Monday, December 22, 2025

On Our "Virtual Route 99" (Final Year End Edition): As We Go Dark Through the End of the Year......


 WE will be going dark throughout properties here at the Daily Outsider through the end of the year.  We leave you with the sentiment above and close out the year with the following courtesy of Ryan Holiday, as we look forward to being of service in 2026

Happy Holidays!!!

The Secret To Better Habits In 2026

Here we are…past the halfway point of the 2020s.

With another year looming before us, I’ve been thinking, if I could flash forward to December 2026, what would it take for me to look back and call it a good year? What challenges will I have taken on? What changes will I have made? What will I have learned? What good will I have done?

I don’t know what 2026 has in store, but I do know that if it’s going to be a good year, it won’t be an accident. It won’t just happen. It will take work. “First tell yourself what kind of person you want to be,” Epictetus said, “then do what you have to do. For in nearly every pursuit we see this to be the case. Those in athletic pursuit first choose the sport they want, and then do that work.”

Here are some habits, some best practices, some of the work I am going to do to try to make 2026 a good year. Many of these were inspired by The Daily Stoic New Year, New You Challenge, which starts on January 1st . It’s a big part of my year each year—kicking things off with something that challenges me—and I hope you’ll join us on January 1st. (Sign up here, and learn more about the challenge below).

Protect The Best Part Of Your Day

This is where it all starts: with how you spend the best part of your day. The novelist Philipp Meyer​ (whose book ​The Son​​ is an incredible read) told me on the Daily Stoic podcast, “You have to be very careful about to what (and to whom) you’re giving the best part of your day.” Well-intentioned plans fall apart as the day progresses. Our willpower evaporates. The world makes its demands. So it’s key that we prioritize the important things and that we habitualize doing them early. Personally, I fiercely protect my mornings—family first, then writing. My assistant knows not to schedule anything before mid-morning because early calls and meetings don’t just take time—they sap the energy needed for the essential work. I want to give my best self to my most important things. Everything else can come after.

Think Small

The writer James Clear talks about the idea of “atomic habits” (and has a really good book with the same title—it was actually the first book someone bought from The Painted Porch). An atomic habit is a small habit that makes an enormous difference in your life. He tells the story of how the British cycling team transformed themselves by focusing on 1% improvements in every area—tiny adjustments that, over time, added up to extraordinary results. It’s a simple but powerful concept: small actions, done repeatedly, accumulate into something significant.

Accept Mediocrity

It's counterintuitive but having high standards can be the enemy of improvement, causing you to avoid or abandon everything that feels beneath those standards. As Churchill said, another way to spell “perfectionism” is p-a-r-a-l-y-s-i-s. One of the best rules I’ve heard as a writer is that the way to write a book is by producing “two crappy pages a day.” It’s by carving out a small win each and every day—getting words on the page—that a book is created. Hemingway once said that “the first draft of anything is shit,” and he’s right (I actually have that on my wall as a reminder). Jerry Seinfeld once said that if he were to teach a writing class, “I would teach them to learn to accept your mediocrity. You know, no one’s really that great. You know who’s great? The people that just put a tremendous amount of hours into it.” It's the same with self-improvement. The first draft of a new habit, a new discipline, a new you—it’s going to be clumsy and awkward and imperfect. Accept that, and focus on just making a little progress each day.

Do Less, Better

When I talked to the great Matthew McConaughey on the Daily Stoic podcast, he told me the story about a moment a few years ago when he realized he was doing too much. “I had five proverbial campfires on my desk,” he said. He had a production company, a music label, a foundation, his acting career, and his family. “What I did was I got rid of two of the campfires.” He called his lawyer and shut down the production company and the music label. “I was left with the three things that were most important to me. And those three campfires turned into bonfires…I had been making C’s in five things, but when I concentrated on three things, I started making A’s.” Marcus Aurelius talked about how doing less brings a double satisfaction: you get to do less and you get to do those things better. As we enter 2026, consider what you might need to say “no” to in order to say “yes” to what matters most.

