20 Vital Questions that Will Help You Find Your Dream Job

The perfect career starts with a little soul-searching.

Reviewed by Chris Leitch

Three people finding their dream jobs and questions

When you were a kid, you probably fantasized about becoming a famous singer and making lots of money along the way. But now that you’re a little older, and hopefully a little wiser, that dream of touring the world and performing on stage might seem a little out of reach — mainly because you sound like a drowning cat when you sing.

But if your childhood dream job is a little more realistic, there’s no need to get comfortable in a dead-end job and forget about what truly excites and interests you — before it’s too late.

And that’s what we’re here for. We’ve created this guide to help you sort through the clutter and focus on realistic goals to find the career that you’ll love.

Here are 20 questions to ask yourself to find your dream job.

1. What was your dream job as a child?

Evidently, not all our childhood aspirations are realistic, but looking over what you wanted to be as a child might uncover other careers that you wouldn’t have otherwise considered.

If you wanted to be a TV presenter, for example, but suck at public speaking, you could think of alternative routes in that field. If you don’t have a degree in media and broadcasting, you could apply to be a runner for TV shows and work your way up the ranks. After all, where there’s a will, there’s a way!

2. What’s your personality like?

Are you an introvert or an extrovert? Do you like to work with people or are you a lone ranger? It’s important to discover what you’re truly like as a person, as this will help you identify which roles best suit your interests.

A good start would be to take a personality test, which will give a list of ideal career paths that suit your characteristics and personality traits. Even if the suggested jobs aren’t really ones you’re interested in, they will help you narrow down the route that you actually want to take.

3. What’s your purpose?

What do you want to accomplish through your job? Do you want to create innovative products that will change people’s lives? Do you want to write informative news pieces? Do you want to entertain people with your comical skills, or perhaps help people in need and work for a charity? Whatever it is, be sure to discover what your purpose in life is and find a job that helps you share those values.

4. What’s your ideal working environment?

Where you work and who you work with is an important part of job satisfaction. You could be working in your dream role, but the environment could completely kill the enjoyment and you could ultimately end up hating your job. It is, therefore, imperative to look at a company’s culture before applying and to figure out what type of environment you want to be working in.

Do you want to work at a laidback office where you have flexibility in your position, like employees at Google and Apple? Is work–life balance an important factor for you?

Spend some time hunting down different companies and make a list of the top 10 you would want to work for.

5. Would you trade your job for your friends’ job?

If you admire a job your friend does and wish that you too could do something related, you should probably research the industry and figure out what steps you need to take to have a similar job. In order to find out if it would be your dream job, connect with people in that industry and have informal interviews.

6. What did your past jobs teach you?

Your past jobs can lead the path to your future. By looking at your previous experiences, you can discover what it is you liked and disliked.

When you’re completing this exercise, make sure you write an equal number of pros and cons so you can fully understand what duties you want to have in your next job and what it is that you don’t want to do. If you’re fresh out of university and haven’t had a full-time job yet, look at previous tasks you completed in your course and what you enjoyed the most.

7. Is money really that important?

A large paycheck will make you happy for a few months, but that phase will soon fizzle out and you’ll be left in a depressive rut, going to work just to get a salary at the end of the month.

Having said that, it’s important to figure out how much money you need to live on and what kind of jobs can give you that income. This will help you narrow down your job search to find the right career.

8. What job would you do for free?

Is there a job that you would do for free just because you absolutely love it? Maybe you’re a talented fashion designer and have the opportunity to intern at a top label like Balmain. If you find something you would do for free, then you’re onto a winning dream job — one that getting paid for would just be an added bonus.

9. What are your hobbies?

Is there something you do in your spare time that you really enjoy? Maybe you’re a fitness fanatic and spend your personal time exercising and creating healthy eating plans and regimes. If so, the answer to your questions is right under your nose, and your dream job is literally in your hands if you will risk a career change for a happier life.

