🐧 How to Negotiate an Extended Leave

‍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:

• Given the business context, I had always wanted to take ~6 weeks off to visit my grandma and family in Shanghai—and this seemed like the right time to pull the trigger
• I had grinded hard for the past 1.5 years and had hardly taken vacation days. This would be my first major recharge
• My plan was to use my accumulated paid vacation days from 2 years. With the rest being unpaid
• Here are the projects I’m working on, why they would not be impacted, and how I would ensure they do not block anyone else’s projects
• I’d really appreciate your feedback - what do you think?

I don’t recall the exact split but believe it was 4 weeks paid, 2 weeks unpaid.

(Side Note: To my surprise later, all my paychecks hit my bank account. So either this was intended or HR didn’t update the system to withhold the payments.)

My manager responded by agreeing that he didn’t see any issues this would cause for the business. He also empathized with my desire to see family.

(I can only speculate but perhaps it helped his family was overseas. In his Latino culture, family was also highly important)

After taking a couple days to review my proposal and checking with the team, he OK’ed it. Boom. I flew to Michigan to see my parents for Thanksgiving, then I was off to Asia for all of December.

‍

Post-Leave

After the holidays, I came back to work feeling re-energized and productive.

I closed the loop by sharing my learnings from the trip, bringing back snacks for the team, and hitting the ground running again.

‍

Why Ask For What You Want (Repeatedly) 🔁 

Most people accept their existing employment landscape as a constraint.

They default to working within the boundaries of their work policies.

But they rarely stop to ask, “What do I really want?”

This is the big, hairy question.

Perhaps it’s a 6-week trip to visit family, a sabbatical to spend time with your kids, or just some time off to backpack across Europe. Whatever it is, this is the starting point.

When people don’t ask this question (or are afraid to), it’s a recipe for misery (I’ve been there.)

Then, the second-order question is:

“How do I get it while navigating my current work landscape?”

This is an important sequence of questions, because it encourages creative, win-win solutions.

To be clear, I’m not suggesting to take advantage of your employer.

You can find creative models to get what you want, while also adapting to your employer’s needs.

In my experience:

By developing a habit of asking for what you want, you’ll start seeing the world differently.

For me, I realized that this practice is a foundation of making “living on your own terms” feasible.

There is a lot of wiggle room in many life and work situations to get what you want.

However, YOU need to ask for it. No one else can do it for you.

The more and more you build this muscle, the more you build confidence in asking for bigger things you want.

Like a raise. Promotion. Business deals.

For many high-performers, asking for an extended leave is a great small step forward:

‍

How to Negotiate an Extended Leave 🪜 

Step 1: Assess your value and timing

Before approaching your manager, evaluate your recent performance. Understand your company's current situation and upcoming projects. Timing is crucial – look for weeks or months when your absence would have minimal impact.

Step 2: Prepare your proposal

Create a clear plan that outlines:

• The duration of your leave
• How you'll use your paid vacation days
• A strategy for handling your responsibilities during your absence
• How you'll ensure a smooth transition before and after your leave
• Get feedback from your manager on options before suggesting unpaid leave

Step 3: Frame it as a win-win

Emphasize how this break will benefit both you and the company. For example:

• You'll return refreshed and more productive
• It's an opportunity for others to step up and develop new skills
• You'll gain new perspectives that could benefit the company

Step 4: Have the conversation

Schedule a meeting with your manager. Present your proposal confidently, but be open to feedback. Be prepared to address concerns and offer alternatives.

Think of this as a collaborative problem-solving discussion.

Step 5: Follow up in writing

After the verbal agreement, send a summary email to confirm the details and express your gratitude.

Step 6: Plan for your return

Before leaving, ensure all your responsibilities are covered. Upon returning, share your experiences, bring back gifts (if applicable), and demonstrate renewed energy and commitment to your work.

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In Summary ⚡️ 

• Negotiating my extended leave was an early step to living on my own terms
• This experience taught me to advocate for your needs, demonstrate your value and find creative (win-win) solutions
• Three Stages: Pre-Negotiation, Negotiation, Post-Leave
• Build the habit of asking
  1. “What do I want?”
  2. “How do I get it while navigating my current work landscape?”
• This skill applies to raises, promotions, business deals, and more
• How to negotiate an extended leave
  1. Assess your value and timing
  2. Prepare your proposal
  3. Frame it as a win-win
  4. Have the conversation
  5. Follow-up in writing
  6. Plan for your return
• You don’t have to wait until retirement to take a longer break. Sometimes all you need to do is ask

🌐 Beyond your borders

🎩 This OP earns $40k/month but struggles to live within his means. He describes his assets as $130k home equity, $120k ETFs, and $80k in paid off car. What you think would help him/her? Hit reply with your thoughts.

🧱 Bloomberg compiled 2025 investment outlooks from major Wall Street firms. The general consensus? According to Bloomberg, “The US economy and assets are once again expected to power ahead, enjoying new momentum from Trump and benefitting from the comparative lack of appeal of other major markets, many of which could be hit by his tariffs.”