10 Of The Best Questions You Can Ask Yourself When Changing Careers

By: Michael Youngblood & Jonathan Kalan, Unsettled Co-founders 

Over the last three years, running nearly 100 experiences in 20 countries for 2,000 people from around the world, we’ve learned one thing for almost certain:

Life is an adventure into the unknown. Knowing how to intentionally navigate uncertainty and build a lifestyle that starts in self-awareness and grows from there may be the most fundamental skill in the world today.

This week, we have officially launched our latest journey: A 30-day online Lifestyle Incubator for mid-career professionals.

Through a unique virtual retreat format, we offer original content, live sessions, peer-to-peer collaboration, and practical tools that will help you identify the core tensions between the lifestyle you want and the career trajectory that fulfills it.

We ask of all Unsettlers, to come to their retreats with a question or intention in mind — what do you want or need out of this experience? On our virtual retreat we are going to ask perhaps the biggest questions of all:

  1. Why are you seeking to realign your career with your lifestyle?

Have you reached a crossroads and feel the need to press pause, reassess, and design your next step to make sure it’s intentional? Navigating toward what you want does not just happen but requires deep intention. It is time to get clear on what’s driving your need for change. 

  1. How has your journey led to where you are today?

What parts of your journey were in your control or beyond your control? What choices did you make or what choices were made for you? If you have asked yourself ‘is this it?’, know you are not alone. You can choose your next move on your journey. 

  1. What are your core values?

We don’t ask this of ourselves enough in today’s world, and it is so essential when designing a life with intention. Our values lie at the core of who we are, what we stand for, and how we make our decisions – big and small. Outlining what they are is a gift to yourself and your future. 

  1. How do you spend your time?

In a world where time seems to be spinning out of control, how can you spend more time on what you value? It’s time to build a bold vision that allows you to visualize a meaningful trajectory for yourself. Once you have vision, you can actively take steps to realize how you will get there.

  1. Why do you work?

It seems silly, but it’s an honest question. Yes, we live in a society where work is a necessity to make enough money to survive (for most). But how can we get clear on where and why we get joy and fulfillment in our working lives? What was it about your past career paths that didn’t sit well? And in what roles did you find meaning? What is the actual daily process – not the title or role – of the work that makes you feel most alive?

  1. What does success look like for you?

Not what society deems successful, but what does success look like for you? Can you get really honest with yourself about what a successful “future you” looks like through your own your eyes? Ultimately that is all that truly matters. 

  1. What are the steps you will take to manifest your vision of success?

“A goal without a plan is just a wish.” – Antoine de Saint-Exupéry. At Unsettled we look at life as an evolution, a continuous process of radical self-discovery and learning through experimentation, exploration, and accountability. How can we ensure we are living each day this way?

  1. What are your career and life non-negotiables?

What are the values you are not willing to compromise on? What are the values that you stand for and build your essence? And how can knowing this help reorient yourself toward action?

  1. What goals do you want to set for your future?

Humans are goal-oriented beings after all, and experimentation and practice will be required to achieve them. You will learn our approach of how to conduct small experiments, throughout life, anytime you are asking, “What’s next for me?”. How to track your progress, stay on course, evaluate decisions, and make micro-adjustments when necessary. 

  1. How will you practice self-compassion when the going gets tough?

You, like all of us, will hit bumps along the road. How will you take care of yourself and ensure that you stay on track when facing uncertain times? Unsettled’s core team will guide you through a process of navigating uncertainty with thought-provoking questions, reflective exercises, personal frameworks for planning, and tools for setting clear intentions for the choices you make that define who you are and what you do.

We can’t wait to ask these big questions with you in the world’s first-ever Lifestyle Incubator. We’ll see you out there!


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Unsettled is a global travel community for those who embrace the unknown and value meaningful human connection. Our mission is to inspire a lifelong pursuit of growth, meaning, and adventure through travel and shared experiences.

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