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7 Common Roadblocks to Clear Communication

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Last night, I had one of my weaker moments of recent memory. I was at dinner with one of the dearest friends I have, casually discussing ideas for our evening together. We exchanged playful banter with one another, taking shots at each other’s inconsistencies with planning and executing.

In what felt like out of nowhere, the conversation leveled-up from meaningless nonsense to abrupt authenticity. I chose to ignore what was best for the conversation’s resolve and blurt out what first came to mind in defense of myself. I reached low for this one — to the depths my own insecurity.

My comment centered around his newfound relationship, that of which he was extremely excited about and invested in. My first attempt to retract my statement was to no avail. I stated that I felt attacked in that moment and that what I said was the only place I felt I could reach to silence anything further. But that wasn’t it.

The reality was my comment came from a much nastier, yet far more relatable place. Where it really came from was my jealousy of his newfound relationship, and my continuation of navigating life without a special person to share it with. I attacked my friend with the very thing I wanted most for myself.

Furthermore, I met his acknowledgement of my inconsistencies with aggression, as it’s clearly an area I’ve refused to confront for quite some time. Sometimes what shows up in the heat of the moment is more about short-term survival than long-term connection. It’s important that we remain grounded in our understanding that what our minds cook up and serve us isn’t always meant to eat.

Here are seven common linguistic patterns blocking us from the fulfilling relationships we always dreamed of:

1. Mind-Reading

There’s arguably no better way to make someone feel limited in their existence as attempting to predict what they’re going to say. One of the most precious gifts in life for human beings is a distinct voice. If I choose to cut it down by robbing them of their expression, I’m effectively taking away both of our voices in the process. If I’m being a truly uplifting friend or partner, I’m listening to them as who they could be and not who the past says that they are.

2. Labeling

Name-calling was once relegated to elementary school bickering, but it’s appalling to see how often it takes place among adults — especially those that care for each other. Labels are defined constructs of language, meaning there is a ceiling on the person they can become when I assign said label.

Moreover, the rapidness in which I want to label is startling — one correlated instance and I’m already inclined to box others in. By calling someone a name, I’m communicating that I’m not willing to put in the effort to understand their unique situation. I’m all for being lazy every now and again, but not at the expense of others.

3. Generalizing

The sister to labeling, generalizing is equally as lazy and equally as diminishing. Just because a person’s behavior repeats itself, it does not mean it’s “always” or “never” going to be a certain way.

By believing this to be true, I not only drive a wedge in my communication with others but the way in which I communicate with myself. I slowly depreciate my sense of curiosity and wonder by assuming that what’s so will always or never be — leaving very little reason to put forth any additional effort.

When I generalize, I check out from life. I throw my mind into neutral and look for what else may be wrong. I must keep my foot on the gas and look — really look — at what may be beneath the surface-level explanation I so desperately want to run with.

“All generalizations are false, including this one.” – Mark Twain

4. Jumping to Conclusions

Actions produce outcomes. We have thoughts about outcomes and feelings about thoughts, but we cannot think or feel an outcome in our external reality. Rather that succumbing to our thoughts and feelings about the events that unfold in our lives, we can take action to gain a firmer grasp on what was being communicated or the meaning behind what transpired.

5. Moralizing

Everyone has had a friend that can not control their temptation to advise what you should or shouldn’t be doing. And odds are, that person didn’t stay your friend for very long. Telling people what they need to do or how to live their life when the advice is unsolicited is a quick way to alienate your closest confidants.

If you really want to give advice that badly, you won’t be asked for it without being a supreme listener. Earn your platform to provide insight by lending both ears, as opposed to steamrolling the conversation with your mouth.

6. Re-directing

I used to have a nasty habit of calling people I care about to share something going on with me by means of asking about them first. I felt uncomfortable simply sharing outright what I wanted to and decided I would ask about them prior to, knowing I had little to no interest in that moment about anything but my issue I wanted to work through.

People can sense this immediately and it doesn’t make for a very empowering experience for either party, often resulting in a breakdown instead of a breakthrough. If I have something I want to confront in my life with another person, I ask them upfront if they would be willing to listen and work through it with me. Giving people a choice results in everything we want from our feeble attempts at manipulation.

