Considering a Career Change? Don’t Skip These 8 Important Questions

Work shouldn’t be something we hate. Yet many people tend to stay in jobs that they absolutely despise – usually for the money or because they are too afraid to make a career change.

This is terrible for our work-life balance and for our physical and mental well-being!

It’s easy to get into the routine of a job, but it’s hard to get out of it. Changing careers and finding a new career can be scary and daunting, even when you are ready to make a switch.

Before you make a career change, there are a few essential questions you should ask yourself first. By making sure you ask yourself the right questions, you can ensure you end up in the role that’s perfect for you. One that you enjoy and that suits the lifestyle you want to lead.

If you’re not sure what you want to be doing job-wise, but you know that you’re definitely not happy as things are, here are pieces of advice and suggestions to help you figure it out.

Below, you’ll find the essential questions that you should ask yourself before you make a career change.

1. What Don’t I Like About My Current Career?

List the things you dislike about your current job. You might realize that certain things are just temporary and will pass, meaning you don’t actually need to make a career move on at all. A simple chat with your current employer or colleague could help you to iron things out.

No job is going to be perfect. There’s good and bad in everything, so you should be prepared to face a few problems and challenges in any career.

However, figuring out the “bad” that you’re willing to accept is a good place to start. For example, if you really love what you do, perhaps you’re willing to deal with the occasional angry client.

On the other hand, if your list just keeps on getting longer, it’s a good indication that it’s time for you to move on. Staying in a toxic work environment will only do you more harm. This will also give you a good idea of what you don’t want from your next career change, too.

2. What Do I Like About My Career?

There must be something you like about your current career – unless you have completely changed as a person since you started. And that happens. People change! 

Take some and think about it. What was it that made you want to pursue this career field or apply to this job in the first place? When were you happiest in this role?

It doesn’t have to be something exceptional. It could be something simple, such as the atmosphere at work, having a short commute, or a decent paycheck. Try to be specific and consider all aspects of your job so that you have an idea of what you want from your next one.

Focusing on the positives, no matter how small or trivial they may be, will also help you cope until you can find something else.

3. What Do I Really Want In a New Job?

To find any level of job satisfaction and have a successful career, you need a role that matches your values. These are the important and appealing aspects you want from a job. Knowing what your values are can help you figure out which careers are right or wrong for you and determine what other characteristics are non-negotiable.

Think about what you want in your next role. What isn’t ideal but you know you could put up with? What do you absolutely need?

If you imagine what you’d like to be doing, what do you picture? That could be a good indicator of where your passion and interest lies.

Get as specific as possible so you can find a career that’s right for you and can rule out anything that is not suitable. Waking up and dreading the day ahead is never a good thing. When you are in a career that you really do not enjoy, it can be quite common to burn out. So what could you be doing instead if you decided to change careers?

4. What Skills Can I Improve Upon To Give Myself A Better Chance Of Landing A Better Role?

There are transferable skills you can improve upon in your own time to show that you are dedicated and worthy of whatever role you want. Depending on where you want to be, you don’t necessarily need to invest a lot of time or money into learning something new.

Do some research.

What kind of qualifications do you need to have a successful career change? Do you have to go back to school to get a specific professional diploma or specialized license? Is there one topic or program you need to learn more about or develop new skills for? Or do you only need a refresher course or two?

Researching the job market and your career options will help you figure out what you need to do to change your career. Once you know this, you’ll be able to move forward from there.

Taking a course online might not give you official qualifications, but there are plenty of them available that can teach you new job skills (many for free). These can be helpful if you want to prepare yourself for a new position.

Search online and on YouTube for “free [topic] training/course” or browse through course catalogs on sites like Coursera, OpenLearn, SkillShare, and Udemy.

There are also options within your community, such as Adult Education centers, Community Colleges, Literacy Centers, and libraries that offer courses, which are great options, especially for those that prefer to learn in person.

