The Most Important Questions to Ask Yourself About Your Career

Dr Kerstin Brehm Career Coach for Global Leaders and Leadership coach for Women at a Leadership conference

7 min read

Your career is more than just a job, it’s a reflection of your values, passions and aspirations. Yet, how often do you pause to truly evaluate where you’re headed? Asking yourself the right questions can uncover what drives you, highlight your strengths and help you align your professional life with what matters most to you.

Taking the time to reflect on your career doesn’t just clarify your goals; it can also boost your confidence and engagement. Did you know that people who use their strengths daily are six times more likely to feel engaged at work? By exploring what excites you, what challenges you and what you want to improve, you can take charge of your growth and create a path you’re genuinely proud of.

So, why wait for a job search or a career crisis? Start asking yourself these 12 important questions to unlock your potential and shape your future.

Why Is It Important to Assess Your Career?

Assessing your career helps you align your work with your personal values and long-term aspirations. If your professional life reflects what matters most to you, it’s easier to stay motivated and find satisfaction in what you do.

Self-reflection enables you to identify your strengths, giving you the chance to leverage what you do best and achieve better results. Research shows people who consistently use their strengths at work are six times more likely to feel engaged, which directly impacts productivity and happiness.

Thinking about your career triggers awareness of obstacles that may be holding you back. If you know your weaknesses, it’s easier to focus on improving them and adapting to changes in your field. Career assessment also reveals opportunities within your current role or industry, helping you position yourself for advancement.

It’s essential to consider how your priorities evolve over time. Life circumstances, goals, and interests may shift, and reassessing your career ensures you’re moving in a direction that suits your current lifestyle and ambitions.

12 Key Questions to Reflect Upon Regarding Your Career

Taking time to reflect on specific questions can guide you towards a career that aligns with your values, skills, and long-term goals. Answering these questions helps clarify your career direction and maximises your professional satisfaction.

1. What Am I Passionate About?

Your passions significantly influence your career choices. Activities you enjoy in your spare time can guide you towards roles that integrate these interests. Considering what energises you at work; working with people, solving problems, or creating something new can help identify fulfilling career paths. Ask yourself:

  • What are my favourite hobbies?
  • Do I enjoy working with people, objects, ideas, or data the most?
  • What tasks or projects make time fly by for me?

2. What Skills Do I Currently Possess?

Mapping out your skills helps you align them with various career opportunities. List your expertise and determine whether they are job-specific (hard skills) or broadly applicable (soft skills). For instance:

  • Hard skills might include coding, financial analysis, or graphic design.
  • Soft skills might include leadership, adaptability, or teamwork.

If you’re considering a career switch, identify transferable skills to smooth the transition.

3. What Type of Personality Do I Have?

Your personality shapes what work environments and roles suit you best. Reflect on preferences such as whether you enjoy leading or following, working independently or in teams, and whether you’re a strategist or action-oriented person. This understanding can steer you towards roles where you’ll thrive, whether in fast-paced, structured, or creative settings.

4. What Education or Training Is Necessary to Achieve My Career Aspirations?

Every career has specific qualifications or skills tied to it. Research educational requirements and certifications needed for your desired role. For instance, healthcare roles might need industry-specific training, while some creative professions emphasise portfolios and hands-on experience. Knowing the time and monetary investment required helps you make deliberate decisions.

5. What Is the Employment Outlook for This Career?

A broader outlook on your preferred career can help you make forward-thinking decisions. Assess the growth potential, demand, and future trends in the industry. For example, technology and healthcare fields are rapidly expanding, whereas saturated fields might offer limited openings. Evaluate job stability and earning potential while planning your path.

6. What Does My Ideal Work-Life Balance Look Like?

Work-life balance directly impacts your overall happiness. Decide how much of your life you want to dedicate to work versus personal pursuits. If career advancement means additional hours, consider whether you’re willing to make that commitment. Balancing ambition with leisure ensures you remain productive without risking burnout.

7. How Satisfied Am I with My Current Career?

Periodic reflection on your current career satisfaction is crucial. Consider aspects like your growth, daily responsibilities, and overall happiness in your role. If you’re unsatisfied, identify whether minor adjustments (e.g., skill development) or significant changes (e.g., a new career path) will bring improvement.

8. Do I Prefer Working Indoors, Outdoors, or Remotely?

Your preferred work environment has a major effect on job satisfaction. Evaluate whether you thrive outdoors in active settings, perform better in a collaborative office, or value the flexibility and autonomy of remote work. Understanding this helps narrow down career roles suited to your preferences.

9. Am I Open to Relocating for a Better Career Opportunity?

Relocation might unlock more substantial career opportunities. If your current environment limits options, consider whether moving to a different city or country aligns with your ambitions. Research industries concentrated in specific regions and assess compatibility with your lifestyle.

10. What Am I Prepared to Sacrifice for Improved Career Prospects?

Career advancements often require compromises such as relocation, additional training, or longer hours. Analyse what you’re willing to give up for growth. Reflect on past job experiences to understand which trade-offs worked for you and whether you’re ready for similar commitments.

11. How Is My Current Role Contributing to My Skill Development?

Evaluate whether your current role offers the growth and learning opportunities necessary for your long-term career goals. If you feel stagnant or unchallenged, explore ways to acquire skills, whether through assignments, mentorship, or external learning platforms.

12. How Significant Is Financial Compensation to Me?

Understanding how much importance you place on financial rewards helps refine your career choices. Consider whether you’d prioritise a high salary over job stability, work culture, or flexibility. For example, high-paying roles might come with added stress, while roles offering work-life balance might have moderate compensation.

Step Into Your Full Potential with Leadership Coaching

True leadership isn’t just about titles, it’s about presence, influence, and clarity. If you’re ready to elevate your leadership style, explore my Leadership Coaching services. Together, we’ll work to sharpen your strategic thinking, build confidence, and help you lead authentically, especially in high-stakes environments where results matter. Whether you’re navigating a new leadership role or preparing for a bold career move, personalised coaching can make all the difference.

Dr Kerstin Brehm - Leadership Training session with Women in Leadership

Targeted Leadership Training – Wherever You Are

Ambitious leaders don’t just emerge, they’re developed. That’s why I offer bespoke Leadership Training programmes designed to help you lead with impact, no matter your industry or experience level.

I work with professionals globally, including:

No matter where you’re based, leadership growth starts with the right mindset, tools, and support.

Negotiation Coaching for Women in Leadership

Leadership often means negotiating for resources, opportunities and sometimes, your own seat at the table. My Negotiation Coaching for Women in Leadership is designed to help women navigate these moments with confidence. Whether you’re leading in male-dominated industries or preparing for high-level negotiations, you deserve tailored strategies that work for you.

Career Coaching to Help You Evolve – Globally

If you’re ready to gain clarity, overcome obstacles, and align your career with your ambitions, consider working with an experienced Career Coach.

I offer specialised Career Coaching across key global markets:

Your career is your story, let’s make sure it’s one you’re proud to tell.

Discover More Articles

Your career journey is unique, and taking the time to reflect on it can lead to incredible growth and fulfilment. If you’re ready to dive deeper, explore our related articles for more guidance and inspiration. Whether you’re looking to uncover your values, boost your confidence, or strike the perfect work-life balance, there’s plenty to help you navigate your path with clarity and purpose.

Remember, your career is more than just a job, it’s a reflection of who you are and what you want to achieve. Keep asking the right questions, stay open to change, and embrace the opportunities that align with your aspirations.

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