The Magic of Attempting Hard Things
Reflections on my experience at the 2026 Female Founders Retreat.
Doing Hard Things
After returning home from the Female Founders Retreat in Palm Springs a couple of weeks ago, I was grappling with how best to synthesize and share my experience.
Yesterday, while on a long run, I finally had a moment of clarity.
When you try to do something really hard, there’s often a certain loneliness that accompanies ambition. You’re choosing a less common path and, in doing so, deliberately pursuing something others may see as impossible, irrational, or simply not worthwhile. Hell, Ben Horowitz literally titled his book The Hard Thing about Hard Things with the subtitle “Building a Business When There Are No Easy Answers.”
There’s a joke that founders are all a little crazy, because no truly rational person would choose a path with such a high failure rate. Most startups fail, and therefore most founders fail too.
Pursuing something difficult requires a surprising amount of vulnerability. You have to care enough to risk embarrassment, rejection, uncertainty, and the possibility that you will fail.
Counterintuitively, I think that vulnerability is also what creates such meaningful connection, especially among people who have chosen unconventional paths of their own. There’s an unspoken understanding between people willing to attempt something hard despite the odds.
The Long Run
I’ve noticed something funny happens when I’m out on a long run wearing a running vest filled with water and snacks, as I was yesterday. Some other runners will smile, nod, wave, or even offer a high-five. But beyond that, people simply going about their day will cheer me on too, even though I’m only racing myself (and usually pretty slowly at that).
I go on walks almost every morning and shorter runs around my neighborhood, but there’s something different that happens when I’m fully geared up for a long run. The running vest becomes a sort of “here is a person trying a hard thing!” bat signal.
I love running around City Park in Denver, Colorado. I’ll pass families heading to the Zoo or the Museum of Nature & Science, someone walking their dog, people biking to work, tourists, kids, strangers. When I’m visibly in “attempting a hard thing” mode, I’m consistently surprised by how much positivity gets sent my way. Smiles. Waves. “You got this!” Fist bumps. Encouragement from people who are just going about their day but want to share a little support.
I try to return the energy whenever I can: a smile, a wave, a “thanks” or “you too!”
There’s a reciprocal positivity that emerges. The catalyst seems to be the hard thing itself — or perhaps simply the willingness to visibly attempt it.
Magic in Reciprocal Positivity
That’s what the Female Founders Retreat (FFR) felt like to me. A 100X magnified version of that same reciprocal positivity in a beautiful setting at Two Bunch Palms in Palm Springs, CA.
An incredible community of female founders, each attempting their own very hard thing, coming together not to compete, posture, or perform competence, but to genuinely encourage one another and support, share experiences, and empower.
One thing I loved from the kickoff of the retreat was the request not to give advice unless someone explicitly asked for it (or said it was welcome). The impact of this was surprisingly freeing.
Rather than constantly signaling competence through advice-giving or trying to solve one another’s problems, we simply got to exist as ourselves. We shared experiences without immediately turning them into prescriptions or lessons.
Counterintuitively, that ended up being far more helpful than much of the well-intentioned advice I regularly receive outside of FFR. There was something powerful about being deeply listened to without the immediate pressure to optimize, fix, or perform expertise.
At FFR, you’re surrounded by people who understand both the ambition and the vulnerability required to pursue an unconventional path. That kind of curated, intentional environment, combined with the people within it, creates something special.
“I Am”: Reflecting on the Female Founders Retreat
The rest of my reflection on this year’s Female Founders Retreat experience will focus mostly on myself, because I want to honor the spirit of confidentiality within the retreat and avoid sharing stories that aren’t mine to tell.
That said, I can’t emphasize enough that the power of this experience was not just in the individual. It came from the collective: this many experienced, brilliant, ambitious female founders coming together with openness, honesty, and generosity toward one another.
