10 Must-Ask Questions for a Fulfilling Career Journey

Achieving Goals, Career Discovery, Career Transitions, Confidence, Mindset & Mindfulness
03/13/23 - Amy Yandell
woman thinking by computer

Have you been feeling stuck or that you don’t have any prospects to advance in your career? Maybe you’ve been trying to figure out how to request the raise that’s years past due? Perhaps you’re overwhelmed by the deluge of titles, companies, paths, job boards, and certifications out there? Or are you feeling like you hustle and grind the best way you know how but it’s just not getting you the results you want?


Take a deep breath. Press pause and suspend the dizzying pace of hustling, proving yourself, and grinding for a minute. Let the world keep spinning around you. It’ll be there when you press “play” again. For now, breathe and open that wondering and wandering part of your brain where amazing ideas come from to consider a different approach.

Spoiler alert: That certainty and clarity you seek for your next career decision? It’s not wandering around out there on your dot.com machine. It’s been right there inside you all along.

The Magic of Questions

2023 already has me asking myself BIG questions about life, work, purpose, and the world. If you’ve spent any time with me, you’ll know I’m a question-asker. I was always that kid who raised their hand in class to ask a question and was politely told through clenched teeth “Ok, Amy. You’ve asked your 3 questions for the day. Let someone else have a turn.”

Asking questions, though, is an extraordinary way to grow and that’s what I LOVE about coaching; the whole profession is based on asking powerful questions! Questions open opportunities to think beyond our usual scope of understanding. Questions don’t tell us what’s wrong or right. Questions give us permission to think without limitations and can spark ideas we’ve never considered.

Clarity is the Goal

Thinking about career advancement is overwhelming. It seems like we simultaneously have no options and are unprepared and/or inexperienced to do anything differently; AND, there are way too many options and paths and we don’t even know where to begin. Clarity is about what you need, what you actually want, and where to access info and connections that lead to growth. Clarity makes this process manageable and life-giving.

Gaining clarity lets you set boundaries around your exploration into next steps. Seeking this information from within will set you up to hold your own needs and wants up in relation to opportunities you discover or that are presented to you. Sort of like a litmus test for weighing your options. Grounding yourself in a foundation of your values, skills, and interests enables you to center your own goals and your own version of what development and advancement mean.

Ask Questions Internally First

When we’re facing a possibly pivotal moment in our lives, our tendency is to look outward for the answer to questions, especially when it comes to work. We query job boards with an infinite combination of words and phrases, we read about different companies’ cultures and how they treat their employees, or we watch videos of other people demanding raises. These are, certainly, part of the journey.

But when we don’t have a strong foundation and articulation of our values, skills, and interests, it just turns into a free-for-all of scrolling and wandering around online, losing hours going down rabbit holes, and looking up 3 hours later with nothing to show except confusion and a little disappointment in ourselves that we lost that time with no results.

We can get hypnotized by claims of the “right” way of asking for a promotion, the “trusted” path to director-level, the “sure-fire” way to hack a career transition. Something about all that doesn’t quite feel “right” for our specific situation, but hey, what do we know about all this?

Here’s the key: You are the expert in your life. If we don’t have clarity about ourselves, our own goals, what drives US the most, how can we look externally and expect to “figure it out?” Getting clear on yourself first means that, when you do face the world of work to find answers about next steps, you have your own language, standards, values, and clarity to shape your questions and decision-making.

You are unique, so one-size-fits-all is never going to work. Answering the questions below often unlocks access to agency you didn’t know you had, confidence to state your needs, and comfort and clarity to go after what matters to you.

10 Questions to Own Your Career Development

For you to get the most out of this questioning process, it helps to suspend any expectations of yourself, any norms of “this is just how things are,” or any perceived limitations of “it’s always been done this way.” Go deep. Get in there. Rustle around. If an idea is sparked, write it down. If you can’t face it now, save it for later. This process is yours.

You get to define work, success, and advancement for yourself
  1. What do I want and need “work” to do for my life in this season?

Examples: financial reward/security; drive my passions; provide an income so I can live my full life outside of work; stellar and comprehensive benefits; make a difference

  1. What do “success” and “career development” mean in my life?

Examples: accomplishments; promotion/raise; learning new skills; overseeing people; a specific job title; focus on relationships; focus on strategy vs. details; less responsibility; growth outward not upward; climbing a ladder

Bonus question: Is my idea of success and advancement based on my own needs and wants, or is it shaped somewhat by societal/familial expectations? Do I need to reckon with this or am I ok with it?

  1. What impact do I want my work to have on me or the world?

Examples: I want to be a millionaire by the time I’m 35 (don’t you dare shame yourself for this!); I need to know I’m making a difference in the world; I don’t want the pressure of changing the world, I just want to do something that uses my skills and then enjoy my life outside of work; I want to be THE global expert in my field.

You get to articulate your values, skills, and interests around work and advancement
  1. What’s my unique value add in my current field vs. a new field/range of fields?
  2. What are my values in life and in work?
  3. What are my dealbreakers moving forward?
You don’t have to do this alone. Sure, a lot of this is your own information-gathering. But you’ve got access to resources too.
  1. What resources do I have access to for growth and advancement? What information do I lack that I need to make this decision wisely?
  2. What growth opportunities are there in my current role/company as compared to if I made a change?
  3. Who can I talk to (hello informational interviewing!), and/or what can I do to learn more about how the answers to these questions fit into real-world opportunities?
You are allowed to not think about and hustle toward advancement 24/7
  1. How can I give structure to my exploration/action items around career advancement to protect my physical, mental, and emotional well-being?

Confidence to take a chance, to have an awkward conversation with your boss, to click submit on a blog you’ve been putting off, to ask a person in your Zumba class what it’s really like to go back to school in your 40s, to formally request the raise you deserve…such confidence comes from getting to know yourself, understanding the infinitely wonderful things you have done and are capable of doing, leaning into your own definition of what growth looks like and plugging into resources around you to feed your fire.

Will your answers change as you learn and grow? Absolutely! Does that make you wishy-washy or indecisive? Absolutely not. It makes you human: a malleable, adaptive, responsive, and beautifully complex human with needs that change over time. That complexity, malleability, and adaptive nature is exactly what we need more of in the world of work.

Here at Ama La Vida, we ask these questions all day long. We partner with you to reveal these answers from within and use that intel to design the career and life you want. Curious about what that’s like? Book a consultation with us and learn more.

Amy Yandell Coach Headshot
Amy Yandell

Hi, I'm Amy, and I'm here to help you break free from the idea that you have to fit into someone else's definition of success. I believe that everyone has the power to define their own path and create a life that feels fulfilling and meaningful. Whether you're feeling stuck in your career, struggling to find your purpose, or just ready for a change, I'm here to help you navigate the journey with clarity, confidence, and a sense of purpose.

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