Hell Yeah or No (Part I)

*Deep thinkers who tend to reject the standard answers given by society to life's most urgent questions, and who want to build a life that's truly their own.

*Young people, especially those thinking of investing large sums of money into their education, who are open to receiving generous, well-intentioned advice from someone who has faced the same challenges as they have and come out the other side happy and free.

*Everyone who sees the value in holding two contradictory ideas in their head at the exact same time, believing aspects of both, and acting intelligently in spite of that contradiction.

*Artists and creatives who want to devote their lives to their art, but who don't feel like starving while they master their craft.

"When life or a plan feels ultimately unsatisfying, I find it's because I've forgotten to find the intersection of all three: what makes me happy, what's smart, and what's useful to others."

-Derek Sivers, Hell Yeah or No

Certain authors just become associated with particular ideas over time, and one that I continue to profit from handsomely – year after year after year – is Derek Sivers’ insight that when making a decision, it’s either a “Hell yeah!” or it’s a “No.”

Either you’re consumed with interest by what you’ve decided to do - it’s just so completely obvious that this is the thing you should be doing/want to do - or you’re better off not doing it at all.

Hell Yeah or No is a fairly quick read, full of exceptionally useful frameworks for thinking, and I ended up with dozens of book notes and brilliant ideas to think about later. The interesting thing, though, is that many of Sivers' conclusions contradict each other!

Derek is a special thinker in that way. He can calmly and wisely approach big, intimidating questions, and he can disagree with himself multiple times (sometimes even in the same essay), all while getting closer and closer to a tentative answer that he then rigorously tests in the lab of his own life.

He's no armchair philosopher either! I'd even say that he's one of the most interesting people alive today. The dude sold his company, CD Baby, for millions of dollars, enabling him to forget about earning more money (he doesn’t need it or want it), and letting him put every single creative neuron in his brain into his creative work and, you know, living his actual life. And what a life!

In the past, he’s been a musician, a producer, a circus performer, an entrepreneur, a TED speaker, and a book publisher, but here in this book, he’s just your friend Derek.

Another really cool thing is that after the first 5000 limited edition hardcover copies he printed were sold out - raising $250,000 in 6 weeks - he donated the entire amount to help others. In his words:

“Yesterday I wired the entire $250,000 to the Against Malaria Foundation. That will buy 125,000 malaria nets, protecting ~225,000 people, averting ~65,000 cases of malaria, preventing ~125 deaths.”

Pretty damn cool if you ask me! Which you didn't haha. But still!

In the book itself, he prescribes the lifestyle of the happiest people that he knows: Having a well-paying job, while seriously pursuing their art for love, not money.

He writes that we all have a need for stability and adventure, certainty and uncertainty, money, and expression, and when we're out of balance, we need to step back a bit into solitude and silence, and really think through these problems for ourselves.

The book is just full of useful wisdom like this, and he lays out numerous simple though profound mental models to help guide our decision-making. He discusses things like:

*Leaving space and time in our lives so that we can throw ourselves completely into the few things that matter most.

*How good goals shape our actions in the present, not in the future.

*Why it's actually good to be a slow thinker and to change your mind often.

*How to relieve overwhelm by saying no to almost everything.

*Finding the intersection of what's smart, what makes you happy, and what's useful to others.

*The best way to sift through the advice (often unsolicited) that you'll often receive from others who think they know more about how you should live your life than you do.

*Why you should do everything that scares you.

*And a lot more....

Throughout the book, Derek Sivers makes a clear, concise, cogent case for the indisputably true assertion that this one life is your own, and you have to live it in a way that makes sense for you.

No one else on the planet has more at stake when it comes to your life than you do. Making good decisions and living fearlessly according to what you've decided takes astounding courage, but no one is more capable of doing it than you are.

#1: If It's Not a Hell Yeah!, It's a No

“Say no to almost everything. This starts to free your time and mind.

Then, when you find something you're actually excited about, you'll have the space in your life to give it your full attention. You'll be able to take massive action, in a way that most people can't, because you cleared away your clutter in advance. 

Saying no makes your yes more powerful."

Every single thing that you've said "yes" to in the past is yet another link in the chain, holding you hostage in the present.

When you think about it this way, you'll be a lot less inclined to start shackling yourself to additional chains, many of which represent commitments that don't even serve the person you've since become.

