Today’s newsletter is inspired by conversations with former government workers, journalists, and others whose industries are undergoing significant disruption. I hope this can be helpful to people navigating stressful transitions. Please share with anyone who may find this useful.
Around the time I left the White House in 2022, a dear friend decided to leave a successful corporate career to become an independent consultant, coach and artist. She pivoted for lots of reasons, but one was a bracing conversation with a mentor about her frustrations with her organization and its resistance to change.
“Anne,” he finally told her, “you’re not happy here because you’re a pirate who keeps trying to join the Navy.”
Our families vacationed together over this past Memorial Day weekend, and, as overeducated nerds are wont to do after a beer or two, we got freaky. With quad charts.
The Socialized ←→ Self-Authoring axis is from Dr. Robert Kegan’s theory of adult development:
Most of us — about 75% of the general population — live predominantly from a Socialized Mind. That means we tend to seek external direction, are shaped by definitions and expectations of our environment, and try to adhere to identities we formed earlier.
Compare that to the Self-Authoring mind, where people align with an internal sense of direction and inner seat of judgment. These people are able to step back enough to question expectations and values, take stands, set limits, and solve problems with independent frames of mind.
The Order ←→ Chaos axis is our attempt to map individuals’ relationships with their environments. It’s not that you are a chaotic or messy person, but rather: do you tend to thrive more in environments that are Orderly (predictable, stable, high-control, hierarchical/structured) or Chaotic (unpredictable, open-ended, creative, flexible)?
Importantly: there’s no “right” place to be on the Order ←→ Chaos axis. Being someone who thrives in chaos doesn’t mean you’re a messy bitch who lives for drama. Being someone who thrives in order doesn’t mean you’re an uptight narc or short-sighted bureaucrat. But understanding where you land does require self-awareness and honesty about both your strengths and weaknesses. It also usually requires experimenting with different kinds of environments to see where you do best.
We could zoom in on any point in this quad, but for now, let’s explore the Navy/Pirate dynamic.
My CV presents as classic “Navy:” a rule follower, standard-bearer, and norm enforcer. For years, I derived an unhealthy amount of my self-worth from being a public servant - a sense of personal achievement, yes, but also the purpose I felt from a career that others recognized as worthy or noble.
Trouble is, I actually thrive in high-chaos environments and get bored and restless in stable, predictable situations. That’s how I wound up in national security comms: my comfort zone is “responding to a terrorist attack.” My brain works best when my cortisol levels are surging, and I have to think about 20 different tasks and eight different perspectives simultaneously.1 At heart I’m a scrappy theater kid, yes-anding with a merry band of misfits, not always sure what we’re going to end up making together but knowing we’re going to have a great time. And I’d like to think I’ve achieved Kegan’s Self-Authorship stage of maturation, maybe even moving towards the Interconnected Mind stage on my good days.
By our framework, that puts me squarely in my Pirate Era. But oops! I spent the last 20 years trying to join the “Navy.”2
Unlike many people who are leaving government today, I left willingly. But it was still a massive, identity-rocking transition.3 I bet that many of the 260,000+ federal workers who have been RIFed, DOGEd, or otherwise forced out of their careers by the Trump administration are experiencing similar feelings of loss and being unmoored.
Kegan talked about this loss in a recent interview4:
When we look at development “from the outside” it is easy to see “maturation” as a kind of “gain.” Each new stage allows us to see more, choose among more options, do more. But experienced “from the inside,” we see that the move to each new level of maturation involves, at first, an exquisite loss. To move beyond the Instrumental Mind, I need to lose my orienting attachment to my own immediate preferences or self-interest. To move beyond the Socialized Mind, I need to lose my ultimate relationship to my tribe and my belongingness within that tribe.
A lot of people are losing relationships with their tribes today, and not always consensually. They’ve been forced out of their workplaces, or expect to be displaced by disruptive technologies like GenAI. They’re examining their relationships with their families of origin or faith communities. Confronted with rising inequality, crushing debt, and flailing leadership, they’re questioning the institutions and power structures in which they were raised.
