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Why I'm learning to disappoint the part of myself that just wants to be safe.
Oct 22, 2025
When I was eighteen, my grandfather gave me a book. Inside, he had written this quote by Thucydides, an ancient Greek historian.
"The secret to happiness is freedom. And the secret to freedom is courage."
At the time, I didn't really get it. I had just graduated high school, I was overthinking every decision about my future, and courage wasn't exactly my thing. I was more the "play it safe" type.
Maybe it's because I grew up with a single mom. I learned early that money is safety – but not just conceptually. I watched her calculate grocery budgets, saw her relief when the electricity bill was lower than expected, noticed how her shoulders relaxed when she got her tax refund. She made sure we were safe, and I never felt we went without. But safety, for her, meant constant vigilance. It meant checking and double-checking, having backup plans for backup plans.
What I didn't realize then was how deeply I had absorbed this. Not just the financial caution, but the entire framework: assess the risks, minimize exposure, always have an exit strategy. It became my default mode for everything – which classes to take, which internships to look out for, which dreams to voice out loud and which to keep safely tucked away.
When I started business school, I found myself surrounded by people who supported this drive for safe, respected choices. Everyone was planning for consulting, investment banking, corporate marketing. The conversations were variations on the same theme: "It's a good first step. You earn a lot. The exit opportunities are great." Always the next thing, always the strategic move.
But here's what struck me: we had all become experts at optimizing for optionality. We were so focused on keeping doors open that we forgot some doors are only worth opening if you actually want to walk through them. The consulting track wasn't just a career choice – it was a sophisticated form of procrastination. A way to feel productive while avoiding the harder question of what we actually wanted.
For quite some time I also thought: Yes, MBBs – that's where I am going to end up. That's the safe choice. But when I started talking to people in consulting, they spoke about the work with detached professionalism. "The projects are interesting. The clients are smart. The hours are brutal but manageable." What I almost never heard was excitement.
Please don't get me wrong – there's nothing inherently wrong with consulting or any traditional career path. Some people genuinely thrive there, find real meaning in the problem-solving, in the variety of challenges. But I was starting to understand the difference between choosing something because it fits you, and choosing it because it fits the shape of safety you've been taught to value.
Because here's what I was learning: how you spend your days is how you spend your life. And the question isn't just whether you're spending them safely, but whether you're spending them in a way that feels like yours.
My grandfather's quote started making more sense. To be truly happy, you need to feel free – not just financially, but free from the exhausting work of constantly managing risk. Free from optimizing for what others consider success. Free from the assumption that the right life is necessarily the safest life.
And that requires a different kind of courage than I had imagined. Not the dramatic, movie-scene courage of quitting everything and starting over. But the quiet, daily courage of paying attention to what actually energizes you. Of admitting when the "smart" choice doesn't feel right. Of being willing to disappoint the part of yourself that just wants to be safe. It's easier to theorize about this than to actually live it, especially when you're still in an environment that rewards the old patterns of thinking.
I'm still figuring out what this means practically. But I've started asking different questions: "What would I do if I trusted myself more?" "What is the worst thing that can happen?" While learning to build this trust in myself, my values and passions.
I know this all sounds privileged – and it is. The fact that I can even contemplate "following my passion" means I've never had to worry about putting food on the table. My mom's lessons about financial security weren't wrong; they were necessary. And I'll probably spend my whole life making sure I earn enough to feel stable. The difference is that I'm starting to question what "enough" really means, and whether optimizing solely for financial safety is the only way to honor her sacrifices.
Maybe the real insight isn't choosing between safety and risk, but learning to recognize when our pursuit of safety has become its own kind of limitation. And maybe courage isn't about abandoning caution entirely – it's about slowly expanding what feels possible.
