Questions to Consider for Career Growth

I had a 6-page pros and cons list. New job. More money. Bigger title. But something felt off. It wasn’t fear—it was something deeper. And the question that cut through it all was this: “Am I running FROM something or running TO something?” The quality of your career isn’t shaped by the opportunities you say yes to. It’s shaped by the questions you ask yourself before you decide. So here are some of the questions I’ve asked myself at every turning point in my career: 1. When you're thinking of quitting... “Am I running from something or running to something?” “If nothing changes in six months, can I live with that?” 2. When you're offered a new opportunity... “Would I still take this if the title and salary were the same?” “Does this move me closer to the life I want—or just the one that looks good?” 3. When you feel overlooked or underused... “Have I actually asked for what I want—or just hoped someone would notice?” “What version of myself am I showing them—my current one, or the one from five years ago?” 4. When you’ve just been promoted... “Do I enjoy the work—or just the recognition that came with it?” “What part of this role gives me energy?” 5. When you're managing people for the first time... “Am I trying to be perfect—or just present?” “What would I need from me if I were on this team?” 6. When you’re constantly busy but don’t feel accomplished... “Am I producing real impact—or just staying in motion?” “What would change if I believed my time was valuable?” 7. When you want more visibility but feel awkward asking... “Who needs to know what I’ve done—but doesn’t yet?” “What’s one small way I can advocate for myself this week?” 8. When the job no longer aligns with your values... “What part of myself have I muted to stay comfortable here?” “What would I be proud to say at a dinner table about what I do?” 9. When you’re on a career break—by choice or not... “What parts of me have I rediscovered that I don’t want to lose again?” “What do I want more of in my next chapter—and what’s non-negotiable now?” 10. When you’re returning from parental leave or a sabbatical... “What boundaries do I need now that I didn’t before?” “What do I want to reintroduce intentionally—and what can stay gone?” 11. When you're bored but afraid of change... “What would I try if I weren’t afraid of starting over?” “Am I more afraid of change—or staying the same?” You don’t have to figure it all out today. You don’t need a 10-step plan. Sometimes clarity doesn’t come from a perfect plan. But maybe—just maybe—you need to ask yourself a better question. So if you’re feeling stuck, overwhelmed, or restless… You don’t need to fix everything. Stop asking "What should I do next?" Start by asking better questions. What’s the one question you asked yourself that changed everything?

When was the last time you asked yourself: ‘What’s really working and what isn’t?’ Most professionals don’t. They keep moving from one task to the next, mistaking busyness for progress. But here’s the truth I’ve seen in 10+ years of coaching: 👉 Your career doesn’t stall because of lack of effort. 👉 It stalls because of lack of reflection. That’s why I use a structured self-reflection framework every week and I teach my clients to do the same. 🟢 My Reflection Framework 1. Core Purpose Questions (Weekly) ✔ Am I still excited about my end goal? ✔ What did I do this week that moved me closer? ✔ Which activities pulled me away? 2. Growth & Learning Check (Bi-weekly) ✔ What new skills am I building? ✔ Have I challenged my assumptions lately? ✔ Who can I learn from right now? 3. Action & Adjustment (Monthly) ✔ Are my daily habits supporting my vision? ✔ What’s working well that I should double down on? ✔ What’s one thing I need to stop doing? 4. Impact & Connection (Quarterly) ✔ How am I helping others while pursuing my goals? ✔ Who are the key people supporting me? ✔ Which relationships need more attention? 5. Vision Alignment (Every 6 Months) ✔ Does my current path still excite me? ✔ Have my priorities changed? ✔ Do I need to adjust my timeline? I keep these questions in my phone’s notes app. Every week, I revisit them. Every month, I review patterns. Every quarter, I reset my focus. And over the last 3 years, this single habit has helped me: ✨ Stay aligned with my vision ✨ Catch blind spots early ✨ Celebrate progress (even the small wins) ✨ Avoid drifting when things got busy 👉 So, when was the last time you asked yourself the hard questions? P.S. If you want more updated insights, practical strategies, and frameworks like this to stay aligned and accelerate your career. 👉 Join my Career Spotlight Group (link in comments). #Goal #PersonalGrowth #Clarity

