How to Overcome Fear in Career Choices

Most people think imposter syndrome is a career killer. But it’s not. It’s a signal. 📍 You’re growing. 📍 You’re stretching. 📍 You’re doing something that matters. 🧠 62% of high achievers experience imposter syndrome at some point in their career. (Salari, et. al, 2025). Yet most don’t talk about it. They just try to hide it, and hope no one notices. And the endless mental loop gets louder: → “Don’t let them find out.” → “I should be more confident by now.” → “Maybe this means I’m not ready.” But I’ve learned that feeling like an imposter doesn’t mean you’re not qualified. It means you’re in the arena. I remember when I became a company officer and joined a board at 27. On paper I felt I had made it. And inside, I was bracing, like someone might tap me on the shoulder and say, “Hey… we made a mistake.” I later learned that feeling didn’t mean I didn’t belong. It meant I was stepping into a new version of myself. And it’s a feeling I’ve seen show up again and again in brilliant, hardworking leaders who are quietly carrying so much. When you stop fighting imposter syndrome, you stop performing from fear, and start leading from power. Here’s how I co-exist with it and teach high-performers who feel it too: 1. Separate feelings from facts → “I’ve done hard things before. I’ll figure this out too.” 2. Use doubt to fuel mastery → You don’t need to feel ready. You just need to keep showing up. 3. Talk back to the critic → “What if this is the version of me that rises?” 4. Track your wins like data → Keep a ‘Wins Portfolio.’ Pull it out when your inner critic gets loud. 5. Redefine success on your terms → Not their finish line. Yours. You don’t need to silence imposter syndrome. You just need to understand what it’s trying to tell you. Because once you stop fearing it… you unlock the part of you that’s been ready all along. Imposter syndrome isn’t your enemy. It’s your upgrade code. ❓What’s one imposter moment that ended up being a breakthrough for you? Tag someone who needs to hear this today. ➕ Follow Loren Rosario - Maldonado, PCC for raw, real career rewrites that feel like coaching. 📊 Sources: Salari, et.al. (’25) 📸 Quote: Steven Bartlett #Careers #LeadershipDevelopment

I moved across the country to join an online bookstore with no job description. A 3,000-mile relocation, a strange city, and ultimately, an Amazon VP role. But at the beginning I was scared I had joined the IT department of a bookstore. Taking the risks you need to take will never be totally rational or logical. To stand out you *must* sometimes take illogical risks that feel scary. Columbus sailing for the new world was not a safe bet, and Jeff Bezos leaving a successful hedge fund role to start Amazon was a huge gamble. Almost all the big successes of our time looked scary and uncertain at the start. The important fundamental here is that the risks you need to take for an outstanding career are not safe, logical, or rational. They never will be. A good friend and fellow executive, Michael Frazzini, recently commented on a post of mine that I write excellent logical frameworks for most situations. He then asked if there are things that I do not cover because they don’t lend themselves to clear, linear steps. The answer is yes. That question led to this post. Big risks and leaps cannot be made easy and comfortable with neat frameworks. Big leaps are big leaps. I can give you a formula to recognize them and reduce the risk, but you still have to take the plunge. Here’s what you can do: 1. Recognize potential opportunity- Invent things and/or spot trends 2. Create a *realistic* worst case. Read Tim Ferriss’ “Fear Setting” essay for this. The takeaway is that the consequences of most risks are reversible and recoverable, and that the price of inaction is higher than the risk. I have had many failures in my career and was laid off twice, but I still became a VP and retired at 50. When things went wrong, I was able to recover. 3. Take the leap. If I have a regret, it is that I did not take more risks. 4. If you succeed, celebrate, learn, and remind yourself that it worked despite your fears. 5. If you fail, implement your plan from step 2, recover, and try again. "The only true failure is when you stop trying." How to lower your fear: 1. Time box your analysis: Dig for rational indicators that you should take the risk, but do not expect to get to a perfect business case before jumping in. 2. Buffer. If you have some savings, a good network, or other recovery tools, you face less true risk in the face of a setback. 3. Remember the risks that DO work out. When you can reflect on the gambles that paid off, it makes you more open to gambling again. Readers: how do you get over the fear and take the plunge? Follow me here for more career success tips.

