By Ethan Maurice | April 15, 2021

Yes or no — which is best? It’s a question that appears to need more context, but actually doesn’t.

Rather, the question of yes or no is about our unconscious tendency to lean towards saying “yes” or “no” when opportunity presents itself in life. 

If you really think about it, even a slight preference towards saying “yes” or “no” to the unfathomable amount of potentials we encounter throughout a lifetime is probably hard to overstate. For this reason, many have argued for conscious consideration of our often unconscious answer.

The kicker is everyone seems to advocate for a different answer.

Some are all about saying “yes.” Others are all about saying “no.” There are books and movies about the power of saying “yes” and writers who say “no” to everything except writing books and movies. A third school of thought also exists in the space between yes and no, interestingly, without the inertia of maybe.

The further you get into it, the more complicated and complex the question of yes or no becomes. It is, however, worth a dive into the complexity because the yes or no we unconsciously lean towards has tremendous influence on the decisions that shape our lives.

I invite you on a little journey with me — through the merit of “yes,” “no,” and the surprisingly enthusiastic space in between — to see if we can’t shake out a more nuanced, situationally-considerate understanding.

My inquiry into the question of yes or no began with a grand summer mucking about the Big Island of Hawaii with a friend I referred to as “the Yesman.”

The Yesman earned his name through a string of yeses. “Yes” to a friend’s suggestion to spend his college summer break in Hawaii. “Yes” to WWOOFing at a small farm he knew next to nothing about far out in the jungle on the rainy side of the Big Island. And a third, “yes” the moment he arrived at that farm, to inhabiting an inconvenient, yet totally epic treehouse thirty-some-odd-feet above the ground.

I had arrived at the farm a week before and said “no” to the treehouse, opting to live below in a pink, primitive shack. The shack was convenient and homey, but I was impressed and a tad envious of this new guy’s willingness to climb thirty feet of sketchy ladder multiple times a day to live the dream of childhood dreams: high-up in a treehouse in a far away jungle.

One of our first days together, the Yesman recounted the string of yeses that transported him from college classroom in Washington State to treehouse in Hawaiian jungle. Together, we explored the philosophical implications of “yes” as a deliberate answer. He then did something that struck me as bold: he vowed to make an experiment of saying “yes” to everything for the entire summer.

We fast became best buds and I soon discovered the Yesman was a man of his word. There is probably a book to be written on the adventures “yes” sent us on that summer—clothing optional hippie drum circles, riding in the back of dump trucks atop piles of fruit down rainforest highways, body surfing empty black sand beaches at sunrise, nearly getting blown out to sea while deep sea fishing in an aluminum rowboat, and a hundred other wilder-than-imagination memories come to mind. I left the Big Island both glad to be alive and forever enamored with that simple word of agreement.

A few years after our summer in Hawaii, I published an interview with the Yesman. 

“Yes” was his tool for encountering the unknown and experiences beyond the scope of imagination — from living in a treehouse in Hawaii and hot air balloon rides to crowdsurfing at concerts he regularly won free tickets to by calling into radio stations and roping himself into trying out for and giving his college graduation speech.

It was also about facing fears. “Yes” was especially to be applied to those “should I” and “what if” questions that pop into our heads when we see a remarkable possibility but fear taking the chance. When those questions arise, a Yesman always knows the answer.

I shared the interview on Reddit to a fantastic response. People reminisced on past Yesmen in their lives. Someone explained that “yes” was one of the tools that helped them out of depression. Someone else mentioned that the Yes Man movie with Jim Carey was based on a book written by an English bloke (I read it and it was a bold and bloody hilarious testament to yes).

Among essentially all positivity and praise of “yes,” though, was (a guy who at least claimed to be) a Hollywood screenwriter. He was no fan of the yes approach. After a few disparaging comments he wrote:

Look. I’ve said yes to a lot in my life and achieved my dreams of being a screenwriter, traveling the world, having a great partner, a group of friends who supports each other, having a body that’s more strong than I ever thought possible, gone skydiving, had an insane mansion in the Hills of L.A., driven across the country three times, fallen in love hard a few times (enjoying it each time regardless of the pain it causes), being diagnosed and getting treated for a mood disorder and addiction.

Whatever who cares. It’s a long list of yes.

I have a life that I couldn’t have imagined in my wildest dreams.

Yes didn’t do it.

Yes isn’t enough.

It took work. A lot of work. It took a lot of hardship and loss. There weren’t any shortcuts.

There seems to be a fascination with “following your dreams” these days.

You don’t follow dreams.

You chase them.

No one is going to take care of your dreams but you. Certainly not the cosmos.

