The Importance of Taking Risks in Careers

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’ve rarely met a successful executive who didn’t take significant, calculated risks. You can’t just play it safe and expect to slowly rise to VP or C-Suite. It doesn’t work that way: I’m lucky to meet dozens of extraordinary people every week. Founders, investors, and long-tenured leaders with strong careers at great companies. These are the profiles of folks teaching on Maven, so I know them pretty well. Everyone knows that founders and investors have to take risks. But the path to executive leadership ALSO requires significant risk-taking. These executives consistently pushed themselves to work on new projects or new industries. They took pay cuts to work at high-flying but smaller startups. They gave their boss tough feedback to help improve the team’s performance. Don’t just take risks for the sake of it. Sometimes people join an early-stage startup because they simply have an itch to take a risk. It almost always backfires. Instead, you need to make calculated and thoughtful decisions. If joining a startup, you better diligence the hell out of it and feel strongly optimistic in both the culture and the company trajectory. If starting a new project internally, you should know that you have the resources and latitude to make it happen. Playing it safe can create a rewarding, steady career. But it’s hard to get to the top levels of a company if you don’t take a few risks along the way.

Career acceleration doesn’t come from playing it safe — it comes from taking bold, strategic risks🧗🏽. 👉🏽Too many talented women are unconsciously holding themselves back by waiting to be “ready.” ✨ For decades, we’ve been taught to be careful, cautious, and calculated — while our male counterparts are encouraged to take risks, ask for promotions, and step into leadership roles before they feel fully prepared. The result? Research shows men apply for jobs when they meet only 60% of qualifications. Women? We wait until we hit 100%. 💡 And here’s the truth no one tells you: playing it safe holds women back more than failure ever could. As a leadership coach, I see this pattern everywhere — brilliant, capable women sitting on sidelines, over-preparing, and under-claiming their worth. And I get it. 👏🏽 Fear of failure, perfectionism, and social conditioning run deep. But the cost of playing it safe is far too high. ✨ So let’s flip the script: ✅ Reframe risk as growth. Every risk teaches you something. There’s no growth in the comfort zone. ✅ Start small. Speak up in meetings. Apply for that stretch role. Pitch your idea. ✅ Shift your “what if I fail?” to “what if I soar?” ✅ Track your risks and celebrate the lessons — whether you win or wobble. ✅ Ask for what you want. Now. Promotions, pay raises, leadership roles. The time is now. And as leaders, we must normalize bold decision-making for women. 1️⃣Sponsor her 2️⃣Give her stretch projects 3️⃣Praise imperfect action.🚀 Build safe spaces for risk and reward. Because when one woman steps forward, she makes it safer for the next to follow. 🔥 💥 You don’t have to be 100% ready. You just have to be 100% willing.💯 The world needs your ideas, your leadership, and your courage — not your caution🎯. So, tell me — what’s one bold risk you’re ready to take this month? Drop it in the comments 👇🏽 — let’s cheer each other on. 🚀✨ Link to WorkersCompensation.com article in the comments below👇🏽 Comment, Like, Follow, Share🔆 #womensupportingwomen  #womenempoweringwomen  #womeninleadership  #leadershipdevelopment  #executivecoaching  #courage  #confidencebuilding  #igniteyourshineownanddriveyourdestiny

Sometimes, the biggest risk isn’t failing. It’s staying exactly where you are. 18 months ago, I was at the height of my NYC real estate career when I made the bold decision to step into the world of real estate syndications and start my own fund. This wasn’t just a career move—it was about answering a deeper calling to help others achieve 𝐟𝐢𝐧𝐚𝐧𝐜𝐢𝐚𝐥 𝐟𝐫𝐞𝐞𝐝𝐨𝐦 𝐭𝐡𝐫𝐨𝐮𝐠𝐡 𝐫𝐞𝐚𝐥 𝐞𝐬𝐭𝐚𝐭𝐞. The decision came with significant risks: → A temporary dip in income, and → Navigating uncharted waters. ↳ I faced 𝐝𝐨𝐮𝐛𝐭𝐬, the 𝐭𝐞𝐦𝐩𝐭𝐚𝐭𝐢𝐨𝐧 to go back to safer paths, and numerous 𝐜𝐡𝐚𝐥𝐥𝐞𝐧𝐠𝐞𝐬 that tested me every step of the way. But my 𝐝𝐞𝐝𝐢𝐜𝐚𝐭𝐢𝐨𝐧 to helping others achieve financial independence became my compass. → Immersing myself in learning, seeking out mentors, and diving into books revealed something I hadn’t expected: my true passion for fund management. This journey reaffirmed one powerful truth: ✅ With commitment and the right mindset, the risks we take can unlock doors to greater impact and personal fulfillment. Have you ever taken a leap that led you to discover your true passion? I’d love to hear your story. #growth #entrepreneurship #personaldevelopment