If you have analysis paralysis, read this: I have a confession to make. When I started my career, I was a chronic overthinker. I leaned hard into being analytical. I struggled to follow Nike's slogan: Just do it. Over the past 10 years, I worked on this A LOT. To the point my weakness has turned into a strength. I have operated in ambiguous emerging markets… … and validated 0-to-1 products in 48 hours. Now I regularly hear: "wow you took action so quickly!" 3 tactics that helped me break through indecision: 𝗧𝗮𝗰𝘁𝗶𝗰 𝟭: 𝗨𝘀𝗲 𝗳𝗲𝗮𝗿 𝗮𝘀 𝗺𝘆 𝗰𝗼𝗺𝗽𝗮𝘀𝘀 😱 20's: I viewed fear as a negative reaction. So fear frequently led to overthinking career decisions. 30's: I view fear as my friend. It's a signal that something is important to me. I lean into fear, instead of pulling myself away from it. 𝗧𝗮𝗰𝘁𝗶𝗰 𝟮: 𝗩𝗶𝗲𝘄 𝗮𝗰𝘁𝗶𝗼𝗻 𝗮𝘀 𝗹𝗲𝗮𝗱𝗶𝗻𝗴 𝗶𝗻𝗱𝗶𝗰𝗮𝘁𝗼𝗿 𝗳𝗼𝗿 𝗹𝗲𝗮𝗿𝗻𝗶𝗻𝗴 🧠 20's: I sought to derisk decisions as much as possible. But going from 70% to 80% confidence was a big lift. And I still ended up wrong a bunch. 30's: I rapidly test my assumptions in the real world. I've learned the hard way that if I don't take action... ... I'm NOT learning about how reality responds. 𝗧𝗮𝗰𝘁𝗶𝗰 𝟯: 𝗧𝗿𝗲𝗮𝘁 𝗲𝘃𝗲𝗿𝘆 𝗱𝗲𝗰𝗶𝘀𝗶𝗼𝗻 𝗮𝘀 𝗮 𝗺𝗶𝗰𝗿𝗼-𝗲𝘅𝗽𝗲𝗿𝗶𝗺𝗲𝗻𝘁 🧪 20's: I put a lot of pressure on each decision. This backfired as I set up myself up for disappointment. Especially when things inevitably failed. 30's: I approach each decision with more curiosity. I start with fewer pre-conceived notions of how it'll go. My experience? The real world often surprises you. Better to test and learn! What tactics would you add to shake off indecision?

Taking the plunge into major changes always brings a sense of unease. Let me elaborate. During my job hunt, especially when targeting my dream companies, I felt this uncertainty acutely. I frequently questioned myself: Am I truly prepared for this career transition? What if I get hired and feel out of place, like I don't belong? What if the job and the environment don't meet my expectations? Acknowledging my fear of change opened my eyes to numerous coping strategies. You just need to convince yourself that while change is daunting, staying stagnant is even more frightening. Here's how: Shift your perspective: Instead of viewing a new job or career path as a plunge into the unknown, see it as an opportunity to gain new skills and experiences. Reflect on your true aspirations: Consider what you genuinely want in the long run and determine if a career or workplace change is essential to achieving that. Identify Your Fears: Understand that fear of the unknown is normal. Take the time to figure out exactly what scares you about the job search – is it the financial uncertainty, the interview process, or the idea of learning new things? Once you pinpoint your fears, you can develop strategies to address them. Embracing change means opening yourself up to more experiences and growth. It might be intimidating, but the fear of looking back with regrets is even more so. Take the leap towards your dream life! (Need job search assistance? https://bit.ly/3SpnYor)

What if I suck? What if it doesn't work out? What if they say something bad about me? What if.... (insert fear-based statement)? This week, I've spoken to founders, executives, individual contributors, those looking for a job, people who have started jobs and feel "duped," and those going through life's big stuff. Every situation is different, but there's a common theme... Fear I've asked myself these questions before, felt that anxious feeling, and have had the fear monster knock on my door. Here's what I've learned to do that has helped me avoid the hypothetical dark rabbit hole while getting out of my own way. Step 1: 🛑 Stop 🛑 Step 2: Use these anxious feelings and questions as a signal to: ~ Chuck the assumptions. ~ Lean into curiosity instead. Step 3: Put your weapons down, go straight to the source, keep an open mind, get curious, and listen to understand their POV. An example of how it looks in practice: "The last time we talked, I heard you say ___. It's stuck with me and was different than I expected. Full disclosure, I wasn't sure what to say at the moment, and I'm curious to learn more about your thoughts. Can we talk about it again?" As they're sharing and the anxious feelings start to percolate, it's another signal to 🛑 Stop 🛑. And say these 3 words: Tell Me More Conversations like this are powerful defining moments. To confirm/deny if your initial thought is true or if there is more to the story. Pro tip: You're part of the story as well. Take the time to do the same self-discovery to ask questions like: What's my part of this story? Why is this still bothering me? Am I clear on what I want from this? How can I use this information to get better or create a solution? Fear is powerful and can play two roles: 1. Paralyzing 2. Motivating It's hard to choose the second option. But it's a lot harder later if you don't. Try this and let me know how it works ✌🏻❤️