Maybe I'm being a little overly dramatic here, but the point still stands: "No" is a complete sentence, and it's your shield against a life of trivia, distraction, and unfulfilled potential.

I don't mean that saying "Yes" to being a parent, or starting a charity, or developing a skill is the same thing as being a slave, but it's important to realize how hard it is to make significant changes in your life if you're burdened by the weight of decisions you've made in the past.

So whenever you're tempted to add an extra time commitment to your already packed schedule, you may want to consider thinking about it in terms of its cost to your time and possibilities in the future, and how it will prevent you from being able to say yes to other things that you may find more important when that future inevitably becomes the present.

A few things to say here before we move on:

By all means, be nice to people when you're turning down their requests for pieces of your time and attention!

There's no need to rudely brush people off, or wail theatrically about the unfairness of the finitude of human existence, but your life is your life. No one owns it but you, and you need to be extremely intentional about how you live it, or the outside world will attempt to tell you exactly what to do with it, and that may not exactly be in your best interests.

Lastly, protecting your time and your attention gives you resources - literally makes you resourceful - and then, once you do find something you want to dedicate yourself to wholeheartedly, you'll have the mental bandwidth, and the time, to fully pursue it. To go all-in on what you actually want to do with your life.

As they say, it's virtually impossible to overstate the unimportance of nearly everything, and so Derek's filter is an excellent one to employ:

If, when presented with an opportunity, you're not jumping at the chance, saying "Hell yeah!" either out loud to yourself, then just say no. Wait for your moment. Wait for your opportunity. And then give it everything you've got.

#2: What If You Didn't Need Money or Attention?

“We do so many things for the attention, to feel important or praised. But what if you had so much attention and so much praise that you couldn’t possibly want any more? What would you do then? What would you stop doing?”

Who would you be if no one told you who you are?

Who would you be if you didn’t do those things that so many of us normally spend our days doing: coveting praise, chasing money, and seeking validation?

As I've said many times, there's absolutely nothing wrong with wanting to make more money - plus, everyone loves to feel good about themselves. And why shouldn't they?

Wanting to be seen in a positive light by others isn't "bad" in itself. But when it consumes the energy and focus of our entire waking lives, we're robbing ourselves of priceless, productive energy that we could direct instead toward something much more meaningful.

These vain pursuits handcuff us to the actions we've already chosen in the present, and it's even worse if your identity happens to be tied up in how others see you and what you're "worth" economically.

Anything that limits your freedom in this way is limiting your ability to maneuver, to choose a different path.

So why do people waste so much time doing these things, even though, if you were to ask them directly, they'd probably concede that those things aren't all that important?

Well, if you want to understand virtually anything, it's always a good idea to look at the incentives. Who stands to gain from me taking this or that action? Believing this or that idea? Who does it serve? What course of action is incentivized?

Making you feel like you're not "enough" is literally a multibillion dollar industry, made up of car companies, jewelry companies, news and media companies, and so on.

Individually, they're just trying to make a fair profit, and there's nothing "evil" about making people want to buy shiny rocks or fast cars. But collectively, they're robbing all of us of our mental freedom to figure out who we are, what we value, and what we want our one and only lives to be about.

But you don't have to get all tangled up in this.

You can slip out of the handcuffs and begin to ask yourself the deeper questions. Questions like, "Who am I?" That's a great one to start with! And you'll never fully answer that question, not for as long as you live. It's always changing, always evolving, the answer forever moving away from you, calling you to keep asking the question.

So let's return to Derek's question. Say you had all the money and attention and praise that you wanted. What do you do now? Where do you go from here? What's important and real?

#3: Fill Empty Time with Great Things

“Empty time has the potential to be filled with great things. Time filled with little things has little potential.”

How's this for an "obvious" truth that most people ignore for basically their entire lives: time is infinitely valuable, terribly finite, and once it slips through your fingers, it's gone forever and ever and will never, ever return.

You could remind yourself of this eternal truth literally hundreds of times a day, and in my opinion, it still wouldn't be enough. I like to keep bringing that obvious truth back to consciousness again and again and again, every single day of my life.

In one of my favorite time management books of all time, Four Thousand Weeks, by Oliver Burkeman, he writes:

“The world is bursting with wonder, and yet it’s the rare productivity guru who seems to have considered the possibility that the ultimate point of all our frenetic doing might be to experience more of that wonder.”

