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19 Questions to Ask Before Making a Career Change

Knowing the questions to ask before making a career change can put everything in perspective and make the transition less stressful.

Almost everyone will consider a career change at some point. In fact, a recent survey of 665 full-time U.S. workers found almost 50% of respondents had actually completed a career change. Moreover, 65% of those who hadn’t made the transition were considering it. However, undertaking a career change is a big step. It involves all kinds of significant life changes like a lower income, a drop in seniority, and more training just to name a few. Plus, you’ll have many questions to ask before making a career change. Therefore, careful thought and research are required upfront to make sure you’re on the right track. Based on the study, the average career change took 11 months, so perseverance is essential.

To help get prepared for a career change, you’ll need all the facts. Below are some of the key questions to ask before making a career change. They are designed to help you find out more about yourself and your decision. Using the information you gather from your answers, you can put together a realistic plan of action to achieve your career aspirations.

The Decision

Exploring the roots of your desire for a career change can help you ask answer the right questions.

Exploring the roots of your desire to change careers is important. If your motivation stems from difficult co-workers or a toxic office environment, a job change may be a better course of action. However, if you are getting no satisfaction from the core activities of your work, a career change could be a better idea. The study cited above found that pay was the largest motivator with 79% of career changers. Other important factors included advancing professionally and experiencing new challenges.

Chances are that if you are seriously considering a career change, you are feeling strongly about leaving your current position. To better understand the root of your dissatisfaction and longing for change, here are important questions to ask before making a career change so you can make an informed decision.

Contemplating 19 questions about your future can take some effort, and keeping the answers straight can pose a problem. That’s why we’ve put together the following 19 questions in a worksheet format. Fill it in online or download and print it to guide you through the questions you’ll need to answer to begin potential career change.

1. Why Are You Dissatisfied in Your Current Position?

Be specific. Take the time to write down the exact things that are bothering you. Then, analyze what you have written to look for patterns. Is it the people, the place, the work, or a combination? Getting to the root of the problem is crucial.

2. If You Were Told You Couldn’t Work in Your Field Anymore, How Would You Feel?

Sometimes the status quo or job stagnation can make you forget why we got into a career in the first place. Try to remember what appealed to you and what you enjoyed previously.

3. Can You Identify What Has Changed Since You Embarked on Your Current Career?

If you were excited about your career at one point, identify what changed since you made that evaluation. Have you experienced changes in the industry that you don’t like? Or changes in your job duties?

4. Do You Enjoy Your Current Work Environment, Why or Why Not?

Examine your feelings about where and with whom you work. Would you like to find the same type of environment, or is this part of your decision to change your career?

5. If You Could Have the Exact Same Job With a Different Company, Would You Take It?

This question is probably the most telling in this section. How would you feel if you were offered the same job again? Use the feelings that arise to help you target the areas of discomfort. Can your situation improve by changing jobs, or is a change of career required?

Use the information you gather here to help you make an informed decision. In addition, come up with a shortlist of lessons learned. Every position and every experience teaches us about our preferences and our aptitudes. We learn about what inspires us and what holds us back.

Knowing now what you didn’t know at the start of your previous position and/or career, what have you learned? Maybe you discovered that you prefer to work remotely. Perhaps you have a preference for teamwork. Take this information and include it in your next job search to avoid past mistakes.

Your Skills and Resources

Knowing what skills and resources translate to another career can help you transition to a new career seamlessly.

In this section, you will answer some difficult questions about the practicality of a career change. Part of undergoing a career change will involve evaluating your current skills and monetary resources to see if you have what you need—and if not, how to get it. Career changes can be stressful, especially if you don’t have the skills to make the transition or the money to last through a job search. In addition, will you be comfortable with a temporary drop in wages or loss of professional status? Below are critical questions to ask before making a career change that identify your current level of preparedness and commitment.

6. What Is Your New Career Goal?

Try to describe in detail where you want to go. Having a vague idea won’t help you in this section. You need to establish your next steps and what resources will get you there.

7. What’s Motivating You to Change?

If you are passionate and dedicated to your new endeavor, you have the ability to overcome obstacles or a temporary reduction in resources. As you make your plan, remember that you will need to balance your practical needs with your higher aspirations.

8. What Are the Top Five Skills Immediately Transferrable to Your New Career?  

Identifying these skills is essential to marketing yourself in your new career. What have you learned that’s transferable to a new career?   

9. Can You Identify the Top Five Skills That You Need to Learn?

Accepting what you don’t know is also essential. You will probably have some gaps to address before you can fully transition.

