Memo 011: High Risk, Higher Self
Why Playing It Safe Isn’t Serving You
Opening Statement
In court, we weigh evidence. In life, we weigh risk. And often, the decisions that lead to our highest selves—the glossiest versions of who we’re meant to be—require a verdict that feels terrifying at first.
But here’s the rule of law: bold moves build better lives.
Not because they’re guaranteed to work, but because they signal to the universe (and yourself) that you’re done settling for safe. That you are ready to be seen, stretched, and transformed. Growth doesn’t happen in your comfort zone. It happens in the moments where your choice looks ridiculous, but you go for it anyway. Where you feel fear but choose alignment. Where you leap without knowing exactly how you’ll land.
This week, we’re raising the stakes. Because playing small doesn’t suit you . . . and you can’t buy your dream life with comfort.
Exhibits
Gloss Docket
Grabbing: a book and lunch for the park
Listening: brat summer (it will never be over for me)
Obsessing: Such Brave Girls season 2 on Hulu (finally); getting my aura read at a function
Styling: white ruffle mini skirt with a waist chain
Stepping into: Big risk and bigger reward
Testimony
Some of the best things I’ve done in my life started with my stomach in knots.
Leaving relationships. Changing careers. Pitching myself. Saying yes to things I technically “wasn’t qualified for” yet. Each of those moments came with a choice: stay small, or risk becoming someone bigger. Someone bolder. Someone who doesn’t wait for certainty to start living with conviction.
When I started posting online and really putting myself out there, it wasn’t some random whim. It was something I’d always wanted to do. I just wasted years wondering if I was allowed. If it would be taken seriously. If it would ruin my “respectable” career. People said, “But you’re a lawyer . . .” as if that was supposed to cancel out the rest of me. Like being analytical and creative, ambitious and expressive, couldn’t coexist. But at a certain point, I realized the real risk wasn’t being seen. The real risk was never finding out what could’ve happened if I’d just gone for it. So I did. I posted. I built. I rebranded. And the only thing I regret is not starting sooner.
Something you don’t learn in school: risk is good for you. It expands you. It reminds your nervous system that you're alive. I spent too long trying to make the "safe" choice, only to feel small inside a life that didn’t fit. Playing it safe never made me feel secure, it just made me stagnant.
Even when its scary, the risk is always the way to reward. I’ve learned to treat my fear like a witness. I hear her out. I let her speak. And then I cross-examine her with truth: Have we done hard things before? Yes. Have we made it out stronger every time? Yes. Has everything always worked out? Yes. So what’s stopping us now?.
Spoiler: nothing. Nothing but the stories you tell yourself about what’s possible.
So tell a new story. One where risk isn't something to avoid, but a rite of passage.
Closing Argument
Let the record reflect: risk is a requirement to become your glossed self.
Not because it guarantees success, but because it guarantees growth. Every time you put yourself out there, apply with no safety net, post the content, pitch the idea, speak your truth, you are building a life that reflects your highest self.
You don’t need to justify your leaps to people who’ve never left the ground. And you don’t need evidence before you take the stand for your own potential.
Your highest self is built by showing up in bold pursuit of the life that lights you up. Go get it.
Briefing Adjourned.
Xo,
Alyssa, CGO