“There is only one you for all time. Fearlessly be yourself.” – Anthony Rapp

7. Lying

My word is all I have. If I lose my word, I lose my ability to create something — anything — with another human being. The short-term resolve, satisfaction or avoidance is not worth it. Tell the truth. And I don’t mean “real talk” — essentially complaining disguised as truth. I mean the authentic truth — the one about where I’m imperfect and I’m pretending not to be. That one gets me much further with the people in my life.

This also includes the friend of mine I referenced earlier. Once I shared with him the source of my comment, I was met with compassion and respect. This wouldn’t have been possible had I not stepped outside of the temptation to leverage one of the aforementioned roadblocks. They may seem like an easy way to transition in the moment, but the cost of a meaningful and lasting connection is far too severe a price to pay.

Which of these seven roadblocks do you run into most frequently?  Let us know your plan to get around it in the comments below!

Dan Whalen is a franchise operator with College Hunks Hauling Junk & Moving, personal development writer, and NLP master practitioner. He has a background in business management and team leadership spanning nearly a decade, and has a deeply-rooted passion for helping people experience fulfilling lives. You can find him on Twitter at @DanielJWhalen.

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Success Advice

JP Conte Took Up Surfing After Decades in Private Equity. Here’s What It Taught Him About Risk

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According to the Outdoor Industry Association’s 2026 participation report, a record total of 183.2 million participants took part in outdoor activities — or 59% of Americans ages 6 and older.

JP Conte is one of them.

Learning to Surf After a Career in Private Equity

Conte, founder and managing partner of his family office, Lupine Crest Capital, is credited with “more than three decades of experience building and transforming companies.” Water sports were not part of that record.

“After decades in private equity, I started sailing my boat around the world and learning to surf and kite surf,” he wrote in a column for Forbes Business Council.

“That unfamiliarity was precisely the point,” he wrote.

The Ski Slope and Risk

In Conte’s column, he breaks risk into three categories. “Smart risk requires understanding what you’re getting into while accepting incomplete information,” he wrote.

Reckless risk is taken when available facts are ignored. Playing it safe, in his telling, means you may never learn anything at all. His rule for staying out of both traps is simple: “Respect the uncertainty, but don’t let incomplete information paralyze you.”

He compared it to approaching a ski run. “You assess conditions, check equipment and commit once you start,” he wrote.

“Hesitation mid-slope is more dangerous than committed execution,” JP Conte wrote.

Real danger sits in the middle, he argued, where a person is neither prepared nor committed. Leaders can get stuck in the same spot.

Building Risk Tolerance One Wave at a Time

Boldness is not something people are simply born with, in JP Conte’s view. “Risk tolerance isn’t a fixed trait; it’s a developed skill,” he wrote.

His method is to practice on small choices and ones that provide rapid feedback. Water works well for that. A surfer who picks the wrong wave finds out within seconds, paddles back out and tries the next one.

“Physical activities like cycling, mountain biking, kiting or surfing involve constant micro-decisions with immediate feedback,” Conte wrote.

Carrying the Habits Back to Business

Executives were the column’s intended readers, and the advice is aimed at people who have spent years getting good at one thing. Conte argued that the core work of running a company, from analyzing data to building teams, carries over to nearly any industry.

He gave an example from two very different fields. A healthcare technology company adopting new ways to run clinical trials and a financial services firm rolling out digital platforms face similar problems, he wrote, even though the products have little in common.

“Many executives stay within their comfort zones because they fear looking inexperienced or making mistakes in new domains,” he wrote.

Before a big move, he urged readers to learn the territory. “Knowledge doesn’t eliminate uncertainty, but it converts wild uncertainty into calculated probability.”

Keep more than one effort going, he advised. “It ensures a setback in one area doesn’t eliminate your ability to take appropriate risks in others.”

And treat a bad outcome, whether it’s a wipeout on the slopes or a project that misses, as information for the next attempt.

“Failure becomes input for better future choices rather than evidence of inadequacy,” JP Conte wrote.

