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The Career Path Dance: Career Coaching for Those in Transition

Updated: Jul 19, 2023

by Stephanie Bickel

career coaching

Career coaching is a huge part of Speak By Design; most of us have been a career coach for over two decades. Whether our clients’ careers are new, narrowing to laser point focus, broadening in depth, or going through great change, being a career transition coach is one of the most exciting and fulfilling parts of our job. The journey of career coaching is a perfect dance of planning, strategizing, and pivoting as the music of the world, and your industry, changes.

Career transitioning is daunting, whether our reasons to change are purely personal desire or a reaction to a lay off or crisis. 2020 has created many different industry and career situations and thus an equal number of opportunities for change. What career do you want to create in our world today? Here are some of the most important questions we help you answer as career coaches and career transition coaches.

1. What Is Your Mountain? As career coaches, we know that choosing and building a career is a feat. Imagining your career as a journey will help you acknowledge, and thus prepare for, its challenges. What are the obstacles you see on the way up? Are there other roles you need to play before you are ready for the top? Your career coach will encourage you on your journey, helping you anticipate challenges and meet the unexpected.

What mountain do you wish to climb? What mountain is worth climbing? What does success look like at the top? Has this mountain been climbed before? If there is a preexisting path, do you want it or do you want to search for a brand new way?

The phrase “pick your battles” is often used to encourage people to fight less. What if “pick your battles” was a question of your ambition? What challenges do you find bracing and thrilling? Any and every job has tough days, but the essence of your career path should be full of challenges you choose— problems you want to solve. Your career coach should help you determine what is worth fighting for.

career coaching

2. What are your Values and Variables? Your values should guide you and shape your every decision; a career coach should continually challenge you to discern and articulate your values. Your variables are negotiable— no one gets their way 100% of the time. What are you willing to give up? What are you willing to do? What are your must-haves and nice-to-haves? Can you identify when you are faced with a challenge to your ethics versus a challenge to your preferences? When is it time to draw a line in the sand and speak truth to power? When it is time to listen, reframe, negotiate, and give ground?

career coaching

3. Would you want to work for you?

Every career transition should involve this self reflection. It is not a question of “do you want to have your own business”; it is knowing your strengths and weaknesses. How will you keep improving throughout your career? When do your strengths flourish?

What do you admire in yourself? If you have trouble answering this question, consider how you might be in your own way. How and what are you holding back? Do you feel the need to minimize your strengths for anyone? Would you want that in your boss? Your employees?

Even if you do not aspire to ‘be the boss,” do your work habits and communication skills bring out the best in others? Are you the kind of employee you would want if you were hiring? Even if you are never ‘the boss’ or even ‘a boss’ — how do you demonstrate leadership in the roles you play and the roles you want? How do you grow? How are you resilient? When have you learned? When have you adapted or pivoted when faced with adversity?


When we coach clients, we insist on tactical specificity and vision during career coaching. Do you understand what needs to happen in order for what you want to happen? Staying abreast of resume trends, corporate buzzwords, and interviewing techniques are important details for job-seeking, but not career building. Vision is exhilarating, but useless if it remains abstract, unrelated to the real world and the market. A good career coach will probe deeply into your ideas, helping you understand your ideas, wishes, and talents, then helps you relate them, perhaps translate them, back to the real world.


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