The Obligation Mindset

The Art of Saying "No" Even When You Want to Say "Yes"

This is for all the people who want to say yes to everything all the time, always and forever. Who maybe, like me, have gotten to a place where they’ve gotten a little bit better because their time has gotten more valuable. When they’ve become a little more disciplined but still in their heart and soul want to say yes to everything.

You just got to look in a different direction. Realize you have the obligation to finish the yeses that you’ve started. And what I mean by that for example, is I get a lot of my companies and a lot of my projects to the 90 percentile and then move on because I have so many more new “yeses.”

The Evolution of “Yes”

One of the great gifts and curses of my life is I want to say yes to everything. It was a remarkably great gift early on in my career because I had unlimited time, unlimited responsibility, unlimited energy, unlimited ambition, and unlimited humility. Nothing was beneath me. No one was beneath me. Thus, everything was yes, yes, yes. And all those incredible yeses created serendipitous outcomes, friendships, memories, inside jokes, and many professional upsides.

As my career started to evolve and my life started to evolve, family, children, personal life, obligations, and then ultimately hitting this crescendo moment where my time just became outrageously valuable. All those things became true. However, my essence still wants to say yes to everything, every ask, every need. And it’s a really interesting challenge. No question.

The Practical vs. The Romantic

The best thing I can do 98% of the time I’m approached with something is to say no. Yet, I still find myself saying yes—whether it’s 80%, 50%, or 30% of the time, I’m not entirely sure. What I do know is that I’m saying yes to things that people with my background and career path are saying no to, and they view that as an incredible strength.

I think that’s right practically, but emotionally I don’t think it’s right. And there’s a part of me that ideologically and romantically believes that one random yes when everyone else would have said no to it, actually leads to something that creates all the other “wasted time” to be net ROI positive.

However, even with that romantic ideological POV that is grounded in me actually believing it’s true, I do sense a need to be better at saying no, to get into a place where I fulfill the obligations I’ve already said yes to all the way through before I add more yeses. But I’m still trying to figure it out. Practically, I should be saying no to many, many things that I say yes to, especially when I have obligations to see through. Aka, how much longer can I just surely use my will to make everything happen? And at what cost?

The optimist’s dilemma.

The 90% Hurdle

Whether it’s Resy, Empathy Wines, or my books...almost everything I do, I take to 90% of my capacity. It feels like 120% effort, but I know it’s only 90%. The only reason I don’t push them to that 100% (which would feel like 400%) is because I’m already onto the next thing, like opening Flyfish Club.

We are working on a new book and I’ll take my foot off the pedal when it gets to a good place. If I didn’t say yes to four more things and just saw that through, it’d be three times more successful. That’s what I’m trying to figure out later in my life and that’s why I’m calling it an obligation.

If I became more romantic in seeing my obligations to 100% (even though my 90% looks like everyone else’s 150%), which would require me saying no to a couple more things, I think everything that I’m working on would work better. It’s very nuanced.

And now I’m trying to be vulnerable and introspective and share some content that might help someone else. This article is for the minority of very successful people which is rare for me. It’s why it’s unusual, which is cool.

Young People Need To Say “ Yes” More

I think the world is grounded in too many people that say no when they should say maybe, which leads to the best yeses of their lives. And I believe that people start saying no out of sheer ego. Those are two things I want to desperately avoid. It would make me sick if I knew how many things young people say no to. For example, saying no to going to a birthday party? Massive mistake. Too many serendipitous things could have happened there. Now the question becomes, why are you saying no? Let’s break it all down. For example, are you a human where small talk with strangers sucks energy out of you and that puts you in a bad place? If the answer is yes, now I understand why you said no. But now I want to know why.

It’s really out of insecurity or ego for not enjoying small talk. There is no other path. What if that leads to such a great thing for you that you need to lean into more humility or more confidence?

How cool is that?

If you say no it’s over. If you say no to playing Monopoly you can’t win Monopoly. But if you play you could win, but you could lose it. But if you don’t play it you’ve already lost it. So it’s very clear to me and when you’re young, there are so many opportunities for love, for new friendships, for money, for exploring your favorite passion that you didn’t know. And to all the kids, you guys all need more friends not less right now.

This leads to the remote vs office conversation. My favorite thing about our office is the culture I’ve created allows people once they get there to know they can say hi to somebody. Like your true best friend in the world might be sitting in the media department right over there. And when you are remote you need to force yourself to get out and meet people.

No Fear

I genuinely do not fear the judgment of others, I have to not waste any time. I’m not worried about people’s opinions because I have the luxury of knowing how good my intent is.

Nice guys finish first, friends. Because when you’re purely a nice guy or gal, you don’t have to think. Because if you’re portraying a nice guy or gal and you’re not, you have to maneuver. And maneuvering is heavy and slow. Authenticity is light and fast.

I make a lot of decisions every day. I prefer all of them to be remarkably good decisions. I just know that most of them aren’t massively important, mostly micro decisions, not huge ones.

I lack fear because of that which means I go fast because I’m not scared of the consequences and I’m also experienced now. So a lot of the mistakes I made are out of the way. I’m not going to replicate them.

So, now I’m just in my prime.