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October 21, 2025

Navigate Your Career Like a Trail, Not a Highway

I’ve always seen my career as a journey rather than as a collection of “next achievements.”  For me, if I’m not learning or contributing where I’m at, it’s time to find something new.  That’s led to four career pivots, building several professional organizations with state-wide, national, and even international reach, and two books on transforming people and organizations (From Chaos to Successful Distributed Agile Teams and The Way Through).  As I see people earlier in their careers struggle with planning a career path, I’ve wanted to share more of my journey.

Woman in a red jacket and black pants hiking through a trail in the woods.
Following my wife on a Tennessee trail

We face many challenges in careers today, including layoffs, technology disruption, and uncertain economies.  There is no map app to guide you smoothly down a career highway.  Instead, I’ve always viewed my career journey as a good hike: a trail that has its ups and downs, that stretches my capabilities, and can reveal some interesting alternative paths.  With a career trail mindset, awareness and adaptability become more important than planning out all your next steps.  You see what emerges on the trail and explore interesting opportunities such as new emerging skills, cross-functional projects that expose you to different disciplines, the problems nobody wants to solve, and pay attention to what in these opportunities energizes you or drains you.  I share more of these ideas in Skip the Path - Find Your Career Trail.

This doesn’t mean you skip planning your career trail.  You want to look for landmarks or waypoints to mark your path.  These career waypoints not only help you move along the current career trail, but they can also help you navigate other opportunities.  Skill waypoints help you develop new capabilities that can help you along many career trails in the future.  Experience waypoints allow you to experience new roles or whole new disciplines with short experiments.  They can help show you forks in your path.  Relationship waypoints help you find hiking companions on the career trail that allow you to get through challenging parts and may point you to alternate routes.  Finally, impact waypoints allow you to contribute beyond your current role to improve the trail you're on.  You never know what new paths open up when you volunteer.  I share more about these waypoints in Setting Waypoints for Your Career Trails.

Of all the things I gathered along my career trail, the relationships were the most treasured.  As an introvert, the idea of networking made me cringe.  Speed networking?  That makes me want to speed away from those events.  What I did value was to “learn and connect” by learning who about the people I met on specific career trails, what got them this far, and what motivated them to continue the journey.  I’ve learned much from these career hiking companions and tried to help them (and others) in return.  I built this habit of connection through simple ABCs: Always Be Curious, Always Build Connections, and Always Build Community.  I’ve not only helped others on their career trails with these ABCs, but I’ve also been able to hike with some of my favorite career companions a few times.  You can read more about connecting versus networking at Find Career Trails Through Connections and Skip Networking.

Where has your career taken some unexpected turns?  What has the unexpected taught you?  What new possibilities opened up for you?  Or what new possibilities may be in front of you now?

Let me know.  Maybe we can walk together for a while and share those trail stories.

Mark

Footnotes:

  • I’ll be speaking at AgileDC next Monday, October 28 at 4:15pm ET, about these career trails.  Tickets are still available if you can hike there in person.

  • If you can’t make that trip, stay tuned as I’ll be sharing tales of these career trails in an upcoming webinar.

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