top of page
Search

From Detours to Direction: A Leadership & Career Success Guide

Recently, I had the distinct privilege of being a guest on the @LeadershipEnlightenment podcast with host Dean Fisher available on YouTube and Spotify. The entire conversation surrounded the story of my building Alignment Advising and my journey from career Chamber and Visitors Bureau professional to entrepreneurship. Dean experienced a similar path to independent employment - leaving the corporate world. As such we discussed what a successful career path looks like for leaders and it's not what we all think! Additionally, if we both had a coach to help us navigate entrepreneurship both of us would we have had a much easier time.


Most professionals are taught—explicitly or implicitly—to expect a linear career: choose a direction, climb steadily, and arrive at ‘success.’ But real leadership rarely develops on a straight line. It’s shaped by pivots, discomfort, and the relationships we build beyond our usual circles. It’s also strengthened by what we give back—especially through mentoring the next generation.


Here's a few nuggets of learnings from our discussion.


1) A leader's career trajectory is never a straight line


If your path includes detours, role changes, unexpected pauses, or a complete pivot, you’re not behind—you’re building range; more importantly you are not alone! The most effective leaders often draw on varied experiences and overcoming challenges of all kinds from navigating different industries, job functions, working with diverse teams, and even dealing with failures.


Takeaway Tip: Measuring progress by your title or a set timeline to achieve something is setting yourself up for failure. Instead, measure your career success by improving on your own capabilities and knowledge, uncovering further clarity on what direction you want to go and understanding how you impact others.


2) Discomfort often is the catalyst for producing real growth


Growth doesn’t usually feel good. Often, it feels like uncertainty: taking on a stretch role, speaking up before you feel ready, leading through conflict, or learning a new skill in public. These are generally uncomfortable situations that you grow through eventually building your confidence and character to new levels.


Takeaway Tip: Normalize discomfort as part of your development and investment in yourself, your team and those around you. Real leaders build cultures where learning is expected and practiced, not penalized or part of an afterthought or wish list.


3) Network outside your typical circles to unlock new opportunities and perspectives


If your circulating in the same networks those networks become echo chambers: everyone has similar backgrounds, are in the same industry and tend to think the same. While this is comfortable, it's not offering you any real challenge or growth. When you intentionally connect outside your usual circles, you gain access to different personalities, varying thought-models, new opportunities, and ways of solving problems.


Takeaway Tip: Treat networking as curiosity, not transaction. Seek conversations that challenge your assumptions. Learn about others before offering details about yourself.


4) Giving back and mentoring are essential leadership skillsets and responsibilities


Leadership is more than merely advancing in your career; it involves nurturing your community and preparing future leaders. By mentoring emerging professionals, you create a lasting impact that extends far beyond your immediate influence. Mentoring is not just for senior leaders to do; anyone can cultivate this essential skill. Engaging in mentoring enhances your own abilities, fostering deeper connections, refining your leadership style, encouraging accountability, and promoting long-term thinking. Ultimately, mentoring enriches both the mentor and the mentee, building a community of leaders ready to tackle future challenges together.


Takeaway Tip: Make giving back and mentoring a core part of your leadership mantra rather than an occasional extra. Mentor early and often—start with one person and solidify your personal impact on your community.


Now here's how you can put this all into practice immediately:


  • Identify one area where you’ve been avoiding discomfort—and take a small step toward it.

  • Reach out to one person outside your usual professional circle and schedule a 20-minute conversation.

  • Offer mentorship to someone earlier in their career (or ask for mentorship if you’re the one growing).

  • Share one lesson you learned the hard way—so someone else doesn’t have to.


Leadership development is seldom linear; it is often advanced through periods of challenge, expanded professional networks, and a sustained commitment to mentorship and service to others.




 
 
 

Comments

bottom of page