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  • Writer's pictureAnna Conrad

5 Important Questions to Ask Yourself Mid-Career + Action Steps

Navigating the midpoint of your professional journey offers a critical opportunity for strategic reflection and deliberate action. As an executive coach, I have guided hundreds of seasoned professionals through this pivotal phase, empowering them to leverage their experience and prepare for future opportunities. I also have the unique perspective of a senior executive who understands what it takes to be successful and common career derailers.

As you crest the hill of your career's midpoint, it is essential to reflect on your journey and strategize your ascent to the summit. Your career midpoint offers a unique vantage point: behind you are years of experience and achievements, and ahead is the potential for growth and new challenges.

Your career midpoint offers a unique vantage point: behind you are years of experience and achievements, and ahead is the potential for growth and new challenges.

Here are five pivotal questions that can catalyze this transformation, supported by compelling statistics and actionable insights.


1. Have I achieved what I initially set out to do?

Begin by assessing your initial career objectives. Revisiting your original goals can ignite renewed motivation and clarity. If there is a gap between your aspirations and your current reality, consider this a blueprint for your future actions. Reflect deeply: write down these goals, then list your achievements and areas of shortfall. Consider if your goals are still relevant, and give yourself to change them if they are not. After all, you are a different person than when you began your career. This exercise isn't just reflective—it's a springboard for your next giant leap.


2. What new skills can I acquire to enhance my market value?

The corporate landscape is ever-evolving; staying relevant means continuously upgrading your skill set. A LinkedIn survey revealed that 72% of successful mid-career professionals attribute their success to ongoing learning and skill acquisition. Identify emerging industry trends and the associated skills needed. Then, commit to a learning plan—formal education, online courses, or hands-on projects.


3. Am I a mentor, a mentee, or both?

Mentorship enriches both the mentor and the mentee. If you still need to take on a mentorship role, now is the time to share your wisdom. Conversely, seeking a mentor can provide insights and advice to navigate forthcoming challenges. Engage actively in your professional community; now is the perfect time to take on leadership roles in industry organizations.


4. How does my work impact my organization and society at large?

Beyond personal success, consider your broader impact. This reflection is philosophical and a strategic alignment of your career trajectory with larger, impactful goals. Evaluate how your role advances your organization's mission and contributes to societal good. Such alignment enhances job satisfaction and amplifies your professional identity and legacy.


5. What would I regret not pursuing or achieving in my career?

Imagine looking back from the brink of retirement. What achievements would you regret not pursuing? This powerful foresight can guide your immediate decisions and long-term planning. It is about crafting a legacy, not just completing tasks. Set bold, transformative goals that challenge the status quo and propel you towards a fulfilling career finale.


Action Steps to Take Today

  • Draft a Revised Career Blueprint: Update your career goals based on today's insights and aspirations.

  • Commit to a Learning Agenda: Choose at least one new skill to learn in the next six months and begin a course or project.

  • Initiate a Mentorship Connection: Within the next week, either find a mentor or offer to mentor someone else.

  • Align Your Career with Larger Goals: Write down how your current role can be leveraged for a more significant impact, and start one initiative this quarter that aligns with this vision.


By tackling these questions and following through with decisive actions, you rejuvenate your mid-career journey and set a trajectory beyond the ordinary. Remember, the goal is not just to climb the ladder but to expand the horizon of what is possible in your professional landscape.


👉🏽Do you want more real-life leadership tips? Sign up for the Monday Morning Mentoring YouTube channel and the ILS monthly newsletter. Also, follow me on LinkedIn.


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