Professional Detours: Driven by a desire to wonder, not wander

This week, we're hearing from Penney Leadership Strategic Career Coach Jessica Crowley. When Jessica joined our team, I was fascinated by the winding road that has brought her career to where it is today—and how her diverse experience is one of her greatest strengths, not a weakness. Here, she tells the story of what that journey has felt like for her. - Carole Ann

"Not all who wander are lost." J.R.R. Tolkien’s famous line in his poem “The Riddle of Strider” is commonly misunderstood, and so are many of us who follow a circuitous career path.

Tolkien wasn't talking about people wandering aimlessly and without purpose, but about those of us who intentionally pursue our life purpose and stay aligned with our values, even when that requires taking detours that others might not understand!

Click here to see a “road map” of the path I’ve taken to get where I am today. Or for a more traditional outline of my experience, check out my LinkedIn profile.

At first glance, it looks like I jumped from one job and one career track to another, from interior architecture to college career services to nonprofit management–all seemingly disconnected and random. Trust me, over the years my inner critic has looooooved telling me how confused and aimless I’ve been compared to my highly successful friends, classmates and family members who’ve nailed the whole upward trajectory career path. I once viewed those times when I left a job or switched career paths as a form of weakness—that if I quit something I’d worked hard to achieve rather than sucking it up and sticking it out, it would mean I lacked grit.

So you can imagine my shock when GRIT revealed itself as one of my core values through the Penney Leadership Values Assignment. It turns out, the research shows there’s an important distinction between GRIT and GRIND:

"People who have a ton of grit walk away from stuff often. They’re not afraid to say, 'This is not working. This is not what I thought. I’m changing course. I’m pivoting. I’m letting this go.' Grind is much more externally focused than grit. Grit is 'this is about me, this is about my grit'...Grind is 'what will people think?'" -Brené Brown

Pivoting careers means admitting when something is no longer working or serving you. That takes confidence, courage, self trust, and putting your own needs ahead of what others might think of you. I wasn’t simply trying out different careers to see what would stick; each pivot was done with a painstaking amount of thought and reflection with the primary intention of staying true to myself. Once I stopped comparing myself to others and judging myself for the detours, I realized my personal career journey is actually a strength and a point of pride.

My multipotentialite journey has also taught me a lesson that resonates with the most important and difficult one I’m learning as a parent: the more I cling tightly to something I cherish, the more I actually need to let it go. This may sound ironic coming from a career coach, but our professions shouldn’t be the only thing that defines who we are. So if you find yourself clinging tightly to the career ladder you’re on, ask yourself “why?” If fear is the driving force, try loosening your grip on it and you might be surprised by the greater sense of connection you have to who you are, not what you DO.

"...cultivating meaningful connection is being able to go anywhere without the fear of getting lost. Even when we have no idea where we are or where we're going, with the right map, we can find our way back to our heart and to our truest self." - Brené Brown, Atlas of the Heart

Will you regret it?

Sure, at times I’ve questioned and judged my detours and missed aspects of previous jobs, but I’ve never regretted changing course.


Before taking a detour or leaving your current job, ask yourself the following 3 questions, recommended by organizational psychologist Adam Grant:

  1. Voice: To what extent do you have a voice in making a shift in your current work situation? If you have at least 20% of a say in the way you design your work life, first focus on what you can ask for in your current work situation to make it closer to your ideal. Otherwise, you might jump ship just to discover that you fixed one problem only to face 3 more unexpected ones.

  2. Loyalty: How much loyalty and connection do you feel to the organization's mission, values, and the people you work with?

    If the answers to these first 2 questions are very low, then it's a good sign to start looking elsewhere. Before you do, check in on the 3rd question:

  3. Alternatives: What alternatives would you be excited to pursue? What have you done to explore those alternative career options? What connections do you have, what do you know about the day-to-day reality of the people working in those opportunities beyond what is marketed to the outside?

If you do decide it’s time to make a big career change, I hope you’ll remember that embarking on professional detours doesn’t indicate a lack of direction or clarity of purpose. Rather, it’s a brave way to pursue your naturally evolving goals, and your own definition of success.

It would have been much easier to believe my inner critic and continue my upward career trajectory than it has been to willingly take pay cuts and title demotions in order to realign with my unique career compass. It hasn’t been the easy route, but it’s honored my continuously shifting priorities at different stages in my life, and fulfilled my desire to continuously learn, grow, and explore a variety of professional interests.

With each detour, I’ve taken valuable pieces of transferable skills and meaningful relationships along the way. Finding the through-lines in a nonlinear, seemingly disparate career path helps build continuity, confidence, and a sense of grounding to a bigger life purpose that transcends any job title. These common themes also help explain your pivots to the people in your life, and serve as a powerful marketing tool for potential employers to see that you’re a purpose-driven professional who brings a wealth of unique experience and curiosity to the table!

Through my own intense work through the Penney Leadership Strategic Career Compass, I discovered my personal through-line is my Mission:

I empower mission-driven leaders with a compassionate blend of challenge and support so they can transform meaningful insight into intentional action and bring their sense of purpose to life.

This has been true throughout my career–even when I was a teaching intern, a project manager/designer, and an administrative assistant.

It can feel scary to stop relying on external directions, but once you learn to trust your internal GPS, it’s freeing, empowering, and allows you to be more present for the journey!

With this in mind, Tolkien’s “The Riddle of Strider” may unveil all new meaning:

All that is gold does not glitter,
Not all those who wander are lost;
The old that is strong does not wither,
Deep roots are not reached by the frost.

From the ashes a fire shall be woken,
A light from the shadows shall spring;
Renewed shall be blade that was broken,
The crownless again shall be king.

Let us know how you interpret this poem in light of your own career path and leadership lessons! - Jessica

Jessica Crowley, Strategic Career Coach

Jessica Crowley, CPC, is a Strategic Career Coach with Penney Leadership where she empowers mission-driven leaders with a compassionate blend of challenge and support so they can transform meaningful insight into intentional action, and bring their sense of purpose to life.

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