When the "Safe" Choice Is Actually the Riskiest Move

Written By Drew English

Episode Overview
Drew shares the full story behind walking away from a $100,000 in-house media position and how that decision led to earning 50% more while staying freelance. He breaks down the red flags that made him trust his gut, the corporate culture problems he encountered, and why alignment with your values matters more than security. This solo episode dives deep into the importance of knowing your North Star and making decisions that serve your long-term creative and personal goals.

Key Topics & Timestamps

  • 00:00 – Why Drew turned down $100K and made 50% more staying freelance

  • 01:27 – Red flag #1: Meetings about meetings and corporate culture chaos

  • 01:50 – No real game plan: throwing everything at the wall to see what sticks

  • 02:34 – The pressure campaign: formal emails, office meetings, and coffee chats

  • 03:17 – The deal breaker: written approval required for any outside freelance work

  • 04:50 – What happened to the colleague who took the job (spoiler: it ended badly)

  • 05:27 – The importance of trusting your gut and staying aligned with your values

  • 06:40 – How saying no opened doors to building multiple revenue streams

  • 07:35 – Drew's current North Star: maximum money, minimum time, maximum family time

Takeaways

  • Trust your gut when red flags appear, even when the money looks good

  • Corporate culture problems rarely improve after you're hired full-time

  • Alignment with your values and goals matters more than short-term security

  • Saying no to the wrong opportunities creates space for the right ones

  • Your North Star evolves as your life circumstances change

  • Write down your goals and priorities to stay clear on your direction

  • Consider practices like morning pages from "The Artist's Way" for clarity

Resources & Links

Connect with Drew

Drew English
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