Figure Out Your Defaults

Another one from James. On the podcast, we were talking about in-between moments in lifeThe lulls. The waiting in lines or between meetings. The extra time you weren’t planning to get. What do many of us do in these moments? We get occupied by mindless and meaningless distractions. We check email. We look up at the TV. We gossip. We just sit there waiting for it to be over. Which is why we have to have “good defaults,” James said. “The way I sometimes phrase it is, What do you do when you have nothing to do? … What I’ve really tried to do—I’m still working on this, I definitely don't have this figured out—is have a better answer to, what do I do when I have nothing to do?” My default is reading. I carry a book everywhere. Yours could be meditating. Or stretching, taking a walk around the block, or calling a friend. Whatever it is, figure out what you do when you have nothing to do. Because those in-between moments? They’re not insignificant. They are your life! It’s time, time you won’t ever get back. So use it. Because it adds up, shaping not just our days but our lives.

Don’t Be Ashamed To Ask For Help

Whenever I speak to military groups, I like to share one of my favorite lines from Meditations: “Don’t be ashamed to need help. Like a soldier storming a wall, you have a mission to accomplish. And if you’ve been wounded and you need a comrade to pull you up? So what?” I love how Marcus Aurelius delivers that line—with a shrug. So what? There’s no shame in needing help. Whether it’s therapy, asking for advice, or hiring someone to support you, seeking help is often the key to breakthroughs, growth, and success. Tim Ferriss has a great question that ties into this: What would this look like if it were easy? Often, the answer involves creating support systems or finding the right kind of help. Building habits, achieving goals, or even just making progress isn’t something you have to do alone.

Use Commitment Devices

At a critical moment in The Odyssey, knowing he wouldn’t be able to resist the sirens, Odysseus tied himself to the mast of his ship. In doing so, he became the first to hear them without steering and crashing into the rocks—where countless sailors before him had been lured to their deaths. On the podcast, behavioral scientist Katy Milkman talked about this as the original example of what’s known in behavioral science as a “commitment device”—a way of deliberately constraining ourselves to help us achieve our goals. What made Odysseus different from every other sailor who had been lured by those beautiful Sirens was not that he had more willpower or discipline. It was that he was wise enough to know he didn’t. He understood that in the moment, with those beautiful voices calling, he’d be just as weak as everyone else. So he came up with a way to protect himself from himself.

It’d be wonderful if we always did what we know we want or need to do. But that’s not how the world is. It is filled with temptations, distractions, and forces tugging us toward the rocks.

We need commitment devices. We need constraints that protect us from our weaker selves, that keep us on the right course.

In 2018, we ran the first Daily Stoic New Year, New You Challenge. It was packed with challenges and exercises inspired by Stoic philosophy. Even I, the person who designed the challenge, found it transformative. Why? Because being part of a group, all working together, created a sense of accountability and momentum. Knowing others were pushing themselves alongside me made it easier to stay committed and go further than I might have on my own.

As we kick off 2026, we’re doing another Daily Stoic New Year, New You Challenge—a 21-day program to build momentum for the rest of the year. If you’re looking to improve your habits, consider finding a similar challenge. It doesn’t matter what it’s about or who’s doing it with you; what matters is having a structure and a community to support you.

Do It Now

Seneca said that it’s the one thing fools all have in common: they are always getting ready to start. It’s pretty funny actually, we see this every year. Starting in early December, we start talking about the New Year, New You Challenge​, but you know what day—year after after—always has close to the most sign ups? January 1st…after it’s already started! Our customer service team spends the first 3-4 days of the year filtering through emails from people saying something like, “I know I’m late but I’d love to do this. Can you still let me in?” (So if you’re considering joining us in this year’s Challenge, don’t wait, sign up now!)

To procrastinate is to be entitled. It is arrogant. It assumes there will be a later. It assumes you’ll have the discipline to get to it later (despite not having the discipline now). It’s not going to be any easier later. It also might not be that difficult right now. That’s the funny thing you find about the stuff you put off—when you finally get around to it, you realize you’ve been dreading something that was actually pretty simple, that only took a few minutes. So in 2026 and beyond, constantly remind yourself: Later is a lie. It’s only going to get harder the longer you wait. Stop putting it off. Do what you need to do. Not Later. Now.