10. Do You Need Additional Schooling or Training, and Can You Fund It?

Gaining additional training in today’s job market is perhaps easier than it’s ever been. In addition to traditional colleges and vocational training options, online certification programs and a growing number of MOOCs (massive open online courses) offer free and low-cost ways to improve your skills and knowledge.

11. What Will Realistically Be Your Entry-Level Position?

Most career changes are horizontal transitions at best. Typically, you will probably drop a couple of rungs on the ladder in the beginning. Are you okay with that?

12. Do You Know What Your New Wage Will Be, and Can You Live on It Comfortably?

A drop in wages is a common characteristic of a career change. Furthermore, a lack of money can be a huge drawback to changing careers. Do you have a plan to get you through the lean times? Do you need to move money around, contribute more, or create a savings account?

13. Can You Identify Any Additional Challenges You Will Need to Overcome?

Undoubtedly, unique challenges will present themselves as you transition from one career to another. Depending on where you are in your career and how divergent your new goals are from your old ones can affect the number and severity of the obstacles you face. Having a realistic understanding and mitigation strategies in place will go a long way to promoting your long-term success.

From the information gathered in this section, come up with a plan for managing and leveraging your current resources to help you through the career transition period. Your approach should also include strategies to overcome foreseeable obstacles and challenges you may encounter. Most importantly, the plan should include a training regimen and financial outlook to navigate your career change.

A Portrait of Your New Position

Now it’s time to zero in on what exactly you are looking for within your new career—one that will get you on the right track, by fitting your current skillset and meeting the parameters of time and money established in the previous section. If the previous section built the foundation for your new career, this section sets your initial trajectory.

One of the most important aspects of identifying your target position is conducting research. Do your due diligence when exploring your new industry, companies, and positions. Check with the Bureau of Labor Statistics for up-to-date statistics on wages, industry growth, and more. Other good sources of information are job boards such as the Virtual Vocations job and company databases and social media, especially LinkedIn. Using these resources, below are position-related questions to ask before making a career change.

14. What Is the Position Title and Description That Best Fits Your Skills, Experience, and Education?

Find a few job ads and determine where you fit in. The closer you can match your current credentials to what employers are looking for, the smoother your job search will be. Meeting the basic requirements is key to getting your resume through applicant tracking software (ATS), so applying for positions you want—as opposed to what you are qualified for—will probably result in disappointment.

15. What Specific Industry Are You Interested in?

Some career paths are easier to transition from one industry to another. However, any industry transition requires creativity and perseverance. If you have no other experience in the industry, you can smooth the way by joining industry associations or trade courses to put on your resume.

16. What Type of Company Do You Want to Work For?

Drawing on your previous experience may help you here. Do you want to work for a nonprofit, private corporation, public corporation, or government? Are you looking for a corporate position or are you happier working for a startup? Is a company’s environmental record or charitable effort important?

17. Do You Have a Preference Regarding Your Working Environment?

Describe your ideal work environment based on what you know about yourself. Maybe you decide that a telecommute position is essential. Perhaps you’re excited about working in the field or traveling in your new position. You might also decide you require a shorter commute. While you may not find your perfect environment, now is the time to try for any improvements.

18. Do You Want a Position Where You Collaborate or One Where You Work Independently?

Based on what you know about how you work, what amount of interaction and oversight is best? Do you want to be part of a team? Are you looking to supervise or manage others? Do you work best on your own with minimal oversight?

19. Do You Know Anyone Who Works in the Type of Position You Are Looking for?

Identifying and interviewing people who work in the position you are interested in will help you discover the reality of where you are headed. Position descriptions, company websites, and industry write-ups are always written in a positive light. The real people who work there can provide essential insights into the day-to-day reality of their jobs and the challenges they face.  

The information you gather in this section will help you target your job search by helping to hone your job search parameters. It will also inform your new job search documents. Make sure to carefully recraft your resume, LinkedIn profile, and cover letters to meet the requirements of your sought-after positions and any industry standards.

A career transition can be an intimidating undertaking. However, this worksheet and list of questions to ask before making a career change can help you develop a solid plan, optimizing your chances of success. If you still have questions, seek out the services of a career coach to help you work through your plan. In addition, you may consider investing in professionally written job search documents. Both of these invaluable services can help you focus your resources and save you both time and money.

Have you made a career change? What steps did you go through to make it successful? Connect with Virtual Vocations on FacebookTwitterLinkedInInstagram, and YouTube to share your advice. We’d love to hear from you!


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