Self-Reflection and Career Evaluation

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?

I used to think reflection was something you did in school, therapy, or after a bad decision. Turns out, when the water is rippling you can’t see your reflection, sometimes you have to stand still and let the water settle to see your reflection. When you’re leading a team, everything moves fast. Ideas are flying, emotions are high, ambition is loud, and everyone wants answers immediately. You can very easily fall into the trap of just reacting. Fixing. Deciding. Moving on. Onto the next thing. No pause. No processing. No thinking about what just happened and why. And that’s where leaders get it wrong. Reflection is what stops you from repeating the same issues dressed up as “new problems.” It’s what helps you understand why the same conversations keep coming up, why certain people disengage, or why you feel constantly exhausted even though, on paper, things are going well. As a CEO and careers leader, especially with a younger team, you are not just managing work. You are shaping how people learn, how they experience leadership, and how they understand their own potential. If you don’t reflect, you end up projecting your stress straight onto them. That’s when you start confusing urgency with importance and control with leadership. And here’s the bit people don’t say out loud: reflection isn’t just about the team. It starts with you. As a CEO, self-reflection is uncomfortable because there’s no one above you to sense-check things. No one is popping into your office to say, “By the way, that came across a bit sharp,” or “You’ve been a nightmare this week, are you alright?” You have to be willing to ask yourself those questions before they turn into culture problems. You have to be honest about whether you’re leading from clarity or from pressure. Young teams feel everything. They notice tone, they read between the lines, they learn what leadership looks like by watching how you handle mistakes, uncertainty, and stress. If you never reflect, you teach them that speed matters more than growth and that being busy is more impressive than being thoughtful. Reflection is what allows you to respond instead of react. It’s what helps you say, “Actually, I could have handled that better,” without seeing it as weakness. It’s what turns mistakes into learning rather than quiet resentment on both sides. Sometimes reflection is five minutes asking yourself why that conversation irritated you so much. Sometimes it’s admitting you’re overloaded and expecting everyone else to absorb it. Sometimes it’s realising your team isn’t the problem, society is. Good leaders don’t have all the answers. Reflective leaders ask better questions of themselves first. Now, off I go to reflect on why I said yes to three things I absolutely did not have the capacity for. Signed, Jackson Chief Careers Officer Mission to inspire 100 million people with career advice globally.

The End-of-Day Reflection: Adding Value to Your Job and Personality In the fast-paced rhythm of modern life, it's easy to get caught up in the hustle and bustle of daily tasks, deadlines, and responsibilities. However, taking a moment at the end of each day to reflect on our actions and their impact can be a powerful practice for personal and professional growth. One simple yet profound question can guide this reflection: "What values have I added to my job and my personality today?" Adding Value to Your Job At the heart of every profession lies a set of core values: integrity, excellence, responsibility, and dedication. These values are not just abstract concepts; they are actionable principles that shape how we approach our work. By asking ourselves what value we've added to our job, we focus on more than just completing tasks. We consider the quality of our work, our contributions to team success, and our alignment with the organization's goals. Adding Value to Your Personality Our professional lives are intrinsically linked to our personal growth. The values we uphold at work can significantly influence our character and personality. Reflecting on how we have developed as individuals each day fosters continuous self-improvement and emotional intelligence. Key Considerations: 1. Self-Awareness: Have I gained insights into my strengths and areas for improvement? 2. Empathy and Compassion:*m Did I show understanding and care for others' perspectives and needs? 3. Resilience and Adaptability: How did I respond to challenges and changes? 4. Ethical Standards: Have I acted in alignment with my moral and ethical values? A Practical Example Consider the case of Rahul, a salesperson at a company that sells medical devices. Each day, Rahul takes a few minutes to reflect on his contributions and personal growth. One day, he realized that while he met his sales targets, he had focused more on closing deals than on understanding the specific needs of each healthcare provider he worked with. The next day, Rahul decided to change his approach. Instead of pushing for sales, he spent extra time with each client, asking detailed questions about their challenges and needs. He provided tailored solutions that better matched their requirements and followed up to ensure they were satisfied with their purchases. This not only helped him build stronger relationships with his clients but also increased his sales in the long run as clients appreciated his dedication and care. By reflecting on his actions, Rahul added value to his job by enhancing customer satisfaction and loyalty, and to his personality by nurturing empathy, patience, and a service-oriented mindset. Conclusion By asking yourself, "What values have I added to my job and my personality today?" you engage in a powerful practice that fosters growth and fulfillment.