I’ve literally seen people die for their dreams. You won’t realize yours just for showing up.

And if you do, no offense, but your dreams are too easy and you’re not living to your full potential, you’re living life in comfort and talking a lot of shit.

Proclaiming the key to life is just saying yes to everything (sort of everything, I’m still not clear on exactly how his yesman ideology works), is a lot of bullshit.

40 years into living, I’ve seen people who just lived yes. They did what they wanted on impulse. They were the coolest when I was in my 20's.

A couple decades of yes later, those people are broke, broken, and have lost their freedom to say yes because they can’t walk, are drug addicts, have no money (which buys a lot of yes) or they’re dead.

Freedom is a tricky thing. You can use it for the short term or you can build it up and use it for the long term.

So yeah, you can feel free everyday by saying yes to random shit and patting yourself on the back for your bullshit courage.

OR

You can put work in, give your life and dreams the respect they deserve and be free forever.

Surely this Reddit Screenwriter Guy was shortchanging his own unconscious orientation to “yes,” but he had a point: yes to everything is indiscriminate.

Should we not commit ourselves to the things we value most? Are the “no’s” required for hard work, focus, and discipline not the tool for turning dreams into reality?

After Hawaii, I continued my wandering, “yes” led lifestyle — a period of five years of deliberate exploration, spending time in different ways in different places, devouring diverse books and saying yes as a means of storming the shores of my ignorance and discovering some blind spots in my secondhand understanding of life.

However, probably because Reddit Screenwriter Guy called my interview with the Yesman a “fanciful metaphysical broride,” my awareness always remained attuned to different perspectives on the question of yes or no.

Six months after Hawaii, I discovered and began regularly listening to podcasts while living in Playa del Carmen, Mexico.

I got into cooking in Playa del Carmen, and often listened to The Tim Ferriss Show while making dinner. One day, I stumbled upon one of my all-time favorite podcast episodes, #125 with Derek Sivers.

Among many legendary stories and little anecdotes, Derek explained how he came to live by the rule of Hell Yeah or No. His argument was short, simple, and sensical. Here it is in its entirety:

Use this rule if you’re often over-committed or too scattered.

If you’re not saying “HELL YEAH!” about something, say “no”.

When deciding whether to do something, if you feel anything less than “Wow! That would be amazing! Absolutely! Hell yeah!” — then say “no.”

When you say no to most things, you leave room in your life to really throw yourself completely into that rare thing that makes you say “HELL YEAH!”

Every event you get invited to. Every request to start a new project. If you’re not saying “HELL YEAH!” about it, say “no.”

We’re all busy. We’ve all taken on too much. Saying yes to less is the way out.

Another blogger, Mark Manson, soon echoed Derek’s idea, but applied it specifically to relationships in an article entitled Fuck Yes or No. 

To avoid the grey area of dating people we aren’t really into and who aren’t really into us, Mark established The Law of Fuck Yes or No:

The Law of Fuck Yes or No states that when you want to get involved with someone new, in whatever capacity, they must inspire you to say “Fuck Yes” in order for you to proceed with them.

The Law of Fuck Yes or No also states that when you want to get involved with someone new, in whatever capacity, THEY must also respond with a “Fuck Yes” in order for you to proceed with them.

Which explicative you attach to the phrase is of less consequence — whether hell or fuck — both are meant to convey great enthusiasm. And by making great enthusiasm a requirement for saying “yes,” we can spend less time in the halfhearted, grey areas of life.

In my circles, Derek’s and Mark’s ideas made a big splash. Friends and others I look up to referenced Hell Yeah or No and Fuck Yes or No surprisingly often. The wandering, renegade “yes” approach I lived by felt increasingly stark in contrast with the more discriminant, value-driven rest of the world.

Then, I read The War of Art — a potent little kick-in-the-ass of a book for creatives by Steven Pressfield.

As artists, Steven argues we should say “no” to everything except our creative work. By saying “no” we devote ourselves to what matters most to us. Like professionals, we show up every day, rain or shine.

“No” is the tool for putting in time and doing the work. 

Dedication to our creative work makes what Steven calls “the Muse” happy. In turn, the Muse provides the artist with gifts — with ideas and inspiration — from a place all artists intuitively know exists somewhere beyond themselves.

It was a damn beautiful, compelling “no” thrown into my inquiry into yes or no question.

Steven’s train of thought offered a ride to not just artists, but everyone. Saying “no” to other things isn’t just how books are written — it’s how businesses are built, habits are forged, relationships are invested in, and meaning itself is made: we sacrifice other things for the thing we value most.