It leads one to ask, "Did I really find myself on this gorgeous planet, full of fascinating and wonderful people, only to passively scroll TikToks and respond to angry Facebook comments all day long?"

Sure, it's probably one of the "easiest" things to do with your time, and it's certainly what nearly everyone else is doing with their precious gift of life, but do you really want to be "everyone"?

Assuming you live to be 80 years old (and modern medicine is getting goddamn futuristic lately, so many people reading this will probably live far longer than that), you'll have had about four thousand weeks to be alive, active, and conscious.

You can spend this time any way you choose! That's your gift!

You can best honor this precious gift by choosing to fill this time with great things, not small ones. Fill it with love, energy, creativity, generosity, and more life.

#4: What's Obvious to You Might Be Amazing to Others

"Hit songwriters often admit that their most successful hit song was one they thought was just stupid, even not worth recording. We're clearly bad judges of our own creations. We should just put them out there and let the world decide. Are you holding back something that seems too obvious to share?"

This is something that held me back for a long time. It still comes up occasionally: I always assume that everyone already knows what I've just learned.

Over the last 10+ years, I've read more than a thousand books, started two businesses, grew a big online following, etc. etc., and I'm often still surprised when someone expresses shock or amazement after I tell them about something I learned years ago. Has this ever happened to you?

It's far too easy to err in the opposite direction, of course, going around thinking that you know the answer to everything and that nobody will ever have the knowledge base that you have. I think you're going to want to avoid adopting that attitude! But you'd be surprised how common the former situation is!

All of this is to say that there is probably something that you know, or that you've done, or learned, or can do, that is just a regular part of your life, but that would absolutely blow someone else away. Something that's obvious to you, but would be amazing to others. Something that you barely even have to think about, but that to someone else would be revelatory. That they might even gladly pay you for!

Not that you have to turn it into a marketable skill or anything; it's just that maybe you should let the world decide if what you can do is amazing or not.

If I can use myself as an example again, sometimes I'll mention something that I read about in a book years ago, the person I'm speaking with will just get it, and they'll get this...look. I've seen it many times, and it always comes out of nowhere. It's the look of someone who's just had the dirt cleared from their mental windshield because of something I said, something that was just a throwaway statement to me, but that made a measurable difference in their life.

The best part is that this is probably true for you as well!

Or, at least it could be true if you kept working on your art. Or your skills. Or whatever it is that you do that most people can't.

Sometimes, we're poor judges of what's actually amazing, and what's worth sharing. Get the world's opinion before you decide that there's nothing special about you, because maybe it's there and you're just not seeing it.

#5: Admit to Yourself What You Really Want - And Then Fearlessly Pursue It

“You don’t want that horrible regret, feeling like you spent your life pursuing what someone said you should want, instead of what you actually wanted.

For example, if you want to make a lot of money, you need to admit that. If you want to be famous, you need to pursue that. If you want freedom and no responsibilities, or want to learn as much as possible, or whatever else, you need to realize it and embrace it.

Whatever you decide, you need to optimize for that goal, and be
willing to let go of the others.”

One of the things Derek Sivers does best is inspire fearless self-reflection and brutal honesty in others. He helps people see their own blind spots, and lets them know that there's nothing to be afraid of when it comes to gaining self-knowledge.

Some part of you might think that your burning desire to get rich is "wrong" or "immoral," or whatever else, or that you shouldn't want what you actually do want. But, as I'll say over and over again, if you getting rich and famous doesn't hurt anyone, then go for it.

Maybe you'll realize that it wasn't worth it in the end, but then again you may find that it's exactly what you wanted. You'd be doing yourself a massive disservice if you didn't go after these authentic desires with everything you have within you.

"And this above all: to thine own self be true," says Shakespeare's Polonius in his play, Hamlet. That advice is literally thousands of years old, and it's so important.

You have to be honest with yourself, no matter what. And that goes for everything. What you want, who you are, what you're willing to do to get what you want, what's important to you, what you believe...everything. The one person you should never, ever, ever lie to is yourself.

Once the truth about what you really want in life is out there, of course, you can't hide from it any longer. That's probably why more people don't admit these kinds of things to themselves: then they'd actually have to follow through on what they said was important to them.

The worst thing that could possibly happen, though, is to defer your dreams and your desires until it's too late to do anything about them.

Make no mistake: people are going to misunderstand you when you start to articulate your authentic desires and pursue them with intention and vigor. They've lied to themselves their whole lives, and on some unconscious level, it bothers them to see someone else live free and unhindered.

