When the "Safe" Choice Is Actually the Riskiest Move

Sep 23, 2025

09:03

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Episode notes

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