Career Decision Risks

Most people think career success comes from making the perfect decision. It doesn’t. It comes from making timely, values-aligned ones. Especially when the next step feels unclear. One of my clients, a brilliant VP, spent 3 months stuck on a single choice: “Do I speak up about being overlooked, or wait for my work to speak for itself?” She called it strategic patience. But it was really fear disguised as overthinking. We ran it through this framework. She made the call. Six weeks later, her promotion was fast-tracked. She was finally seen, heard, and most importantly, included. Because here’s what I tell every high-achiever I coach: You don’t need more time to decide. You need a better way to decide. Try the 2-Minute Decision Framework™ (Career Edition): 1. QUICK DECISIONS → Handle it NOW For low-stakes tasks that clog your mental bandwidth: → Can you respond to that email in < 2 minutes? → Is the request low risk and easily reversible? → Are you spiraling on something that just needs action? ✅ Do it. Momentum builds trust and confidence. (Your career doesn’t stall in the big moves, it drips away through tiny indecisions.) 2. TEAM DECISIONS → Resolve it TODAY For collaborative work or project bottlenecks: → Who’s recommending this approach? → Who’s doing the work? → Who’s accountable for the final call? ✍️ Assign roles. Align expectations. Move forward. (Most team confusion comes from no one knowing who’s driving.) Use this anytime you’re: – Leading a cross-functional project – Navigating performance reviews – Building team trust through shared clarity 3. CAREER DECISIONS → Make it THIS WEEK For decisions that affect your growth, visibility, and voice: Use the 3–2–1 Method: → 3 options: Brainstorm career paths, scripts, or solutions → 2 perspectives: Ask two mentors, not the whole internet → 1 call: Choose the path aligned with your long game 🎯 Clarity > complexity. Every time. This works for: – Deciding whether to advocate for a raise or promotion – Considering a lateral move for growth – Navigating visibility or speaking up on tough issues The truth is: courageous careers aren’t built on perfect plans. They’re built on small, aligned decisions made with intention. That’s C.H.O.I.C.E.® in action. So here’s your coaching moment: 🔥 Pick one decision you’ve been avoiding. Run it through the framework. Make the call within the next hour. Then ask yourself: What changed when I finally decided? ❓ What’s one career decision you’ve been sitting on too long? Share it below, or DM me, and we’ll run it through together. 🔖 Save this for your next “Should I…?” moment 👥 Tag someone who needs this framework in their toolkit Because alignment isn’t found in overthinking. It’s built through C.H.O.I.C.E.®. ➕ Follow Loren Rosario - Maldonado, PCC for tools that actually work in real life. #CareerCoaching #LeadershipDevelopment

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)

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.

I spent the first 17 years of my career on the options trading floor. When I chose the wrong position, we lost money. Real money. We acknowledged it. Moved on. Made the next trade. But rarely would a trader freeze for two weeks, analyzing how and why they were wrong. The market kept moving. Yet that analysis paralysis is precisely how I see manufacturing companies operate in the face of uncertainty. They get stuck. Over-analyze. Sit in uncertainty and wonder why things aren’t getting better. You can be wrong 40% of the time and still make money. If you’re decisive and take action. Equally, you could be “right” 100% of the time, but without action it’s meaningless. Decent decisions now are better than a perfect decision later. A few ways I’ve seen this bleed margin in manufacturing: 🏭 Equipment breaks down. The team debates “repair vs. replace” for three weeks while production limps along at 60%. 🛩️ Supply chain shifts. Contract negotiations with a vendor drag while inventory sits dead on the warehouse shelves. ❌ Key person quits. You’ll never find the “perfect” replacement AND the team now realizes the value of SOPs. No owner, operator, or team can avoid making wrong decisions. But you can practice making decisions you can recover from. Most folks don’t love this. Strategic planning, risk mitigation, and contingency plans are nice boardroom exercises that stay theoretical. Until they realize that every day with indecision IS a decision. One that bleeds margin over time. Your org doesn’t need a Big L to learn this. Just permission to move forward with 70% certainty vs. 100%. Make the best decision you can with the info you have. Make a new one when new info rolls in. Whether it’s trading or manufacturing, the market doesn’t wait. Neither do your competitors.

