9 Journal Questions to Help You Navigate a Transition with Dan Cumberland

April 20, 2023
Meet Your Guide
Transitions, whether personal or career-related, can be exciting yet daunting at the same time. For this reflection journey, Dan Cumberland offers a series of thought-provoking questions that he used to navigate his own meaningful transition. 

For this reflection journey, Dan Cumberland offers a series of thought-provoking questions that he used during a time of personal and professional transition. 

Transitions, whether personal or career-related, can be exciting yet daunting at the same time. Taking a moment to reflect during these pivotal periods will help you navigate your journey and make the most of the changes ahead.

Meet Your Guide: Dan Cumberland

Dan is a serial entrepreneur, podcast host, and SaaS founder with over a decade of experience in helping online companies achieve seven-figure launches. After overcoming personal and professional setbacks, he's dedicated to helping entrepreneurs avoid similar mistakes. Dan is now building an Accelerator Program for mission-driven entrepreneurs, growing VideoSnap, and hosting The Meaning Movement podcast. 

Questions to Help You Navigate a Transition

About You:

What are you proud of from your recent work (skills, accomplishments, relationships)? 
Where are the biggest disappointments and regrets?

The Transition:

How did you get here? What are the major events from the recent season?
What is the biggest source of tension? How can you let go of it?

Your Work:

What do you want to spend more time on? What do you want to spend less time on?
What are you craving?

What’s Next:

What does success look like in the next season?
What do you want to be remembered for during this season?

Next Steps:

Who might be able to help? Who can you help along the way


We hope you enjoyed this guided reflection. Embracing change and transitions is an integral part of our personal and professional growth. By asking yourself these crucial questions, you can gain valuable insights, clarify your goals, and find the direction you need to move forward confidently. Remember that every transition is an opportunity for self-discovery and growth, so take the time to reflect and make the most of the journey ahead.

Learn more about Dan and follow his journey:

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