30
When I was first asked in January what I wanted for my 30th I wasn’t functioning on a whole lot of sleep. I think I said something pretty uptight about wanting to crush our fundraise, and this one specific bralette from Anthropologie.
(Pan 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 and a
ll I had energy for was meandering, sloth-like, around my neighborhood.
For obvious reasons, turning 30 feels significant.
Looking ahead to “Chapter 3” - a new decade with new responsibilities
Family forming
Aging parents
Heading the household
Getting to that “next frontier” in your career
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?
Instead of focusing on the splashy, somewhat obvious ripples of one’s 30s, I thought I’d go deeper and spotlight some of the precious stones I’ve found down in the river beds of my 20s (across which the proverbial stillest waters of them all run deep).
One thing that founding (as opposed to employee-ing) has taught me is what it feels like to lean into fighting a different fire (or eating a different flavor of shit sandwich) every single day. Over this last year, out of necessity (story for another day), I’ve explored a couple ways to cope with that craziness e.g. investing in nervous health.
It turns out the least cool but most effective way has been doubling down hard on my values and being unapologetic about them.
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At the risk of sounding very strengthsfinder / gartner 360, and never being invited to a party again, here’s my real answer to the question “what I really want for my 30s”:
A: To unapologetically embody 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 it comes with 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.
And let’s call a spade a spade: these things are kind of uncool because:
They run the risk of making their owners seem really uptight and intense.
Like, just look at them. Not a shot glass or happy hour to be seen.
They may be wisdom-compatible but I’m not sure they elicit respect in corporate circles.
Where is the profit motive? Where is the founder mode? Who cares about coming alive when you can get ahead?
They are incredibly hard to implement well in practice (details below).
They sound good on when waxed about on yet another podcast. Means nothing when it comes to implementation.
So yes, they’re sharp river rocks. But the currents of my 20s have hewn these smooth and I’ve found myself reaching to them repeatedly for relief — so, I’ve decided to embrace them honestly and champion them in myself and other people.
4 uncool things: A manifesto
[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. Like many 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 the people I really respect most are all idealists with fire and I love them for it. 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: Idealists seem like idiots, at least for a while.
Some notable idealists were… literally burned in town squares.
Many people won’t agree or empathize with your belief.
And so you’ll just have to live with a lack of external validation for a (long?) while. Sucks to suck.
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: A temporary stopping point, the only way is through.
Dictionary definition of naivete is a lack of experience / judgment.
That literally means that all truth seekers must at some point be brave enough to be naive on their journey.
All this to say: Idealism is really just conviction at an earlier stage. I would like to embrace it.
(And I’m quietly confident that people can tell the real thing VS when it’s being faked for a sell, but I could be wrong here.)
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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. Now I, insufferably, won’t stop going on about it.
“Servant leadership” is easy to talk about in keynotes and the closing speeches of leadership conferences (the ones with bad pastries, freezing A/C and self-aggrandizing linkedin posts afterward). 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 your team 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
There’s no clear stopping point - only you can decide what you’re personally willing to do -
ASSK’s house arrest hunger strikes?
Mandela years and years in prison?
Korea’s prime ministers stepping down when vessels sink?
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.
But the fact is that for me, the only leaders I’ve ever been really down to follow in the long run are servant leaders. I am unable to shake the idea that servant leadership / leading from the back is critical.
So here’s how I reconcile it all:
We practice servant leadership for ourselves — not for anyone else.
You do it for you — so you can lead with more conviction.
This is 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, maybe that’s wasted effort. But at the 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 now watching 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”.
Frequently I have then looked at them over time and thought “meh.”
In contrast, there is a different, rarer breed of leader I’ve started paying more attention to… who comes across at first sniff a lot softer. But in the longer run, they earn my followership. And I’d drop many things to follow them.
Softness isn’t weakness.
We have been trained to equate strength with sharp edges, but there is something powerful about a person 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 right way. But it’s not weakness.
I have had the good fortune of getting to live my life alongside personalities across the soft/hard spectrum by this point, so I’ve had the benefit of testing out different dispositions and whom I personally have the stomach to build with in the longer run. I am constantly refining my desired collaborator aperture but I thought I’d share some of the heuristics I’ve come to look out for:
A strong back. I’m looking for people with conviction and belief. (I don’t much care what you believe in.)
A soft front. I’m looking for people who genuinely want to be useful in the world - not have power over it.
Warm eyes. I’m looking for people whose smiles reach their eyes.
Both hands. I’m looking for people who give generously, and take responsibility for their teams.
In leaders (aka. someone I need to report into or ultimately defer to) I have 3 more criteria I look for:
Vision — the ability to create from scratch. (It’s harder to have a point of view than you think.)
Reliability — discipline both at work and in their personal lives, too. (The lines blur).
Low ego — most founders don’t role model this but imo w/o this, you won’t have a shot at dependably closing the gaps on what you 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.”
Sometimes you talk to a business person who dazzles (hard, icy), and you’re like “OK, you’re impressive”. Other times you talk to someone who is kind and whole (softer), and you find yourself finishing the sentence “… and I feel like I can trust you”.
I’m coming to realize that successful long-term businesses are ultimately built on sustainable relationships. So, the former is P2 and the latter is P0.
It’s not the way, it’s just my way.
Soft.
[4] I will not be ashamed of …. taking an axe to my frozen sea
Through startup haze and concept pivots and even the identity fog of stepping into founding, I have found myself leaning constantly back on the core question of What do I know to be true?.
Someone I know who made it to Series C 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.
It turns out amid all the noise, the truth seeking and telling is the only thing that will help you sleep at night.
Kafka’s reference to taking an axe to the frozen sea within each of us speaks to the importance of doing brave, confronting things and reveling in the truth and peace on the other side. There is also a really lovely short poem that goes “Barn’s burned down / Now I can see the moon”.
Axes to frozen seas evoke splintering ice, rocking waves, and ripples. They require honest, un-minced, clear thinking to [A] find the right path quickly, and [B] not overstay when you sense something won’t work in the long run. Whether this involves:
Making a quick left turn to course correct (a pivot)
Getting off the wrong train before it’s too far from the original station to return
Doubling down on an anchoring drishti to outlast a temporary headwind or off-center balancing pose
There is such relief that comes with pursuing what feels true, whether you define this as “there is real PMF to be found here” truth, or “this is the mission I signed up for” alignment.
Thank you to my community
OK, well, anyway, I had the best 30th. My in-the-city friend group had a really lovely pizza + cocktail hangout.
Another recent discovery: the highest leverage unlock for a successful gathering is 100% the guest list.
I was 75% brain dead (like “an hour beforehand unconvinced I had energy to attend my own party level” brain dead). But 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, really cherish the people who have made it in there.
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 being here (and tolerating the pontification).
Whatever comes next, I’m here for the ride.
