30
On New Year’s Day this year my husband gently asked me what I wanted for my 30th.
I wasn’t functioning on a whole lot of sleep at the time. I think I said something pretty uptight about wanting to crush our fundraise, and this one specific bralette from Anthropologie. (He didn’t know my cup size, so he got me an Aesop candle instead.)
On my actual 30th, I was running on empty from a pell mell launch season. All I had energy for was meandering, sloth-like, around my neighborhood with my husband (who took photos to remember the day).
For obvious reasons, turning 30 feels significant.
Looking ahead to “Chapter 3” - the start of the women’s health minefield
Everyone I know who has family forming intent is watching the clock.
Half of us are exploring egg freezing.
The other half are buying ovulation thermometers.
Many of us are examining the social expectations passed down from the women before us:
Becoming a parent (at all)
Becoming a birthing parent — with all of its postpartum / recovery gifts
Becoming head of the home / default primary caregiver (ideally more equitably with a partner).
Glancing back at “Chapter 2” - the end of formal education, early career adventures
How much have we achieved? With what we started out with?
What life-altering decisions have we made? Do we regret any? (Can they be reversed?)
Are we happy? Are we living up to our potential? Are those two things — oh no — at odds?
Staring down “Chapter 2.5” - the life transition equivalent of platform 9¾
Money - where are our finances? What does this mean for what we can afford?
Time - how much of it do we have left before Chapter 3 hits?
How much money would we trade for time, or time for money, right now?
There isn’t a single right answer. Everyone has different personal things at stake.
So instead of these splashy, somewhat obvious ripples, I thought I’d go deeper and spotlight some of the precious stones I’ve found down in the river beds (across which proverbial still waters run deep).
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Answering that question again (with an ounce more sleep in me than before):
What I really want for my 30th year around the sun is to embrace 4 uncool things.
Idealism - which involves being a patriot, not an optimist
Servant leadership - which is about me, not other people
Having a soft front - as long as I also have a strong back
Taking an axe to my frozen sea - to live my life awake
You can call these principles or values. I call them things I’m starting to realize I'm willing to suffer for.
I call these uncool things because even though they’re generally thought of in good regard, they’re incredibly hard to implement well in practice. They’re like sharp river rocks on the river bed. But currents of time through my 20s have hewn them into gleaming, smooth stones that I’ve found myself reaching to for cool relief.
So in my 3rd decade I’m going to champion these 4 things more — both in me and in other people.
So, a manifesto of 4 uncool things
[1] I will not be ashamed of … idealism
Picture credits to Slauson & Co.
(That’s me starting to rant about something, I can tell)
Recently I watched a founder pitch his product. Like many presenters do, he included a feel good story about why what he is building matters — a personal why. The story: how he had watched the caregiving responsibility fall heavily and unfairly on his mom and grandma for a decade, and wanted to be part of the systemic change that reduced this caregiving burden.
I ran into him after the session, and he smirked and asked me if I enjoyed his “sappy story”. I think he thought he was being funny. He stopped short of saying it was made up.
In case you couldn’t tell, I am the wrong audience for such a confession. I care so much about the burden of caregiving and the way it is systematically taken for granted.
I kind of wanted to slap him. (I didn’t.) But the interesting thing is that I felt immediate shame for having this reaction.
My brain went: I know founders tell stories. I know that so much of this is for show. There is nothing wrong with this. But to me, this feels like more than just showmanship, it feels wrong and disingenuous and I don’t like it and its gross and arrrrrrrggghhhhh
I didn’t say anything but I looked at him with what I hoped was disappointment and I don’t think he noticed.
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A few days later I had another conversation with another founder.
We were talking about the larger state of the industry and some of the controversial parts of what customers in our space want, and they remarked, very well intentionedly, “at the end of the day it’s not up to us to change the system.”
Again. Wall of shame flung up. Like Prius airbag inflating on impact.
I wanted to say but I am here to change the system. If no one is here to actually make things better why are any of us doing this? Are you not? Do you not care? If you don’t care why are any of us here? why wouldn’t we just all go work at FAANG and take home a cushy salary and argggggghhhh
But I didn’t dare to say this out loud, because I wanted to seem pragmatic, and more importantly I didn’t want to seem naive. And again I just kind of smiled and let it go.
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I’m still reflecting on why my voice catches in my throat in these situations.
“I don’t want to be thought of as an activist or self righteous”
“I want to come across grounded and practical and competent”
“I don’t want to be a fiery or intense person”
People may tell you to hold on to your idealism in conference keynotes but when push comes to shove most of us of us role model the opposite.