10 questions that could change your career... Most people look for the next step in their career, but the real transformation starts with asking better questions. Here are 10 I come back to again and again for myself, my clients, and in building Pivotr. They’re not comfortable, but they’re powerful. 1️⃣ What am I avoiding because I fear being seen? → Often, visibility is the edge, not skill. 2️⃣ What if I didn’t need to be the best (just the bravest)? → Progress begins the moment you stop performing and start choosing. 3️⃣ What could I do in the next 5 minutes that future me would high-five? → Bold moves don’t have to be big. They just have to begin. 4️⃣ What truth am I whispering to myself lately? → There’s wisdom in the quiet. Pay attention. 5️⃣ If my career was a story, what chapter am I in right now? → Are you building tension, rising, or rewriting the plot? 6️⃣ What parts of me have I been hiding to stay ‘professional’? → The future of work needs your whole self, not a filtered version. 7️⃣ Whose permission am I still waiting for? → Bold careers aren’t granted… they’re claimed. 8️⃣ Where am I confusing comfort with alignment? → Just because you’re good at it doesn’t mean you should stay. 9️⃣ What would I do if I trusted myself completely? → Let that version of you lead even for a day. 🔟 What dream have I downsized to make others more comfortable? → Reclaim it, rewrite it, and then start again… LOUDER. Try this: Pick one question and journal on it. Discuss it with someone you trust, and let it shape your next move. Your next bold move might not start with a plan, it might start with the right question. ♻️ Share this with your network to help others seek career clarity on their next bold move.

The market isn’t tough just because there are too many people. It’s tough because too many are trying to be the same person. The answer isn’t to compete harder. It’s to know who you are and show it fully. When you define yourself, you stop chasing what everyone else is doing. Here are a few questions to help you find your direction, sharpen your focus, and define your own way to cut through. Clarity: What work excites you? Where do your passions lie? What’s the thing you’re best at? What type of environment helps you thrive? Are you clear on what you really want to do next? Does your work feel like you, or like what you think they want? What conversations give you energy rather than drain it? What would a fulfilling next chapter look like? Mindset: Is there any baggage you can put down? What beliefs might be holding you back? What if what seems like a weakness is actually your differentiator? What would you try if you knew the industry was about to completely change anyway? What does progress mean to you right now? Are you being honest about what no longer fits? Reality Check: What assumptions about how things work might no longer be true? If you had to work in a studio, remotely, or relocate, what could that open up? Who’s succeeded with the same disadvantage you think you have? What roles or paths didn’t exist five years ago that might suit you now? What would your 25-year-old self think of your experience? What would your 55-year-old self tell you to try? What story are you telling yourself that might be holding you back? What’s changing faster than your current plan? What industry next to yours might value exactly what you know? Skill and Growth: What kind of work makes you forget the clock? What skills do you already have, and what would you like to develop? Have you identified your transferable skills? Do you have the range to step into the role you want? What do you understand that others find complex? What are you learning right now that excites you? Visibility: Is your folio distinct and does it tell a story? Are you visible online in a way that shows who you are? Could someone describe your perspective in one sentence? Does your work reflect the kind of opportunities you want next? Would someone remember you after seeing your work once? Does your work reflect your taste, or just your skill? What work best shows your point of view, not just your capability? Connection: Are you connecting with people or with positions? Have you researched beyond the same familiar agencies? Have you researched the people in the company? Who’s solving problems in ways that make you jealous in the best way? Are you comfortable talking about your work? Are you present at events and in the real world? Who inspires you, and have you told them? Who could you help today without expecting anything back? It’s hard to stand out, but knowing who you are gives you a far better chance. 🤝 Si

I made this mistake early in my career. (And it almost broke me) I said yes to an external promotion. Most people think every promotion is progress. Smart professionals know not all progress is growth. Here are 7 questions they ask before accepting a bigger role: 1. Am I chasing growth or validation? ↳ Titles impress others, but they don’t develop you. ↳ Growth comes from challenge, not approval. ↳ Promotion isn’t proof, it’s purpose. 2. Does this role align with my long-term goals? ↳ Not every “step up” moves you forward. ↳ Direction matters more than elevation. ↳ Growth without alignment leads to burnout. 3. Will I still have time for life outside work? ↳ Bigger roles often come w/ bigger trade-offs. ↳ If balance breaks, success won’t feel like success. ↳ Protecting your energy is leadership too. 4. Will I learn or just repeat what I already know? ↳ Repetition feels safe but stalls your development. ↳ Smart professionals pick learning over comfort. ↳ Growth hides in discomfort. 5. Do I respect who I’ll be working under? ↳ A great boss accelerates your growth. ↳ A poor one limits it fast. ↳ Mentorship matters more than money. 6. Will this build skills that make me more valuable? ↳ Titles fade, capabilities compound. ↳ Always choose the path that multiplies your value. ↳ Invest in skills, not status. 7. Does this role make my life better, or just my résumé? ↳ Growth should feel meaningful, not mechanical. ↳ The right role fits your goals and your values. ↳ Progress means moving toward the life you want. Promotions shouldn’t be automatic. They should be intentional. Which question will you ask yourself next time? 👇 📌 Save this post to revisit later. ♻ Repost to help your network. ✅ Follow me Alec Rickard for career growth strategies.

