s not just because I’ve become more professional, but because I’ve become street-smart and resourceful.

After learning how lengthy and complicated the U.S. job search can be under immigration visa constraints, I realized that job security isn’t about skills — it’s about the network.

You’ll always grow skills as you work more, but the shortcut to landing a job under the 60-day U.S. visa constraint (since the U.S. will kick you out if you don’t have a job after 60 days) is to know people who are hiring. Fortunately, placing myself in an incubator where there’s a constant influx of new founders needing team members gave me awareness of who needs help. Even though people post hiring announcements, they often ignore the applications because they’re busy and don’t know you. However, if they meet you, get to know you, and like you, you’re in a completely different game — even if your skills aren’t the best among all candidates. People are people.

You might ask, how about the money? Yes, I sacrificed money and comfort from bigger companies, but I built strong resilience for difficult times. I know that even if I get fired today, I’ll get hired next week. Not only will I get hired, but I’ll also have a choice in who I want to work with.

Mission matters, but day-to-day work might matter more.

In Startup 2, I didn’t bother too much with learning the business because I wasn’t interested in LLM observability. But even in Startup 4, where I was working on prompt tuning and spending most of my time in meetings, I found it so boring that I couldn’t continue after a month. Day-to-day satisfaction really matters. My current work only has one meeting a month, so the rest of my time is spent in the flow of coding. I feel concentrated and fulfilled every day. And yes, since I’m aligned with the mission, I spend extra time learning about EdTech products on the side and applying them in my work. But still, it’s not how I spend most of my time. I need to work on something intellectually challenging and not have too many meetings every day.

Work in a place where you love, love, love the people. It will auto-resolve many problems, and shape who you are.

Most people underestimate how much the people around you matter. But picking the right people means picking the right place to spend your energy, and those people will help shape you into a better person.

Many problems get solved with the right people and vice versa. Let me give you a practical example: Our company recently hired a new engineer, and here came an extremely smart but intense candidate who made me really uncomfortable. Sitting with them made me feel suffocated, and I was so worried they would hire them because they seemed so incredibly talented.

I thought,

Interestingly, none of us liked them, and they were immediately rejected without consideration. And I realized, wait, we really have similar tastes when it comes to people. So I said, “Yeah, hire whoever you like, because I’ll probably like whoever you pick anyway.”

On the other hand, in Startup 2, the YC co-founders seemed like a golden match but ended up having a terrible experience. They were talented and experienced engineers and designers, but their personalities clashed. They fought, broke up, dealt with legal problems, and eventually couldn’t align, so they closed down the company very quickly.

My second reason to pick people you love is that, as you sit next to your coworkers for at least 8 hours a day, they shape who you are. In one startup, the founders were constantly anxious, and I felt stressed and terrible sitting next to them. On the other hand, my current founders are mostly happy and calm, and I’m happy and calm too, which allows me to stay curious every day. So nowadays, if a founder tells me they only hire “top-tier engineers” with elitism as a value (which is something people sometimes put in the values section of their job boards), I stay the f*** away from them. Thank you, next time!

I feel immensely grateful to work with my team, who work hard but also value rest and relationships outside of work. I’ve learned a lot from them, not just about work but also about having a positive attitude in life.

If you work in a startup, having customers is an important foundation for progress.

I fought a lot with founders who didn’t have customers. Not having customers almost means not having direction, because when someone says we should do A, there’s no way to measure whether A is actually good.

You might ask, shouldn’t you just follow the founder then?

Well, things are more complicated because, as an early team member, you have to make tons of important decisions when responsibility isn’t clearly defined. I fought with some founders because we only had < 100 non-paying daily users, and I started trusting them less and less on product decisions. In my current job, we still fight about ideas, but we look at metrics together and make decisions based on 750K users.

People have very different philosophies on how to run a company. Some founders believe in iterating on quality first before releasing to users, while others believe in launching fast. The thing is, if you don’t have customers yet, no one can really tell who’s right other than by trusting and believing in the founders. In the beginning, I didn’t care because I just wanted a job, but nowadays, as a founding member, I do care, because I want to work in a sustainable business.

Ending: Discovering what I want for work

When I was first laid off from my job at Startup 1, I was devastated. It felt like breaking up for the first time, and I thought I’d never find love again. How on earth would I find another EdTech startup where I liked the work so much?

Looking back, I find it hilarious because, compared to my current work, I didn’t like the people and the work nearly as much! I was like a frog in a well!

I didn’t really know what I wanted for my work because I can still recall so much career advice I got during my job search, like:

• “You should prioritize finding a mentor over everything, because people don’t leave companies — they leave managers.”
• “You should find a medium-sized startup because early startups don’t have time to teach you.”
• “Don’t worry about money at all right now, because it’ll pay off in the future.”

None of them are completely wrong, but none of them are completely right from my experience. Nowadays, when people say they want to work with me, I’m able to get a gut feeling. And I realized it’s thank to f**king around so much in my first year. Now, I want my work to be a meaningful space where I can learn and explore, surrounded by supportive, secure, and fun relationships that challenge me to grow, all built on the foundation of financial stability.

Ahh…why does it sound like marriage?