Fear is nothing more than untested risk. That's why I always look for cheap ways to buy down risk. Here are 5 practical examples: 1. Fear that my business won't succeed. Tactic: Sell -> Build -> Launch If you can't sell the idea to the perfect customer, you can't justify investing to build the product or service. Iterate until you can. 2. Fear my feedback will be received poorly. Tactic: Become a Jeopardy contestant Take your observation and transform it into a question. Make sure it's a question that leaves open the possibility you're wrong. 3. Fear my career change won't work out. Tactic: Saturday Side-hustle Find a way to "try on" your new job. Freelance. Work for one client on the weekend. Use a vacation week to "intern." Try before you buy. 4. Fear I'm wasting my time. Tactic: Realistic Benchmarks "I posted online and got no engagement." Take a course. Learn what the adoption curve really looks like. Find a small support group. Set a milestone of 1-3 months out and commit to showing up until then. 5. Fear I'm hiring the wrong person. Tactic: Paid Projects No interview will ever simulate working together. So work together. Find a real piece of work and pay them to do it with you. That's infinitely cheaper than making the wrong hire. ---- I suspect you noticed some themes across those examples: Fast Knockouts - Optimize for fast elimination, not slow completion. Two-Way Doors - Make it just as easy to go out as it is to come in. Real Data - Pressure test your theory with reality ----- The only path I know to success is action. So how can I take the smallest possible step? If it's a good one, I build momentum. If it's a bad one, I learn a better direction. The only failure we should fear is letting fear keep us from starting. ----- Need an idea for reducing your risk?  Drop your challenge in the comments, and I'll offer you some ideas. And if you found this post helpful - Follow Dave Kline for more - Please repost so others can benefit - Subscribe to my free MGMT playbook mgmt.beehiiv.com You get 60+ leadership playbooks and working management templates. Like the image on this post? Make sure to follow Janis Ozolins for more just like it.

𝗘𝘃𝗲𝗿 𝗵𝗲𝗮𝗿𝗱 𝗼𝗳 '𝗳𝗼𝗿𝗰𝗲 𝘃𝘀 𝗳𝗹𝗼𝘄'? It's not just a catchy phrase, it's a game-changer for career transitions. Let me share a story that'll resonate with many of you. My client Lisa was stuck in "force" mode after 17 years with the same company. She was ready for a change but found herself overthinking every move. Sound familiar? Most of us are guilty of over-analyzing everything in our careers, especially during transitions. We try to force square pegs into round holes, getting caught up in the "shoulds" and "what-ifs" until we're paralyzed by anxiety and stress. Lisa was no exception. She was frantically applying everywhere, second-guessing every decision, and feeling more trapped by the day. That's when we decided to switch gears and embrace the "flow" approach. Instead of forcing outcomes, we focused on optimizing her resume and LinkedIn profile to attract the right opportunities. We let go of the constant analysis and trusted the process. To facilitate this shift, we incorporated strategic tools designed to cultivate a flow state of mind and being. We introduced daily mindfulness practices, used visualization techniques to align her goals with her authentic self, and implemented a structured 'idea capture' system to channel her creativity without overthinking. These tools helped Lisa step out of the anxious, over-analytical mindset and into a more intuitive, flow-based approach to her career transition. 𝗧𝗵𝗲 𝗿𝗲𝘀𝘂𝗹𝘁? One strategic application, one interview, and boom - Lisa landed her dream job with a 40% pay increase, all within 30 days! 𝗛𝗲𝗿𝗲'𝘀 𝘁𝗵𝗲 𝗸𝗶𝗰𝗸𝗲𝗿: Flow doesn't mean passive. It means being attuned, responsive, and open to opportunities you might miss when you're stuck in analysis paralysis or bulldozer mode. So, here's my challenge to you: This week, try loosening your grip on one aspect of your career. Stop over-analyzing and let things flow a bit. You might be surprised at the doors that open when you're not trying to force them. What's your experience with force vs. flow? How has over-analysis affected your career journey? #CareerTransition #SuccessMindset #CareerAdvice #PersonalGrowth #OvercomingAnalysisParalysis #AuthenticLeadership #JobSearch

