"The simplest path to freedom is low overhead" and 49 more Rubyisms

Useful life lessons about relationships, money, fear, looking good, and more.

This is the Rubesletter from Matt Ruby, comedianwriter, and the creator of Vooza. Sign up to get it in your inbox weekly.

The return of Ruby’s House of Gems

Rubyisms are things I’ve learned along the way that make me seem deep and witty but also provide valuable life guidance in a faux Zen kinda way. It’s all very wisdomish.

  1. What you’re outraged by isn’t nearly as interesting as what you feel guilty about.

  2. If they’re not paying rent, don’t give them emotional real estate.

  3. Just because a relationship ends doesn’t mean it was a failure. 

  4. Every dollar you spend is a vote for more of that thing.

  5. A plan that can’t survive reality is merely a fantasy. 

  6. There’s a reason it’s called due process and not due reaction. 

  7. If you’re too broke to buy a gift, make one instead. The person will like it more anyway. 

  8. The problem with life is it takes time.

  9. There is no easy way. if there was, everyone would do it and then it wouldn’t be the easy way anymore.

  10. The meaning of life is the experience of being alive. You’re already doing it.

  11. Quality over quantity is the wrong way to look at it. The way you get to quality is by traveling through quantity. Quality through quantity.

  12. Good soldiers never make great art.

  13. The best thing to teach is something you learned recently but wish you had known years ago.

  14. Often, fear shows up as anger and growth shows up as pain. 

  15. Don’t be afraid to take a pause before you respond. It shows you are answering with intention. (Related: One of the most underrated answers is “Let me think about it.”)

  16. You need a practice. Something healthy you do on the regular. “Practice, practice, practice” isn’t just how you get to Carnegie Hall, it’s also how you get to sanity.

  17. The more someone insists something is true, the more likely it is they’re lying. Example: Nowhere feels like less of a party than Party City.

  18. It’s always tempting to fight the last war. After all, it’s already been outlined for you. We waste time preparing for the past instead of imagining the future.

  19. If I pass away in my sleep, just know I died doing what I love.

  20. Never let them see your strategy. It should be hidden just out of view, like a nipple. 

  21. Hire an accountant. It pays for itself. At least that’s what my accountant keeps telling me. 

  22. Words are an imperfect attempt to repair the failure of silence.

  23. Just because it’s not your fault, doesn’t mean it’s not your problem.

  24. Never mistake someone’s telling you how young you look for a compliment.

  25. We constantly see how we’re mistreated yet rarely notice how much we mistreat.

  26. The ultimate escape is accepting there’s no way out.

  27. Seeing past the BS is only the first step. The hard part is figuring out what to replace it with that is not BS. Example: Substituting capitalism for religion is a lateral move at best.

  28. If it’s part of your story, walk with it.

  29. The first step to getting someone to act sexy is making them feel safe. 

  30. When it happens in your brain, it’s spirituality. When it happens in someone else’s brain, it's religion.

  31. The things you hate about what you do are the obstacles that keep everyone else from doing it too. So love those things; they are your moat. 

  32. People say that money changes you. Nah, being broke forces you to hide your true self.

  33. Find your book, a little known one you love to talk about. Then, gift it to anyone in your life that might enjoy it.

  34. For every “it’s easy” claim, there’s someone else thinking, “If they only knew how much work it took to make it look this easy.”

  35. If you know you’re right, not being assertive is actually pretty rude. 

  36. A super question that cuts through tons of life’s nonsense: “If you were me, what would you do right now?” Works great on customer support reps, waiters, and spouses.

  37. Appearance hack: Spend more money on haircuts, jackets, and shoes – and less on everything else. 

  38. Never get offended by the truth. Choosing to get upset by something that’s accurate is a path to misery. Life is relentlessly accurate.

  39. The more “time saving devices” you use, the busier you’ll wind up feeling.

  40. Be your partner’s accomplice to joy.

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  41. Write thank you notes. (Related: Martha Stewart is usually right, she just doesn’t have to be such a Karen about it.) 

  42. The thing you least want to talk about is the thing people most want to hear.

  43. You’re almost never fighting about the thing you’re fighting about. Get to the unmet need or untreated wound that is the actual cause or you’ll just fight again in some other way.