My goal going into this year’s retreat as a second-timer was to really lean into the experience and, as I wrote beforehand, “be a sponge, learn a lot, find inspiration, and build meaningful connections.”
Especially with so much shifting in my life beyond the usual chaos of startup founder life, I wanted to show up fully open and present. The degree to which that actually happened surprised me.
I also wanted to push myself toward new experiences rather than simply repeating my favorite conversations and workshops from last year. While that sometimes led to difficult-feeling choices about where to spend my time (though there truly were no wrong answers), I consistently chose the newer experiences and was repeatedly delighted by what I learned.
There was something powerful about intentionally stepping into rooms, conversations, and ideas that felt unfamiliar rather than optimizing for comfort or certainty. Again and again, those choices led to unexpected insight, connection, and inspiration.
One especially bright spot was Amy Jin’s ConfidenceOS workshop, which continues to influence me daily as I realize how much power there is in rewiring the way I perceive and present my own confidence.
The roundtables were equally impactful. I attended those led by Kristen Hamilton (Alongside Advisors) and Helen Kontozopoulos (Founder & CEO), as well as the one co-led by Amelia Lin (VC Backed Moms Founder) and Jenny He (Founder & CEO of Ergeon).
On the last morning, I also co-facilitated one final roundtable with Partners Marcia Hatch and Sogol Salari from law firm and Female Founder Retreat sponsor, Gunderson Dettmer.
Each night’s Jeffersonian Dinner seemed to deepen both self-exploration and connection through conversation and discussion.
On the last night of the retreat, during an evening of celebration, I sat with Donna Sacks. She spoke about paying attention to my “energy GPS system” and feeling empowered to create and co-create. She also encouraged replacing words like “want,” “need,” and “try” with the much simpler phrase: “I am.”
“I am” felt strangely grounding to me. Simple, but powerful and an anchor point.
I am someone who tries to do almost-impossible things, especially as a founder.
Balancing creating space for all that I am, while being supported by and learning from such an extraordinary group of female founders, left me buzzing with creative energy and ideas.
It took me a while to figure out how to share even a small piece of this experience, but I’m leaving the retreat feeling unstuck and emboldened: clearer in my sense of self, my leadership, and the kind of company and life I want to continue building.
Gratitude and Joy
After last year’s retreat, I left feeling deeply inspired and grateful. This year, those feelings only intensified, alongside a strong sense of joy. I left feeling more centered, inspired, and excited to return to the startup trenches with renewed energy.
I’m immensely grateful to everyone who helped make Female Founders Retreat what it is. Thank you.
Special thanks to this year’s hosts, Emily Dong (Founder and CEO, Snout), Mada Seghete (Co-founder, Upside and Co-founder, Branch), Amy Jin (Leadership Coach for Founders and Teams), and Tracy Lawrence (Leadership Coach & Facilitator) for creating an environment where this kind of connection, mutual support, and magic can exist.
The host team are incredibly successful and busy founders and creators themselves, which makes the intentionality behind building this space even more meaningful. Creating an environment that encourages learning, vulnerability, exploration, sharing, and radical candor among dozens of talented female founders, from first-time founders to serial entrepreneurs with multiple exits, is no small thing.
Thank you as well to everyone who volunteered, sponsored, facilitated, and showed up to help make the retreat possible. You each helped create an experience that felt deeply thoughtful, supportive, and special.
Your time, energy, care, and contributions are deeply appreciated.
And thank you to the founders who shared their experiences so openly in workshops, roundtables, dinners, spontaneous conversations, and moments in between — even in airport chats on the way home.
With my upcoming move to New York City, I’m especially excited to be closer to so many of these incredible women and continue deepening those friendships and connections beyond the retreat itself.
It was incredible to see you for a second year! I find myself having a similar experience with pregnancy, where people smile at me and cheer me on. Everyone's excited about the final stretch of this long and hard run, especially women and moms. I feel you!
I attended the retreat last year and it left a lasting impression on me! such a magical experience.