Make Time For Strenuous Exercise

Adopting a new habit, making a change, doing anything challenging always seems daunting at first. As I write about in Courage is Calling: Fortune Favors The Brave, we can’t just hope to be brave when it counts. Courage has to be cultivated. To do the big things that scare you, start with smaller things—start with developing the ability to push yourself to do stuff you’re reluctant to do. To be able to endure the cold reception of a bold idea, start with enduring a cold shower. To be able to step forward when the stakes are high, regularly do that when the stakes are low. To be able to embrace the discomfort of a major life change, accustom yourself to minor discomforts. We treat the body rigorously, Seneca said, so that it may not be disobedient to the mind. We push ourselves in little ways so the big ways stop seeming quite so big, quite so out of character. We minimize fear by making the act of overcoming it routine. We test ourselves to prepare for the tests of life. By methodically and deliberately exposing ourselves to small challenges, what once seemed daunting becomes manageable, even routine.

Go The F*ck To Sleep

All the other habits and practices listed here become irrelevant if you don’t have the energy and clarity to do them. We have to follow the advice of a book I love to read to my kids: Go the F*ck to Sleep! What time you wake up tomorrow is irrelevant…if you didn’t get enough sleep tonight. In the military, they speak of sleep discipline—meaning it’s something you have to be good at, you have to be conscious of, something you can’t let slip. We only have so much energy for our work, for our relationships, for ourselves. A smart person knows this and guards it carefully. A smart person knows that getting their 7-8 hours of sleep every night does not negatively affect their output, it contributes crucially to their best work.

Get Back Up When You Fall

The path to self-improvement is slippery, and falling is inevitable. You’ll sleep in and not be able to read that page, you’ll cheat on your diet, you’ll say “yes” and take on too much, or you’ll get sucked into the rabbit hole of social media. That’s okay. It doesn’t mean you’re a bad person. You’re only a bad person if you give up.

It’s wonderfully fitting that in both the Zen tradition and the Bible, we have a version of the proverb about falling down seven times and getting up eight. Even the most self-disciplined of us will stagger.

All of us have fallen short in the last year…and the years before that. We broke our resolutions. We lost touch with people we care about. We made the same mistakes again and again. We were “jarred, unavoidably, by circumstances,” as Marcus said. But now it’s time to pick ourselves up and try again. It’s time, Marcus continues, to “revert at once to yourself, and don’t lose the rhythm more than you can help. You’ll have a better group of harmony if you keep on going back to it.”

In other words, when you mess up, come back to the habits you’ve been working on. Come back to the ideas here in this post. Don’t quit just because you’re not perfect. No one is saying you have to magically transform yourself in 2026, but if you’re not making progress toward the person you want to be, what are you doing? And, more importantly, when are you planning to do it?

I’ll leave you with Epictetus, who spoke so eloquently about feeding the right habit bonfire. It’s the perfect passage to recite as we set out to begin a new year, hopefully, as better people.

“From now on, then, resolve to live as a grown-up who is making progress, and make whatever you think best a law that you never set aside. And whenever you encounter anything that is difficult or pleasurable, or highly or lowly regarded, remember…The true man is revealed in difficult times. So when trouble comes, think of yourself as a wrestler whom God, like a trainer, has paired with a tough young buck. For what purpose? To turn you into Olympic-class material.”

Saturday, December 20, 2025

On Our "Virtual Route 99" : Out & About in America




This is our final edition of the "Virtual Route 99" for the year as we decided to headline the key excerpts of the White House Chief of Staff Interview with Vanity Fair--and as the War With Venezuela Looms.  

We share thoughts from leading thinkers we consult as we gear up to go dark through the end of the year, with thoughts courtesy the Brennan Center, Defense One, Pod Save America,  Zeteo, and concluding with an analysis of President Trump's Speech On Wednesday, December 17: 

 

Rep. Ayanna Pressley speaks alongside Senator Elizabeth Warren during a news conference on March 4, 2025. Photo by Kayla Bartkowski/Getty Images

The libs are out of the wilderness, and they want every institution that’s bowed before Trump to know they’ll soon be out for blood.

