What If I Said No? (And Other Questions to Consider Daily)
Voltaire said the way to judge a person was by the questions they asked. I think that’s right. Because none of us are perfect and we all fall short of our own standards, what matters are the questions we ask—of ourselves and other people — in our pursuit of self-improvement. What matters is the wrestling we do as we work to find the answers.
A few years ago I wrote a piece about 12 questions I think we should ask ourselves on a daily basis. They included questions about the company we keep, the worries we indulge, and the purpose we set for ourselves. They are questions whose answers have changed a lot for me as I have asked them throughout my life, but they have never failed to make me better or give me something to think about.
I’ve also realized they don’t address everything I believe is important. So here are 13 more questions that will change your life, if you let them — if you ask them consistently and try to answer them honestly.
How can I be stronger for this?
Ernest Hemingway supposedly said the first draft of everything is shit — which, of all the beautiful things Hemingway has written, applies most of all to the end of his novel, A Farewell to Arms.
One passage clearly challenged Hemingway more than the others — and it’s there in the final pages, which he rewrote something like 47 times. It appears after the protagonist Frederic’s wife Catherine has died after delivering their stillborn son and he is struggling to make sense of the tragedy that has just befallen him. “The world breaks everyone,” Hemingway wrote, “and afterward many are strong at the broken places. But those that will not break it kills.”
The world will break us. It breaks everyone. It always has and always will.
The question: Will we futilely resist it? Or will we accept the will of the universe and instead become stronger where we were broken?
Because those that cannot break cannot learn, and cannot be made stronger for what happened. There is a form of Japanese art dating back to the 15th century called kintsugi. Masters take broken plates, cups, and bowls and repair them by fusing the cracks and chips with gold. The legend is that the art form was created as a way to turn the scars of a break into something beautiful.
That’s what we can be, too: better, more beautiful, and stronger for everything that happened.
What books changed your life?
When I was a teenager, I began a habit that would change the course of my entire life. Every time I would meet a successful or important person I admired, I would ask them: “What’s a book that changed your life?” And then I would read that book. (In college, for instance, I was lucky enough to meet TV host Dr. Drew, who was the one who turned me on to Stoicism.)
If a book changed someone’s life — whatever the topic or style — it was probably worth the investment.
I loved books and was very hungry for the good stuff — what economist Tyler Cowen has called “quake books.” The ones that shake you. That knock everything over and turn it upside down. But I also understood that there are so many books out there, and only so much time. It was overwhelming.
If a book changed someone’s life — whatever the topic or style — it was probably worth the investment. If it changed them, I thought, it might at least help me. It’s a habit I continue to this day. There’s no better way to find out what to read or what subjects to explore than by asking and benefiting from the experiences of the people you admire.
Does anger make this better?
You gave them very careful instructions, which they disregarded, leading to costly consequences for you both. You’re a very courteous driver, yet this person is still honking and flipping you off. You’ve asked your kid 50 times to work on their school project, and here they are the night before, complaining that they need help.
These are trademark frustrating situations. Ones that are very easy to get angry about — it’s natural, even.
But just because it’s “natural” doesn’t mean it’s a good idea. Marcus Aurelius wrote in Mediations, “how much more harmful are the consequences of anger… than the circumstances that aroused them in us.”
Anger almost always makes things worse. It almost always compounds the harm — it takes a situation that was already unfortunate and makes it more so. Getting angry isn’t good for your heart. It’s not good for your mind. It’s not good for the people around you. So leave it alone.
Am I being kind or clever?
When Jeff Bezos was a young boy, he heard an anti-smoking public service announcement on the radio that explained how many minutes each cigarette takes off a person’s lifespan. His grandparents were both smokers. One day, like a typical precocious kid, he applied his recently acquired knowledge and proudly told his grandmother, “You’ve lost nine years of your life, Grandma!”
Bezos’ grandmother quite understandably burst into tears. Bezos’ grandfather took his grandson aside and taught him a lesson that he says has stuck with him for the rest of his life. “Jeff,” his grandfather said, “one day you’ll understand that it’s harder to be kind than clever.”
