5 Questions to Ask Yourself When Changing Careers

Last updated: Jan 17, 2023

If you feel stuck in a dead-end job you despise, it’s natural to have an overwhelming desire to get out. The mistake too many people make is making a career leap without looking to see where they’ll land first. Before hopping the fence to greener pastures, there are five questions to ask yourself when changing careers.


When you explore the deeper reasons for a switch, you’ll have a better chance of finding a position that inspires and energizes you. Making a career change to get a sense of fulfillment should be a calculated, planned decision, never an act of desperation.


5. What Are the Best and Worst Parts of My Current Job?

This question will help you identify exactly what’s lacking and what’s working in your current role. To find the answer, make two lists: one will detail the parts of your job you love and the other will record the things you loathe. Not sure where to start? There are some common areas people often cite that relate heavily to their workplace satisfaction:

  • Flexibility and work-life balance
  • Work culture
  • Management styles
  • Company mission
  • Day-to-day responsibilities
  • Location

Your list will act as a road map when you start the actual job search by showing you the company and position details that you want to avoid and embrace. This list will also help you ensure you’re looking for a new role for the right reason. For instance, a surprisingly large percentage of people who leave a job are quitting their work colleagues, especially bosses, not their actual role. Knowing this ahead of time can have a huge impact on your choices moving forward.


Male employee researching questions to ask himself when changing careers.

4. What Am I Passionate About?

When searching for a new career, many career coaches believe your best option lies at the intersection of your passion and what is needed in the world. Finding your passion will help you escape the endless cycle of wandering from job to job that so many adults find themselves in. According to some estimates, as many as 70 percent of Americans are dissatisfied with their job! When you identify your passion, you’ll stop chasing money that won’t make you happy and instead find a career that leaves you feeling fulfilled.


Counter to what you may think, identifying your passion isn’t always as simple as it seems. Fortunately, there are some steps you can take:

  • Learn how your hobbies, skills, and talents differ from your passion.
  • Find out exactly who you want to help.
  • Narrow down the problems you want to work on and the solutions you want to provide.

Still unsure what you’re passionate about? Some signs that you hold a deep, abiding love for a particular role include a willingness to put in extra effort, losing track of time, and looking forward to the next day.


3. What Are My Career Values?

Jumping to a high-paying position is a great move. However, if your career values conflict with your new role, that extra money won’t sustain you for long. Perhaps more than any other factor, career values should dictate your workplace decisions because they play such a big part in your long-term happiness.


When your work aligns with your values, you will likely be more successful in your career because you’ll find more inherent satisfaction. You’ll also be more willing to fully invest yourself in your role, setting you up for continued success. Although important, narrowing down these standards can be overwhelming because of just how many exist:

  • Adventure
  • Autonomy
  • Creativity
  • Helping others
  • Prestige
  • Structure
  • Teamwork
  • Work-life balance

These are just a sampling of potential career values. The list is practically endless, and you likely feel strongly about several. Experts recommend you either rate your top picks or brainstorm two lists that can be categorized as “essential” versus “nice to have.” Then, evaluate how many of your values show up in the career you’re considering.


Find out how the Birkman Method can help you better understand your personality and the emotions and actions that drive your life.


2. What Barriers Do I Face to Changing Careers?

Before you make a move towards changing careers, it pays to consider the barriers that are standing in your way. If the barriers are too tall, they can significantly delay or completely derail a career transition.


No matter how seamless you may think the path to your dream career, there’s almost always friction that goes beyond simple resume issues:

  • Lack of training and credentials
  • Strong competition in the workforce
  • No professional network for support
  • Employer hesitancy and risk aversion

Identifying these barriers up front allows you to prepare for them. For some of these barriers, like lack of experience, you can volunteer or do freelance work to pad your resume and ease employer concerns. For missing credentials, a new college degree may not be realistic, but you can consider certification programs that may only take a few weeks to complete.


1. Am I Willing to Work My Way Into the Career I Want?

When you’re daydreaming about a new job, it’s easy to gloss over all the difficult steps to getting there. This may include gradually moving into the position you want because you may not be able jump into the exact career role you envisioned. Particularly if your new career requires you to cross into an entirely new industry or lead others, you may need to invest significant time working your way up the career ladder to make it to that metaphorical corner office.


Unsure what that path looks like? Connect with individuals who hold similar roles and learn about their career trajectory. Take notes on which positions they held before making it to their current position. Don’t forget to ask about their educational background, certifications, and special skills as well.


Once you’ve talked to a few individuals to get some different perspectives and stories, you’ll probably have a realistic idea of the steps you’ll need to take. At this point, ask yourself if it’s worth it. If you’re mid-to-late career and looking at a timeline of 10-15 years to secure your dream job, maybe it’s time to rethink that dream. There may be another, more accessible career for you that can scratch the same itch. On the other hand, finding out that you can expect an easy transition should help finalize your decision and give you the final push you need to make a change.


Female employee on an ipad exploring questions to ask herself when changing careers.

Start With the End in Mind

When making a career transition, you always want to ensure you’re running towards an opportunity, not away from something. Escaping a role that you resent is only the back half of the equation. First, you need to identify your new destination. More than anything, that involves discovering what’s important to you.


Once you’ve fully explored your motivations and barriers to a career change, you can start forming your strategy. Whether that’s immediately applying for a new position or putting in the work to boost your qualifications, you’ll at least have a plan to follow. After asking yourself all of the questions above, you’ll probably have a good idea of what to expect on your journey.


If you need any support along the way, our Corporate Training and Professional Education team at USF is here to help with a variety of certification courses, test prep, and professional development programs. Don’t settle for a career that just pays the bills. We’ll help you find one that satisfies your inner needs and goals.


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