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Success Is Not a Solo Journey: Why Entrepreneurs Grow Faster Through the Right Connections

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Success is often described as the result of hard work, discipline, and the ability to keep moving forward when things become difficult. These qualities are important, but there is another factor that can influence an entrepreneur’s journey just as much: the people they surround themselves with.

Building a business requires more than individual ambition. Entrepreneurs need fresh perspectives, honest feedback, useful knowledge, and relationships that encourage them to think beyond their current limitations. While personal determination provides the motivation to begin, the right professional connections can help turn ideas into meaningful progress.

Personal Growth Begins With the People Around You

The people we interact with regularly can influence how we think, approach challenges, and define success. Spending time with individuals who are curious, ambitious, and willing to learn can encourage us to raise our own standards.

For entrepreneurs, this influence can be especially valuable. Business ownership involves constant decision-making, and having conversations with people who understand similar responsibilities can introduce ideas that might not emerge when working alone.

A founder who regularly exchanges experiences with other business owners may discover a better way to manage a team, approach a customer problem, or evaluate a new opportunity.

Personal development is not limited to books, courses, or individual routines. It also happens through conversations and shared experiences.

Why Entrepreneurs Should Look Beyond Their Own Industry

It is natural for business owners to focus most of their attention on their particular industry. However, limiting professional relationships to people doing similar work can restrict the range of ideas they encounter.

Some of the most useful business lessons come from completely different fields.

A technology entrepreneur might learn valuable customer service practices from a hospitality business. A marketing professional could discover new approaches to leadership by speaking with someone managing a growing manufacturing company.

Different industries may operate under different conditions, but many challenges remain similar. Hiring, communication, customer retention, leadership, and business development are concerns shared by companies of all sizes.

Connecting with people outside one’s immediate professional circle can help entrepreneurs question familiar approaches and consider new possibilities.

The Difference Between Networking and Building Real Relationships

Networking is often associated with attending events, exchanging contact information, and adding new connections on professional platforms. These activities can create opportunities, but they do not automatically lead to meaningful relationships.

Strong professional connections require consistency and mutual interest. People need time to understand each other’s goals, experience, and working styles.

A valuable relationship is not built around asking what someone can do for your business. It develops when both individuals are willing to share knowledge, offer support, and contribute to each other’s progress.

This is why entrepreneurs should focus on the quality of their connections rather than the number of people in their contact lists.

Finding a Community That Encourages Entrepreneurial Growth

Building meaningful professional relationships can be challenging when most of an entrepreneur’s time is spent managing daily operations. A structured environment that brings business owners together can make it easier to connect with people who understand the realities of entrepreneurship.

For those seeking an entrepreneur community in Los Angeles, a focused professional network can offer opportunities to exchange ideas, learn from other founders, and develop relationships beyond occasional business events.

A strong Los Angeles entrepreneur community can also bring together people from different industries and business backgrounds. These interactions can create opportunities for collaboration and expose entrepreneurs to perspectives they might not encounter within their usual circles.

The most valuable communities encourage participation rather than passive membership. Members should feel comfortable discussing challenges, sharing lessons, and learning from one another.

How the Right People Can Improve Decision-Making

Entrepreneurs often face situations where there is no obvious answer. Expanding a company, hiring a senior employee, changing a pricing strategy, or entering a new market can involve considerable uncertainty.

Discussing these decisions with experienced peers can help business owners examine different possibilities before taking action.

For example, a founder considering expansion may benefit from speaking with someone who has already managed a similar transition. Another entrepreneur might share lessons about an unsuccessful decision, helping others recognize potential risks earlier.

This does not mean every suggestion should be followed. Each business has its own customers, resources, and priorities. However, additional perspectives can help entrepreneurs make more informed choices.

Building a Stronger Professional Circle in Los Angeles

Los Angeles offers opportunities across industries such as entertainment, technology, real estate, professional services, and digital business. For entrepreneurs operating in such a diverse business environment, building relationships with people outside their immediate industry can be especially useful.

A private entrepreneur network in Los Angeles can provide a more focused setting for connecting with other business owners who value meaningful conversations and professional development.