Reflection is one of the most powerful tools for growth. Yet, its so easy to overlook. I've always asked myself: What’s working? What isn’t? What can I do better? Make this happen: 1. Block Time: Put an hour on your calendar at the end of each month. Treat it as a non-negotiable meeting with yourself. 2. Ask the Right Questions: I use these prompts: • What were my biggest wins this month? • What challenges did I face, and how did I handle them? • What lessons did I learn? • Where did I spend my time, and was it aligned with my goals? • What do I want to do differently next month? 3. Write It Down: There’s something powerful about putting pen to paper (or fingers to keyboard). Documenting your thoughts helps clarify them and gives you something to review later. 4. Set Intentions: Based on your reflection, identify 2-3 priorities for the next month. Keep them actionable and specific. Reflection is about learning from your experiences. It’s about stepping back, recalibrating, and moving forward with intention.

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?

Your best career investment? Study yourself. 📌 How I do a "career retro" in 7 steps: AKA, "Yudi’s Personal Growth Breakdown" (Yeah, still working on the name 😅) 👀 Never done a career retro before? It's just a fancy way of looking back at your journey to understand what worked, what didn’t, and how to grow from it. TLDR; When things don’t go as planned (no job offers, internship rejections), instead of self-blame, run a "blameless retrospective" — a candid analysis of your steps, without judgment. Here’s my 7-step process to boost your growth: 1. 𝗦𝗰𝗵𝗲𝗱𝘂𝗹𝗲 30-60 𝗺𝗶𝗻 𝘄𝗶𝘁𝗵 𝘆𝗼𝘂𝗿𝘀𝗲𝗹𝗳. → Find a quiet space → Remove distractions → Grab a pen and paper (yes, the old school way) 2. 𝗗𝗲𝗳𝗶𝗻𝗲 𝘁𝗵𝗲 "𝘀𝗶𝘁𝘂𝗮𝘁𝗶𝗼𝗻" 𝘆𝗼𝘂 𝘄𝗮𝗻𝘁 𝘁𝗼 𝗿𝗲𝗳𝗹𝗲𝗰𝘁 𝗼𝗻. Maybe it’s your last round of interviews, or that application you never heard back from. Use neutral language: ❌ "I always fail." ✅ "I’ll reflect on what I can improve and grow from this." 3. 𝗖𝗿𝗲𝗮𝘁𝗲 𝗮 𝘁𝗶𝗺𝗲𝗹𝗶𝗻𝗲 𝗼𝗳 𝗲𝘃𝗲𝗻𝘁𝘀. Write out the key steps, from the moment you started applying or preparing, to the final result. Be objective, and avoid blaming yourself: →Job search started in April →Applied to 10 companies in May →First interview in June →Got to the final round with two companies (Your goal is to break down each part of the journey like movie scenes 🎬) 4. 𝗕𝗿𝗮𝗶𝗻𝘀𝘁𝗼𝗿𝗺 𝗰𝗼𝗻𝘁𝗿𝗶𝗯𝘂𝘁𝗶𝗻𝗴 𝗳𝗮𝗰𝘁𝗼𝗿𝘀: → How did you prepare for applications? (Resume, networking, skills) → Who influenced your results? (Mentors, recruiters, friends) → What was your mindset during the process? → What did you communicate well/not-so-well? 5. 𝗙𝗼𝗿 𝗲𝗮𝗰𝗵 𝗳𝗮𝗰𝘁𝗼𝗿, 𝗮𝘀𝗸: → What was in my control? → How did each step connect to the final outcome? This is key to figuring out what you can adjust for next time. 6. 𝗗𝗶𝘀𝗰𝗼𝘃𝗲𝗿 𝘆𝗼𝘂𝗿 𝗹𝗲𝗮𝗿𝗻𝗶𝗻𝗴𝘀: Shortlist 1-3 growth areas: → What patterns did you notice? → Have you seen these patterns before? → What will you start, stop, or continue? My favorite question here: "If I repeated every action I took, would I get where I want to go? If yes, why? If no, why not?" 7. 𝗖𝗹𝗼𝘀𝗲 𝘄𝗶𝘁𝗵 𝗮 𝗿𝗲𝗳𝗹𝗲𝗰𝘁𝗶𝗼𝗻: → How do you feel about this process now? → What will you do differently next time? 📌 The goal is self-awareness, not self-judgment. That’s how you grow from setbacks and bounce back stronger. Whether you’re applying for internships, struggling to get interview calls, or breaking into tech from scratch—it’s all part of the process. Reflect, adapt, and most importantly, keep going. You got this 💪 P.S. Have you tried reflecting on your career growth? Would love to hear your tips! 👋 Follow for more career content. Helpful? ♻️ Repost to share it!

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!

