• tl;dl
  • Posts
  • #25 Should You Leave Your 9–5 for a Startup?

#25 Should You Leave Your 9–5 for a Startup?

I was inspired by my sister this week so this one's for her.

Author

Senda from tl;dl
August 01, 2025

Have you ever wondered what it feels like to leave a corporate job to join a startup?

So many of you have asked me this exact question over the past few weeks: "Is now the right time to leave my safe 9–5 job and try something new?" Whether it’s joining a scrappy early-stage startup or finally starting that thing you’ve been thinking about for years—the fear and the excitement are both real.

Why So Many Are Thinking About the Leap

Maybe you’re bored. Maybe it’s the creeping burnout. Or maybe it’s that itch that corporate life just isn’t it anymore. Here’s what the numbers say:

  • Only 13% of employees are engaged at work globally (Gallup).

  • 65%+ of Gen Z and Millennials want to start their own business (LinkedIn).

  • But more than 50% feel stuck in traditional jobs due to finances, family expectations, or visa limitations.

If this feels familiar, you’re not alone.

Why It Feels So Scary

Because you’re not just walking away from a job. You’re leaving stability, routine, and identity behind. It’s terrifying to tell your family you’re quitting a big-name company. It’s even scarier to explain why.

But when you do take that leap, something shifts.

You start building. You talk to different people. You wake up excited—and afraid. But that mix? That’s where the real growth happens.

What Can Help You

Over time, I’ve spoken to dozens of people who made the leap. Here are 5 things they all say helped:

  1. Start before you quit: Freelance, test, shadow, or build on weekends.

  2. Follow your energy: Notice what you can’t shut up about. That’s your clue.

  3. Plan a financial runway: 3–6 months of savings makes decisions easier.

  4. Find expanders: Talk to people who’ve done it, not just those who haven’t.

  5. Start messy: No one feels 100% ready. Starting is the point.

The leap might look different for everyone, but the desire to build something more aligned is real. If this is you? You’re not crazy. You’re waking up.

Some inspirational TLDL episodes

Listen to (one of) these episodes if you’re looking for weekend inspiration:

Helpful resources for job applications

Feel free to reply to this email if you have specific topics you’d like me to write about next week! 💜