How to stop saying yes when you want to say no

Have you ever said yes to something, but immediately wished you could take it back?

There’s that nit-picky client who won’t sign the proposal. Do we need an internal meeting to discuss? Yes.

Your ex-boss’ son is looking to get into consulting. Could you grab a coffee with him to give him the lay of the land? Yes.

Your second cousin is hosting a “cousins reunion.” It’s just a three hour drive, right? Yes.

Yet after every “yes,” you feel a pit in your stomach.

It’s been four months since you read your kids Goodnight Moon without your mind sifting through your inbox. The end of Q1 is approaching and you’ve taken zero steps towards your personal BHAG of overhauling your firm’s investment process.

But mostly, you’re tired, overcommitted and just want to go for a long run by yourself.

In her 2016 TED talk, my year of saying yes to everything Shonda Rimes (the brains behind Gray’s Anatomy and Scandal) declared the “power of one word” and how “Yes changed my life; Yes changed me.”

Yes, in my own life “yes” has been an engine of serendipity, opportunity and inspiration. (Heck, it’s why RadReads exists.) Yet it’s also accompanied with a nagging feeling of frustration, resentment and burnout.

“Just beyond yourself is where you need to be” writes the poet David Whyte. But how on earth do you toe the line to actually get there?


Let’s start with an easy heuristic. This simple test works quite well as a solopreneur, as it protects your most precious resource: your time. The author Derek Sivers proposes two modes of action when evaluating an action:

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

Admittedly, there’s more nuance than these two states of the world. So how could you more deeply triage your decisions?

Decision overload

I’m going to bet that your “yes” come from a very noble starting place: curiosity. Whether it’s a new person to meet, a new book to read or a new rabbit hole to explore, the mysterious promise of what lies on the other side can be quite tantalizing.

In his post finding the one decision that removes 100 decisions Tim Ferriss explains how he was looking to make decisions “from a place of calm” as opposed to a “place of turbulence and blurred judgement.”

In order “to create space for seeing the bigger picture and finding gems” Ferriss identified a big domino in his own life: not reading any books written in 2020. For him, reading was a source of FOMO (being “wedded to the identity of being a well read guy”) and a “socially acceptable” form of procrastination.

Now this specific strategy may not be applicable to you individually, but the concept of aligning your “nos” with a your broader vision is a powerful one. As the investor Pedro Sorrentino said, “If you don’t guard your time, people will steal it from you.”

Stop paying it forward?

We stand on the shoulder of giants.

I stand on the shoulder of giants.

I would not have been pushed to go to Yale without my a college counselor invested in my future.

Phenomenal mentors propelled my rad career on Wall Street.

And every day a global tribe of radvocates fervently spreads the word about my creative endeavors.

How on earth could I say no that younger, eager version of me… looking for their life-changing break?

My answer: “You cannot give that which you don’t have.”

This mantra (from an untraceable source) helps me when I feel overwhelmed by meeting and Zoom requests, particularly from folks looking to learn from my career experiences.

The combination of a 15 year career and a regular online presence means that my inbox is inundated with requests to “pick my brain.” Yes, I’d love to answer each one – but that would come at a great cost.

My family. My health. My sanity.

Here’s where the mantra kicks in. If I am stretched on my giving, it still has a sneaky way of showing up. I come to the conversation distracted. Close-minded. Ego-centric. Or the worst: resentful.

I never want to show up like that. Not for my family. Not for an Internet fan who appreciates my work.

Two “pick your brain” strategies

I’ll concede that relying on existential questions might not pragmatically solve the onslaught of meeting requests. So here are two strategies you can immediately use.

First, set an internal quota. Doing this with a clear head (and with input from the key stakeholders in your life such as your spouse or business partner) can shift your decision-making from reactive to intentional.

You might decide that two mentoring meetings are in line with your current life priorities. Then stick with it. If you get three requests for February, roll one to March. If you get 24 in February, your year’s been set.

Next, find a mutually beneficial way to deflect. In his post my magic response to ‘Hey, can I pick your brain’ internet entrepreneur Alex Hillman has a stock answer (presumably in a text expander) to this frequent request:

I’m happy to help! I do keep my limited 1-1 time available for my consulting clients, students, and Indy Hall members, so right now the best way for me to help will be to know what questions you have upfront. Try to pick 1-2 that are most important to you, and the more specific the better!

For starters, Hillman reports that 70% “won’t bother to think about what their questions are ahead of time” and just drop the request. Think about that. You’re probably saying yes to 70% of people who can’t be bothered to think of what question they want to ask you!

For the remainder, Hillman then uses their questions as a vehicle for understanding customer pain points, writing ideas and even sales opportunities! He adds that this approach:

Makes it possible for me to help thousands of people, and all the while makes me look like a goddamned wizard who can read minds.

FOMO and the scarcity mindset

We haven’t really addressed the elephant in the room: the Fear of Missing Out. In an age of social media peacocking, infinite choice, and ummmm INSTAGRAM we’re terrified of missing that one big thing that snaps our lives into place.

In her post on JOMO (or, the joy of missing out) Ness Lab founder (and RadReader) Ann-Laure Le Cunff shares the familiar dilemma:

You are invited to a dinner party, maybe drinks, or an event. But you can’t make it. Maybe it’s a deadline at work, maybe a call with a customer, or a kid on holiday who you need to stay with for the day. You can’t help but wonder: what am I missing out on? Are they having lots of fun without me? Are they going to bond over conversations I’m not able to join?

There’s a Twitter trope that says “Don’t tell me your priorities. Show me your calendar” and Le Cunff recommends a review of how you spend your time (with a calendar or a time audit), taking breaks from the Internet and reconnecting with “yourself and the people you care about.”

Furthermore, is your FOMO (and the fear of saying no) driven by your scarcity mindset? As an entrepreneur, are you asking yourself: what if that coffee could have landed your first client? Or your future spouse could be at that museum opening? Or speaking at that conference might have increased your slice of the bonus pool?

Yes, we’ll never definitively know the answers to these what ifs. But they do arise from the zero-sum worldview that life is one giant fixed pie with only winners and losers.

Do you really believe this to be true? Can you recall prior instances from your life when you were part of a win-win?

Might saying no today actually increase your potential for a future hell yeah?

Remember, you’re a good person

Now to the people pleasers (thumbs pointed inwards) out there, please hear me out:

Saying no, doesn’t make you a bad person.

It doesn’t make you selfish.

It doesn’t make you ungrateful for the generosity you’ve received.

And it doesn’t shut the door on serendipity and opportunity.

Returning to Rimes’ Ted Talk we see that saying “yes” did help her overcome her fear of public speaking, appear on live TV and learn acting. But her most important yes:

“I made a vow that from now on, every time one of my children asks me to play, no matter what I’m doing or where I’m going, I say yes, every single time.”

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