The Highlands Company Blog


By Anna Bray, PCC, of Jody Michael Associates. Anna employs a collaborative and integrative approach to empower her clients. She helps them enhance self-awareness, cultivate talents, and make informed decisions to achieve desired outcomes, both professionally and personally.

Making a prudent career change requires careful consideration, pointed soul-searching and intentional preparation. It’s tempting to switch career gears when the going gets tough — or to fall prey to the shiny object syndrome when a new opportunity presents itself. How can you gain the clarity you need to decide if a career shift is right for you?

The following questions can help you get the ball rolling. Be honest! Don’t let your answers be clouded by how much you’ve already invested in terms of education, years of experience or others’ expectations.

1. Am I already in the right career?

Many times, people talk themselves (or are talked) into the wrong career for the wrong reasons — or feel locked into a mismatched career for reasons that are no longer relevant or true. If that rings familiar for you, reexamining your career path makes sense.

But before striking out for greener pastures, it’s important to consider whether a smaller change — like shifting your focus to work on projects that interest you more, or moving to another team within the company — might bring you greater career satisfaction. If your earning potential, opportunities for advancement or professional development have maxed out, then it might really be time to move on.

2. What am I proud of?

What kind of work has given you the most satisfaction thus far? Why was it satisfying? Keeping in mind that we often receive confirmation of our gifts through the feedback of others, think about praise you’ve gotten in the past — and how it made you feel. Being good at something doesn’t necessarily mean it’s the right career fit. The things that make you feel proud can provide room for growth, whereas the things you’re good at can breed boredom.

3. What are the pros and cons of my career?

Any time you say “I hate my job/boss/career,” you bring emotion into the equation, which can cloud your lens. Taking a more objective look at your career can be very helpful in evaluating what kinds of changes you might consider. Maybe you’re frustrated by the bureaucracy of a large organization and want to work for a smaller company. Or maybe it’s time to launch that freelance business you’ve been contemplating so that you can be your own boss. Whatever the answer, use it to evaluate your current career, as well as potential alternatives.

4. What are my natural talents?

Your innate abilities determine how you think, how you approach challenges and even how you communicate with others. Natural talents transcend skills, which can be learned and honed over time and with practice. When considering a career change, think about how it feels when you work for — versus against — your natural abilities.

Related: 4 Surprising Insights the Highlands Ability Battery Can Reveal

5. What am I willing to learn?

Are there certain degrees or certifications you need to advance in your current career, or to transition into a new career? How far are you willing to go — i.e., what sacrifices are you willing to make — to enhance your skillset or expand your qualifications? As important as it is to dream, it’s also critical to honor your reality and its limitations before setting your sights on a career that will require more effort than you’re willing to expend, at least for now.

6. What’s my ideal lifestyle?

Are you a morning person or more of a night owl? Do you perform well under stress and tight deadlines, or would a slower pace suit you better? Do you enjoy dressing up for work, or would you love a job where you could wear jeans? Is flexibility that allows for maximum time with family a priority right now, or are other concerns more important? How much time do you want to spend commuting between home and work? If you have specific standards in this area, keep them in mind as you think about making a career change.

Related: Does Your Life Align With Your Purpose?

7. How much money would make me happy?

It’s hard to be happy when you’re worried about meeting basic living expenses, but loads of cash and a stressful job with long hours aren’t that great, either. How much money do you need for the lifestyle you desire?

8. What compromises can I accept?

No job or career is perfect, so where are you willing to compromise? Would you accept lower pay for fewer hours of work? What about the risk of joining a startup for the opportunity to learn the hot new skills in your field?

9. What are my long-term professional goals?

It’s not the right job if it will derail you from your long-term career goals. However, this doesn’t mean the right job has to be your dream job. If a temporary job that pays good money allows you to stash some cash for your “Great American Novel Adventure,” it could very well be the right job for you right now. By the same token, that high-paying, high-stress, high-visibility job could be all wrong if you’ll be doing something you hate, or if the time commitment doesn’t allow you to explore your next best career move.

The right career lives at the intersection of your natural talents, work (and life) experiences, skillset, values and aspirations. Discovering the career for which you’re best suited isn’t always easy — but it is always worth it. When your work aligns with who you are —  and who you want to be — the return on your investment of time, energy and resources is beyond measure.

Other Posts You Should Read:
4 Surprising Insights the Highlands Ability Battery Can Reveal
Does Your Life Align With Your Purpose?

 Highlands Consultant, Anna Bray, PCC, Executive and Career Coach,

“For over twenty years, I have successfully coached hundreds of clients from a breadth of industries, working with rising leaders, mid-level professionals, and C-Suite executives. My primary goal in any coaching engagement is to help individuals achieve desired results in their careers. I support executives as they manage complexity and competing priorities within their organizations; and I help leaders develop essential competencies they need to drive their business units forward with skill and ease. I encourage authenticity, and I provide a judgment-free, supportive environment for uncovering blind spots and building new behaviors.”


This blog is reposted with permission by Jody Michael Associates –

The Highlands Ability Battery is included in JMA’s Career Discovery program. It is also available as a stand-alone offering, including the assessment and a debrief session with one of our certified career coaches, trained by the Highlands Company to help you understand your results — and to use them to create alignment with your career.