The Hidden Power of Saying Yes

Saying Yes can open doors you didn't even know existed

One of the most common pieces of self-improvement or business advice is to make a habit of saying No. They say you ought to say No more often - a lot more. They say you need to be ruthless in saying No so you can have relentless focus on your mission.

There are good reasons that most of us ought to be saying No more often than we do:

• There are a lot of things we already want to say No to, but just don’t do it because we’re too afraid to say so.

• Some people are just taking advantage of us with their asks.

• Sometimes the things people ask for pose moral or ethical conflicts - and even then we can struggle to say No.

• If we say Yes too often, it can put our mission at risk and even cause us to neglect our own responsibilities.

It’s not wrong to tell people to say No, but it’s incomplete. There’s a case for saying Yes that’s too often ignored.

Here are three big reasons why you should be saying Yes.

1. Yes is much more powerful than No.

Yes is more powerful than No because Yes has more optionality. There are more things that can come out of saying Yes than saying No. Saying Yes opens up entirely new possibility spaces, and maybe even entire new futures for you that you didn’t even imagine existed.

Focus is important, but the most important breaks in life are often the ones that seem random, that come from unexpected places. Writer Nassim Taleb talks about this in his books like Fooled by Randomness and Antifragile.

Taleb says, “You make forays into the future by opportunism and optionality…Look for optionality; in fact, rank things according to optionality.”

Optionality is part of the reason industries cluster in a small number of places, like tech in Silicon Valley. These places, where lots of top people in the same field congregate, grease the skids for serendipitous encounters that lead to an investment, a sale, a key new hire, a hot bit of industry news, a book contract, or the solution to a problem. They are places where opportunity and optionality abound.

Saying Yes to someone who wants to grab coffee creates the possibility, the option, for that kind of magic to happen. Saying No does not.

That’s why Taleb talking about saying Yes to invitations to parties or meeting invitations. He writes:

Seize any opportunity, or anything that looks like opportunity. They are rare, much rarer than you think. Remember that positive Black Swans have a necessary first step: you need to be exposed to them. Many people do not realize that they are getting a lucky break in life when they get it. If a big publisher (or a big art dealer or a movie executive or a hotshot banker or a big thinker) suggests an appointment, cancel anything you have planned: you may never see such a window open up again. I am sometimes shocked at how little people realize that these opportunities do not grow on trees. Collect as many free nonlottery tickets (those with open-ended payoffs) as you can, and, once they start paying off, do not discard them. Work hard, not in grunt work, but in chasing such opportunities and maximizing exposure to them. This makes living in big cities invaluable because you increase the odds of serendipitous encounters—you gain exposure to the envelope of serendipity. The idea of settling in a rural area on grounds that one has good communications “in the age of the Internet” tunnels out of such sources of positive uncertainty. Diplomats understand that very well: casual chance discussions at cocktail parties usually lead to big breakthroughs—not dry correspondence or telephone conversations. Go to parties! If you’re a scientist, you will chance upon a remark that might spark new research. [emphasis added]

I’ll give a real life example from my own life.

When I was working in consulting, I started a blog called the Urbanophile, the lover of cities. Growing up in a rural area, I fell in love with cities when I moved to Chicago. I was passionate about discussing urban issues in a way I no longer was about consulting. So I started my blog. And it turned out to be very popular. It occurred to me that I might want to do something in this space professionally.

One day I put up an article contrasting the ideas of the major urbanist writers Joel Kotkin and Richard Florida. Joel must have had a Google alert set because he wrote to me and asked if I’d write for his website New Geography. NG was basically a group blog itself. It didn’t pay anything to writers. I might well have decided I needed to focus on building up my own site and said No.

But I ended up saying Yes and writing a bunch of free pieces for Joel. Later he introduced me to the editor of City Journal magazine, where I wrote a few articles that performed very well. Eventually, the Manhattan Institute, which publishes City Journal, hired me as a full time senior fellow and I moved to New York City and worked there for five years.

Saying Yes to writing free articles for Joel turned into a dream opportunity for me - an opportunity I had no idea would come from that first Yes. Had I said No to him, who knows were I’d be today.

This pattern has recurred multiple times for me. I met the person who ended up becoming my biggest financial supporter when he cold emailed me asking to meet for a drink while he was visiting New York City. I had no idea who this guy was, but saying Yes to the meeting again opened up possibilities I had never imagined.

