Skip the Path - Find Your Career Trail

The classic career path implies you have complete control. The last five years of the job market prove that it is no longer possible to plan every career step due to layoffs, shifting technology, frequent mergers and acquisitions, and unexpected market changes. Instead, you want to look for career trails that lead to new opportunities in your current or next organization.
- What markers are there for these career trails?
- What happens when you find something blocking your career trail?
- What if you need an unexpected turn?
- Can you see the forks in the career trail and how do you choose?

Transcript

1. Skip the Path & Find Your Career Trail A fresh perspective on navigating your professional journey in an uncertain world. Mark Kilby Oct 2025
2. Our trail for this session& Laying Out the Map Understanding Career Trails Setting Waypoints On Your Career Trail Finishing Today's Trail
3. Laying Out The Map
4. The Classic Career Path Illusion The traditional career path implies you have complete control over your professional journey. It suggests a clear, linear progression from one role to the next, with predictable milestones and destinations. But here's the truth: You don't have complete control over your career. The world of work has fundamentally changed, and the old maps no longer match the territory we're navigating.
5. The Path Is No Longer Clear Several factors fundamentally disrupted how we think about careers. Remote work, economic uncertainty, and rapid technological change have made traditional career planning obsolete. The question we must ask ourselves&
6. Can we look at careers differently?
7. The Rule of Personal Mobility If you are neither learning or contributing where you are, go somewhere you can. It's not about chasing titles or salaries4it's about ensuring you're growing and making an impact. When both learning and contribution stop, it's time to find a new trail.
8. Understanding Career Trails
9. The Career Path: A Closer Look Career paths show a clear direction and remain unobstructed, indicating a specific destination. Study this picture closely4notice how the "road" appears solid and predictable. But what happens when conditions change? When the road becomes blocked, when industries shift, when your interests evolve? The rigid path becomes a limitation rather than a guide.
10. The Career Trail: Embracing Exploration A career trail requires you to explore and may not always be clear, but it pulls you in a direction. Unlike a path, a trail adapts to the terrain, winds around obstacles, and reveals new possibilities as you move forward. Trails invite curiosity and discovery. They acknowledge that the journey itself shapes the destination.
12. Skills for Navigating Career Trails Career trails require a different set of capabilities than traditional career paths. These skills help you navigate uncertainty and seize opportunities as they emerge. Adapt to Changing Conditions Flexibility and resilience when the landscape shifts Awareness of Surroundings Understanding the environment and context you're operating in Spot Emerging Opportunities Recognizing possibilities before they become obvious
13. More Essential Trail Skills Navigate Uncertainty Willingness to move forward even when the path ahead isn't perfectly clear Stay Curious Maintaining curiosity about unexplored possibilities and new directions
14. The Organic Nature of Career Trails Career trails take an organic, non-linear nature. They wind, branch, and sometimes double back. This isn't a failure of planning4it's the natural way growth happens in complex environments. Embrace the meandering path. Each turn teaches you something new about yourself and the landscape of possibilities.
15. Identifying Career Trail Markers As you navigate your career trail, watch for these markers that signal opportunities for growth and direction. New Capabilities Opportunities to develop skills you don't currently have Cross-Functional Projects Work that bridges different areas of expertise Problems Nobody Wants Difficult challenges that others avoid but offer learning Energy Markers Work that energizes rather than drains you
16. What if &?
17. Setting Waypoints
18. Setting Waypoints on Your Career Trail Waypoints are markers you can set to map out better career trails. Unlike rigid goals, waypoints provide direction while allowing flexibility in how you reach them. Skill Waypoints Specific capabilities you hope to develop Experience Waypoints Projects that test new skill combinations Relationship Waypoints Key connections you want to establish Impact Waypoints Contributions that improve your workplace
19. Skill Waypoints Skill waypoints represent specific capabilities you hope to develop along your career trail. These may require creative approaches outside normal work experience. Practical Example: Developing meeting facilitation skills Volunteer to lead team retrospectives Take an online course in facilitation techniques Observe skilled facilitators and note their methods Practice in low-stakes environments first
20. Experience Waypoints Experience waypoints are projects or challenges that help you understand new skill combinations and test potential career directions in low-risk environments. Test Before Committing Try new roles or responsibilities without making permanent career changes Practical Example Volunteer to organize a community event to test project management skills Learn Through Doing Hands-on experience reveals whether a direction truly fits
21. Relationship Waypoints Relationship waypoints represent key connections or networks you want to establish. These are people working in areas of interest who can provide insights, guidance, and opportunities. Practical Example: Finding thought leaders in your area of interest Follow their work on social media and blogs Attend conferences or webinars where they speak Engage thoughtfully with their content Seek informational interviews when appropriate
22. Impact Waypoints Impact waypoints focus on contributions that improve your current workplace and leave things better than you found them. These create value while building your reputation and skills. Mentoring Programs Guide others and strengthen your leadership abilities Improved Processes Streamline workflows and increase team efficiency Community Building Foster connections and strengthen organizational culture
23. If you don't go where your interests are, you don't really find that next possibility This insight reminds us that exploration isn't optional4it's essential. Your interests are signposts on your career trail, pointing toward opportunities that align with who you are and who you're becoming.
24. Finishing Today's Trail
25. Avoid the "Golden Ticket" Trap There's no perfect job (or role) waiting to be discovered 4no golden ticket that will solve all your career challenges. This mindset keeps you stuck, always searching for something that doesn't exist. Instead, encourage exploration. Try different things, learn from each experience, and let your trail emerge organically from your interests and strengths.
26. Remember: The Rule of Personal Mobility If you are neither learning or contributing where you are, go somewhere you can. This rule serves as your compass on the career trail. When you find yourself stuck4neither growing nor making an impact4it's time to explore new territory. Your career trail is uniquely yours. Trust the process, stay curious, and keep moving forward.
27. Don't hike the trail alone The world of work has become a difficult journey. Finding companions for your career trail4mentors, peers, coaches, and communities4makes the journey more sustainable and rewarding.
28. Continue Your Journey Thank you for exploring career trails together. Remember that your professional journey is an ongoing adventure, not a destination to reach. Learn More Visit markkilby.com for more resources and insights Get in Touch Contact me at mark@markkilby.com or on LinkedIn
29. Thanks!