Entrepreneurs can make the most of these relationships by following a few simple practices:

  • Be genuinely interested: Ask about other people’s experiences instead of focusing only on introducing your own business.
  • Share knowledge: Offer useful insights or resources when they can help someone else.
  • Stay consistent: Keep in touch after initial conversations and make an effort to develop lasting connections.
  • Welcome different opinions: Constructive feedback can reveal weaknesses in an idea before they become costly mistakes.
  • Look beyond immediate benefits: Some of the strongest professional relationships take time to become valuable.

These habits help turn introductions into relationships that can support long-term professional growth.

Success Requires Both Individual Effort and Collective Learning

Ambition and personal discipline remain essential to entrepreneurial success. No professional network can replace the effort required to build a company, serve customers, and overcome difficult situations.

However, individual effort does not mean working in isolation. Learning from others, exchanging experiences, and developing trusted relationships can make the entrepreneurial journey more informed and rewarding.

A LA founders community can give business owners opportunities to connect with people who understand their ambitions and challenges. These connections may lead to new ideas, valuable conversations, and collaborations that develop over time.

Ultimately, success is not only about how far someone can go independently. It is also about the knowledge they gain, the relationships they build, and the people who contribute to their growth along the way.

The right circle will not do the work for an entrepreneur, but it can help them see new possibilities and approach their goals with a stronger perspective.

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Why Founders Beat Professional Managers When Industries Change

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Founders vs professional managers comes down to one question: who can run a company when the industry stops standing still? Marc Andreessen’s answer, built on James Burnham’s theory of the managerial class, is that interchangeable professional managers are good at protecting a stable machine but tend to freeze when the product or the market changes underneath them. That is why Andreessen Horowitz would rather teach a founder to manage at scale than ask a manager to become a founder.


The managerial-capitalism section of this Dwarkesh Patel interview with Marc Andreessen starts around the nine-minute mark, and the founders section around fifty minutes in. A shorter clip from a separate Andreessen interview, where he walks through the same Burnham frame with a SpaceX example, has been circulating on X. One note if you watch that clip: the captions say “James Byrne.” He is talking about James Burnham.

The Advice That Sounds Smart Until the Market Moves

I have heard the same sentence in green rooms, on podcast calls and over dinner with founders for more than a decade: “Hire great people and get out of their way.” It sounds mature.

And I have watched what happens when founders take it literally. The founder hires a polished operator with a beautiful resume, hands over the product roadmap, and steps back to “work on the business.” For a year, everything looks cleaner. Then the market shifts. A new tool shows up, a platform changes its rules, customers start wanting something different. And the polished operator does exactly what they were trained to do: protect the plan.

That is the moment the company stalls. Not because the manager is lazy or dumb, but because they were hired to run a machine, and the machine just became obsolete.

Here is the line I keep coming back to: a manager protects the machine you built; a founder notices when the machine is pointed at the wrong target. You need both. But only one of them can turn the ship.

Burnham’s Frame in Plain English: Bourgeois Capitalism vs Managerialism

James Burnham was an American political theorist who wrote The Managerial Revolution in 1941. That book is where his core argument lives: ownership and control of big organizations were splitting apart, and a new class of professional managers was taking control. Andreessen also often cites Burnham’s 1943 book The Machiavellians, which is about how elites actually hold power.

In the Dwarkesh interview, Andreessen lays out two kinds of capitalism.

Bourgeois capitalism is the old model. One person owns the business, runs the business and often puts their name on the door. Andreessen’s examples include Ford Motor Company, and Andreessen Horowitz itself. He describes it as the owner, builder and CEO being “one person with a direct link between ownership and control.”

Managerial capitalism is what replaced it across most of the economy. Ownership is spread across thousands or millions of shareholders who are not paying attention, so a professional managerial class steps in and runs the company. In Andreessen’s summary of Burnham, the managers end up in control even though they might own only a sliver of the company.

