Overcoming Career Obstacles

I was lucky enough to have my team grow from 6 to 800 people in 9 years. I was promoted from Senior Manager to Director to Vice President, and I had imposter syndrome the whole time. Here are 4 ways I fought it, and how you can too: It is no surprise that when my team grew 130x from 6 to 800, I ended up not fully knowing what I was doing. At the same time, it is hard to say no to opportunities when you have experienced downsizing and setbacks. So, as the chance to take on new tasks and challenges was available, I said yes. There was definitely an element of "fake it until I make it" in the whole process. It is also true that most of the leaders above and below me were in the same situation. Because of the unprecedented growth of Amazon through these years, most of my managers and direct reports were also in the largest and most complex jobs of their lives. While I cannot know the inner workings of their minds for sure, I feel confident that many of them had similar feelings of imposter syndrome. Action 1: If you worry that you are in over your head, or that people might find out you don't completely know what you are doing, realize that this is normal. Action 2: Understand that it is normal to be in the largest and most complex job of your life for much of your career. If you are not, it often means you have either stepped back intentionally or that you have suffered a setback (like a layoff). Growth inevitably means doing harder things than ever before. Action 3: Get help. Be open with your mentors on what you need. You do not have to share all your worries to lay out your challenges and ask for advice. If you are in an environment where admitting “development areas” is unacceptable, turn your language around and ask for "help optimizing performance and delivery." No one will be against optimization, and it amounts to the same thing - getting insight on any gaps and places to improve. Action 4: Hire a coach, therapist, or counselor if you need one. To be top performers, we need a strong mental game. As leaders, particularly of knowledge work, our whole performance comes from our minds. None of us would hesitate to go to a doctor if we were sick, or a trainer to develop our bodies, so getting help with our mental performance should be a no-brainer. However, there is hesitation and sometimes shame in getting help with our mental game. Readers: I really want to create a short course on fighting imposter syndrome and developing a strong mental game to help with these common challenges. What mental challenges are you fighting? If you have overcome typical worries either in a specific job or long term, share what you did please.

Dear software engineers, It stings when you see your college friends or ex-teammates posting about new job offers, hikes, or “finally made it to FAANG” while you’re still hustling for your shot. Every “I’m thrilled to announce…” on LinkedIn can feel like salt in the wound. And it’s natural to wonder: >> Why not me? >> Am I not good enough? >> Will my turn ever come? But please understand that everyone’s journey in tech runs on a different timeline. Some folks have been grinding DSA or building side projects for years. Some get lucky with a referral or the right timing. None of it means you’re lagging behind, or that you don’t deserve that shot. Instead of letting comparison eat you up, try this: → Cheer for them. Their win doesn’t mean your story is over. → Ask questions, how did they prep, what mistakes did they make, what would they do differently if they started over? → Stay consistent with your own prep. Every coding problem you solve, every project you finish, every application you send, these count. You might feel stuck now, but your breakthrough might just be around the corner. Keep building, keep learning, keep shipping, even if it’s lonely. One day, you’ll look back and realize this phase taught you resilience, focus, and the kind of grit you can’t learn in any bootcamp. You’ve got this. Keep going.

I have been an Instagram and LinkedIn creator for 7 years now. Several videos and posts of mine have gotten over a million views. And, that’s not all. I get 10-20 inbound leads daily without a single cold dm/mail. My students and clients often ask me - “Saheli, how do you get such creative ideas?” With the growing creator economy, there is an increasing misconception around this topic. You may think that creativity comes naturally to these creators, but you cannot be farther from the truth! Creativity isn’t inherent. You need to use your creative muscles enough times to truly hone the skill. Yes, it’s a skill and not a trait. How do I do it?, you may ask. I look for inspiration outside these social media platforms. Here are the Top 5 things that gets me going- - Books - Essays - Writing - Movies - Movement This helps me connect dots, and produce high quality outputs for my personal brand and clients. As freelancers and entrepreneurs, we always have to keep our creative hats on. However, it does get exhausting after a point. ➝ Here’s how you can train your brain to be more creative- Doing these 3 things regularly will help you come up with novel ideas every now and then- 1. Movement Block time for walks, cycling,or gym so that those endorphins come into play. 2. Indulge in new experiences New experiences trigger your creative thinking. It forces you to think in a different direction altogether. 3. Journal in Third Person POV It is an incredibly powerful technique, which means you will have a bird's-eye view into your own brain. I understand that it can be difficult to get out of your head sometimes. It happens to the best of us, don’t worry. P.S - How do you get over your creative blocks? Tell me in the comments below?