In Tuesday’s edition of ‘First Draft,’ I detailed how MAGA-friendly billionaire oligarchs are intent upon warping American reality by any means necessary.

The latest plot, hatched by father-and-son duo Larry and David Ellison, involves a mass consolidation of US media. In mere months, the Oracle co-founder and his Silicon Valley scion have seized control of Paramount and its library of subsidiaries, including Showtime, MTV, BET, Nickelodeon, Comedy Central, and CBS News. They’ve managed to wrap their tentacles around TikTok, and now they’re trying to gobble up Warner Bros. Discovery – thereby planting a flag in HBO, CNN, and a host of other properties.

It seems Democrats on Capitol Hill (or perhaps a handful of their staffers) are fans of ‘First Draft.’ .....Yesterday, Semafor’s Max Tani first reported Democratic lawmakers sent a letter to the WBD board and Treasury Secretary Scott Bessent, warning them in no uncertain terms that when (not “if’!) Democrats return to power, they may very well go nuclear.

Future Congresses… will review many of the decisions of the current Administration, and may recommend that regulators push for divestitures, which would undermine the strategic logic of this merger,” Reps. Ayanna Pressley of Massachusetts and Sam Liccardo of California vowed, “We urge the Board to weigh… regulatory liabilities in evaluating a transaction burdened by uncertain but potentially extensive mitigation obligations, foreign influence risks, or adverse regulatory action.”

The pair went further, explicitly laying out their concerns about the Ellisons getting into bed with Gulf state actors like the Saudis and Qataris in order to launch a hostile bid for WBD.

These [foreign] investors, by virtue of their financial position or contractual rights, could obtain Influence — direct or indirect — over business decisions that bear upon editorial independence, content moderation, distribution priorities, or the stewardship of Americans’ private data.”

Pressley and Liccardo, both members of the House Financial Services Committee, warned that any pushback on the part of either WBD or the administration in allowing the interagency Committee on Foreign Investment to review any Paramount bid would constitute “a serious lapse in fiduciary judgment and could expose the company to significant regulatory… harm.”

Is the day finally upon us? Have Democrats, at long last, summoned the resolve to stop bringing a butter knife to a bazooka fight?

Pressley and Liccardo’s letter is a good sign. It’s, dare I say, a great sign. But we need so much more from the party of Hakeem Jeffries. We need a clear plan. We need a true and proper Project 2027 that lays out all the many, many ways in which congressional Democrats will make MAGA’s life a living Hell after the midterms. And, no, I don’t mean merely impeaching Donald Trump. Perhaps this is a hot take for another time, but, personally, I worry about giving Republicans a rally around the flag opportunity. The GOP is rapidly becoming a circular firing squad; why give them what could turn out to be a political gift?

No, believe it or not… and I can’t believe I’m saying this… I now want strongly worded letters. I want clear, explicit communications sent to all the major institutions and corporations that bent the knee to the Bad Orange Man, warning them that they better lawyer up.

Get ready to be subpoenaed out of the wazoo.

You bet on a permanent fascist autocracy – and you bet wrong.

Now, yes, the House is coming to collect.

🗞️ What You Need to Know

  • Epstein update: A New York federal judge ruled to unseal grand jury records in Jeffrey Epstein’s 2019 sex trafficking case at the request of the Justice Department. The move comes a day after another federal judge ordered the release of grand jury material in the sex trafficking case against Ghislaine Maxwell.

  • Mad about Maduro: US forces seized an oil tanker off the coast of Venezuela. The Venezuelan government called the move “a blatant theft and an act of international piracy.”

  • So much for free speech: All foreign tourists must provide their social media histories from the last five years to enter the United States, according to a new notice from Customs and Border Protection. Tourism numbers are already plummeting, and the World Cup is just months away.

  • Zeteo late-night scoop: The Trump administration is in talks to revoke the visas of two European green card holders – former European Union Commissioner Thierry Breton and Imran Ahmed, CEO and founder of the Center for Countering Digital Hate – who are prominent critics of Elon Musk’s Twitter, Zeteo scooped. If implemented, the move would mark one of the administration’s first attempts to revoke the visas of those they deem to be engaging in the “censorship” of Americans.