  44. Luck is just showing up at the right place over and over again until it’s the right time.

  45. We constantly mislabel apathy and ignorance as malevolence. They might hate you, but it’s more likely they simply don’t care.

  46. Acting morally superior is silly. Instead, admit you're awful. Now the worst they can call you is a hypocrite. And that's fine because we're all hypocrites.

  47. In a disposable culture, being consistent is a rebellious act. 

  48. The simplest path to freedom is low overhead.

  49. “In love” is a misnomer. You either do love or you don't do love. Love is an action, not a feeling.

  50. Closure is overrat

50 more Rubyisms: ”You have to go first" and 49 other life lessons (July, 2020)


Video: I was not alerted

I wrote, performed, shot, and edited this video about what it was like growing up without Steve Jobs in my pocket. Some comments received on it so far:

“Beautiful montage.”
”Loved this.”
”I love everything about this 👏❤️”
”This is excellent: in my opinion your best ever”

This essay originally appeared in the Rubesletter with the subject “The most unbelievable things about life before smartphones.”

Help support this newsletter and videos like this by subscribing



👩🏻‍⚕️: After your vaccine, you may experience fever & chills–
🕺: I could get chills?
👩🏻‍⚕️: Yes.
🕺: Could they start multiplying?
👩🏻‍⚕️: I guess.
🕺: And I might start...losing control?
👩🏻‍⚕️: Kinda.
🕺: Phew, the vaccine you're supplying–
👩🏻‍⚕️: OK, you can go now.
🕺: It's electrifying.
👩🏻‍⚕️: I get it. Bye.
🕺: Wait, one last question.
👩🏻‍⚕️: What?
🕺: Which vaccine was it?
👩🏻‍⚕️: J&J.
🕺: Great, that's...THE ONE THAT I WANT.
👩🏻‍⚕️: Next!

🌀 “Vaccine passports will create a two-tiered society.” We already have that with iPhone and Android. That green text bubble is the digital version of being unvaccinated.

Tech’d up

🌀 I don't want to tell you how many times i have opened my air pod case to find my air pods missing and gotten upset and then realized they were in my ears.

🌀 Algorithms are our new ruling party.

🌀 My startup mission is to have a bankruptcy that elevates the world’s consciousness.

🌀 Everyone should do everything the way software developers create apps. Minimal viable product, get feedback, iterate, etc. Too bad we associate it with tech geeks instead of sexy people.

Politicked off

🌀 America 2021: Sometimes you're outraged but then you're like "well, let's wait until we hear all the facts" and then you hear all the facts and you're even more outraged.

🌀 Cancel culture is the war on drugs brought to ideas: A bogus "problem" is met with never-ending, aggressive prosecution. Severe punishments are imposed yet yield no meaningful change. The result: It forever breaks the trust of those who are overpoliced.


🌀 "You can't have your cake and eat it too." Um, WTF is the point of having cake if you can't eat it?

🌀 “You know what’s cooler than video games? Watching other people play video games.”
-No woman ever

Podcast: “Ayahuasca” on Hell & Wellness

Newest ep of Hell & Wellness is up and it’s a doozy. I 🖤 ayahuasca and explain why…but my cohost Rob ain’t so sure.

Ep 10 // Ayahuasca
Ayahuasca, a hallucinogenic tea from the Amazon has become a trendy, life-altering brew consumed by hipsters, Silicon Valley, and the yoga crowd. Many say it’s the most significant spiritual experience of their lives. Others claim it’s like “10 years of psychotherapy in one night.” But what is it? How do you take it? And how did drinking a South American psychoactive brew become just as popular as microdosing, CBD, and partying in Tulum? Matt and Rob go deep to discuss the benefits and misconceptions surrounding this traditional spiritual medicine. Buckle up.


1) “You are here to be swallowed up,” explains Louise Erdrich in The Painted Drum.

Life will break you. Nobody can protect you from that, and living alone won’t either, for solitude will also break you with its yearning. You have to love. You have to feel. It is the reason you are here on earth. You are here to risk your heart. You are here to be swallowed up. You are here to be swallowed up. And when it happens that you are broken, or betrayed, or hurt, let yourself sit by an apple tree & listen to the apples falling all around you in heaps, wasting their sweetness. Tell yourself that you tasted as many as you could.