Those institutions are often Navy-coded, because 1) most adults, per Kegan, are somewhere in the Socialized Mind phase of development, and 2) institutions typically value order over chaos. It stands to reason that many people - especially the laid-off feds out there - have been trying to fit in that Navy space for a long time. And perhaps some of them are now where I found myself a few years ago: grown beyond the Socialized Mind stage, discovering their true inner values and strengths, and realizing that not all of them are a good fit with the institutions that shaped their lives to date.
As someone socialized to prioritize gold stars, credentials, and the mission/team over my individual wants, U.S. national security communications was my dream “Navy” career. I could be part of something bigger than myself, working for a higher purpose, trying to improve complex organizations from within. For a long time I insisted that’s what truly motivated me, because that was what the systems I was in rewarded - and I cared more about success within those systems than understanding what my actual talents and instincts were.
I knew I was good at my work. So why did I often feel like I was experiencing resistance? Why did I always feel cast as the change agent in places that said they wanted change, but fiercely resisted it in practice?
Now that I’ve been out of government and doing consulting/teaching/portfolio living for several years, I’m SO MUCH HAPPIER. I understand that the systems I was working in (federal government, think tanks, academia) were built for Navy people, not Pirates. My innate strengths - eagerness to improvise, willingness to question why things were done this way, a bias towards action - were often received as liabilities, not assets. In the end, working so hard to mask my Pirate traits and force myself into the “Navy” quadrant pushed me into cycles of unsustainable pace followed by burnout, and left me constantly doubting myself.
It took leaving those systems to question them. When your job is literally explaining and defending the actions of elite institutions, there’s very little room to acknowledge the realities of elite institutional failures, whether that’s Israel policy, the failure to prevent a terrorist attack, or disdaining new forms of communication as unserious or unworthy.
Massive upheaval is an opportunity to ask tough questions about why things are the way they are, and how we can improve them. To challenge the structures and systems that failed to prevent the upheaval, and are now failing to provide real solutions for managing the fallout. To experiment, and push our tolerance for risks - because, if we don’t try now, when would we?
Meanwhile, public trust in institutions, from government to media, from academia to corporations, has never been lower in our lifetimes. There are sectors where that trust could technically fall a bit more, but mostly it has nowhere to go but up.
In other words: it’s a Pirate-y kind of moment, isn’t it?
Pirates are definitely ascendant in comms and media. It’s no wonder that so many individual journalists are fleeing their version of the Navy and striking out on their own via Substack, YouTube, etc. Granted, there’s not much of a “Navy” left for most journalists to try to join. But what remains has often failed to live up to its own goals and aspirations in profound ways.
Look at the front office failures of leadership and moral courage at legacy media institutions like CBS and the Washington Post. See how legacy media’s inability to find sustainable business models led to the collapse of local journalism. Watch the consolidation of national media under corporate megabrands whose priority is protecting their operating space, not holding the powerful accountable.
Seeing these trends in media and journalism has me thinking about how cohorts of displaced knowledge workers, RIFed and DOGEd feds, and other Americans experiencing destabilization in 2025 will react to their own displacements. How many of them may realize that they were also Pirates trying to join the Navy this whole time?
Healthy societies need to have work and structures that support both Navy people AND Pirates. Generally, I’d prefer that Pirates not, say, guard nuclear weapons, or administer vaccine clinical trials. But I also reject the false binary that says embracing Pirate traits like independence and willingness to improvise inherently means compromising rigor or ethics.
My Pirate self is resourceful. She’s creative. She doesn’t waste time pushing boulders uphill because that’s what the Department of Boulder Pushing has always done. She’s direct. She puts things out into the world, and if they don’t work, she fixes them. She works well with others, especially her fellow Pirates, but she doesn’t wait for permission to tackle a problem or help where she can.
