EPISODE · Sep 23, 2025 · 9 MIN
When the "Safe" Choice Is Actually the Riskiest Move
from No Set Path: Creative Entrepreneurship Growth Stories · host Drew English
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 & Timestamps00:00 – Why Drew turned down $100K and made 50% more staying freelance01:27 – Red flag #1: Meetings about meetings and corporate culture chaos01:50 – No real game plan: throwing everything at the wall to see what sticks02:34 – The pressure campaign: formal emails, office meetings, and coffee chats03:17 – The deal breaker: written approval required for any outside freelance work04:50 – 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 values06:40 – How saying no opened doors to building multiple revenue streams07:35 – Drew's current North Star: maximum money, minimum time, maximum family timeTakeawaysTrust your gut when red flags appear, even when the money looks goodCorporate culture problems rarely improve after you're hired full-timeAlignment with your values and goals matters more than short-term securitySaying no to the wrong opportunities creates space for the right onesYour North Star evolves as your life circumstances changeWrite down your goals and priorities to stay clear on your directionConsider practices like morning pages from "The Artist's Way" for clarityResources & LinksThe Artist's Way - Julia CameronUpstate Podcast Studio: www.upstatepodcaststudio.comConnect with DrewNo Set Path Newsletter: https://thedrewenglish.substack.com/Drew's IG: https://www.instagram.com/drewenglishhDrew's LinkedIn: https://www.linkedin.com/in/drewenglish/Drew's Website: www.drewenglish.com
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When the "Safe" Choice Is Actually the Riskiest Move
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