40 Career Questions: Assess Your Job & Plan Your Next Moves

Are you content in your career, or are you itching to make a change? Are you worried about where the job market is headed and wonder how to maintain a competitive edge?

Your job is a big part of your life. The more thoughtful and strategic you are about it, the more rewarding it can be. We’ve put together 40 career questions that will help you evaluate your career, assess your professional self, navigate career challenges, and plan for a second career.

Continue reading for these questions that could set you up for greater success and fulfillment.

Questions to Evaluate Your Career

The following two exercises contain career questions that will help you assess your current and past jobs and consider the role of chance in your career.

Exercise: Assess Your Current Job

In How Will You Measure Your Life? business consultant and Harvard professor Clay Christensen shows how economic theories that help businesses succeed can also help individuals make better life decisions. He presents theories and business case studies that show you pitfalls to avoid (such as marginal thinking and outsourcing your parenting), and also how to build a career that makes you happy, how to deepen your relationships with your spouse and children, and how to live with integrity. Together, they offer a philosophy for living a fulfilling life.

People choose jobs based on 1) hygiene factors (money, status, perks, security, working conditions), or 2) motivating factors such as having challenging work, responsibility, learning, the chance to grow, and the chance to make a meaningful contribution. The motivators rather than hygiene factors are what make you happy.

  1. What factors made you choose your current job? Which were hygiene factors (money, perks, security, working conditions) and which were true motivators? Which were most important in your decision?
  2. How do you feel about your job now? (Do you love or just tolerate it?)
  3. What factors will you prioritize in choosing your next job?

Exercise: Debunk the Passion Hypothesis

In So Good They Can’t Ignore You, author Cal Newport considers the question: What makes people love their work? Drawing on interviews with professionals, performance science, case studies, and experimentation with strategies in his own career, Newport discovered that the popular recommendation to follow your passion is very much not the path to loving your work.

In fact, the path to loving your work is to become so good—so highly skilled—that no one can ignore you. Then, you can cash in your skills for work that comes with desirable traits.

Following your passion isn’t going to make you happy—the three factors that most contribute to workplace satisfaction are independence, capability, and connection.

  1. Think back on all the jobs you’ve had in your life. Describe two or three jobs that you’ve enjoyed. 
  2. Of the jobs you’ve enjoyed, what characteristics did they have in common? Did they offer independence, capability, or connection? 
  3. Of the jobs you’ve enjoyed, did any of them match a pre-existing passion? Why or why not?
  4. List two or three jobs that you didn’t enjoy. What characteristics did they have in common? Did they discourage independence, capability, or connection?
  5. Of the jobs you didn’t enjoy, did any of them match a pre-existing passion? Why or why not?

Exercise: Consider the Role of Chance in Your Career

In Fooled by Randomness, former options trader Nassim Nicholas Taleb examines the outsized role luck plays in success, how and why people don’t generally understand luck, and how we can accommodate randomness in our lives once we’re aware of it. Taleb primarily focuses on examples from the world of investing, but his principles are applicable to any field ruled by unpredictability (such as economics or politics) and demonstrate how we’re fooled by randomness in many aspects of our lives.

People often underestimate the influence of luck on success. We very often attribute luck to skill and randomness to determinism.

  1. Look back on your own career progression. What were the major turning points along the way—the pivotal moments where you were either faced with a choice or an opportunity found you?
  2. Do you think these pivotal moments were due either in part or in whole to chance? Why or why not? 
  3. Describe a time along the way when a choice you made regarding your career—or a gamble you took—might have turned out differently. 
  4. Had you made this choice differently, how might that have affected your career path?

Questions to Evaluate Your Professional Self

The following exercises contain career questions that will help you assess your purpose, strengths, weaknesses, and goals.

Exercise: Find Your Why

Purpose-driven people and organizations are more successful and fulfilled, and they contribute more to the world around them, according to Simon Sinek, best-selling author, coach, and popular TED Talk speaker. Find Your Why distills Sinek’s theory and his experience working with organizations and individuals into a workbook you can follow to discover your own purpose and strengths, or those of your organization.

Consider how clarifying your purpose could improve your life.

  1. Think of a time when you felt fulfilled. What were you doing?
  2. Do you feel fulfilled with the work you’re doing now? If you do, where does that sense of fulfillment come from? If not, how would your life be different if you were working at a fulfilling job?
  3. If you were working at a fulfilling job, what kind of decisions would you make more confidently and why? For example, knowing your purpose might help you choose a new path for your career or choose between competing career opportunities.
  4. Consider your “What,” including your work, personal life, and other projects. What overlap or similarities do you see between them? Is there a common thread?