The secret to accelerating your career isn't spamming mentors with cold DMs or wasting time with small talk at networking events. Instead, ask these 7 key questions to learn from the people ahead of you: 1. What is something most people think is important that I can skip entirely? As a beginner, everything looks important. But as you progress, you realize most things aren't. So instead of wasting your effort in dozens of directions, ask this to figure out what to avoid. 2. What part of your daily routine do you wish you had started sooner? People ahead of you got to where they are with simple daily actions compounded over time: • Figure out what they are • Build them into your days • And stick to them for years 3. What channels led to the building of your highest-quality relationships? It's cliché, but you are the average of the 5 people you surround yourself with. But finding the right people isn't easy—unless you know where to look. So use this question to get some directions. 4. What is something you did differently than your peers 5 years ago that led to pushback, but served you in the long run? If you do what everyone else does, you can expect to achieve what everyone else achieves (mediocrity). Use this question to identify behaviors to shed. 5. What can I expect to struggle with along the way? Growth is having problems today you would have begged to have had years ago. So if you know which struggles are coming, you can prepare for them and continue to grow (which means unlocking new problems). 6. What is something you believed 5 years ago you had to "unlearn" to take the next step? Progress comes from the constant cycle of: • Identifying a bottleneck • Removing it • Repeat Most of the time, that bottleneck is a behavior or belief you have to "unlearn." 7. What's something you didn't pay enough attention to early on, then had to learn the hard way? Early on, you're flying blind. You don't even know what you don't know. So the faster you can uncover these blind spots, the faster you can improve.

It's surprising how many people have never had meaningful career conversations with their managers (or their direct reports). I don't mean conversations that are solely backward-looking about recent performance or forward-looking about the next promotion. I mean holistically taking stock of the journey: where you've come from, where you are now, where you're headed, where you'd like to go, the tools you need in your toolbox to get there, and the people you need in your support crew. Several years ago, I created a framework to guide career conversations with my direct reports. It's a somewhat cheesy framework, but it leads to rich conversations and strategic, as well as tactical, action plans. It's not meant to be prescriptive, but rather a guide for meaningful reflection and action. I offer it in case it's helpful to anyone here. (I'd also love to know how others approach leading or engaging in career conversations. Do you have your own framework that you'd be comfortable sharing?) Here’s mine: GROWTH G is for Goals. Personal and professional aspirations: How do you think about these today, and how have they evolved over the past 2, 5 years? What matters to you when you reflect on your career adventure thus far? What do you want to build on and carry forward, or leave behind? R is for Reflection. Self-awareness and feedback: What significant milestones or achievements have you accomplished in your career so far? When have you felt strongest and most fulfilled? Least? Where are you currently stretching and reaching the most? Where do you feel most uncomfortable – both positively and negatively? O is for Opportunities. Skill development and growth path: Together, we’ll identify the skills needed to develop further on the current path, or to strike out on a new path. W is for Wellbeing. Personal and professional balance: How are you balancing your work and personal life? What strategies do you use to maintain your wellbeing? Are there any areas where you feel you need more support or resources to ensure a healthy balance? T is for Team: Collaboration and mentorship: Who are the key people in your professional network? How are you leveraging relationships for growth? How are you contributing to others' growth? Who can and should we expand your network to include? H is for Holistic Action Plan. Actionable steps and accountability: What specific actions will you take to move toward your goals? How will we track your progress? What milestones will we set to ensure accountability and continuous growth?

