These Three Insights Will Help You Thrive During Life Transitions

by Jeff Hittner

Transitioning to more purposeful work is a messy process.

We listen in awe to the stories of our heroes at work, in our communities, in politics and religion who describe their ascension in logical terms. They make it sound as if it was meant to be. But the real, messy story of transition is hidden below the surface. Why does it get overlooked?

Vulnerability is courage

It has a lot to do with vulnerability: the emotions, the fears and especially the triggers that launch us into our uncertain journey forward are personal and sometimes painful. Transitions are the in-between time. A period of stability has ended and, looking forward, you don’t yet know what is in store for you. This can be destabilizing and scary.

Our vulnerable moments are not ones we tend to scream about from the tallest rooftop. Yet, what I find so beautiful in the vulnerability of transitions is that opening up about it is the definition of courage — the type it will take to get you over the finish line to your purposeful future. We mistake vulnerability for weakness and define it as self-doubt. But what it really signifies is that by opening up, you are taking the critical first steps to thriving in transition.  

The messiness inherent in a transition is why we have so many “Monday Miserables” — individuals unhappy in their jobs but not prepared to quit. In our work, we see a consistent series of activities leading up to and through a transition that help many individuals thrive: triggers, support, and action. Each forms part of the graduation process to a more purposeful future, and each requires courage.


A range of events from the mundane (eating the best pizza of your life) to the traumatic (the death of a loved one) can be classified as triggers. What they all have in common is the spark they ignite, launching us into a period of reflection. This reflection can bring up profound questions about purpose, spirituality, family or community.

For example, before committing to launch Project X I had a new job lined up. I thought that getting this job signified it wasn’t the right time to pursue my purpose and my dream. Then the start date kept getting pushed back, and suddenly the funding for the company fell through.

I had been waiting for two months to start working at this new company. Now I was unemployed and not sure that I had the courage to launch a business full-time. It brought up so many fears about money (could I support my family with a startup?),  time (could I commit to launching a business and being a good dad?), and even fears about my skills as an entrepreneur (would it succeed?). The trigger was the lost job. It catapulted me into my transition.

Related: How to Reign In Fear and Invite Curiosity Instead

By opening up, you are taking the critical first step to thriving in transition


When will this uncertainty end?! The only sure thing in these transitions is that we don’t have a clear end date. This is incredibly disconcerting and surviving such ambiguity requires finding people to lean into for help and encouragement. Find individuals that won’t judge and won’t help you find a solution, but who will instead focus on caring for you and allowing you to be vulnerable. How do you find these people? They are already in your circle. We go through all kinds of triggers and transitions in our lives. Think back: which relationships gave you hope and energy in your last transition? Was it a specific community, a particular friend or a family member?

When I was preparing to launch Project X, I met every day with a different mentor or friend. I lined up a coffee chat with someone that I could get support, insight, and encouragement from. I also kicked my community engagement into high gear. I participated more fully in the spiritual community I belong to. I asked more questions from the group and got more prayers and more unconditional love.


With no clear ending in sight, we have to commit to action every day to move forward. It’s the opposite of raising a child: we want to act first and reflect later. We want to gain momentum as we take the small consistent steps towards our purpose.

In our programs, we build accountability groups: small teams that work together each week setting three small goals that their group helps them develop, motivates them to complete and supports them when they get stuck. The process ensures you aren’t alone and you’re all moving forward together — even when you move in different directions.

With no clear ending in sight, we have to commit to action every day to move forward.

Get ready for your transition before you begin

Too often we leave the story of our messy transitions on the sidelines. We share our accomplishments but not enough of the struggle that got us there. Committing to a purposeful future can be messy. The more we acknowledge this reality, the less likely we will be to run from it into the open arms of a stable but soul-sucking career. Get geared up for your transition before it begins and you’ll be in great shape to take on the uncertainty with the vulnerability needed to thrive in it.

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