Here is the rough timeline, in plain English:

  • 1880s to 1920s: Railroads, steel, oil and early auto companies grow too big and too complex for one owner to supervise. Layers of salaried managers appear to coordinate them.
  • Early 1900s: Business schools such as Harvard Business School and later Stanford’s business school turn management into a teachable, portable profession. The idea spreads that a well-trained manager can run almost anything.
  • 1960s and 1970s: The conglomerate era pushes that idea to its extreme. If management is a universal skill, why not run a hotel chain, a bakery and a defense contractor under one roof?

Burnham’s argument was that this shift was inevitable because of scale and complexity. Andreessen agrees that big organizations do need people who can run things at scale. This is not an anti-manager rant.

Where Professional Managers Shine, and Where They Freeze

In the Dwarkesh conversation, Andreessen puts it bluntly: managers “don’t build new things.” They are not trained for it, and their incentives point the other way. If you are a manager, your number one job is “not to upset the applecart.” You want to keep the job, keep the comp and avoid introducing risk.

In the clip circulating on X, he sharpens the point. Managers may be good at running something that is “going to be status quo for a long time.” But “the minute things change,” he says, the manager personality type “doesn’t know how to deal with change.”

Think about it as two kinds of terrain:

Situation Professional manager Founder
Stable product, stable customers (a soup brand, a regional bank, a legacy car line) Strong: optimizes cost, process and predictability Can get bored, may over-tinker
New technology changes the product itself Weak: defends the old plan and the old metrics Strong: has the knowledge and authority to rip up assumptions
Company needs to run 1,000+ people Strong: knows how to manage managers Weak, unless they deliberately learn it
Long-term bet that hurts this year’s numbers Weak: paid on quarterly and annual targets Strong: the company is their life’s work

Look at that last row. Ben Horowitz made the same point back in 2010 in Why We Prefer Founding CEOs: professional CEOs are effective at maximizing a product cycle, while founding CEOs are better at finding the next one. His example: record-label executives who would not let go of their old business model when the internet arrived.

The SpaceX Example: What Good Are Management Skills Now?

Andreessen’s sharpest illustration in the clip is rockets.

For decades, orbital boosters were treated as expendable. You built an extraordinarily expensive machine, launched it, and most of it was gone. If you were a professionally trained manager at a launch company, your skill was running that system well: hitting schedules, managing contractors, controlling cost overruns.

Then, as Andreessen tells it, “this crazy guy in California comes up with this thing where the rockets land on their bottom and you can’t replicate it.” His question is the whole thesis in one line: “What good are your management skills at that point?”

The point is not “be like Elon.” It is structural. When the core assumption of an industry breaks, the person who is best at executing the old assumption is often the worst-positioned person in the building. Their expertise is in the thing that just stopped mattering.

This is where, in the clip, Andreessen says Burnham’s thesis “collapses.” Yes, there is a need to run things at scale. But managers “can’t adapt.” That is a stronger stance than his Dwarkesh-era framing, where he treated the drift toward managerialism as close to inevitable. The through-line in both: managers can run scale, but they will not build the next thing.

The a16z Operating Theory: Teach Founders to Manage at Scale

So if managers cannot adapt and founders cannot run 10,000 people, what do you do?

Andreessen’s answer, in the clip: “The founders can actually learn how to do this.” He frames it as a big part of how his firm thinks. Horowitz’s 2010 post says the same thing from the inside: teaching a founding CEO how to maximize the product cycle is easier than teaching a professional CEO how to find a new one.

In the Dwarkesh interview, Andreessen names the specific breakthrough a founder has to make: learning to manage managers. Even a CEO of a 100,000-person company only has eight to twelve direct reports. If you can lead a team of managers, that skill scales. He describes the best case as a founder-minded CEO “managing a team of managers who are doing all the managerial stuff required at scale.” Best of both worlds.

He also tells founders the honest part. In his estimate, nearly every founder they back is smart enough to run a big company, but maybe half have the temperament, and fewer still actually want to be doing it twenty years later. Horowitz is even more direct: almost no founder has the CEO skill set on day one, and learning it on the job is often “a miserable, debilitating experience.” He did it anyway, because it is the most reliable way to build something great.

That is the real choice in founders vs professional managers. It is not founder or manager. It is founder who learns to manage versus manager who tries to become a founder. The first one is hard. The second one rarely happens.

