Season 1, Episode 24

When to Leave the 9-5

When I started  my entrepreneur journey, I was a 9-5 employee. For those who, like me, are embarking on their own journeys while currently in the 9-5, there will come a time when you ask yourself, “When should I leave my 9-5?” This question can bring up a lot of excitement, anxiety, and anticipation.

In this episode, I share my insights from having to decide when I should leave my 9-5. Ultimately, every entrepreneur must answer this question for herself, but it is my hope that this conversation will help listeners feel a bit more prepared when the exciting time comes!


Episode Highlights


Hosts & Guests

Jackie Kossoff, Host


The Millennial Success Society

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Inside This Episode

(1:00) Intro
(1:36) Dreaming about leaving the 9-5
(3:15) Knowing when to leave the 9-5
(3:25) Jackie’s story on leaving the 9-5
(9:55) Jackie on having her parents’ support and understanding
(12:25) Not planning on leaving the 9-5 so soon
(13:43) “My leaving the 9-5 was kind of spur of the moment and unexpected”
(15:00) Business success when leaving the 9-5 and gaining your friends and family’s support
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Links Mentioned
How to Leave the 9-5 in 90 Days Checklist
Jackie’s Instagram