Exercise: Identify Your Current and Future Self

What do master chess players and master businesspeople have in common? Both always plan five steps ahead. In Your Next Five Moves, entrepreneur Patrick Bet-David argues that what distinguishes exceptional business leaders from average ones is their ability to anticipate future events and plan effectively for them—ideally by thinking five steps ahead. To turn you into a master business planner, Bet-David presents five strategic steps you must start taking now: learn about yourself, improve your problem-solving skills, create a winning team, expand your business, and position yourself as an industry leader.

Take Bet-David’s first strategic step by understanding who you are now, who you want to be in the future, and how to get there from here.

  1. Being as objective as possible, write down your personal qualities, your strengths and weaknesses, the circumstances in which you thrive, how others perceive you, and anything else that comes to mind about your personality. (For example, you might be extremely sociable, have a hard time focusing on long-term projects, be perceived as a social butterfly, and thrive in fast-paced work environments.)
  2. Next, write down three to five career goals you hope to achieve. (For example, you might aspire to work for a high-profile tech company.)
  3. Finally, write down ways you can take advantage of your strengths (and avoid triggering your weaknesses) to pursue those goals. How can you best leverage your unique personality to realize your aspirations? (For example, as an extrovert who doesn’t like long-term projects, you might achieve your goal of working for a high-profile tech company by seeking roles in public relations, where you’ll need good people skills and projects are short-term.)

Questions to Navigate Career Challenges

The following exercises contain career questions that will help you compete in today’s fast-changing job market.

Exercise: Develop a Competitive Edge in Your Career

Do you feel like the job market is changing faster than ever? Does job stability seem like a thing of the past? In The Startup of You, LinkedIn co-founder Reid Hoffman and entrepreneur Ben Casnocha argue that, to build a successful career in the modern world, you must approach your career as if it were a startup company—something that’s always growing and adapting. By applying principles of entrepreneurship to your career, you can overcome unexpected career obstacles and react quickly to opportunities.

As Hoffman and Casnocha point out, many startups leverage their unique value to stand out from the competitors and achieve success. Apply the authors’ strategies to define your competitive edge.

  1. What hard assets do you currently have (finances, possessions, and so on)? How might these give you an advantage over others? For example, you might own the latest technologies related to your field.
  2. What soft assets do you have (knowledge, skills, connections)? These might be tasks that other people find difficult but you find easy. What’s one specialized skill you can learn that can help you stand out in your field?
  3. Stand out from competitors by identifying your unique values and aspirations. What motivates you? What do you consider important in your life? This might be freedom, the ability to express your creativity, or the promotion of diversity in your field.
  4. What market is your job catering to? What popular or trending market might your skills be valuable in?

Exercise: Create Multiple Career Plans

Hoffman and Casnocha advise that, to navigate the ever-changing job landscape, you should plan out three possible career paths instead of a single one. They explain that many startup companies became successful not because they had a brilliant idea from the start but because they could pivot quickly when their idea failed or when a better direction opened up. Like these successful startups, make plans so that you’re prepared to switch paths easily, take risks, and be resilient to setbacks. Here are the three plans you should have in place:

Your Current Path (“Plan A”): This is the path that you’re currently on or the field that you’re working in.

Your Alternative (“Plan B”): Your alternative plan should be in a field related to Plan A, one that you can turn to if you run into problems with your current path or if a promising opportunity suddenly appears. The authors advise you to shift to Plan B before you think you should or consider starting it up on the side.

Your Last Resort (“Plan Z”): Your last resort plan is where you go to regroup if opportunities fall through or if the risks you take don’t work out. This could mean moving back in with your parents or working temporary gigs like driving for rideshare services. When you have a Plan Z, you feel more comfortable taking risks and acting quickly on potential life-changing opportunities.

Develop three career plans so you can adapt to changes in the modern work world.

  1. First, describe your Plan A. What is the current career path you’re on? In what ways are you currently using your skills and knowledge?
  2. Next, to make a Plan B, consider something that you’re interested in, which is different from yet related to Plan A. For example, if you work in HR, you might be interested in a career in coaching.
  3. What’s one way you can prepare yourself to pivot to your Plan B? For example, you could take courses, intern, or volunteer in that field.
  4. Lastly, form a Plan Z by considering what you can fall back on if your first two plans don’t work out. What’s a temporary job you could take up to support yourself financially?