I see many people struggling or confused when switching into AI. Don’t jump straight into frameworks like LangChain or LangGraph. Frameworks are accelerators, not starting points. Without foundations, you’ll end up building fragile demos instead of production-grade systems. Here’s a step-by-step path to transition your career into Generative AI: 1. Build Core Foundations --Python (APIs, JSON, virtual envs, packaging) --Git, Docker, Linux basics --Databases: Postgres + pgvector, or FAISS for embeddings 2. Learn Just Enough Math & Data --Vectors, cosine similarity, probability --Tokenization, chunking, normalization 3. Understand LLM Basics --How transformers work at a high level --Different types of models: base vs. instruct, hosted vs. local --Prompt engineering patterns (instruction, few-shot, tool-use) 4. Get Hands-on with RAG (without frameworks first) --Ingest → chunk → embed → store → retrieve → re-rank → generate --Add logging, caching, retries --Evaluate outputs with ground-truth sets 5. Learn Evaluation & Safety --Handle hallucination, PII, toxicity --Define and track metrics (accuracy, latency, cost) 6. Explore Reliability & MLOps --CI/CD for prompts/config --Observability, tracing, cost dashboards --Error handling and fallbacks 7. Then Explore Agents --Start simple: one-tool agents --Add planning and memory only when metrics prove value 8. Finally → Use Frameworks Wisely --Adopt LangChain, LangGraph, or LlamaIndex as orchestration layers --Keep your core logic framework-agnostic 9. Showcase Projects --Document QA system with metrics --Structured extraction pipeline with redaction --A small but reliable agent automating a real workflow 10. Be Interview-Ready --Explain RAG pipelines on a whiteboard --Compare models and providers --Justify design choices (chunking, caching, re-ranking) Learn the primitives first. Frameworks make you faster after you understand what’s under the hood. That’s how you build systems that last.

To Every Young Lawyer (or Professional) Who Feels Like a Fraud—Read This When I started practicing, I felt a pit in my stomach every single day for the first four years. You know the feeling—the part where you’re just faking it, hoping you’ll make it? Exactly. Every matter was unfamiliar. Every client brought something I hadn’t seen. And every time I got a question I couldn’t answer, I questioned whether I belonged. If that sounds familiar, take a deep breath. You’re not an imposter—you’re just new. And you’re not alone. Imposter syndrome is the fear that everyone else knows what they’re doing—and you don’t. But here’s what helped me move past it: 1. I learned that every lawyer—even the most seasoned—encounters problems they’ve never seen before. The law evolves. The facts shift. The people involved are never the same. You don’t stop facing the unknown. You just get better at working through it. 2. Confidence doesn’t come from knowing everything. It comes from knowing how to find the answer—and who to call when you can’t. When you run into an issue outside your subject matter, find someone who knows it well. Listen. Learn. And take notes for next time. Build a network of problem-solvers. Get a mentor. Know lawyers in other fields. Build relationships with expert witnesses. Their insight will elevate your thinking and your practice. You’ll know your network is strong when you’re two phone calls away from any answer you need. Be the kind of professional others respect and want to support. And return the favor when your phone rings. You don’t outgrow imposter syndrome—you outsmart it.

Receiving a rejection letter stating you are "too experienced" or that the position "won't be challenging enough for you" is incredibly frustrating. It feels like the company is making a decision for you, rather than letting you decide what the right fit is for your own career trajectory. When a hiring manager says a role isn't "challenging enough," they are rarely critiquing your skills. In reality, this is corporate code for a few specific things: – The Fear of Attrition: They are worried that you will get bored, feel underutilized, and quit the company within six months. – The Budget Constraint: They assume your level of seniority means you will be too expensive to retain long-term. – The "Junior" Mismatch: They decided to hire someone more junior whom they can easily mold, and pay significantly less. Because this happened at the final round, instead of trying to argue your way back into the job (that rarely works), use your response to position yourself for future opportunities. You should reply within 24 hours using a strategic, low-friction framework. Try this template: "Hi [Hiring Manager Name], Thank you for the update and for the transparent feedback. While I am disappointed, I appreciate your clarity regarding the role's current scope. I understand the concern about the challenge level. However, I viewed this position as a distinct opportunity to [bring stability to the operations team / mentor junior leaders/master X-specific market skills], which is exactly what I am looking to focus on in my next professional chapter. If a more senior role opens up down the line, or if the requirements for this position evolve, please keep me in mind. I truly enjoyed meeting the leadership team." If you genuinely respected the organization, don't let the connection freeze at the rejection email. Send a LinkedIn request to the hiring manager and the peers you interviewed with, and note how much you valued the conversation (please add a note). In future interviews, explicitly state why you want to do this specific level of work right now. Framing your intentions early eliminates their fear of attrition before it turns into a rejection letter. Have you ever been hit with the "overqualified" or "not challenging enough" rejection message after a great interview process? How did you respond to the hiring manager? —----- 👋 Hi, I’m Ana. I help introverted managers & directors land their next role through strategic positioning. Every Thursday, I send out tactical job search tips in my newsletter. Check my FEATURED section to join the list.

