The Career Scaries

because they just hit differently midlife

Hi! Three quick things before we dive into this week’s newsletter:

1. I want to acknowledge that this post was written prior to the LA fires, as it feels strange to share anything unrelated. I went home to LA this weekend, hugging far too many friends and strangers who lost everything. The devastation is indescribable, a truly inconceivable nightmare that feels so unfair.

Yet amongst the tears and beneath the pain and heartbreak, there is a profound sense of perseverance. A sentiment driven by community, hope, showing up for one another, and a deep, unshakable love for LA. In moments like these, I’m reminded not only of how resilient this city is but how resilient people are. How neighbors become family, strangers step up, those in crisis dive deep to find a way forward, and how every small act of kindness ripples outward. LA’s spirit has always been rooted in creativity and grit, and even in the face of unimaginable devastation, that spirit continues to shine through.

As the healing process begins, so does the effort to find some sense of normalcy, something I’ve personally found hard to embrace when hearts are so deeply tied to the pain and all we want to do is help.

I know this is supposed to be “three quick things,” so I’ll wrap this up: what I’m trying to say is that this newsletter isn’t fire-related, even though it’s all I can think about and talk about. And this is me trying to get back to some semblance of work.

2. We’re returning to our OG newsletter day: Thursday. It just feels right and works better with my schedule. I hope this feels good for you, too.

3. The Weekly Edit will be back next Sunday.

And as always, thank you for being here. I hope you’re all well (I know it’s been a week!). xx

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The Career Scaries

The first time I hiked Runyon Canyon, Hollywood’s notable loop, I was 21 and in pretty great shape. I went into it with the kind of arrogance only a 21-year-old can muster, as though I had the stamina of Caitlin Clark. I got this! I started strong, throwing caution to the wind, and approached the initial incline with fearless determination.

Half a mile in, I hit the stairs - those uneven, vertical steps carved into the mountain, forcing hikers to lunge and leap at varying heights. A shift in the walk that demanded more of your athletic ability, mental strength, and thighs - a true challenge for anyone with a heart and lungs. After a few pauses to catch my breath and some internal pep talks along the climb, I made it to the top, rewarded by the breathtaking view of the sweeping city. The reward was so sweet that I chalked it up as the halfway mark, took a few swigs of water, and continued on, feeling pretty good about myself with a rejuvenated pep in my step. Around the bend I went, only to be greeted by yet another steep hill, prompting a nice, big gulp of demoralization. One more push later, I reached the descent - a relief - but the road ahead was still long. Even so, I cruised along with optimism.

The next time my girlfriends asked me to go for the hike, I declined as I wasn't in the mood to get my ass kicked. The third time, I mentally prepared, paced myself, and went into it with humility. The point of my story? This feels like a good analogy for my career, particularly as an entrepreneur, in my 20s vs now. In my 20s, I had a level of naivete so pure it could have been bottled up and sold as an adaptogen. I was bold, fearless, unknowingly arrogant, fiercely ambitious, and leaped without looking, telling myself, “You’ve got this,” and figured everything would work out because, well, why wouldn’t it? And if it didn’t, I’d keep pressing on. But now that I understand what it takes, how hard it is, and how high the stakes are, I approach big career moves with careful consideration and trepidation.

At this stage in the game, taking on a new career endeavor can feel like signing up for your fourth marathon knowing how much it’s going to hurt around mile 18. Yes, I have far more experience and confidence, but you know what else I have less of? Time. An indulgent ingredient in your 20s that made the thought of failing at something feel like a minor inconvenience - a bump in the road. In your 20s and 30s you can take all sorts of shots but the older you get, it can feel like you don't have as many shots left, you've played a lot of the game and need to be strategic before the buzzer.

Now, in my early 40s, with many miles and mountains behind me, I find myself contemplating the next climb, the next shot - and career choices feel more daunting than they ever have before. There’s less margin for error, and career moves feel existential.