2) The hottest take you can have these days is that things are actually getting better. Why the World Is Doing Better Than You Think, According to Steven Pinker (Men’s Health). If things are actually good then why does it feel so bad? Pinker: "In general, our personal danger calculation has more to do with instinct and optics than reason and logic."

“We’re biased toward negativity,” he tells me. We erroneously expect destruction.

To understand why, you need only make two lists: one of every glorious thing that could transpire on a typical day, and the other of every bad, nasty inconvenience. Pinker suspects your latter list will be longer; since these include the things that can actually hurt us, it makes sense for our emotions to be tuned toward the negative, says Pinker. Essentially, we’re wired for pessimism…

In general, our personal danger calculation has more to do with instinct and optics than reason and logic, notes Pinker. Someone intending us harm causes more worry than something that buzzes and doesn’t. Danger can be difficult to accurately cognize. And so too can "progress."

3) New York, Finally, Taxes the Rich (NY Times). Will New Yorkers flee to Florida? Nah. This is a devastating paragraph (in a fun way).

Opponents of tax increases on the wealthy have forever argued that even the slightest incremental change will send New Yorkers fleeing to income-tax-free Florida. Now we will have an opportunity to see how many people making more than $2 million a year will really move from the Upper East Side to South Beach — a location where climate models predict two feet or more of sea-level rise by 2060 — for a savings roughly equal to the cost of a used Chevy Malibu. These are people who essentially require grief counseling when their children are forced to go to Vassar. Are they really going to pull their children out of elite private schools that have fed the Ivy League for hundreds of years to settle down in a place with a diet named after it?

4) If You Want to Make It As a Writer, For God's Sakes, Be Weird by Freddie deBoer points out how the lack of conservative voices in the mainstream media is a market failure.

You could, if you were a masochist, go one by one through the Twitter feeds of people at prominent newspapers and magazines, at sites like Vox and Buzzfeed and the Daily Beast, at NPR and the biggest podcasts, at think tanks and nonprofits, at the whole vast constellation of people involved in writing our culture, and you will find almost total unanimity in support of a self-defensive style of social justice politics.

Again, this is has nothing to do with the question of whether the politics media has adopted are correct. The point is simply that it’s not hard to see why many writers can’t get off the landing pad: they’re all saying the exact same things. In a profession where you are what you say, that’s death. I don’t know why people aren’t grasping this.

Related: I’m constantly astounded by the lack of southern accents on television. There’s one guy on ESPN who covers college football and NASCAR who talks with a drawl and that’s it. But think about the percentage of the country which speaks that way. No wonder they don’t trust the media. “Representation” cuts both ways. If one side wants it, the other probably does too.

5) “The last time I bought a microwave oven I asked the saleswoman which ones beeped only once and stopped.” Electronic Narcissism by J.F. Riordan explores the increasing volume of gadgets with, well, increasing volume.

It used to be that appliances would sit silently and make themselves useful. Now, for reasons I do not understand, they seem to feel a need to call attention to themselves, as if, like electronic toddlers, they are announcing: Look at me! Look what I’ve done!

It strikes me as an indication of a deeply flawed society. What personal failings have led us to develop narcissistic appliances? Is it a reflection of modern life, the electronic equivalent of so-called influencers, who must announce their doings on Twitter, Instagram, Pinterest, and Facebook, or be forced to question the value of their own existences? Have we created appliances like ourselves? Is there anyone who likes this incessant mechanistic signaling? Or is there something about the electronic miasma in which we all exist that assimilates our nerves into a state of noise acquiescence? Is there some consumer movement I need to join to dissuade manufacturers from this evil path?  

The last time I bought a microwave oven I asked the saleswoman which ones beeped only once and stopped. It was clear by her reaction that no one else had ever asked this question, but she dutifully investigated the beeping of each one, no doubt thinking bad words that I am grateful not to have heard. But each time I buy a new appliance, I find that the noise factor has intensified, as if this has become a signal—as it were—of improvement. I believe it is, instead, an instrument of consumer torture.

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About the Rubesletter: Weekly musings from a standup comedian and startup veteran. If you like my comedy or writing; if you dig tech, politics, art, wellness, & pop culture; if you enjoy smart/nuanced takes & hate BS; if you’d like me to turn you on to other people making cool stuff: Sign up.

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My latest standup special is free on YouTube. And you can stream my standup albums “Feels Like Matt Ruby” and “Hot Flashes” too.