My candidate landed her 12 LPA dream job after a 2-year career gap… Most recruiters and job seekers treat career gaps like a red flag. Every week, I see talented professionals sabotaging their comeback because they hide, apologize, or downplay what those years actually taught them. A gap on your resume is not a gap in your value. If you’re still letting your “break” break you, you’re missing out big time. Here’s how my candidate turned her break into a breakthrough: 1. She Flaunted the Gap, Not Hid It Instead of shrinking away, she owned her story: “During my sabbatical, I upskilled in data analytics, freelanced for two startups, and volunteered to build digital processes for an NGO.” Recruiters at top companies love candidates who show initiative even off the clock! 2. Quantified Every Achievement She replaced generic lines with hard numbers: “Automated reports, saving 15 weekly hours for a non-profit.” “Managed 6 campaigns as a freelancer, boosting client traffic by 40%.” Resumes with quantified impact get 2x the recruiter callbacks! 3. Nailed Her Story in the Interview We practiced a clear, honest narrative for the “career gap” question. Example: “I took time to care for my family and during that time, I built digital workflows and launched a side project that solved a real problem. Those skills are relevant for your team at Deloitte.” She shifted focus from absence to VALUE. 4. Used Smart Networking (not just applications) She reached out to former colleagues working at her dream companies, attended webinars, and asked for informational interviews. Result? Insider referrals and warm intros, no “cold” interviews. 5. Upgraded Her LinkedIn for 2025 Profile before: “Looking for opportunities.” Profile after: “Data Analyst | Delivered digital strategy for non-profits. Passionate about driving impact with numbers.” She also shared a short post about her upskilling journey (which got recruiters DMing her!). 💡 My top pro tips for candidates returning after a gap: ➡ Add a short “Career Break” entry in your resume. ➡ Highlight any freelance project you worked on, or courses you completed during your gap. ➡ Prepare a 60-second, positive story about your break. ➡ Focus on what you bring NOW, not what you “missed.” Your career gap is only a problem if you let it be. It can be your power move — the proof that you’re adaptable, proactive, and resilient. It’s not about the time you took off. It’s about how ready you are to grow next. #career #careergap #careerbreak #interviewtips #jobsearch #interviewpreparation #linkedinforcreators

The most limiting belief is "I already know." You’ve built expertise over years. You know your domain. You’ve solved the problems. You’ve earned your credibility. And now you’re stuck. Not because you don’t know enough. Because you stopped asking what else you could learn. I remember early in my career I had to ask questions. I didn’t have a choice. I had to listen. I had to absorb. I was uncertain about everything. That uncertainty was fuel. It kept me growing. But somewhere along the way, that changed. I started answering before I’d fully understood. Solving before I’d explored. Knowing instead of discovering. I’d become "the one who knows." And that identity – the expert, the reliable one – created a ceiling I didn’t even see. I realised this wasn’t just me when I met H. Brilliant change expert. Built change service frameworks from nothing. But she kept second-guessing herself. She’d been offered a role with a consultancy firm twice. Bigger salary. Bigger company. Bigger opportunity. Both times, she turned it down. "Who am I to walk into an organisation and say I’ll show you how to do this?" In one session she said: "I don’t know if I’d be staying or leaving for the right reasons. Even now, my brain is just throwing things at me." That was the moment. She wasn’t limited by what she knew. She was limited by believing she hadn’t paid her dues. What shifted wasn’t more knowledge – it was trust in her own judgement. One simple tool helped: Write down your evidence. Not how it felt. What she’d actually done. Three functions built from scratch. Seven years of impact. Nominated for industry award. A few weeks later she said: “My inner monologue has switched. It’s not attacking me anymore – it’s backing me." Same expertise. Different posture. Growth doesn’t come from accumulating more knowledge. It comes from staying open when you already know enough. A jar that’s already full can’t receive anything new. Where do you see this showing up for you? —— I share reflections like this here, and go deeper into the work in my newsletter: James Compton