Eventually, it occurred to me that I had heard, saw, and felt the merit to the entire spectrum of responses to the question of yes or no.

There were compelling arguments for “yes,” “hell yeah or no” and “no” collectively covering the entire spectrum of possible responses.

We can visualize this on what I will dub The Yes or No Spectrum:

In one way or another, every answer on The Yes or No Spectrum makes perfect sense. So what’s the best answer to the question of yes or no? How can there even be one?

Fortunately, there is a best answer. Unfortunately, the best answer is this:

It depends.

It depends because “yes,” “hell yeah or no,” and “no” are the best answer to the question of yes or no depending upon one’s current life situation.

As we begin our adult lives, it makes sense to start on the right of The Yes or No Spectrum with “yes” because we are discovering ourselves and the world. The younger we are, the more our values and ways of being come secondhand from the past experiences of others, mainly, from our parents and community.

Saying “yes” is an intentional means of indiscriminate experience — a tool for random encounters with the whole of life that test our values and exposes shortcomings in the ways of being we have adopted that were developed in the past by others. “Yes” takes us places wilder than our imaginations can go.

Saying “yes” also spurs us to face fears. And as Joseph Campbell once so profoundly put it: “the cave you fear to enter holds the treasure you seek.”

In the freedom and time abundance of youth, before we set upon more defined and specific paths, “yes” is a means of exploring the world at large and entering the caves we most fear, where we may have the good fortune of finding — and then — investing in a lifetime of our kind of treasures.

Reddit Screenwriter Guy was right. At some point, we must stop saying “yes” to everything to invest in our earned values and the treasures we have found. What would be the point of testing and improving our values if we never invested in them?

So, eventually, we slide left on the The Yes or No Spectrum to “hell yeah or no.” We devote our time — our most valuable resource — to our values and only let new things into our lives for which we have great enthusiasm.

If we find a calling — something we value as much as Steven Pressfield values the creative act and conferring with the Muse — then saying “no” to everything else is the means of making the largest investment in that thing.

To put it graphically, The Yes or No Spectrum functions like this:

Here’s what I’m suggesting: as we go through life, the general pattern to follow here is to start on the right of The Yes or No Spectrum with “yes” to find, test, and develop our values and then slide left to “hell yeah or no,” or even “no,” to invest in them.

When we take the whole arc of life into consideration, not just the point we are currently at, it becomes clear that there is no, singular best answer to the question of yes or no. Each answer is the best answer at particular, different times in our lives.

However, over a lifetime, there’s a problem with simply starting with “yes” and permanently sliding left to “hell yeah or no,” or “no.”

When we leave “yes” on The Yes or No Spectrum, we switch from testing and improving our values to investing in them:

In crossing the dashed line in the chart above, our values switch from dynamic and evolving to static and rigid. For this reason, over time, ceaseless “no’s” and even “hell yeah or no’s” can be problematic.

Perhaps you also know an older someone who’s stuck in his or her ways, often complains about the way things are, and wishes that things were the way they used to be?

A permanent crossing of the dashed line in chart above is likely the cause.

They crossed that dashed line and started saying “no” to everything except their set-in-the-past values and familiar experiences. Over time, the dynamic, ever-changing world went on changing — and they didn’t. Whenever they crossed that dashed line, that’s probably the time they so fondly gaze back upon and refer to as “the good old days.”

So, saying “yes” to things we do not feel “hell yeah” about once-in-a-while is essential to not becoming too set in our ways and stuck in the past.

The other thing nobody really wants to admit is that our values aren’t perfect. All of us experience and understand but a sliver of the whole of reality — a vast sea of ignorance stretches far, wide, and unfathomable fathoms deep for all of us. If we permanently stick with no and thus never venture beyond the shores of our knowledge, it’s easy to convince ourselves that we’ve got it all figured out, when in truth, we can only be sure that we don’t.

So, throughout life it’s good to shake things up and deliberately say “yes” to things we don’t feel like saying “yes” to every once in a while. Otherwise, we run the risk of getting stuck in the past and losing touch with the present.

In a most general fashion, we can graphically summarize all this by somewhat confusingly flipping The Yes or No Spectrum vertically and adding time as a second axis:

In short: “yes” is for seeing anew and surveying the land. 

“Hell yeah or no” and “no” are for doubling-down and settling the places worth calling home.

The best answer to the question of yes or no is to slide our default answer from “yes” to “hell yeah or no” to “no” across a lifetime, while periodically — when the time is right — jumping back to “yes” to drop our patterns and renew ourselves in the ever-new, ever-evolving present.