A dangerous assumption we seem to have made as a culture these days is that being right is a license to be a condescending jerk, that it exempts you from the need to persuade or even to have human decency. Being right is not enough. We need people who can be kind, who are willing to put in the time to understand those who think differently and convince them. To respect them. We need a lot less humiliation and a lot more humility.
And that starts with you. Catch the sharp or clever works before they come out of your mouth and replace them with respect, with patience, and with kindness.
Is this getting me closer to my ideal life?
I think a lot of people make the mistake of trying to build a life toward their perfect day instead of building a life around their perfect day.
People think they have to live a life they don’t want for a long time so that eventually, off in the distant future, they might get to do what they want someday. They need to make millions or get famous or earn their big break. Then, and only then, can they achieve their goals.
So many of us are focused on achieving big goals, but I think it’s better to know what your perfect day looks like. Then, with each opportunity and choice, ask yourself: Is this getting me closer or further away? Does saying yes to this job in New York City make you a lot of money… but come at the cost of deferring your dreams? Does driving across town to be interviewed for a television show seem cool? Yes… but it’s actually a lot of time away from the real work you should be doing, and what is the real ROI to this ego-booster?
Knowing what you want your life to look like day-to-day helps you separate the essential from the inessential, the optional from the necessary. These are rarely easy choices, so we can all use the help.
Does this stop me from acting with justice, temperance, courage, or wisdom?
No question, things go wrong. Often all at once and in public. But the question we should ask ourselves when that happens — when basically anything happens to us — is not, “Is this fair?” “Whose fault is this?” or “How will I recover?” Instead, we should ask questions the Stoics asked themselves: Does this stop me from being a good person? Does this affect my character?
More than 99% of the time, the answer is no. Which means you know exactly how you respond. By keeping on, keeping on. By falling back on virtue and the standards you set for yourself.” As Marcus Aurelius reminded himself: “Just that you do the right thing. The rest doesn’t matter.” Nothing can stop you from acting with the so-called Cardinal Virtues. Nothing is made worse by their appearance.
It doesn’t matter if other people get away with doing wrong. It doesn’t matter if people won’t appreciate the sacrifice of what you’re about to do. It doesn’t matter if it might not work. It doesn’t matter if you’ll be criticized or judged — if it’s right, it’s right for you. And nothing can stop you from trying to do that.
Why do I care what they think?
There’s a moment almost everyone remembers from their childhood. They’ve just received something they liked — a new shirt, a new toy, a haircut they thought was cool — and showed up for school with it… only to be mercilessly teased and mocked for it. Many a trash can has been filled by this experience — the toy, the shirt, the opinion no longer the same now that some jerk has weighed in.
Marcus Aurelius spoke of it 2,000 years ago in Meditations. “It never ceases to amaze me,” he said to himself, and now to all of us. “We all love ourselves more than other people, but care about their opinion more than our own.”
We’re proud of the job we did until our insecure boss attacks us for it. We’re excited about the book or movie or product we’re launching until we read the critics’ reviews. We feel like we’re making progress at the gym until somebody makes a nasty remark. We believe them more than we believe ourselves. And then we are miserable.
This is no way to live. We must cultivate our own high standards, our own strong opinions about what is right and good and important. This is what we need to use to evaluate reality. Other people’s opinions? We need to stop caring about them. Especially because deep down, we know they don’t know what they’re talking about. Why should we let them determine our sense of self-worth?
It’s not their judgment that should be guiding our lives. It’s our opinion that matters.
What if I said no?
It’s one of the hardest things to do in life — to say “No.” To invitations, to requests, to obligations, to whatever everyone else is doing. All of us regularly say yes unthinkingly, or out of vague attraction, or out of greed or vanity, or out of fear of disappointing a friend or acquaintance.
Roman philosopher Seneca wrote that if all the geniuses in history were to get together, none would be able to explain our baffling relationship with time. “We’re tight-fisted with property and money,” he writes, “yet think too little of wasting time, the one thing about which we should all be the toughest misers.”
Always think about what you’re really being asked to give. The answer is often a piece of your life, usually in exchange for something you don’t even want. In every situation, to every invitation or request, to everyone who asks for “just a little” of your time, ask yourself: What if I said no? If the answer is, “I’d be happier” or “No one would care,” then guess what? Say no!