I’ve got an offer from Microsoft. eBay has offered a better sign-on bonus. Looks like Salesforce is also ready to match. Which one should I take? I received this message from a client who needed help in deciding on the right job offer. While it’s a great problem to have, it’s also one of the most misunderstood. When people get multiple offers, they tend to focus only on salary or brand name. But the right question is: Which offer creates the strongest compound return for your career? Here’s how I walk clients through offer selection (especially in tech): 1. Assess the 24-month runway → Will you still be learning and growing 2 years from now, or will you plateau after 6 months? → Will this team give you mentorship or treat you like a fire extinguisher? 2. Study the team structure & decision-making power → Are you working in a core product org or a side initiative that could shut down tomorrow? → Will you own features, influence roadmaps, or be a ticket-taker? 3. Check the track record for promotions → How long do people usually stay in your level before moving up? → Ask: “Who was the last person in this role and where are they now?” 4. Evaluate long-term visa & location safety (especially for international hires) → H-1B sponsorship, green card timelines, internal mobility not all companies are equal. → Get clarity upfront so you don’t scramble later. 5. Don’t forget: your manager > your brand → A great manager will open doors for you. → A bad one will block your growth, erode your confidence, and slow your career down. My client didn’t take the highest offer. She took the smartest one. Today, she’s working at a top company, and she’s thriving there. 📌 Save this if you're comparing offers. Repost if you know someone who's comparing multiple offers. P.S. Follow me if you are a job seeker in the U.S. I share practical advice to help you land your dream role. 

Happy TGIFFF! (Free Fry Friday!) Over the past six months, I have witnessed layoff notices and "open for work" announcements almost every time I log onto LinkedIn. The trend has been constant since late 2024. I'm trying to help and offering pro bono coaching to people who’ve been affected. In that time, I’ve noticed a few common threads among those who are managing to land new roles. Not easily, but with some clarity. Here are three things I’ve seen help: They separate their identity from their job. They’re not using work to fix deeper issues or prove their worth. They see work as just one part of life — important, but not everything. That mindset helps them avoid toxic roles and recognize red flags, both in companies and in themselves. They understand their values and act accordingly, not in a corporate or abstract way, but in a lived way. They know what matters to them (time, stability, autonomy, family) and stop chasing roles that conflict with that. They’re honest about what they’re good at and what they’re not. They’ve let go of the “fake it till you make it” approach. They know their strengths but don’t pretend to be experts in everything to get a foot in the door. None of this guarantees a job. The market is still hard. But this kind of self-awareness helps people navigate it with less confusion and sometimes, with better results. Sharing in case it helps someone else trying to find their way through. #jobsearch #layoffs #careertransition #honestadvice

Here’s why it’s so difficult to assess whether your parental leave policy is “hurting” your retention rate: Because 94% of women do return to work after parental leave. Most stay over 12 months. And then - on average - 36% of them leave 18 months after their return. Many companies look just at that initial return to work % and declare success: “We have great retention for new mothers! 94% in fact!” But under the surface? There could be huge problems brewing. Because, of course, most women return to work at first. Most people aren’t in a financial position to just quit. Most women do want to work for pay. Most women can’t possibly handle interviewing while on parental leave taking care of a new child 24/7 (often without a partner also on leave). So they return to work. And maybe they “give it a go” so to speak. Maybe they really do try to make things work. But what happens is this: All of the things that were broken in their roles before become intolerable now that they’re exhausted and stressed. They return to work to find they’ve been frozen in time - their projects stalled, their coworkers got all the high priority work, they missed major growth opportunities. Perhaps they also have a new manager (this happens so often!) who isn’t aware of their prior successes and has no idea about their career goals. A mountain of work is dumped at their feet. So they begin to crumble, slowly but surely. They may decide to keep their head down for 6-12 months. After all - who wants to throw their career up in the air when they’ve just added a new human to their family? Too much change at once. But around that 1-year mark? They’re feeling like themselves again. They realize how capable they are, and they start to truly assess their job. And if they had a negative return to work experience that has this many long-term repercussions? They start to interview. And by 18 months post-return they are gone. So for companies that really want to know if you have a “return to work” problem? Look at your 18 month retention rate for ALL new parents.