An earlier, shittier version of this essay read like refried Sheryl Sandberg: embrace your inner pirate! Ok, great, but how does that help the thousands of laid-off feds watching their life’s work be dismantled by wannabe edgelords, wondering how they’re going to pay for their kids’ educations and elderly parents’ care? Or the recent grad looking for her first job in an economy where entry-level knowledge work is being increasingly automated? Or a 50-something worker worried he can’t keep pace with the rapid adoption of AI in his field?
Look, it’s a profoundly destabilizing time for so many of us. The last thing I want to do is offer glib, airport book-ish advice for people dealing with the messy realities of this tough moment.
And truly, I’m not saying that everyone is or should be a Pirate. Far from it! Being a Pirate isn’t inherently good or bad. The trouble comes in trying to force someone to be something that they’ve evolved past, or are not naturally wired for.
For people experiencing destabilizing change - whether or not we invited it on ourselves - there’s value in looking back and asking, “Was I truly a match for that institution I left? Or was I contorting myself to be what I thought was required? If I was willing to change so much of myself for the institution, why couldn’t the institution change even a little to help me help it?”
It’s a worthy inquiry that can help inform your next steps, and how you’ll adapt for the future. I don’t think I could have started my own business without this kind of self-inventory. I certainly wouldn’t have the confidence to put myself forward and ask for what I’m worth, instead always being the gal behind the guy and waiting for an institution to reward me accordingly.
I’m keenly aware that when so many of these institutions are under existential attack from bad-faith actors, critiques from formers can feel gross. But it’s not disloyal or kicking people when they’re down to look at the systems we sprang from and ask, “how do we do better when we’re in charge?” It’s an act of respect: for the good those institutions try to do, for the people doing their best within them, and for yourself, on your journey to greater self-knowledge.
Finally, for those living through this upheaval: you may be forced into being a Pirate for a while. Maybe that will be a natural fit and you’ll keep swashbuckling forever. Maybe you’ll go back into a Navy someday. If so, try to use this liminal Pirate period wisely. How will you help build a future Navy that doesn’t talk only to others like it? A Navy that welcomes Pirates who help it innovate and avoid groupthink? What from your own Pirate days can you take back into the Navy with you?
Because I bet you have some secret Pirate in you, too. I’m convinced even the most Navy among us does.
Yes, I’m also ADHD, and no, I didn’t figure it out until my 40s, because absolutely no one can mask neuro-spiciness like a midwestern Millennial eldest daughter who was “always a pleasure to have in class.”
To be clear: not the actual U.S. Navy. My “Navy” quadrant was over a decade as a State Department civil servant, two National Security Council stints, and a DC think tank. But I can see how it could be confusing when the metaphor is also literally a part of the thing it’s describing.
Or, as willingly as a mom working 100+ hours a week with two children under four can. But that’s a different newsletter.
Kegan also has one of the more interesting explanations for the whiplash of the Obama-to-Trump change, offering a different take on the “polarization” narratives to which we’ve all become numbed: “The reality is that most US Presidents, unsurprisingly, reflect the same levels of mental maturity most prevalent in the general adult population—namely, the Socialized Mind, the Self-Authoring Mind, or the gradual transition between the two. This is where most of us are at, and most Presidents, be they from the political Left or Right, occupy these positions, as well. So while we may elect leaders who differ in political party or personal temperament, they do not differ greatly in their level of mental maturity. Obama and Trump, however, both look to be exceptions. At least in the initial years of his Presidency, Obama’s appeals to a Havel-like post-partisan “common ground,” and his penchant for “disinterestedly” addressing limitations both in race-relations at home and foreign policy abroad, suggested a capacity to transcend the Self-Authoring mind. On the other hand, Trump’s stark view of the world as a jungle of self-interests, and his dismissal of all appeals to higher values as naïve (“Don’t be a baby,” is a common retort), suggest that, despite his appeals to an America First tribalism, his own mental maturity is more reflective of the Instrumental Mind.”
This is SO GOOD.