Almost every college and university offers distance education or online courses that you can apply to. If you are changing jobs into a new industry, you could complete a degree or certificate program online without needing to quit your day job.

5. Does This New Career Align With My Passions, Interests, and Strengths?

When looking at your career path or job prospects “follow your passion” is a piece of advice that you’ll hear a lot. But what if you’re not sure what you are passionate about?

This is a question that people who are just starting out in their career face, as well as people already in the workforce. Especially if their dream job has turned into a nightmare thanks to a horrible boss, or they are stuck in a job that isn’t fulfilling or interesting.

Finding your passion doesn’t have to be too hard. But you need to put in a little effort to discover what you are passionate about.

To start off with, ask yourself a few questions, such as:

  • What books could I read and re-read and not get bored of?
  • Is there something that I would volunteer to do just because I love it so much?
  • If I didn’t have to work for financial benefit, what would I spend my time doing?
  • As a child, what did I want to be when I grew up?
  • What topics, blogs or organizations do I follow on social media?
  • What documentaries do I watch?

If something springs to mind like working with animals, helping people, or traveling, for example, you could be on your way to finding the area of work that could bring you the most joy.

If nothing comes to mind, take some time to figure it out before you change jobs. Reach out to a career coach or career counselor to explore the ideas that interest you. Or take online career assessment tests like Myers Briggs to learn what career opportunities match your personality type.

Make sure you have a strong idea of what your passions and interests are, as well as what you’re good at. In an ideal world, the best jobs for you will align with these. Try your best to find a job that does.

6. Would a Hobby Fulfill the Gap?

When you think about what you enjoy in life and are passionate about, there will be some things that will make great career paths. But some hobbies and passions shouldn’t become a career. Unfortunately, not all passions make money.

Don’t worry if the things you enjoy doing can’t be turned in into a full-time job. Not everything in your life has to be monetized. It’s okay to just enjoy doing things in your spare time.

It is also perfectly acceptable to include relevant hobbies in your resume and cover letter, particularly if it demonstrates your talents, strengths, or skill set.

What you may need instead is to find a new career path that will allow you to have the work-life balance you want. Something that will give you the time (and money) to do the things you love outside of work.

Or, if your job is alright and you’re thinking about making a change of career out of boredom or because you feel like it’s time for a change, maybe a hobby is all you need?

7. Does This New Career Align With My Long Term Goals?

Having an idea of your professional goals is also a must, as your career choices should align with these goals, too. You want to make progress towards your ultimate career goal and not stand still. Or worse yet, go backward.

You may not know what your career goals are. That’s okay! But start thinking about it, even if it’s just in the back of your mind. It may take some time to figure it out, and it might change as time passes.

Don’t forget to consider how your other, non-career-related long terms goals may be impacted. For example, if having kids and raising a family is important to you, what career would allow you to put your family first?

8. Why Are You Considering a Career Change?

There are many valid reasons to change careers. Better pay, better hours, more (or less) responsibilities, less stress, a more prestigious title, following a passion, wanting a new challenge.

What is YOUR reason? Why are YOU considering changing careers?

Knowing your why will determine your next steps.

If you are desperate to escape a stressful work environment, bad management, or bad coworkers, it might be in your best interest to make a move sooner rather than later, even if it is a lateral move. On the other hand, if you like your job but are looking for a career change because there’s no room for advancement, you have time to job search and explore other options where there are opportunities for job growth.

Before making a career change and switching careers, take some time to answer these questions so that you can find something you love!

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Amanda Kay, the founder of My Life, I Guess, provides valuable career advice and support for anyone striving to make a living and, more importantly, make a life. Whether it's navigating job searches, learning new skills, overcoming unemployment, or dealing with debt, My Life, I Guess has been a go-to resource for career guidance and financial stability since 2013. Amanda's expertise and relatable approach have been featured in trusted publications such as MSN,, Yahoo! Finance, the Ladders and Fairygodboss.

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