  • Judge slams LA deployment: A federal judge in San Francisco ordered the Trump administration to end its National Guard deployment to Los Angeles in the latest blow to the MAGA militarization agenda. Judge Charles Breyer wrote that the administration’s “argument for a president to hold unchecked power to control state troops would wholly upend the federalism that is at the heart of our system of government.”

  • NDAA passes the House: The House passed the National Defense Authorization Act, thereby approving a $900 billion budget for the Pentagon and enacting several provisions, including increased pay for service members and reduced diversity efforts.

‘Make Europe Great Again’ and more from a longer version of the National Security Strategy

By Meghann Myers

A fuller version reviewed by Defense One outlines the Trump administration’s plans for shedding old relationships and creating new ones.

Brennan Center for Justice The Briefing
The 2026 election will take place in a political system that is divided, discordant, flagrantly gerrymandered, and marked by widening racial discrimination. Thank Chief Justice John Roberts and his colleagues on the Supreme Court. And the supermajority of highly activist justices seems poised, even eager, to make things appreciably worse.
In 2019, in Rucho v. Common Cause, the Court refused to adopt any standard to police partisan gerrymandering, and it even prevented federal courts from hearing that claim. Fast-forward through a census, six years of line-drawing, and a flurry of lawsuits, and predictably, our democracy has become much less fair.
Redistricting is supposed to take place once a decade, after the census. In fact, that’s why the census is written into the Constitution. But earlier this year, Texas abruptly drew new congressional maps in a gambit to squeeze out five extra seats for Republicans. It was in the middle of the decade and at the behest of someone who doesn’t live there (President Trump) — and all at the expense of Black and Latino voters. Even though 95 percent of population growth in the state came from those communities, the map’s main feature was fewer districts where those voters can elect their preferred candidates.
Bad, right? The very conservative Fifth Circuit Court of Appeals agreed, temporarily blocking the map from being used in the upcoming election until a full trial could be held. Texas first resisted allegations of a partisan gerrymander, then insisted it was actually acting at the behest of the Justice Department for racial reasons, then said it was, in fact, a partisan power grab. (“I don’t see race. Just Democrats.”) Talk about a Texas two-step! Amid these gyrations, the court found it illegal.
Enter the Supreme Court. Last week it blocked the lower court’s ruling, thus allowing the election to go forward with freshly gerrymandered maps. It’s yet another brazen use of the shadow docket — the Court’s supposed emergency docket (with limited briefing and no oral argument) — to hand Trump a win with only a few sentences of explanation.
Where does that leave things? The Texas seat grab set off a partisan arms race across the country. Furious Democrats acted. California voters overwhelmingly supported drawing new Democratic-leaning congressional districts there to counter the GOP gains in Texas. Republicans in Indiana and Florida are moving to redraw lines, while Democrats in Illinois, Maryland, and Virginia aim to do the same.
With all this headbutting, the gerrymander war of 2025 could turn out to be close to a wash in partisan terms. Moreover, voters may have their own ideas. If Democrats win big, as recent races have suggested is possible, the Republican gerrymandering might produce extra GOP losses. (The technical term for this, believe it or not, is a “dummymander.”)
All that sound and fury, in short, might signify . . . not exactly nothing, but not a decisive partisan gain.
That’s where the next big intervention by the Supreme Court would come in. And its impact could well be even more dramatic — and if possible, more harmful.
The Court seems poised to demolish the effectiveness of what’s left of the Voting Rights Act. Two weeks ago, in Louisiana v. Callais, it heard arguments about whether the law’s Section 2 remains constitutional. For decades, that provision effectively barred states, particularly in the South, from enacting maps that dilute or cancel out the voting power of racial minorities. As our friend-of-the-court brief pointed out, the provision has transformed both Congress and legislative bodies across the country. And the disparity in registration rates between white and Black voters dropped from nearly 30 percentage points in the early 1960s to 8 percentage points just a decade later. Now the justices seem ready to wreck Section 2 if not strike it down entirely.
This would not only mark a shameful retreat from federal action to protect racial equality and fair representation. It could have a dramatic and specific impact: A bad ruling, especially early, could be followed by another wave of redistricting in coming months, maybe even in time for the 2026 election.
As my colleague Kareem Crayton writes, “The argument invites a return to the era when race was a barrier to entry for political representation — the cruel and painful experience of political exclusion that made passage of the Voting Rights Act necessary in the first place.”
Nate Cohn of The New York Times has crunched the numbers and predicts that an extreme Supreme Court ruling could allow Republican states to eliminate between 6 and 12 districts currently held by Democrats. That would be a margin larger than the House majority either party has had in recent years.
When politicians pick voters — whether based on race or politics — instead of the other way around, our elections become less fair and less democratic. The country would slide toward even greater division and balkanization. Republican voters in Massachusetts (where there are no Republican members of Congress even though Trump won 37 percent of the vote) have no party representation in Congress, while Democrats in Texas (where Kamala Harris won 42 percent) would have only about 7 of the state’s 38 seats. John Adams famously said that the legislature must be an “exact portrait of the people at large.” The current portrait doesn’t bear much of a resemblance.
So what’s the answer?
There must, above all, be national standards that apply to red states and blue states alike. The Constitution gives Congress that power. It should enact national redistricting rules that would ban partisan gerrymandering, bar mid-decade redistricting, and ensure fair representation for voters across the country. In 2022, it almost did: The Freedom to Vote Act would have banned mid-decade redistricting and set other standards. And the John R. Lewis Voting Rights Advancement Act would have strengthened protections against racially discriminatory maps. Both came achingly close to enactment.
And then the ideologues on the Supreme Court should stop meddling in elections. Over the past 15 years, the Court demolished campaign finance rules in Citizens United, wrecked the Voting Rights Act starting in Shelby County, and gave ex-presidents vast and unprecedented immunity from prosecution for crimes committed in office — thus ensuring no legal accountability for candidate, now president, Trump.
In a season when it seems increasingly clear that the justices plan to hand President Trump even more power, inexcusable rulings and interventions in partisan politics will leave a very sour taste for many voters. The Supreme Court itself, increasingly, will become an issue in American politics. That’s as it should be.