The world is changing faster than ever. 🌍 If you're thinking about a pivot, you're on the right path. AI is reshaping industries. Remote work is standard but back to office is an increasing likelihood. Skills that were hot yesterday might be obsolete tomorrow. Sticking to one linear career path? That's a 20th-century myth that no longer applies. In 2026, adaptability is your superpower. If you're sensing burnout, boredom, or a pull toward something bigger... It's time to pivot. You're not quitting. You're evolving. But don't leap blindly. Most people skip the introspection and regret it. Here are 11 questions to gain clarity before you make the move: 1️⃣ Why do I want to pivot? ✅ Is it burnout, boredom, or a deeper calling? ✅ Be brutally honest, escape won't lead to evolution. 2️⃣ What parts of my current work still energize me? ✅ Don't torch everything. ✅ Identify the sparks to carry forward. 3️⃣ What am I running from—and do I need to face it first? ✅ A pivot won't fix unresolved issues. ✅ Distinguish between fleeing and growing. 4️⃣ What would a 10x better day look like? ✅ Design your ideal workday. ✅ Reverse-engineer a path that gets you closer. 5️⃣ What kind of problems do I want to solve next? ✅ Every job is problem-solving. ✅ Choose problems that fascinate you, not just fund you. 6️⃣ Who do I want to learn from or work alongside? ✅ People trump titles. ✅ Select mentors and teammates who elevate you. 7️⃣ What am I naturally great at—and am I using it? ✅ Align pivots with your unique edge. ✅ Double down on strengths for real leverage. 8️⃣ What skills do I want to invest in next? ✅ Think career compounding. ✅ Build skills that multiply your value over time. 9️⃣ What's my risk tolerance—and how will I manage it? ✅ Can you handle an income dip? ✅ Or do you need a bridge plan first? 🔟 What does success actually look like now? ✅ Status? Income? Freedom? Growth? ✅ Update your personal scoreboard. 1️⃣1️⃣ Who's already doing what I want—and what can I learn? ✅ Success leaves clues. ✅ Study, shadow, and ask. These aren't just questions. They're a framework for intentional change in turbulent times. Take 30 minutes today to journal your answers. Clarity beats a perfect plan every time. What's your biggest pivot challenge right now? 👇 — john — ♻️➕ John Brewton 📬 Subscribe to Operating by John Brewton for daily perspective on the history, economics, and future of operating companies.

Not Thriving in Your Career? Thinking About Making a Change? Before you jump ship, here are some things to consider that might just change your perspective… Unpopular opinion: Sometimes, the uncomfortable season you’re in is preparing you for what’s next. Here’s what I mean:  1️⃣ What am I supposed to be learning through this? That toxic teammate? They might be developing your conflict resolution and resilience muscles. Sometimes the challenge is about learning to thrive in difficult environments.  2️⃣ Are you running away from conflict because you don’t know how to deal with dissent? If you say you champion “diversity,” which includes differences of opinion, yet you abort ship every time you disagree with how something is done, that’s the antithesis of resilient and inclusive leadership. Discomfort is where we grow, and disagreement is often a less-than-courageous reason to disengage.  3️⃣ Are the interviews wearing you down or building you up? Those seemingly relentless interviews are actually giving you the space to sharpen your storytelling, helping you articulate your greatness more clearly each time. Your next “yes” could come because you’re better at telling your story.  4️⃣ Is it toxic, or is it growth? Sometimes the discomfort you feel isn’t toxicity, but the stretching that comes from growth. Are you being challenged to step into a new level of leadership? Don’t mistake growing pains for stagnation. 5️⃣ What skills are being cultivated right now? The tedious projects or tasks might be sharpening your attention to detail or your ability to handle high-pressure situations. Don’t miss the hidden gems in the mundane.  6️⃣ Have you done everything you can to change the situation? Before you decide to leave, consider if there are conversations you haven’t had yet, boundaries you haven’t set, or opportunities for growth you haven’t explored.  7️⃣ Are you leading yourself well in this season? You might be feeling stuck, but how are you showing up for yourself? The ability to lead yourself through tough situations is the foundation of thriving in any career. 💡 Before you make a move, ask yourself: What’s this moment trying to teach me? Sometimes the most uncomfortable seasons are the ones that shape us into leaders who thrive through change. #thrivethroughit #leadership #careerchange #selfleadership #growthmindset

Ever wondered if you’re truly satisfied with your career path? It’s easy to get caught up in the daily grind and overlook how you really feel about where you're headed. Taking a moment to reflect can make all the difference. Here are a few questions to ask yourself: 🔍 Am I excited about my work every day? If not, what parts of my job bring me joy, and what parts don’t? 🔍 Do I feel challenged and valued? Are there opportunities for growth, or do I feel stuck? 🔍 How does my current role align with my long-term goals? Is this job helping me get closer to where I want to be? 🔍 Am I balancing work with personal fulfillment? Do I have time for the things that matter most outside of work? If you're considering a change, start by reflecting on your strengths and passions to find roles that truly align with your interests. Research potential paths and network with professionals in those fields to gain valuable insights. Set clear, realistic goals to stay focused and motivated, and seek advice from a career coach or mentor for objective guidance and strategies for a smooth transition. When was the last time you assessed your career path? Share your reflections and insights below!