7 Things a Scaling Founder Can Do This Month

If you are a founder somewhere between ten and a few hundred people, here is how I would put this into practice. All of it requires you to stay in the building.

  1. Learn to manage managers before you need to. Pick one leader who already has a team and coach them weekly. This is the skill Andreessen says separates founders who scale from founders who get replaced.
  2. Keep your hands on product taste. Review the roadmap and sit in on at least one product or customer session every week. Delegating execution is smart. Delegating judgment about what to build is how founders lose the company.
  3. Hire operators who amplify your judgment, not replace it. In interviews, ask candidates how they handled a time the strategy changed under them. You want someone who builds systems around a moving target, not someone who needs the target to hold still.
  4. Run skip-level conversations. Once a month, talk directly with people two levels down. You will hear about market shifts weeks before they reach a slide deck.
  5. Write down your company’s core assumptions. List the five beliefs your business model depends on. Once a quarter, ask your leadership team which one is most likely to break. This is the founder’s version of watching for the rocket that lands.
  6. Protect your own capacity. Founders who burn out hand the company to the managerial class by default. Build a founder energy operating system so you can still think clearly at 200 people.
  7. Delegate without disappearing. The opposite of micromanaging is not vanishing. Most founders struggle with the psychology of letting go, so they swing from doing everything to doing nothing. Hand off outcomes, keep the feedback loop.

Don’t confuse this with Paul Graham’s “Founder Mode.” Graham’s 2024 essay, sparked by Airbnb’s Brian Chesky, is about how founders should run their own companies day to day, including skip-level meetings, instead of following conventional delegation advice. It is related and worth reading. Andreessen’s Burnham frame is a bigger, economy-wide argument about who runs organizations and why professional managers stall when industries change.

The Bottom Line on Founders vs Professional Managers

Andreessen describes the economy as roughly 99% managerial, with venture capital trying to keep the other 1% alive so new things still get built.

Managers are not the enemy. The enemy is a company that forgets why it exists the moment the ground moves. If you are the founder, your job is not to hand the keys to someone with a better resume. Your job is to become the person who can drive the bigger vehicle, without losing the instinct that told you where to go in the first place.

The industries that matter most are the ones that are about to change. Make sure the person in charge can change with them.

FAQ

What is the difference between founders and professional managers?

Founders start companies and usually hold both ownership and control, so they can change direction fast. Professional managers are hired to run existing organizations, are often trained in business schools and are typically rewarded for predictable results rather than reinvention.

What did James Burnham mean by the managerial revolution?

In his 1941 book The Managerial Revolution, Burnham argued that ownership and control of large organizations were separating. Dispersed shareholders owned companies, but a new class of professional managers actually ran them, gaining real power without holding much ownership themselves.

Why does Marc Andreessen prefer founder-led companies?

Andreessen argues that managers are good at running things at scale but do not build new things and struggle when industries change. Founders, he says, can learn to manage at scale, which is easier than teaching managers to innovate.

Can founders learn to manage at scale?

Yes, but it takes deliberate work. Andreessen says the key breakthrough is learning to manage managers, because that skill scales. Ben Horowitz adds that almost no founder starts with CEO skills, so most learn them on the job, often painfully.

Is founders vs professional managers the same as Founder Mode?

No. Paul Graham’s Founder Mode essay is about how founders should operate inside their own companies. Andreessen’s Burnham frame is a broader argument about managerial capitalism and why professional managers tend to stall when an industry changes direction.

Disclaimer: This article is for educational purposes only and is not business, legal or investment advice. Quotes from Marc Andreessen are drawn from his public Dwarkesh Patel interview and a widely shared interview clip; summaries of James Burnham’s work are simplified for a general audience. Make leadership and hiring decisions with advisers who know your company.

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Memento Mori Meaning: How to Practice It Every Day

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Memento mori meaning, in plain English: it’s Latin for “remember that you must die.” In Stoic philosophy it isn’t a gloomy slogan or a skull aesthetic, it’s a daily practice of keeping your mortality in view so it sharpens what you do today. You practice it with short, regular reminders that end in action: cut the trivial, stop postponing what matters and treat each day as if it could be complete.