Navigating today’s job market? It’s not just you - it’s the system.   Let’s be honest: • Exceptionally qualified candidates are struggling to get noticed • Job postings go live, then disappear • Hiring processes stretch on for months • ATS filters continue to screen out the very people companies are trying to hire   The issue isn’t a lack of effort or talent - it’s that many hiring systems are broken or misaligned with how great talent actually shows up.   If you're feeling stuck or overlooked, you’re not alone.   Here are a few strategies I’ve seen work in today’s environment:   1. Build strategic visibility - being qualified isn’t enough if no one sees you: • Share insights and reflections on LinkedIn • Engage in relevant industry conversations • Create content or resources that highlight your expertise   2. Activate your network intentionally - most roles are still filled through relationships: • Reach out before you’re in crisis mode • Be specific in what you’re asking for • Offer value before expecting help in return   3. Keep moving forward - relying solely on job applications limits your options: • Consider consulting, freelance, or contract work • Reach out directly to companies or decision-makers • Stay open to projects that build momentum   4. Protect your confidence - rejection in this market is often systemic, not personal: • The hiring process is imperfect - and your value isn't defined by it.   The people landing great roles right now aren't always the most experienced.   They're the most visible, strategic, and resilient.   What strategies have helped you navigate today’s job market?   Check out my newsletter for more insights here: https://lnkd.in/ei_uQjju   CC: TikTok @fine_ten   Dm for removal.   #executiverecruiter #eliterecruiter #jobmarket2025 #profoliosai #resume #jobstrategy #jobsearchrealities #careerresilience

🤮🤮 300k tech workers laid off since Jan 2023, >10% in the past 30 days - it's brutal out there... Bringing back some practical advice for facing the job market: 𝗚𝗼 𝗜𝗻 𝗘𝘆𝗲𝘀 𝗪𝗶𝗱𝗲 𝗢𝗽𝗲𝗻 - A search could take >6 months - You have less leverage - Competition is much fiercer for posted jobs 𝗙𝗶𝗻𝗱𝗶𝗻𝗴 𝗔 𝗝𝗼𝗯 = 𝗬𝗼𝘂𝗿 𝗡𝗲𝘄 𝗝𝗼𝗯 - Maintain a regular schedule - Spend 40+ hrs a week on the hunt - Treat applications like work projects (high effort / quality) - Spend several hours researching / learning about companies before applying 𝗔𝗽𝗽𝗹𝘆 (𝗦𝗲𝗺𝗶-)𝗟𝗶𝗯𝗲𝗿𝗮𝗹𝗹𝘆 - Titles mean very little - Apply --> use process to assess fit - Don't avoid applying because of perceived seniority diff - Best way to make a company want you: crush an interview process, and decline an offer (respectfully) 𝗡𝗲𝘁𝘄𝗼𝗿𝗸 - Activate your relationships - Try to get referred for open jobs - Ask for intros to hiring teams <<< - But don't be pushy 𝗔𝗽𝗽𝗹𝘆 𝗪𝗲𝗹𝗹 - Custom resume + cover letter every time - Cover letter should not be a novel - "Unique" resumes are bad resumes (eg unusual formatting, images, etc.) - Apply to MAX 2-3 roles per company - Submit ASAP, but not at the expense of high quality customization 𝗜𝗻𝘁𝗲𝗿𝘃𝗶𝗲𝘄 𝗪𝗲𝗹𝗹 - Know the company's stated goals - Know who the competitors are - Know the company's market advantages - Be able to explain why working there / in that role will advance your career goals - Avoid language like "I'll take anything" or "I'm open to [x] because of the market" 𝗥𝗲𝗮𝗱 𝗧𝗵𝗲 𝗧𝗲𝗮 𝗟𝗲𝗮𝘃𝗲𝘀 - The layoffs aren't done... - Low ratio of open jobs to current employees = BEWARE (eg: 30 jobs / 5000 employees) - Ask about recent budgeting / headcount processes, try to understand the funding direction of the biz - Incumbent businesses (big ones) are facing pressure to become efficient, meaning upstart + growth businesses are good options right now 𝗖𝗼𝗻𝘀𝗶𝗱𝗲𝗿 𝗔𝗱𝗷𝗮𝗰𝗲𝗻𝘁 𝗜𝗻𝗱𝘂𝘀𝘁𝗿𝗶𝗲𝘀 - If you need a job, be willing to industry-switch - Taking a detour out of current industry is generally better than going unemployed 𝗔𝗱𝗼𝗽𝘁 𝗣𝗿𝗼𝘀𝗽𝗲𝗰𝘁𝗼𝗿𝘀 𝗠𝗶𝗻𝗱𝘀𝗲𝘁 - >99% of your applications will not warrant a job offer - >90% of your networking requests will go unanswered - If you accept the two above statements, won't see time and effort as "wasted," or feel like you're failing. You are just in the process of finding the 1% outcome. Remember: you only need to "win" once, and the cycles of applying and interviewing will both better prepare you for future encounters, and also enrich your understanding of the broader market. #layoffs #jobsearching #google #activisionblizzard #paypal #block #okta