Exercise: Reflect on the State of the World Today

These days, the world is moving faster than ever. Every day new scientific discoveries are announced, conflict breaks out somewhere in the world, and nature and the climate behave unexpectedly. If you feel overwhelmed or destabilized by this, you’re not alone—no period in the history of humanity has ever been subject to such quickly changing conditions as today.

In Thank You For Being Late, Thomas Friedman explains how these conditions arose—the three forces that shape the world, technology, globalization, and climate change, all accelerated at once—and how we can adapt to them.

  1. What discoveries and world events have significantly changed how you do your work or live your day-to-day life?
  2. What’s a change that affects your job that you struggle with? What have you done so far to adapt? What could you do to further adapt? 
  3. What technologies currently exist that you’re not taking advantage of? What’s preventing you from engaging with that new technology?

Exercise: Adapt to Changes in the Workforce

Friedman writes that the three accelerations of technology, globalization, and climate change drive change in the workforce.

  1. Which parts of your job could be automated? Which parts can’t? 
  2. If you had full control over your job description, how would you change it so that it more evenly requires both people and technical skills? 
  3. Where might you find lifelong learning opportunities? Consider professional development programs at your workplace, online classes, and so on.

Exercise: Consider Your Career in the Flat World 

Around the turn of the 21st century, the world changed more dramatically than perhaps at any other time in history. Seemingly all at once, shifts in the political landscape, technological advancements, and collaborative business practices came together to create a new globalized society. In this new world, free markets reign supreme, global trade is the centerpiece of economies, and people have access to more information and are more connected than ever before. The global playing field has evened out. In other words, the world has become flat.

In The World Is Flat, Thomas Friedman explains that, for individuals, the most important aspect of globalization may be its effect on the job market. With the following career questions, you’ll reflect on how you can remain gainfully employed in a flat world by building your versatility, cooperative skills, and ability to integrate ideas.

  1. If you’re in school now, how do you feel about the future job market? If you’re currently working, how might the industry you work in change in the coming years? Now, jot down some skills and knowledge you might acquire to be versatile and able to take on new roles and tasks in the changing labor market. (These might be skills like coding or learning a new language.)
  2. The ability to cooperate and communicate is vital in today’s society. Think about a time recently in which a lack of cooperation made your job or your life harder. What could you do in the future to work more effectively with others? (These might be things like improving your listening skills or developing a stronger relationship with coworkers.) 
  3. Thriving in a flat world may require combining multiple skill sets in new and interesting ways. Think about two or more skills or abilities you have. How might you combine these skills to add a new form of value to a company? (For instance, if you have a strong social media presence and can also code, you might offer to create a video series about coding to help others in the company learn.)

Questions to Embark on a Second Career

Perhaps you’re considering making a major shift in your career, branching out to a second or third career. The following exercises contain career questions that will help you plan and make the most of such a move.

Exercise: Prepare for the Second Half of Your Life

In From Strength to Strength, management expert Arthur Brooks says that, as we get older, our professional skills start to decline, and we can no longer succeed in our current jobs. Despite this, with the right mindset, the second half of your life can be even happier and more meaningful than the first. If you find a job that suits your changing skill set, and if you change your idea of “success” from career achievement and material wealth to happiness and fulfillment, you can continue to thrive.

  1. What position or career path could you aspire to that lets you use your knowledge and experience as you age? (For example, if you’re currently an office worker, becoming a training manager for your company could play to these strengths.)

Exercise: Plan Your Second Career

Managing Oneself is a guide to finding success in your career. Peter Drucker asserts that, through careful self-management, you can build a career where you thrive and feel rewarded. Drucker likens managing yourself to taking responsibility for yourself and your own career development so that you can grow and achieve throughout your entire working life. 

Drucker encourages everyone to have a second career, to keep their working life interesting and to increase their chances of career success. These questions will help you to plan out your transition to your second career.

  1. First, identify what your ideal second career would be. (Would it be a shift into a totally different field or a change to a different role within your current industry?)
  2. Now, consider which route into a second career would be best for you: a gradual career transition or a sudden switch. Why this route?
  3. What three actions could you take within the next year to lay the foundations for your second career? (For instance, you might take a training course relevant to your ideal new role or professionally network with people in your desired industry.)
40 Career Questions: Assess Your Job & Plan Your Next Moves

Elizabeth Whitworth

Elizabeth has a lifelong love of books. She devours nonfiction, especially in the areas of history, theology, and philosophy. A switch to audiobooks has kindled her enjoyment of well-narrated fiction, particularly Victorian and early 20th-century works. She appreciates idea-driven books—and a classic murder mystery now and then. Elizabeth has a blog and is writing a book about the beginning and the end of suffering.

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