A £120k HR Director I worked with last year took a 14-month career break to care for her mother. When she returned to the job market, she applied for 23 roles at or below her previous level. She received 4 interviews. She was told in two of them that her 'gap' was a concern. 14 months. Not 5 years. Not a decade. 14 months, caring for a parent, and it was enough for panels to question her 'commitment' and 'currency.' I have worked with returners throughout my career. The pattern is consistent: the career break itself is rarely the issue. The issue is how panels interpret it when they see it on a CV. ❌ Listing a career break as a gap on your CV with no context. ✅ Frame the break as a deliberate decision. '2024-2025: Career break, full-time carer for a family member. During this period, I maintained my CIPD membership, completed a Level 7 module in Employment Law, and consulted informally with two former colleagues on restructuring projects.' The break should read as a chapter, not a gap. ❌ Apologising for the break in interviews. 'I know I've been out of the market...' ✅ Own it without apology. 'I made a decision to prioritise family care for 14 months. During that time, I stayed connected to the profession through [specific activities]. I am returning because I am ready to lead at this level again, and this role aligns with where I want to take my career.' ❌ Accepting a significant salary downgrade as 'the cost of coming back.' ✅ Benchmark your market value using current data, not guilt. 14 months out of a 20-year career does not reduce your worth by 25%. If a company offers £90k for a role worth £120k because you have a gap, that is not a reasonable adjustment. It is an exploitation of your perceived vulnerability. I call this The Return Penalty: the informal devaluation that happens when a career break is treated as evidence of reduced capability rather than evidence of a life lived outside work. Here is the follow-up question most companies cannot answer: if your organisation genuinely supports returners, how many of your hires in the last 12 months had career gaps of more than 12 months? If the answer is zero, the policy is not the problem. The process is. Have you experienced the return penalty? Or have you been on a panel where a career break changed the way you assessed a candidate?

Even top performers get slowed down by mental blocks. The difference? They know how to break through. These mental blocks can feel really tough to deal with. I used to struggle with perfectionism - and spend hours tweaking things instead of actually finishing them. The day I embraced ‘good enough’ was the day I started making real progress. Here are 8 common mental blocks - and how to break through them: ❌ 1. Analysis Paralysis: Overthinking keeps you stuck in decision-making mode, freezing you into inaction. ✅ Take one small step: Movement creates clarity. Focus on one actionable task to build momentum. ❌ 2. The Self-Doubt Tax: Believing tasks are too big or beyond your abilities leads to procrastination. ✅ Look back at your wins: Remind yourself of challenges you’ve overcome. Every past success proves you can rise again. ❌ 3. Fear’s Grip: Fear of failure or mistakes stops you from trying at all. ✅ Shift your mindset: Every expert started messy. Embrace the process, and keep moving forward. ❌ 4. Comparison Trap: Looking at others’ progress makes your own success feel far away. ✅ Focus on your own growth: Track your personal metrics. Celebrate your progress, not someone else’s. ❌ 5. Purpose Blindness: When work feels meaningless, it’s hard to stay motivated. ✅ Reconnect to your "why": Link daily tasks to your bigger mission or goals. This brings meaning back to your actions. ❌ 6. The "Too Late" Trap: Feeling like you’ve missed your window for success keeps you from trying. ✅ Start where you are: Growth begins the moment you take action. It’s never too late to start moving. ❌ 7. Identity Chains: Labelling yourself as “unmotivated” or “not good enough” locks you into limiting beliefs. ✅ Let actions shape your identity: Take small, consistent steps. You’ll begin to see yourself as the capable person you truly are. ❌ 8. Perfection Prison: The pursuit of perfection keeps you from finishing - or even starting - important tasks. ✅ Embrace "good enough": Allow yourself to start with imperfect work. You can always refine and polish later. The first step is recognising these mental blocks. The next step? Taking action to overcome them. -> I'd love to hear in the comments, which of these mental blocks you've overcome? ♻ Share this post with someone who needs a reminder that progress starts with action. ➕ Follow me, Jen Blandos, for actionable daily insights on business, entrepreneurship, and workplace well-being.