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Welcome to our first edition of 2025! 🎉 

After celebrating the holidays with karaoke and a Mexican wine country trip, I’m excited to get back to writing juicy deep dives for you.

Today, in 5 minutes or less, you’ll learn:

• 🧑‍💻 How a 23-year-old product manager negotiated a 6-week leave

• 💪 The hidden power of asking for what you want at work (and in life)

• 🪜 A step-by-step guide to negotiating extended leave (even as a newbie)

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🤝 How to Negotiate a 6-Week Leave

In 2013, I started my first full-time job in marketing just 1 week after I graduated from Dartmouth.

I was hungry. I wanted to prove myself.

1.5 years later, I was promoted to a product manager role at this Series B edtech startup. I received a 40% salary bump. My hard work had paid off.

However, I sacrificed other parts of my life. Family. Travel. Personal growth.

As a 23-year-old without much life experience, I desperately wanted a break to prioritize life outside of work.

So for the upcoming winter holidays, I dreamed up a plan to visit my grandma, newlywed cousin, and aunt/uncle in Shanghai, as well as visit friends in Seoul and Taipei for my first time.

But there was only one big problem.

I had just 3 weeks of paid vacation leave.

So what’d I do?

I negotiated for a 6-week leave. And to my complete surprise, my manager agreed without any hesitation.

Little did I know, this was a small step forward on my journey of living on my own terms.

It wasn’t until later in my early 30’s that I realized the bigger picture. The reason why I pursue financial independence has not been about retirement. It’s been about having the flexibility that money provides.

And sometimes, you can achieve this flexibility by simply asking for it. Even in your full-time job.

In this newsletter, I share how I negotiated a 6-week leave as a recent college grad, why build the muscle of asking for what you want—and how to negotiate an extended leave.

How I Negotiated My 6-Week Leave 🧳 

I break down what I did in three stages:

• Pre-Negotiation

• Negotiation

• Post-Leave

Pre-Negotiation

Before I setup the conversation with my manager, I took an inventory of what I had accomplished and the overall business context:

• What I accomplished: I had a new manager who was pushing the org for more experimentation. I was the only person running growth experiments to drive website engagement and revenue, which helped accelerate his initiatives. He gave positive feedback on my performance.

• Business context: At the same time, my projects were slowed by the lack of data/technical resources. My manager was onboarding new talent, but they would take time to ramp up to support my initiatives. The winter holiday period was looking to be a transition period.

Given this situation, I knew I had a 1-2 month window where if I took a break, there’d be minimal impact on the organization.

Negotiation

I setup a short conversation with my manager, saying something along the lines of: