April 8, 2024

Soul Searching: 7 Key Questions to Define Your Career Path

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His career path was in doubt. Three years of drudgery were all that Matthew could put up with before deciding to throw in the towel. Commuting to work daily with ‘a bee in his bonnet’, he realised that this wasn’t the job he wanted. Like many in his situation, Matthew was aware of what he didn’t want but remained clueless about what his desired career looked like. 

A good place to start discovering your career pathway is to dig deep within by asking some helpful questions.
A good place to start discovering your career pathway is to dig deep within by asking some helpful questions.

June on the other hand had a razor-sharp focus on pursuing a career in accounting. But as her job hunt journey unravelled, many career pathways seemed plausible, leaving her unsure and unclear about what to do and how to begin, as she was a fresh graduate. 

Embarking on a career journey is akin to embarking on a quest—it requires self-reflection, courage, and a deep understanding of one’s desires and aspirations. Yet, in the hustle and bustle of everyday life, many individuals find themselves adrift, unsure of their true calling. If you’re feeling lost, uncertain about the next step, and mulling over the impending question of how to find a career you love, fear not. By asking yourself the right questions, you can unearth hidden truths and pave the way for a fulfilling and purpose-driven career.

Question 1: What am I passionate about?

Passion is the fuel that propels us forward, igniting our enthusiasm and driving us towards our goals. Take a moment to reflect on the activities, subjects, or causes that light a fire within you. Whether helping others, solving complex problems, or expressing your creativity, identifying your passions is the first step towards aligning your career with your innermost desires.

Helpful tip: List the experiences and conversations you have had that made you feel passionate about something. The process of introspecting and writing them down may guide your journey of discovering your innermost passion. Having conversations with others can help you gain clarity as well. 

Question 2: What are my strengths and weaknesses?

Understanding your strengths allows you to leverage your unique talents and abilities to excel in your chosen field. Conversely, acknowledging your weaknesses provides an opportunity for growth and development. Conduct a thorough self-assessment to identify your strengths, weaknesses, and areas for improvement, then seek out opportunities that allow you to capitalise on your strengths while addressing any areas of weakness.

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Helpful tip: Try to recall the times you were complimented for a job well done or for a trait that others have given you an honourable mention for. These help to inform where your strengths are.

Likewise, as far as it is safe for you to do so, reflect on the times when things didn’t go well because of a shortcoming on your end. What lessons did you learn from them and how have you worked on those areas? It can be confronting to think about our weaknesses. But be assured to know that everyone has weaknesses and blindspots that can be addressed over time. Be kind to yourself knowing that there is always room for improvement. 

Question 3: What are my core values and beliefs?

Our values and beliefs shape who we are and guide our decisions and actions. Take the time to reflect on your core values—integrity, honesty, compassion, etc.—and consider how they align with your career aspirations. Choosing a career path that is congruent with your values ensures a sense of fulfilment and authenticity in your work.

Helpful tip: One helpful exercise to consider is to write your personal manifesto. If you were a brand, what values define you? This can be a fun exercise that compels you to examine your principles and beliefs, which will shape your work ethic and direct you towards your ideal career.

Beginning with the end in mind will help you determine the steps you need to take in finding your career path.
Beginning with the end in mind will help you determine the steps required to finding your career path.

Question 4: What are my long-term goals?

Visualise your ideal future and set clear, achievable goals to work towards it. Whether it’s advancing in your current field, transitioning to a new industry, or starting your own business, defining your long-term goals provides direction and purpose in your career journey.

Helpful tip: In his book, 7 Habits of Highly Effective People, Dr Stephen Covey defines habit #2  as ‘Beginning with the End in Mind’. What does the final picture look like in your mind’s eye? With the end in mind, you will understand which direction to take. 

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In a world where things are rapidly changing and often unpredictable, it may seem counterintuitive to think too far ahead. However, having a reasonable view of what your future might look like can help with your goal-setting. You could think in terms of a long-term view, a mid-term view and a short-term view. Do I see myself owning a business in 10 years? What are some milestones I should work towards over the next three to five years? In a year, will I have gained enough experience from this job to move up in the ranks or have a competitive edge in the industry? 

Question 5: What brings me joy and fulfilment?

Happiness and fulfilment are the ultimate markers of success. Reflect on past experiences or moments when you felt truly fulfilled and alive. Was it collaborating with others, making a difference in someone’s life, or achieving a challenging goal? Identifying what brings you joy allows you to seek out career opportunities that align with your intrinsic motivations and passions.

Helpful tip: A step further in making sense of what brings you fulfilment is to identify the components of those experiences and memories that brought you joy. For instance, if you had organised a successful event before, what elements made you feel accomplished? Was it your ability to plan the logistics well? Was it your natural flair to network with the guests effectively? Were your time-management skills and foresight in preparing for the event the confidence boosters? Identifying these gives you a deeper insight into what makes you happy.

Question 6: What lifestyle do I envision for myself?

Consider how your career choice will impact your lifestyle and overall well-being. Do you value flexibility and work-life balance, or are you willing to sacrifice personal time for career advancement? By aligning your career path with your desired lifestyle, you can create a harmonious balance between work and leisure.

Helpful tip: In today’s world of mixed working arrangements, there are a variety of work options that enable employees to produce their best while adhering to the company’s culture and expectations. It would be crucial to consider your circumstances, work ethic, goals and expectations when trying to find the right career match. For some, striking a work-life balance is the way to go, while for others, a work-life integration approach helps them harmonise their personal and professional needs.

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Having considered all things, are you willing to take risks and embrace uncertainties?
All things considered, are you willing to take risks and embrace uncertainties of your career path?

Question 7: Am I willing to take risks and embrace uncertainty?

Embarking on a new career path often entails stepping out of your comfort zone and embracing uncertainty. Ask yourself whether you’re willing to take calculated risks, learn from failure, and adapt to changing circumstances. Embracing uncertainty opens doors to new opportunities and growth, ultimately leading to greater fulfilment and success.

Helpful tip: Our appetite for risks varies over the years. While the general assumption is that the younger and more agile you are, the more capacity you have for risk and changes, it is important for us to correctly assess our needs, wants and aspirations. Am I looking for a stepping stone into a more definite career path with this job? Am I playing roles that may impact dependants if I had to embrace this company culture? What barriers are preventing me from pursuing these new opportunities for growth and development?


By delving deep into these soul-searching questions, you’ll gain valuable insights into your true desires, passions, and aspirations. Armed with this self-awareness, you can chart a course towards career paths that not only align with your values and strengths but also bring you joy, fulfilment, and purpose. Remember, the journey to discovering your true calling may be challenging, but the destination is well worth the effort. So dare to dream, dare to explore, and dare to create the career of your dreams. Your destiny awaits—you just have to ask yourself the right questions.

You are never alone on this job search labyrinth! If you are looking for coaching advice on how to find your ideal career match, or if you are looking for more self-assessment questions and tips, reach out to us now.