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How to Choose a Career You Love – 6 Questions to Ask Yourself

January 9, 2024

I'm the woman who transformed adversity into triumph: I left my economic development job, navigated through divorce, and built a business that realized my dreams. Blending support with strategy, I turn dreams into reality. My mission? To empower women to boldly chase their entrepreneurial ambitions every day!

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Are you at a crossroads, feeling that your path isn’t the one you were meant to travel? If you’re reading this, chances are, you’re seeking something more — a career that not only sustains you but also fills you with excitement and a sense of purpose. It’s astonishing, isn’t it, how we’re often expected to chart out our entire life’s course by the time we’re 18? Like many, when I graduated from high school, I was far from understanding what truly ignited my passion, let alone choosing a career that aligned with it. Over time, I’ve realized that too many of us fall into the trap of conforming to expectations set by others, losing sight of what makes us truly come alive.

This might hit close to home for you. Perhaps you’re feeling unfulfilled, even though you’ve followed the path that was expected of you. Maybe there’s a business idea you shelved, a dream career you put on hold because the voices around you — voices of caution, of traditional wisdom — drowned out your own. It’s not too late. The first step to reclaiming your dreams is to stop listening to everyone else and start tuning in to your own desires and aspirations.

In this article, we’ll explore six critical questions to help you rediscover what truly lights you up. These aren’t just questions; they’re keys to unlock the door to a career that resonates with your deepest aspirations. I invite you to grab a pen and paper or download this worksheet (complete with additional thought-provoking questions) and set aside some uninterrupted time to delve into your true self. Ready to take this journey with me? Let’s dive in and start redefining your path to a career that’s not just a job, but a reflection of who you truly are.

#1. What Are Your Core Values?

Understanding your core values is the first step toward career fulfillment. These values are the principles that you hold dear, guiding your decisions and actions. They’re your compass, dictating what feels right and doesn’t. When your career is in line with these values, work doesn’t just feel like work; it becomes a reflection of who you are.

Consider this:

Imagine waking up each morning to the sound of your alarm, feeling a sense of dread at the thought of going to work. It’s not that the job is bad; it’s quite the opposite. It’s a prestigious position at a well-respected company, and it comes with a handsome paycheck and commendable status. Your family and friends often remark on how lucky you are to be in such a position. But deep down, you feel a persistent tug of dissatisfaction, a sense that something just isn’t right.

Picture yourself sitting in your well-organized office, surrounded by the trappings of success. The job demands precision, adherence to strict protocols, and a consistent approach. However, you’ve always been someone who thrived on creativity and independence. You long for the freedom to innovate, to take risks, and to express yourself. But in this environment, your ideas are often stifled by rigid rules and the ubiquitous “this is how we’ve always done it” mentality.

Each day, as you navigate through a labyrinth of policies and procedures, you can’t help but feel confined. It’s like wearing a suit that’s impeccably tailored but suffocatingly tight. The work, which should be a source of pride, feels more like a golden cage. You excel in your role, yet each accolade feels hollow because the work doesn’t resonate with your inner self.

This dissonance between your job and your core values – creativity, autonomy, expression – casts a shadow over even the brightest moments of your career. You begin to realize that no amount of prestige or salary can fill the void created by not being true to yourself. It’s a realization that whispers to you in quiet moments and echoes loudly in your achievements: True fulfillment in your career can only come when what you do aligns with who you are at your core.

Why your core values matter when choosing a career

This scenario is a stark reminder that when our careers are misaligned with our core values, it doesn’t just affect our job satisfaction; it permeates our entire sense of self and well-being. As you reflect on your own career, ask yourself: Does my job reflect my true values, or am I conforming to someone else’s idea of success?

To identify your core values, think about times when you felt most fulfilled. What were you doing? Who were you with? What aspects of those experiences can you trace back to your core values? This reflection will help guide you toward a career that meets your professional goals and resonates with your personal beliefs and values.

#2. What Am I Passionate About?

Passion is the fuel for career fulfillment. It’s what gets you excited to wake up in the morning and keeps you engaged throughout your workday. Passion can stem from hobbies, interests, or subjects that captivate you. When your career aligns with these passions, work becomes more than just a means to an end; it becomes a source of joy and fulfillment.

Think about your childhood or early adult years – what activities made you lose track of time? What subjects could you read about for hours without getting bored? These memories can be key indicators of your underlying passions. It’s also important to recognize that passions can evolve. What excites you five years ago might differ from what excites you today, and that’s totally fine! 

Rediscovering or uncovering your passions might require some exploration. Try new activities, read broadly, and engage in diverse experiences. This exploration is not just about finding what you love; it’s about understanding yourself better, which is a critical component of choosing a fulfilling career.

#3. What Are My Strengths and Skills?

Identifying your strengths and skills is crucial in finding a career that challenges you and feels rewarding. Your strengths are the things you naturally excel at, while your skills are the abilities you’ve developed over time. Understanding these helps you pinpoint careers matching your innate talents and acquired competencies.

