Why I Left Amazon at My Peak: Scarcity, Growth, and the Search for Purpose
Learn the cognitive strategies and practical tips to overcome your fear and make that career switch or take that leap you've been dreaming of
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We’re thrilled to feature a guest post by Rajdeep Saha, a former L7 Principal Solutions Architect at AWS and former Distinguished Cloud Architect at Verizon. He has designed and delivered multiple world-scale projects, presented all over the world, and mentored hundreds of students to switch careers to cloud. He has over 350,000 worldwide followers.
This essay shares the cognitive strategies and practical tips Raj relied on to dismantle his flawed mindset, reframe risk, and move toward purpose instead of letting fear keep him stuck. You can apply these principles to make that career switch, take the leap, or start the thing you've always wanted to do!
Leaving Amazon at the peak of my career to found a stealth startup was the hardest decision I’ve ever made, and also the most life-changing.
Like many ambitious professionals, I was tempted to cling to security and status, especially with a scarcity mindset rooted in my childhood. But confronting that mindset and choosing purpose over (perceived) security reshaped my trajectory, and has rewarded me in ways I never imagined.
On paper, I had everything. I was presenting at the biggest cloud conferences, helping architect world-scale projects, and publishing official Amazon blogs that conferred real status. I was well compensated with salary and stock, and I had the respect of my customers and peers. By every external measure, I had reached the pinnacle of professional success, which is exactly what made it so hard to walk away.
And yet, I began to feel restless. The customer meetings, no matter how big the company or project, no longer excited me. Even stepping on stage, once a thrill, felt hollow despite the crowd’s enthusiasm. That dissatisfaction was especially strange for someone who grew up on the razor’s edge of poverty in a small village outside Kolkata, in a home where the roof had caved in and we simply lived with the hole. I still remembered the nights when we couldn’t afford to light the whole house, so my parents lit only my bedroom so I could study late. Their sacrifices were the reason I had built the life I was living at Amazon. For that kid, financial security and status were the very definition of safety. So why, in my middle age, did it suddenly feel like they were no longer enough?
At the same time, I found myself drawn to something that felt like purpose. I had started a YouTube channel, Cloud with Raj, where I offered free content to teach people about the cloud, hoping to help others like me use technology to elevate themselves. I wanted them to dream big, and then achieve those dreams, just as I had at Amazon. The more I taught and the more I heard from people who had benefited from what I was doing, the more motivated I became. I would think to myself, I want to do more of this; maybe this could be something more than a pastime. But even as that purpose became clearer, the scarcity mindset that kept me safe began to hold me back, and I was stuck.
I eventually realized, or rather, my therapist wife helped me realize, that the problem wasn’t external at all. It was an inside job. My doubts and fears, fed by a scarcity mindset, were what kept me stuck. To move forward, I had to challenge those thoughts and question the mindset behind them. What follows are some of the thinking strategies I used, rooted in Cognitive Behavioral Therapy, that helped me dismantle irrational fears and take real steps toward my goal.
Cognitive Restructuring in Action
(CBT technique: identifying the thought, testing the evidence, reframing the belief)
Reframe Action #1
Fear/Automatic Thought: “If I leave Amazon, I’ll lose financial security and plunge myself into ruin.”
Restructuring (Challenge & Evidence Check): I had savings, lived humbly, and had in-demand skills. Worst case: the startup fails and I return to tech. Not catastrophic.
Reframe (Balanced Thought): “I have a safety net. Even if this venture doesn’t succeed, I’ll land on my feet. The real risk is never trying.”
Reframe Action #2
Fear/Automatic Thought: “If the startup fails, people will see me as a failure and I’ll lose status.”
Restructuring (Challenge & Evidence Check): Many respected entrepreneurs have failed before achieving success. People close to me care about who I am, not my title. At worst, a few people might judge, and their opinions fade.
Reframe (Balanced Thought): “Trying and failing shows courage. Status isn’t just about titles - it’s about growth, integrity, and impact.”
Reframe Action #3
Fear/Automatic Thought: “Leaving Amazon means throwing away everything I’ve worked so hard for.”
Restructuring (Challenge & Evidence Check): My career and skills don’t disappear; they come with me. Amazon was one chapter, not the whole story.