I’ve watched this idea change people more than almost any productivity system I’ve seen. Not because it scares them, but because it cuts through the noise. When a founder genuinely remembers the clock is running, the inbox gets smaller, the hard conversation finally happens and the “someday” project gets a start date. Two words, and suddenly you know what matters.

Before we get into the practice, here’s Ryan Holiday from Daily Stoic explaining memento mori in about five minutes. It’s the clearest short take I’ve found, and he shows the coin he carries in his pocket as a reminder.

What Does Memento Mori Mean?

Word for word, memento means “remember” (a command, not a suggestion) and mori means “to die.” So the phrase is an instruction to yourself: remember that you will die. Over the centuries it also became a noun. A memento mori is any object made to remind you of death, which is why Tate describes old paintings full of skulls, hourglasses, guttering candles and wilting flowers.

Here’s a detail most explainers skip. The exact Latin phrase is a later label, mostly medieval and Christian. The early Christian writer Tertullian recorded something close to it from Roman triumphs, where a victorious general was reminded, “Look behind you; remember you are a man.” The practice though is older, and the Stoics are the ones who turned it into a working tool. They never said “memento mori” as a catchphrase. They just did it, every day.

That’s the line I want you to take from this section: memento mori isn’t a mood, it’s a filter. Its only job is to make your next decision clearer.

How the Stoics Actually Used It

Three Stoics, three angles, all from the primary texts.

Marcus Aurelius, the most powerful man in the Roman world, wrote this to himself in his private notebook: “Since it is possible that thou mayest depart from life this very moment, regulate every act and thought accordingly” (Meditations 2.11). Notice the second half. The thought of death isn’t the point. Regulating the next act is. If you want more from his notebook, I’ve pulled together the best Marcus Aurelius quotes with their book and section sources.

Epictetus gave it a frequency: keep death “daily before your eyes,” and “you will never entertain any abject thought, nor too eagerly covet anything” (Enchiridion 21). Daily. Not once a year at a funeral.

Seneca gave it a bedtime ritual. In Letter 12 he suggests going to sleep able to say, “I have lived,” and treating any extra day as a gift. In his words, the person who can say that receives a bonus every morning they wake up.

Put those together and you get the whole system: a reminder (Epictetus), a decision rule (Marcus) and a way to close the day (Seneca).

Why Memento Mori Sharpens Your Priorities

Most high performers I meet aren’t lazy. They’re busy on the wrong things. They’re answering every message, sitting in meetings that could have been an email, defending a decision they already know was wrong, and pushing the work that actually matters to “next quarter.” Nobody does that on purpose. You do it because, deep down, you’re acting like time is unlimited.

Steve Jobs said it better than anyone in his 2005 Stanford commencement address. For 33 years he looked in the mirror each morning and asked, “If today were the last day of my life, would I want to do what I am about to do today?” When the answer was no for too many days in a row, he knew he needed to change something. He called remembering that he’d be dead soon “the most important tool I’ve ever encountered to help me make the big choices in life,” because pride, external expectations and fear of embarrassment “just fall away in the face of death.”

That’s the mechanism. Death doesn’t add motivation. It removes the junk that was blocking it. Status games, people-pleasing and the fear of looking stupid all lose their grip when you remember none of it is permanent. We already have a deeper piece on why remembering you’re going to die will wake you up. This one is about the how.

How to Practice Memento Mori Daily: 6 Steps

Here’s what I’d do if I were starting from zero tomorrow. None of these take more than a few minutes. Pick two, run them for a month, then add more.