The thoughts and opinions of those people are no concern of yours. If you have a strong sense of self, a clear direction and vision for what you want your life to be, the words and opinions of those other people will start to lose their hold on you. As Derek Sivers writes:

“But whatever you choose, brace yourself, because people are always going to tell you that you’re wrong. That’s why you need to know why you’re doing what you’re doing. Know it in advance. Use it as your compass and optimize your life around it.”

#6: Become a Bat (Yeah, a Bat)

“The problem is taking any one person's advice too seriously. Ideally, asking for advice should be like echolocation. Bounce ideas off of all of your surroundings, and listen to all the echoes to get the whole picture.

Ultimately, only you know what to do, based on all the feedback you've received and all your personal nuances that no one else knows."

Learning whose advice to take and whose to ignore is one of the most valuable skills that you could possibly develop. It's also fraught with difficulty, because even well-meaning, good-intentioned people tend to give advice based on their experiences, and their worldview, not advice that's going to be specifically useful to you.

It's not usually their fault. Many of these people genuinely want to help you. They just don't know you, could never know you, and that's why you have to be extra careful.

As Derek points out in the book, even people commenting online aren't responding to the real You; they're responding to your online avatar, their representation of you that's taken up residence in their own minds, and you really do have to learn to ignore most of it. Even the good things they say!

This being the case, it's actually rare and valuable to be someone capable of giving great advice, and ultimately, you have to learn to trust yourself.

The same goes for the Stairway to Wisdom, by the way! Of course, I try to present the authors' views and ideas relatively dispassionately, and try to pick out the key ideas and takeaways that are going to be most helpful to the widest range of people. But I write the damn things, and there's just no way that my own personal viewpoint isn't going to seep through into what I write and the advice I give in these pages.

These book breakdowns are an interpretation, and even though I put a tremendous amount of time and effort into preparing them for you, it's still you that has to decide what's relevant to you and what to ignore.

So become a bat! Bats listen to the sound waves bouncing off the objects in their environments, and that's how they "see." Chiropterologists (people who study bats, and a word I looked up just now) are probably cringing right now at my 1-second explanation of echolocation, but that's the basic idea.

You sift through the sound waves - feedback you're getting from others, and the information you consume - and you slowly, over time, begin to build up an idea of what you think. You create your own representation of the world, and become your own chief counsel.

If you ask a thousand people about your business idea and they all tell you that it's a complete waste of time, maybe you'll want to reconsider. But then again, if 1,000 people tell you that it's a waste of time and 3 actual, successful business owners in a similar industry tell you that it might work, those are signals too.

It all comes down to this: don't take advice from people who don't have your best interests at heart, and who haven't achieved the kind of success that you're looking to achieve. Don't take financial advice from broke people, health advice from unfit people, or relationship advice from sixteen year olds.

#7: The Standard Pace is for Chumps

“The system is designed so anyone can keep up. If you're more driven than most people, you can do way more than anyone expects. And this principle applies to all of life, not just school."

One of the things that makes Derek's writing so special, as I've mentioned elsewhere, is that he's able to hold at least two conflicting ideas in his head at the exact same time and see how they might both be true in different situations.

Case in point: "the standard pace," i.e., go through school, get a job, stay there for years, retire, etc., is fine for some people. That might even be the life you want. You can complete a 4-year degree in 4 years, apply for a normal job, raise a family, and be perfectly happy with your life.

But then there are those other people.

You might even be one of them. Those people who crave challenge, who relentlessly pursue freedom, mastery, and creative expression. Those people who are so obsessed with what they're learning that they decide to do the 4-year program in six months, cold email dozens of professionals in their field, practice and/or study for hours and hours every night after work or school, and surge ahead in their chosen craft.

It's just that you have to be brutally honest about which one of those things most accurately describe you, and then do whatever it takes to build a life around what you value.

If you truly and honestly cannot stand to be held back by the "average" expectations reserved for the masses, then you have to acknowledge that, prepare yourself to go all-in on what you say you believe, and then actually go for it.

No one says that you have to slow down so that other people can keep up. Or that you have to downplay your accomplishments just so other people don't feel "bad" about themselves.

Again, it's about keeping two ideas in your head at the same time. You don't have to make a big deal out of the fact that you're moving faster or achieving more than everyone else...you just do it.

You realize that their path is theirs and yours is yours.

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