Yes has optionality. Yes is powerful. Yes can open doors you don’t even know exist.

2. Saying Yes is a way to do things that don’t scale.

One of the classic pieces of advice to new tech startups is to “do things that don’t scale.” Although you want to be in a business that theoretically has very high scale and “flywheel” effects, you often have to do a lot of non-scalable pump priming to get there.

For example, the founders of Stripe, the dominant online payments processor, used to personally install and configure their software on prospects’ web sites. If they were meeting with a prospective customer, they would offer to install the software personally right there on the spot. Obviously they couldn’t keep doing this, but it was key to getting their business off the ground.

Taking all those coffee meetings or Zoom calls, being a guest on all those small podcasts, answering the random email from someone who asks you a question are all things that don’t scale, but are part of helping you achieve escape velocity.

Let’s be honest, most of us aren’t so busy that we can’t do these things. Few of us are celebrities that get besieged with requests every day. I’m a busy person, but even I am able to respond to most requests and say Yes to a lot of them. I’m only now reaching the point where I’m pondering whether I should be transitioning to saying No more often.

One of my guiding principles is to “pay it forward.” I want to help out others who are getting started in this business the way bigger name people helped me. So I go on a lot of smaller podcasts, most of which probably will never do anything to help me out.

I want to pay it forward regardless of whether it benefits me or not, but like many things in life, it sometimes turns out that you end up doing well by doing good. For example:

• All it might take is one high value person finding me through one of those podcasts to make the investment of all that time on all those small podcasts more than worthwhile.

• Some of those people who are much smaller than me today in terms of audience might one day be much bigger. Just as I never forget the people who helped me when I was trying to get off the ground, maybe they won’t forget it either.

3. Saying Yes helps you stay relevant.

Saying No is related to the bigger self-improvement idea you also hear that you should ruthlessly prune people out of your life that aren’t pulling you up.

This an example of the “too cool for school” attitude that I can’t abide. There are a lot of people - I’m sure you’ve come across them in your life - who spend all of their time networking up. They only want to talk to or invest time in relationships with people that they think can do something for them.

The problem with this approach comes when you succeed at it. It ends up isolating you from contact with the real world, you end up losing touch, and ultimately end up not being relevant anymore.

This happens to almost everyone who gets famous, even if they don’t do it intentionally. Being forced to winnow a flood of requests disconnects you from anybody else who isn’t a VIP, which ultimately cuts off from contact with the world.

This seems to have happened to journalist Thomas Friedman, for example. Tanner Greer wrote a great piece about Friedman’s story arc that explores what happened. Friedman studied the Middle East, then ended up as a New York Times correspondent in Beirut and Jerusalem. This gave him profound insights into the globalizing world that he used to write multiple influential books like The Lexus and the Olive Tree and The World is Flat. It’s hard to overstate the extent to which the latter book made Friedman into a prophet like figure for corporate America.

Fifteen years later, Friedman was something of an internet joke. People would write parody columns in which he explained the world through a conversation with his cab driver. As a superstar columnist, he spent his days doing things like hobnobbing with other elites at the Aspen Ideas Festival. He wasn’t on the streets of Beirut anymore gaining insight into what was coming next. Those elite conversations are important, but they are also one dimensional. Perhaps Friedman overly relied on his proverbial cab driver because riding in a cab became one of the few times he interacted with the kinds of people he used to talk to daily when he was a foreign correspondent.

For people who hit Friedman’s level, or say the Hollywood celebrity tier, avoiding this trap is almost physically impossible. So they can’t be judged too harshly for it.

But the same thing can easily happen to us if we detach ourselves from the everyday kinds of contacts that come from saying Yes to people who aren’t in a position to do us immediate favors.

Young people in particular are a great source of insight, a great way for older folks to keep at least some connection to the zeitgeist. Helping them or meeting them when they ask for it is a free chance to learn something. That’s why I love talking to college students. They are my pipeline to the now.

Despite the abundance of advice to say No more often, it’s not obvious whether most people’s problem is that they aren’t saying No enough or whether they aren’t saying Yes enough, letting opportunities pass them by. For the average person, my guess it’s more likely that they should be saying Yes more often, not less.

Note: I originally gave the case for saying Yes in a podcast two years ago. When I posted it, a bunch of people used it as an opportunity to ask me for things. I admire the hustle, but please don’t do that this time. There’s a time to ask me for things, but this isn’t it.