Thank you to Strawberry.me for sponsoring this episode. Get 50% off your first coaching session at strawberry.me/thefiveyearplan.
How do you know when it’s time to quit your job, change careers, end a relationship, or walk away from something you’ve spent years building?
In this solo episode of The Five Year Plan, Anna breaks down 5 questions to ask yourself when you’re trying to figure out whether you’re going through a difficult season — or whether something is fundamentally no longer right for you.
Drawing from her own decision, along with lessons from more than 50 hours of conversations with people who have made major life and career pivots, Anna explores the difference between temporary discomfort and knowing it’s actually time to move on.
In this episode, you will learn:
- How to tell the difference between “this is hard” and “this is wrong for me”
- Why you should try changing your circumstances before changing your entire career
- The question: Do I actually want the future this path is leading me toward?
- Why your gut feeling can matter even when you can't logically explain it
- The physical and mental signs we sometimes normalize when we're unhappy
- Why apathy can be a bigger warning sign than hating your job
- What it means when you haven't lost your ambition — your ambition has just moved
- Why knowing it's time to leave doesn't mean you have to leave tomorrow
- How to start making a plan when you know something needs to change
Because sometimes the question isn't whether you can keep going. It's whether you actually want the life waiting for you at the end of the path you're on.
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Sponsors:
Thank you to Strawberry.Me for sponsoring this episode. Visit Strawberry.me/fiveyearplan for 50% off your first coaching session.
Want to partner with us?
anna@thefiveyearplanpodcast.com
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Timestamps
00:00 Should You Quit
01:55 Season Or Forever
09:41 Track The Patterns
14:00 Try To Fix It
19:19 Do You Want That Future
25:11 Health Warning Signs
28:37 When You Stop Caring
33:47 Make A Quit Plan
36:32 Final Thoughts
00:00 Should You Quit
01:55 Season Or Forever
09:41 Track The Patterns
14:00 Try To Fix It
19:19 Do You Want That Future
25:11 Health Warning Signs
28:37 When You Stop Caring
33:47 Make A Quit Plan
36:32 Final Thoughts