10. What are your strengths?

Are you good at solving mathematical problems? Do you have a calm nature, and are you talented at guiding people and delegating tasks? If so, you’ll make a great leader. By determining your key strengths, you’ll be able to match them to different job positions which, in turn, will help you find your dream position.

11. What are your weaknesses?

It’s great to know your strengths but, with that, it’s important to know your weaknesses too. Maybe you were really bad at science in school, or perhaps you’re not great with kids — if that’s the case, then you might want to avoid jobs in science or teaching.

Your weaknesses don’t have to define you, but they can sure shine a spotlight on areas to avoid as you strive to find your dream job.

12. What makes you happy?

What’s your passion? What truly makes you feel happy and content?

You want a job that has limited stress, and one where you can go home at the end of the day without feeling miserable. When you find this sense of tranquility, you’ll know that you’ve bagged the perfect job.

13. What motivates you?

Beyond your passion and what truly makes you happy, think deeper: what motivates you to keep going every day?

Think outside the money and job security factors you are evaluating thus far, and dig down deep. Motivation will forever be your “push factor”, something on the outside that’s pushing you to take action. Find out what yours is to achieving a specific standing in life, and let it continue to push you towards your dream job.

14. What’s your preferred style of work?

Would you rather work for a large company, a small startup, or on your own? It’s important to identify what kind of working style you prefer. For example, if you want to work on your own and determine your own schedule, you could either freelance or start your own business to ensure you have the ideal job.

List of Careers to Explore Your Options

15. What jobs would you really like to do?

There are probably a handful of jobs that you would love to do but might not actually have the skills to complete them. Make a list of your dream jobs — well, at least ones you think that would make you happy.

16. What skills do you need?

Following on from the previous point, once you have your list of positions, spend about 30 minutes researching the skills, qualifications and experience needed for each job. You should then circle the roles that you actually can and are currently equipped to do.

17. What are the ups and downs of that career?

Once you’ve gathered your answers to all the above questions, consider the pros and cons to the careers that are on your current list. Be sure to do your research and discover what a life in that path looks life; if it ties in with all your hopes and dreams, you may be on to a winner.

18. What’s your current daily schedule?

There’s no use reinventing the wheel here — maybe your current schedule is what makes your life currently work, so why change it?

For most jobs, though, you may not be able to stay in the same spot in your comfy clothes all day watching Netflix, but that doesn’t mean you can’t find the job of your dreams that allows you to work from home.

Analyze what specifically you love about your current schedule, and look for your dream job that can complement that lifestyle and doesn’t throw some night shifts into your schedule.

19. Is work–life balance important?

When it comes to your dream career, be sure to ask yourself about the importance of work–life balance.

Let’s say you’re evaluating the potential of retail industry job. Consider the working hours and see if that fits your desire for the evolving definition of work–life balance as it pertains to you. Before you commit to your dream career, you need to ensure it fits with your forever outside-of-work goals too.

20. What are your non-negotiables?

At the end of the day, you may have to compromise on some of this list, as you are asking and answering questions to help you find your dream job. You may not find the right career that ticks all the boxes, but that doesn’t mean you should compromise on the most important items for you.

Perhaps working overtime is a no-go for you; add it to the list! One of the most important questions you can ask yourself to help you find your dream job is “What am I not willing to compromise on?” — and don’t compromise. Create a list of your non-negotiables and stick to them.

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Key takeaways

It’s completely okay to not know what your dream job is, even if you’ve been in the working world for a number of years. Some people end up spending their whole life jumping from job to job, trying to find their ideal path. However, finding your dream job isn’t impossible, and this guide should help you narrow down the search.

When you're asking yourself questions that will help you find your dream job, remember these pointers:

  • Consider your strengths and weaknesses. Don’t let them define you, but allow them to help steer your direction for selecting your dream job.
  • Learn from your past to help define your future. Consider your previous jobs, skills and hobbies, and allow them to foreshadow what could come in your future.
  • Define your no-go list early, and stick to it.

How do you envision your dream job? Let us know your thoughts in the comments section below.


Originally published on February 20, 2018. Updated by Shalie Reich.