"Who am I to be giving advice?" When I started this business, I asked myself this question every day.  Even though I had helped hundreds of colleagues, team members and resume clients make career moves, I didn’t feel qualified to be a job search coach. Imposter syndrome was real and deep for me. What fascinated me most was discovering how widespread this phenomenon is among high performing leaders. I've witnessed senior executives, with decades of success, question their ability to step into new roles. The difference wasn't that they didn't experience doubt—they had simply developed strategies to navigate it. Through research and experience, I've identified these key patterns of imposter syndrome: - The perfectionist trap: fixating on minor missteps while dismissing major achievements - The attribution error: crediting success to luck or external factors, while internalizing every setback - The comparison complex: measuring yourself against idealized versions of peers - The expertise paradox: believing you need to know everything before speaking on anything - The acknowledgment avoidance: deflecting praise and struggling to own your accomplishments What are ways we can overcome this syndrome? - Create evidence: write a list of my achievements from childhood through today - Reframe obstacles: see how they helped me learn and grow and led me to an even better place or understanding - Ask questions like is this even true? Oftentimes it isn’t and isn’t based on any facts! - Build a support team: talking to mentors, peers and specialists who can provide honest and constructive feedback. Their perspective can help bridge the gap between misperceptions and reality - Get comfortable with the uncomfortable: recognize that fear and anxiety is part of a new experience and is a sign of growth, not inadequacy When it comes to your career, you may not feel qualified to get the job you really want or take your career to the next level. If that’s the case, remember this: your doubts are not defects nor the truth—they're shared human experiences that can be transformed into catalysts for growth. Ready to transform your career but feeling uncertain about the next step? My team and I specialize in helping professionals move from self-doubt to strategic action. Let's explore how we can help you reach your full potential. You can learn more + book a call here: https://lnkd.in/g7WY3iGY #impostersyndrome #resilience #careermove

Reminder: You are not the problem. If you’re applying online via job boards (LinkedIn, Indeed, Glassdoor, etc), feeling invisible, and tired of getting ghosted, it’s not because you’re not qualified. It’s because the game has changed, and you need a new playbook. The first thing that I coach clients on is their Mindset and Confidence. With how competitive the market is, many high performers are having a tough time finding a job. Many of them have not had to look before. They got referred in or better yet, recruited by their Former Manager. I hear " I don't know what is happening. This is not normal. I usually can get a job fairly quickly". Then I hear, "Now, I am questioning myself. My skills, abilities - maybe they weren't enough?" Or imposter syndrome is creeping in. 🛑 STOP doubting yourself. These are the things I want to encourage you to do to regain your confidence and improve your mindset. 1️⃣ Self Reflection - Better clarity: Identify and understand your current situation and limiting beliefs. Take the time to evaluate your career. Think about the job you loved the most and why. Think about what you don't want. Get crystal clear on the job you want - BEFORE you start applying. Recognize any negative thought patterns or beliefs that may be holding you back from pursuing your goals. 2️⃣ Adopt a growth mindset: Embrace setbacks and challenges as learning & growth opportunities. This builds confidence. Identify and develop the skills that you may be missing that can help you round out your experience or fill that gap on that job you want! (Remember, when you fail, you learn.) 3️⃣ Ensure you have a supportive environment: Surround yourself with positivity. Avoid negative people or demotivating influences. In fact, the other day I reached out to a former leader & manager of mine, sharing an idea and a fear I had. She said just "DO IT" - you will learn what works and doesn't work. Regularly reflect on the things you are grateful for - both personal and professional. Build positive habits that promote a positive mindset - journal, mindfulness, or spend time outside. (I talk about this a lot). 4️⃣ Set Goals and Actions: Define your SMART goals (Specific, Measureable, Achievable, Relevant and Time bound) that align with your SMART goals. Take Action - break down your goals into smaller, manageable steps and take consistent action towards achieving them. You will need to evaluate your progress and adjust goals and strategies as needed. 🌟 By consistently implementing these steps, you can cultivate a more positive and growth mindset which will lead to great career success. 👉 If you are struggling with your mindset and confidence level, download my Clarity Worksheet Guide in the comments. Feel free to schedule a 1-1 with me to review and set a very strategic plan for you. I am rooting for you! Coach Kat

🚨 What if our fear of failure is doing more harm than failure itself? As senior professionals, we’re no strangers to pressure … pressure to get it right, to have the “perfect fit,” and to only make moves when success feels guaranteed. But here’s the truth: at this stage, it’s not failure that’s holding most of us back - it’s the fear of it and can even be fear of success! Fear keeps us silent when we should be visible. It keeps us waiting for job postings instead of reaching out. It tells us we’re “over-qualified” or “too old” or that the market is “too competitive.” But fear doesn’t get you hired. Action does. Here’s a reframe: Companies don’t always know they need you until you show up! These are tips I’ve personally done and professionally done with my clients and had tremendous success: ✅ Reach out directly to leaders at companies you admire, even if there’s no role posted. ✅ Share your perspective online (doesn’t have to be just LinkedIn) especially on industry challenges you’re passionate about. ✅ Reconnect with peers and mentors; they’re more open to helping than you think. Senior-level roles are often filled through relationships, visibility, and timing, NOT job boards. Don’t let fear keep you waiting for a door to open. Sometimes, you have to knock and keep knocking! 🚪 So, are you making yourself visible, or waiting for permission? #JobSearchStrategy #CareerGrowth #JobSearchTips