Reframe (Balanced Thought): “I’m building on what I’ve done, not erasing it. My experience gives me more tools to succeed in what comes next.”
Laying my fears out on paper and challenging them with CBT gave me clarity I hadn’t had before. But even with those reframes, I still found myself circling the same doubts. That’s when I learned another lesson: sometimes you can’t think your way out of fear alone. You need the perspective of someone who has already walked the path you’re trying to take; you need the right mentor. For me, that person was Ethan Evans.
Ethan Evans first entered my life when he agreed to an interview for my tech podcast, an honor that felt almost unbelievable when he said yes. I couldn’t have imagined that just a few months later, he would drive his RV across the country and end up on my back porch, sharing a bottle of wine with my wife and me. It was surreal: a man I admired as a paragon of Amazon leadership, sitting at my table, chatting like an old friend. But that night, Ethan did for me what even my CBT work hadn’t: he challenged me. He listened to all my reasons for staying and then cut through them with one sentence: ‘You should leave.’ He told me there was no good reason not to. And here’s the thing, sometimes you need to hear the hard truth from people who are closer to your goal, not just closer to you. My wife had said the same thing, but I knew she was motivated by love. Ethan was someone who had left Amazon at his peak and built something new helping others. He had actually walked the road I was only imagining. So when he said it was time to go, it hit deep.
After that night, the excuses I’d been clinging to lost their power. Between the CBT tools I had practiced and Ethan’s blunt clarity, I finally found the courage to do what I had been circling for months: I resigned from Amazon. It wasn’t without fear; leaving behind security, status, and colleagues I respected was painful. But the decision felt like alignment. With the help of a few key mentors, I came to see a simple truth: security is an illusion. None of us can avoid struggle. None of us can avoid death. But while we are here, we have the chance to truly live; to take risks, to go big, to follow our passions, and to elevate one another. For the first time in years, I was moving toward purpose instead of away from fear.
If there’s one thing I’d leave you with, it’s this: find the places in your life where fear is keeping you small and challenge them.
Drag those fears out of the dark and into the light. Look at them dead on. You’ll be glad you did. And don’t do it alone. Surround yourself with worthy mentors. Not slick gurus, but people who’ve walked the path you want to walk and will tell you the hard truth when you need to hear it. Remember: iron strengthens iron.
The payoff for me has been more than a startup that supports me financially. It’s a life with presence and purpose. Twice a week, I take my family to the park and ground myself by pressing my bare feet into the grass, something I could never do at Amazon. Recently, I even I spent an unplanned week in Colombia with a friend, free from the laptop tether that once defined me. And I’ve been able to give back: teaching cloud technology and watching students achieve their dreams. Like Sumanjit, who once believed he couldn’t crack FAANG without coding and now works as a Senior Solutions Architect at Amazon. Or Anuj, who had the technical skills but struggled with executive communication and now leads as a Senior VP at JP Morgan.
Not only am I still immersed in the tech I’ve always loved, but I get to use education, the very thing that changed my life, to change the lives of others. That’s the kind of dividend no paycheck or title can buy. The world needs your passion and your purpose more than ever; a bet on yourself is something you won’t regret.
These days, I spend most of my time teaching and building. Through SA Bootcamp, I help people across tech become Solutions Architects with live classes, hands-on projects, mock interviews, and career coaching. Alumni have landed roles at AWS, Microsoft, Google, Databricks, JP Morgan, Reddit, and more. The next Bootcamp begins September 20th–visit SA Bootcamp for the details or to join the waitlist. Readers will get a special discount if they join the launch webinar on Sept 20th. Webinar details will be shared close to the date. But beyond the bootcamp, I love connecting with people who are curious about career growth, mindset shifts, or just the messy, human side of making big transitions. If any of this resonated, I’d love to hear from you. You can find me on LinkedIn, Instagram, or YouTube.
I’m always up for a good conversation.
See you in the Cloud!
Thank you, Raj, for sharing such an honest, deeply personal, and inspiring story. You remind us that courage starts with a mindset shift and your journey is proof that real personal growth begins the moment we stop letting fear dictate our choices
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Inspirational!
Your story is empowering and transformational. Thank you for sharing it with courage and humility. What hit home is that security is an illusion and surround yourself with real mentors. And yes, Ethan is great and so is Jason Yoong!!