  1. Ask the morning question. Before you open your phone, borrow Jobs’ line: “If today were my last day, would I want to do what I’m about to do?” You don’t need to overhaul your life on a Tuesday. Just notice the answer. If it’s no three or four days in a row, that’s data.
  2. Use it as a decision filter. At every fork in the day, ask: would I be okay if this were the last version of me people saw? It’s amazing how fast it kills the sarcastic email, the pointless argument in a group chat and the third hour of “research” that’s really just avoidance.
  3. Run a quick reverse visualization. Pick one thing you keep postponing, the product, the trip, the call to your dad. Picture yourself five years from now and it still hasn’t happened. Sit with that for 60 seconds, then schedule the first step today. Keep it short and practical. The goal is a calendar entry, not a spiral.
  4. Keep a physical cue. The old painters used skulls. You can use a coin in your pocket, a sticky note on your monitor or a life-in-weeks calendar, where an 80-year life is roughly 4,160 small boxes. Every time you see it, ask one question: what’s the next useful thing?
  5. Apply it to people, not just projects. Epictetus told his students to remember that the people they love are mortal too. That isn’t cold, it’s the fastest way I know to become more patient, more present and quicker to say the thing you’ve been meaning to say. Make the call. Send the message.
  6. Close the day like it was complete. This is Seneca’s version. At night, look back and ask: did I spend today on purpose? Then let it go. If you get tomorrow, you’re playing with house money, so treat it that way.

Quick daily checklist: morning question asked, one decision filtered, one postponed thing moved forward, one person reached out to, day closed without carrying it to bed.

Memento Mori Done Right vs. Done Wrong

This idea gets misused a lot, so here’s the simple version I’d want any founder or team leader to understand:

Done right Done wrong
A short reminder that ends in a clear next action Long rumination that ends in dread or doom-scrolling
Cutting trivial work so the important work gets done “Nothing matters anyway,” so nothing gets done
Being more present with the people you love Pulling away from people because everything is temporary
Bold, considered decisions you won’t regret Reckless “you only live once” decisions you’ll pay for later
A private practice that changes your behavior A skull tattoo or aesthetic with no change in behavior

Common Mistakes to Avoid

Mistake 1: Turning it into nihilism. “We’re all going to die, so why bother?” is the exact opposite of what the Stoics meant. Marcus remembered death and then went back to running an empire. Finite time makes your choices matter more, not less.

Mistake 2: Morbid rumination. If the thought lingers for twenty minutes and leaves you anxious instead of clear, it’s stopped being a practice and become brooding. Set it down and pick up the next task. And if you’re grieving or anxiety about death is heavy right now, be gentle with yourself and talk to someone you trust. The tool should serve you, never the other way around.

Mistake 3: Using it as an excuse. I’ve seen people quote “life is short” to justify blowing up a business, skipping the boring work or treating people badly. Life is short. That’s exactly why the boring work, done well, matters. Memento mori asks for wisdom, not impulsiveness.

Mistake 4: Keeping it as decoration. A coin or a print on the wall is fine, but only if it triggers the question. If you stop noticing it, move it or swap it.

The Real Point

Here’s what I believe after years of watching people build things: the people who remember they’re going to die tend to live like they mean it. They say no faster, they forgive faster and they start sooner. They stop treating their best work like something they’ll get around to.

You don’t need a skull on your desk. You need one honest question each morning and the courage to act on the answer. Ask it tomorrow before you touch your phone, and see what changes.

Frequently Asked Questions

Is memento mori a Stoic phrase?

The exact Latin phrase became popular later, mostly in medieval Christian art. The practice is classically Stoic: Marcus Aurelius, Epictetus and Seneca all wrote about keeping death in view daily to guide better choices.

What are common memento mori symbols?

The classic symbols are a skull, an hourglass or clock, a snuffed or guttering candle, wilting flowers and fruit. Modern versions include engraved coins, life-in-weeks calendars and simple written reminders.

Is memento mori morbid or depressing?

It shouldn’t be. Practiced well, it’s brief and ends in action: a clearer decision, a call you’ve been putting off, less time on trivia. If it leaves you anxious rather than clear, shorten it or set it aside.

How often should you practice memento mori?

Daily, but briefly. Epictetus said to keep death before your eyes every day. A 30-second morning question and a short evening review are enough for most people to feel the difference within weeks.

What is the difference between memento mori and carpe diem?

Memento mori is the reminder: your time is finite. Carpe diem, “seize the day,” is the response. Done right, remembering death leads to using today well, not reckless “you only live once” choices.

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