Often, people overlook their natural strengths because they come so easily to them. Take time to reflect on the feedback you’ve received from peers, mentors, or during performance reviews. What are the common themes? These are likely your innate strengths. Similarly, consider the skills you’ve honed over the years, whether through formal education, work experience, or personal pursuits.

Leveraging your strengths and skills in your career leads to greater satisfaction and success. When you’re doing what you’re good at, work feels less like a chore and more like a natural extension of your abilities. This alignment can lead to greater career fulfillment and a sense of accomplishment in your professional life.

#4 What type of Lifestyle do you want to live?

Your career choice has a profound impact on your lifestyle. It dictates your work hours and flexibility, overall stress levels, and day-to-day happiness. Therefore, it’s crucial to envision your ideal lifestyle when choosing a career. Ask yourself: what matters most to you? Is it work-life balance, the ability to travel, or spending quality time with your family? Your career shouldn’t just be about the work you do – it should support and enhance the lifestyle you aspire to have.

My journey

My own career journey offers a real-life illustration of how significant this alignment is. As the economic development director for my city, I had a role that many would consider impressive and enviable. It was a stable position with a consistent paycheck. More than that, the work was fulfilling – I loved helping business owners grow, assisting them in finding new locations and teaching marketing strategies for expansion. On paper, it was a dream job.

However, despite the satisfaction I found in the work itself, there was a disconnect between the demands of the job and the lifestyle I yearned for. As a divorced mother of two young children and the owner of a lively golden doodle, I craved more flexibility. I remember the frustration of having to request an afternoon off to attend my daughter’s basketball game or the stress of managing my PTO to ensure I could enjoy family events like camping trips and weddings. No matter how rewarding the work, the rigid structure of a 9-5 job was at odds with the family-oriented life I wanted to lead.

Fast forward to today, as a women’s entrepreneurial coach, my work hasn’t drastically changed in nature – I’m still empowering others to grow and succeed. But how I live while doing this work has transformed completely. I now have the flexibility to work from home, tailor my schedule around my family’s needs, and even work on the go. This flexibility means I no longer have to choose between my career and being present for the small yet significant moments in my family’s life. I’m writing this blog post while traveling. I’m excited about attending every basketball game school event and planning a three-week family vacation to Yellowstone National Park following my sister’s wedding next year.

The work is the same the lifestyle is different.

The essence of the work I do remains similar to my role as the economic development director. Still, my lifestyle looks vastly different – and it’s a change that brings me profound happiness and fulfillment.

I encourage you to ponder a typical day in your ideal life. What time do you start work? What environment are you in? How much free time do you have? How does your work integrate with your personal life? Answering these questions is not just about planning your future; it’s about sculpting a career that fits seamlessly into the tapestry of your desired life.

#5. How Much Financial Security Do I Need?

Financial security is a significant factor in career decisions. It’s about finding the balance between a job you love and one that meets your financial needs. Reflect on what financial security means to you. Is it having a steady paycheck, saving for the future, or having the financial freedom to enjoy your hobbies and travel? Your career should align with these financial goals to ensure overall satisfaction.

For many, the fear of financial instability can be a barrier to pursuing a dream career, especially if it involves entrepreneurship or a career shift. It’s essential to acknowledge these fears and address them realistically. Consider the worst-case scenarios and plan for them. Remember, financial security includes having a safety net, like savings or an emergency fund.

Financial mindset plays a crucial role in this journey. Many people harbor unconscious beliefs about money that can limit their potential earnings. It’s essential to explore these beliefs and challenge them. Books like “You Are a Badass at Making Money” by Jen Sincero can be a great resource. Understanding and shifting your financial mindset can open new career fulfillment and success possibilities.

#6. Am I Open to Continuous Learning and Adaptation?

The willingness to learn and adapt is crucial in today’s ever-changing job market. Careers evolve, and new opportunities arise often. Being open to continuous learning means staying relevant and competitive in your field. Ask yourself if you’re willing to invest time and resources into learning new skills or adapting to new technologies and methods.

Continuous learning isn’t just about formal education. It includes attending workshops, reading industry publications, networking, and staying curious about your field. This openness to growth enhances your skill set and keeps you engaged and excited about your career. It’s a vital component of career fulfillment, as it allows you to evolve with your career.

Remember, adaptability is also about flexibility in the face of change. It’s about embracing challenges and being willing to step out of your comfort zone. This could mean changing industries, starting a new venture, or even relocating for a job. Consider how adaptable you are and how that trait can influence your career path.

You got this!

Choosing a career you love is a journey of self-discovery and courage. It involves understanding your core values, passions, strengths, and the lifestyle you aspire to lead. It’s about balancing financial security with job satisfaction and being open to continuous learning and adaptation. Reflect on these six questions to guide you toward a personally and professionally fulfilling career.

I’d love to hear about your journey to finding career fulfillment. Share your experiences in the comments, or reach out for a deeper conversation. If you’re looking for personalized guidance, book a free discovery call with me here. Together, we can explore the path to a career that lights you up.

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