But I was thinking about it recently and actually, the people I really respect most in life are all idealists. And I love fire. They’re not always easy to get along with but man they are definitely living their biggest lives.
My father in law (whose idealism does not always make for easy dinner table conversation when he does not agree with you, but): One of his biggest shticks is that the smartest people with the most privilege need to work on the biggest problems for society.
That how you made an honest living is what really matters. That there is no glory in making big bucks pushing paper and creating no value.
One of my previous employers: He wasn’t easy to work with but man — the guy had fire. I think everyone could tell it wasn’t about dollars and cents or shareholder value, the guy believed. And I really respected that.
Anyway, the way I come to terms with all of this is
Accept the occupational hazard: Most people will think you’re an idiot.
Many famous idealists were… literally crucified. (Some were subsequently beatified, many were not.)
Many people won’t agree or empathize with your belief. And so you’ll just have to live with a lack of approval.
Naked idealism is crotchety: It requires packaging.
In its original, emotive form, idealism is not consumer-friendly.
But when successfully packaged, it can remind people that they could reach for more.
Accept naïveté: It’s a temporary stopping point, the only way is through.
Dictionary definition: a lack of experience / judgment.
That literally means that all truth seekers must at some point be brave enough to be naive on their way forward.
All this to say: I think idealism is really just conviction. And I will try to be more proud of having conviction.
I’m quietly confident that idealism is important to hold to — and that people can tell the real thing VS when it’s being faked for a pitch.
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[2] I will not be ashamed of… servant leadership
With my day to day servant leader role model.
Ugh what a self aggrandizing word. I can’t even look at it without cringing a little.
I first heard about servant leadership in the Girls Brigade when I was 9. You could literally not inhale without bumping into this phrase on the way, I think it was like a part of the creed or something.
I pretty much never ever used that term aloud or in public because of how cliche / navel gazing it sounded. But when I was at Carrot, an engineering leader I really look up to — who role models servant leadership — talked about it in an interview and made me realize it was, unfortunately, the perfect way to describe what it stands for.
Now I, insufferably, won’t stop going on about it.
“Servant leadership” is easy to talk about in keynotes and closing speeches or - the worst - “leadership conferences”. It’s way harder to execute in real life, because it is a hard balance to strike.
Feels weird and manipulative somehow to do something for the express purpose of eliciting a specific reaction in someone else who has the freedom to… not have that reaction.
Like … again, what if they don’t have that reaction?
Will you feel they didn’t live up to their side of the bargain and be resentful?
How is that fair to enroll them in an emotional contract they didn’t even know existed?
Hello burnout - navigating land mines of “savior mentality”, or holding yourself to unnecessarily high standards
I think most of us will fall into these traps before we course correct.
Only you can decide what you’re personally willing to do - there’s no clear stopping point.
ASSK house arrest hunger strikes?
Mandela years and years in prison?
Korean prime minister stepping down when a vessel sinks?
Objectors against servant leadership include:
College curriculum: A class I took with Dr. Rosemarie Siino on different leadership styles specifically called out the futility of traditional servant leadership. This archetype often resorts to intense personal heroics to get things done + constant “walking the talk” may not be sustainable or effective.
Founder breakout groups: I recently found myself in conversation with other founders who were discussing exactly how far one “should” go for our companies — and whether it was dumb, or respectable, to put too much of ourselves on the line given very real stakes. (Assumption: This is a game but it’s also real life.)
I’ve thought a lot about these objections and their obvious validity. But have been unable to shake the idea that servant leadership / leading from the back is as critical as everyone says it is. And the fact is — the only leaders I’ve ever been really happy to follow are servant leaders, so maybe there’s a personality component to this as well.
What I’ve come to terms with:
Practice servant leadership for yourself — not for the other people whom you hope will benefit from it.
Do it for you — so you can lead with more conviction.
It’s about holding yourself to your own highest standards, and being the kind of person you would want to follow.
(Why on earth would you do that? Well - who else is your life for?)
Everyone has different standards. If yours happen to be too much higher than other people’s, well, sucks to suck, what a shame (wasted effort?) — but end of the day, you will sleep better at night.
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[3] I will not be ashamed of … having a soft front
“Do not mistake my kindness for weakness, my silence for acceptance … etc etc.”
I have spent a lot of time watching other people present in ways that feel forceful and sharp and compelling. I have looked at them, both close up and from a distance and thought “w0w leader”. Then I have looked at them over time and thought “meh.”
In parallel, I’ve looked at a lot of people I’d drop many things to follow — who come across at first sniff, a lot softer.
And I am realizing that softness isn’t weakness.
We have been trained to equate strength with sharp edges but there is something powerful about a person — woman or otherwise — who owns their softness and refuses to be hardened.