Is this something only I can do?
Two thousand years before Peter Thiel famously said that “competition is for losers,” Greek philosopher Epictetus quipped, “You can always win if you only enter competitions where winning is up to you.”
When you’re the 40th Indian restaurant in town, the 4,000th health podcast, the four millionth life coach, your success is dependent on so many things outside your influence. The margins of victory are small. The spoils are split between so many competitors. Your happiness depends on a difficult contest.
If you didn’t go work on Wall Street, would someone happily take your place? Probably. But what about moving back to your hometown and helping revive it? Maybe only you can do that. Plenty of other people can write clickbait, but only you can speak your truth.
The wise, whether they’re Epictetus or Peter Thiel, know the real race is between mimicry and uniqueness, and most of all: purpose. When setting out on some new endeavor — building a business, producing a creative project — the question has to be: Is this something ONLY I can do?
Who owns who?
“Be careful that the things you own don’t end up owning you,” as the age-old warning against materialism goes. Chinese Confucian philosopher Xunzi explained: “The gentleman makes things his servants. The petty man is servant to things.”
As you consider buying this or that in the course of a day, ask yourself if it is making you more or less free. Ask: What hidden obligations does this come with? How much time will owning it take from me? How will it change me?
Examine your possessions and your privileges. Make sure you have an accurate accounting — an honest assessment — of who owns whom. Make sure you’re in control. Make sure what you buy and do serves you and not the other way around.
Where does this person fit into the world?
Marcus Aurelius, a guy who met his share of jerks, had a great line. “When you run up against someone else’s shamelessness,” he said, “ask yourself: Is a world without shamelessness possible?” The point was to help him realize: “There have to be shameless people in the world. This is one of them.”
Epictetus had an interesting word for gratitude — eucharistos — meaning “seeing” the whole picture. He said, “It is easy to praise providence for anything that may happen if you have two qualities: a complete view of what has actually happened in each instance, and a sense of gratitude.”
The stubborn or lazy or obnoxious people we bump up against? They are just playing the role assigned to them (and it’s probably not a role they enjoy). Same too for the evil or the stupid, the unlucky or the sad. We can understand and empathize with them when we can see the whole picture. It can remind us what our role is — to not be one of those people. To mitigate the damage they do. To be the best version of ourselves.
What am I working to get better at?
In Brazilian jiujitsu, they say the goal every day should be to improve in one particular area. When facing opponents whose sole focus is finding a weakness to exploit, it’s easy to see why. If a fighter is not learning and practicing and improving every day, if he is not self-aware, relentlessly asking where he can get better, he will be destroyed.
There is no excuse for ever ending the process of improving.
Is it all that different for the rest of us? Are we not fighting for or against something? Are we the only ones who have goals and aspirations? Is there anything but upside to waking up in the morning and taking a minute to ask yourself, “What am I going to work at today?”
The legendary MMA fighter Frank Shamrock put it best, “Always stay a student.” Pick up a book on a topic you know next to nothing about. Put yourself in rooms where you’re the least knowledgeable person. Technology has eliminated the barriers to learning. The information available to us has never been easier to access. There is no excuse for ever ending the process of improving.
What can I let go of?
We all carry wounds and grudges. People have wronged us. We have been hurt. We have been deprived. The question is: How long are we going to carry this around? What would we be better for letting go of? For dropping off our shoulders?
The truth is, in some form or another, we ourselves are guilty of most of the slights we hold grudges against. We don’t like someone because of something they said, yet how many cruel and unfair things have we said? We were hurt by our parents, but are we perfect mothers and fathers ourselves?
Every day we should take a few minutes to think about the baggage we carry and decide whether to keep carrying it. Some of it we do need to keep lugging around. Some of it we are not ready to part with — the wound is still too rare, and we are still too vulnerable. But there is plenty we can let go of. We can forgive. We can forget. We can move on.
We can be better (and lighter) for that.
Are these all the questions we should be asking ourselves? Of course not. But they’re a start.
Try asking and try answering. You won’t always get it right. People won’t always understand. But that’s the point, right? What do you care what they think?
What matters is that you’re never stopped from acting with justice, courage, temperance, and wisdom. That’s the goal.