 

Campaign Finance Laws Could Take Another Hit
Today, the Supreme Court heard arguments in a case challenging long-standing federal rules that limit how much political parties can spend in coordination with their candidates. It’s fair to question the effectiveness of these rules given the radical changes to the campaign finance landscape in recent decades. “But evaluating those sorts of policy considerations is the job of Congress, not the Supreme Court,” Eric Petry writes. Read more
SCOTUS Weighs Expansion of Presidential Power
The Supreme Court heard arguments yesterday in another pivotal case, Trump v. Slaughter, which challenges the president’s decision to fire a member of the Federal Trade Commission. Long-established federal law bars the president from firing the heads of independent agencies, such as the FTC, without cause. As Lauren Miller Karalunas told Roll Call, the justices “won’t just be deciding the technical question of whether President Trump can remove these officials, they’ll also be deciding a much more profound question of whether the president can override the will of Congress.” Read more
How to Fix NYC’s Jails
New York City Mayor-elect Zohran Mamdani will inherit a jail system plagued by mismanagement that has allowed neglect, abuse, and violence to run rampant. Soon a federal court will appoint an outside administrator to help run the jails. “One important task for the incoming Mamdani administration is establishing a productive and optimal relationship with the remediation manager,” Hernandez Stroud writes, adding that the new mayor should also heed long-standing calls to shutter the notorious Rikers Island. Read more
The Legacy of Bush v. Gore
This week marks the 25th anniversary of Bush v. Gore, the infamous Supreme Court decision that “changed the trajectory of election law and painted the Court in a partisan light like never before,” Stephen Spaulding writes. He recaps the issues that marked the 2000 election, the controversy and confusion surrounding the justices’ opinions, and the case’s impact on the public’s trust in the Court and American democracy writ large. Read more