Followership is the actual metric that matters — and there are many ways that can be achieved effectively.
Leadership is bandied about more, but leadership is actually a lagging indicator because it’s an outcome.
This is not to say that softness is the way. But it’s not weakness.
I have had the good fortune of getting to live my life alongside a good number of personalities across the softness spectrum by this point and am constantly refining my desired collaboration aperture. As a result I’ve had the benefit of testing out different kinds of people that I want to work alongside and do life with (and I have also learned valuable expensive lessons from my mis-steps).
This list isn’t close comprehensive, but I’m looking for folks with:
A strong back. I’m looking for people with resolute conviction and vision, even if the way they get there may vary.
A soft front. I’m looking for people who genuinely want to serve the world - not have power over it.
Warm eyes. I’m looking for people who are gentle and warm.
Both hands. I’m looking for people who are others-centered first. I believe the rest follows.
Additionally, in the workplace, I need to see 3 more things to work with or report into something:
They need to have vision — a point of view, the ability to create from scratch, not just move things around.
They need to be reliable — in their personal lives, too. (The lines blur).
They need to be low ego — so that they can have a shot at closing the gap on what they don’t know.
I always remember someone telling me that a useful litmus test for whether or not you’re in the right relationship is:
“If someone said “you and X are so alike”, that had better feel like a compliment in your gut — not an insult.”
It is important that everyone can respect and admire each other.
And all of these things coexist beautifully with a soft front.
You know how sometimes you talk to a business person who dazzles, and you’re like “OK, you’re impressive”, and other times you talk to someone who is just profoundly comfortable and kind and whole, and you’re like “- and I feel like I can trust you”?
Well, for me, I’m coming to realize the former is P2 and the latter is P0. It’s not the way, it’s just my way.
Soft.
I will not be ashamed of …. taking an axe to my frozen sea
There is a really lovely short poem that goes “Barn’s burned down / Now I can see the moon”.
I also really love Kafka’s famous reference to taking an axe to the frozen sea within each of us. Both speak to the importance of doing brave, confronting things and reveling in the peace that waits on the other side. Through startup haze and concept pivots I have found myself leaning constantly back on the core question of What do I know to be true?.
A Series C+ CEO I really respect and trust once told me that any founder’s goal assembling a venture-scale initiative is at the end of the day, really just truth seeking and compulsive action - nothing else. That has brought me huge comfort and constancy as I ride the waves. The truth seeking and telling will help you sleep at night.
Axes to frozen seas involve asking the hard questions to [A] get on the right path quickly, and [B] not overstay your welcome when something isn’t working or set to last. Whether this involves:
Making a quick left turn off the wrong path to course correct (often called a pivot)
Getting off at the wrong train before it’s too far from the original station to return (it’s going around the internet)
Having a longer-term goal on the horizon that holds constant as an a drishti amid the small waves
There is such relief, and focus, that comes with pursuing what feels true. Whether you define this as true “there is PMF to be found here”, or true “this is right or wrong for me”.
I would hazard the struggle to be totally personally honest about what you need is relatable to anyone who, like me, grew up in fairly high competition, “keep the peace” environments —
Where the focus regularly prioritized getting ahead over coming alive
Often for entirely necessary and valid reasons
But ones that we may have outgrown — that are no longer relevant.
I think it would be very helpful to reframe “live the life you’ll be proud of at death” chest pumping nonsense to “first, you have to give up the fight for the things that just don’t matter enough at the end of the day”.
The latter is a necessary condition for the former.
Finally, a big hug to my community
I had the best 30th birthday celebration ever — my husband invited my SF friend group out a couple days in advance, and we had a really lovely, intimate, cosy pizza and cocktail hangout.
A recent thing I realized - the highest leverage unlock for a successful gathering is the guest list not even the prep.
I was 75% brain dead — and an hour beforehand I wasn’t sure I even had energy to attend my own party. But I’m so glad I did. The glow of that night lasted all weekend and carried me through an intense season at work.
I find it challenging to maintain a large social circle, so I really like the people who make it in there. So many of them have seen me stepping and bleeding on these river rocks and helped me through.
Whatever you’re doing you truly cannot do it alone.
Thanks to my house for organizing everything for me so I could just sit there and talk to people.
(Not my actual birthday. We did it a little early.)
If you’ve made it this far, thanks for putting up with all this pontification.
No idea what’s coming next, but that’s probably the way it’s supposed to be.
I’m here for the ride. I’m here for idealism, servant leadership, unapologetic softness, and axe to frozen sea truth seeking. Please remind me of this when I forget.