I vividly recall when I realized my career had hit a wall. Despite pouring my energy into my work, I wasn’t seeing the growth I had hoped for. Every day felt like I was going through the motions—no direction, no joy. I knew something had to change. The turning point came when I acknowledged that I was following someone else’s path instead of carving out my own. For years, I tried to mirror the success of others, thinking it would lead me to my goals. But it only slowed me down and left me feeling unfulfilled. I needed to refocus on what I truly wanted from my career. Here’s how I started my journey to break free from stagnation: ↳Self-Assessment: It took time for me to evaluate my strengths, weaknesses, and passions. Believe me, this was one of the toughest exercises. ↳Seeking Guidance: I never hesitated to reach out to mentors who could provide valuable insights and guidance. ↳Investing in Growth: I attended workshops, read books, and engaged in activities that aligned with my career goals. ↳Taking Action: Gradually, I began to apply what I learned, leading to job offers, promotions, and recognition. These steps transformed my career. More importantly, I found joy in the journey that helped me remain consistent. Breaking free from stagnation wasn’t easy, but it was a critical move toward the growth I desired. Are you feeling stuck in your career? What first step will you take to ignite your growth? Drop a comment below—I’d love to hear your plans!

Self-awareness—or the lack of it—can make or break your career. I’ll be honest—I've had moments where I was unknowingly passive-aggressive with a coworker. Or defensive. Or dismissive. Later, someone on my team would confidentially tell me how I came across. I have many blind spots. Do you have a blind spot? Are you aware of how your behavior is impacting your fundraising or promotion chances? 📌 You might think you’re confident but perceived as arrogant. 📌 You might think you’re being helpful but come across as micromanaging. 📌 You might believe you’re overperforming, but others see you as disorganized and unreliable cause you have too much on our plate and fail to deliver. And the list goes on and on! Here’s the harsh reality: People who are unaware of their own behavior in the workplace are: ↘ Less likely to be promoted. ↘ Less likely to win over investors. ↘ Less likely to receive praise or recognition. Why? Because if you don’t see how your actions impact others, you can’t correct course. And if you can’t course-correct, you’ll struggle to build trust, influence, and respect—the very things that drive professional success. So, how can you become more aware of your blind spots and address them? ↗ Seek feedback regularly: It’s easy to overlook your own behavior. Ask trusted colleagues for honest feedback—they’ll often see what you can’t. Investors and leaders pay attention to those who can listen and adapt. ↗ Practice self-reflection: At the end of each day, take a few minutes to reflect on your interactions. What went well? What could have been handled better? Awareness breeds growth, and growth gets noticed. ↗ Embrace mindfulness: Being present helps you catch those passive-aggressive tendencies before they happen. The more aware you are, the more positively you’ll impact your team and stakeholders. ↗ Hold yourself accountable: When you slip up, own it. Investors and leaders respect those who can admit mistakes and show a commitment to improvement. ↗ Embrace vulnerability: Embracing vulnerability shows strength. Just as you need understanding, so do others. Authentic relationships lead to deeper connections, more opportunities, and greater recognition. Self-awareness isn’t just about feeling good—it’s about being the kind of person who can lead, influence, and ultimately succeed. Do you have a blind spot? #ThinkAboutIt Artwork: Aykut Aydogdu

One startling realization that is common among young professionals is their lack of self-awareness. Young professionals simply go from school to the workplace without taking the time to consider their strengths, weaknesses and uniqueness. If you would like to build self awareness, do this: 🌎 1. Journaling: Regular journaling is one of the best ways to build self awareness. Journal regularly about your experiences, thoughts, and emotions can enhance self-awareness. 🌎 2. Take personality assessments: If your company allows it, take personality tests such as the Myers-Briggs Type Indicator (MBTI) or the Big Five Personality Traits, to gain insights into your personality and preferences. 🌎 3. Seek Feedback: Request feedback from peers, mentors, or supervisors. Other perspectives can provide insights into your strengths and areas for growth. 🌎 4. Reflect on Your Values: Identify and prioritize your core values. Consider what matters most to you in life and in your career. ___________________________ Specifically to your career, here are some questions you should ask yourself: 🍀 1. Observe how you work. What aspects of your job excites you? What aspect do you not mind doing over and over again? 🍀 2. What aspect do people say you excel in? What aspect do superiors like you working on? 🍀 3. How would you rate your work ethic? How would your colleagues and supervisors rate your work ethic? 🍀 4. How aware are you of the office dynamics going on around you? How do you fit into the mold? 🍀 5. What are your key strengths and how can you leverage them in your career? 🍀 6. In what work environments do you thrive best – collaborative, independent, fast-paced, etc.? 🍀 7. What are your long-term career goals, and how can you align your current path with them? _______________________ The essence of this is to help you develop self awareness. Now note, self awareness is not necessarily a goal. It is a journey. You arrive at new destinations of knowing yourself. To your best self, cheers 🥂