‘Why did I agree to that?”

That’s exactly what I caught myself thinking a couple of weeks back, dashing between four back-to-back meetings, a lunch with a founder, a conference I’d promised to speak at months ago and a late evening flight. At the time of each invitation, I’d felt sure I could squeeze them in—what kind of leader would I be if I didn’t show up for my team, founders, or peers? Yet, there I was, mentally kicking myself: “Damn, why did I say yes to all of this?”

I’m hardly alone in this struggle; it’s a scenario that plays out for most of us. We sign up for conferences we’re only half-interested in, commit to extra meetings we know we don’t have time for, and volunteer for initiatives that won’t actually move the needle. In the moment, our reflex is to say “yes.” When the day finally comes, we’re left lamenting our overstuffed calendar.

This gap between an optimistic “yes” and a regretful “damn” is what is called the Yes-Damn Effect. In this week’s post, let’s take a closer look at why we keep saying “yes” and how we can break this cycle.

Where the Yes-Damn effect comes from

Social psychologists have studied why we overestimate our future capacity. One explanation is temporal discounting – we treat future commitments as if they’re easier to handle than present ones. There’s also the classic desire to please others: we want to appear available, supportive, and opportunity-ready. Throw in some personal aspirations (“I’ll totally have the energy for that next month!”), and you have a recipe for chronic overcommitment.

Overcommitment itself isn’t new. It’s been around for as long as people have tried to juggle competing demands. But in leadership circles, the stakes can be especially high. Each “yes” might seem like a chance to impress your boss, nurture a new client, or support a team member. Yet each misguided “yes” also edges out time for strategy, rest, or genuine connection with the people who rely on you.

How this impacts our effectiveness

When you’re stuck in a cycle of “yes-damn,” your effectiveness suffers in a few key ways:

• Eroded trust: If you end up cancelling at the last minute or arriving ill-prepared, people start doubting your reliability.
• Wasted time: Every hour you spend on low-impact commitments is an hour you’re not using to mentor your team, think creatively, or resolve core challenges.
• Emotional drain: It’s exhausting to keep up a frantic pace. Burnout is the natural byproduct of chronically saying “yes.”

Three key reasons we overcommit

1. We have an aspirational view of our future self.

We picture ourselves morphing into someone with unlimited energy and enthusiasm—someone who runs daily 10K races, travels for every conference, and never declines a speaking gig. But when the day comes, we realise we are not that person after all!

2. We think we’ll have more free time in the future,

even though prior experience proves otherwise. As a result, we overschedule ourselves. There’s a popular internet saying that reflects this thinking: Adulthood is saying “But after this week, things will slow down a bit.” over and over till you die.

3. Our default answer is “yes”.

People-pleasing tendencies can make it tough to say no, even to casual acquaintances or distant relatives. The desire to be liked and seen as nice trumps all else. As a result, we end up clogging our calendars with things that don’t bring us joy or satisfaction.

Breaking the Yes-Damn cycle

The good news is you can avoid the “why did I say yes?” trap with a few strategic shifts. Here are six suggestions:

1. Check your recent calendar.

Are you debating whether to attend an event that’s a few months away? Your schedule may be wide open right now, but that isn’t a good indicator of what things will actually look like.

To counteract the fantasy of endless free time in the future, glance over the last two weeks of your calendar. If it’s filled with work, household chores and social commitments right now, then it’ll likely look much the same a few months down the line.

2. Pretend it’s happening sooner.

It’s easier to say yes to things in the distant future. Let’s say your neighbour invites you to watch a play next month. You’re unsure how you feel about it – but you accept it anyway because it’s so far off.

To create clarity in your own mind, move the timeline up. If the play was this week, would you want to attend? If you’re not excited about it now, you’re probably not going to be excited about it later either. Such events are top contenders for the yes-damn effect – it would be best to decline graciously.

3. Assess the true value.

Weigh the cost vs. payoff when choosing how to spend your time. Some things are worth doing even if they cause inconvenience or temporary reluctance. Showing up for a friend during an important time in their life. Attending a conference that could lead to strong connections. Going for an event that supports a worthwhile cause. In her NYT article, Jancee Dunn also suggests asking the following question:

Will showing up be low stakes for me, while making a big difference for someone else?

It can be illuminating to see how the event fits with your personal goals and purpose. For example, if you’re trying to build a new community of friends, then social gatherings could be greatly beneficial, even if they strain your schedule. If you’re on the verge of starting your own business, then those “not again!” industry events could generate valuable opportunities. It all comes down to what you see as worthwhile.

4. Reset your default.

If your instant response to any invitation is “yes”, it’s time to break the habit. Declining outright might feel too hard in the beginning, so why not settle for something like: “Thank you for asking, let me check my calendar and come back to you.” This will give you the breathing room you need to apply some of the above steps (look at your schedule, weigh the cost/payoff, etc.).

If you judge the event to be a yes-damn threat, turn down the invitation gently with an acceptable excuse. (Don’t worry, it gets easier with practice – just think of all the free time you’ll have for things and people you genuinely love!)

5. Track your “no” wins.

Did you, after much back-and-forth, finally say no to an event that doesn’t interest or inspire you? Go ahead and make a note of it in your calendar at the relevant slot: “Said no to X event.” When you’re enjoying that day, hopefully doing something more fulfilling, a notification will pop up to remind you of the rewards of saying no. (This is the no-yay technique created by Dr. Dilip Soman, a behavioural scientist at the University of Toronto.)

6. Build time buffers.

Do you have a habit of scheduling multiple things in quick succession, leading to endless rushing around and no time to transition between activities? If so, start building buffers into your calendar and provide a cushion for delays and problems.

For example, if you’re going for a cocktail from 7-9 pm, block your calendar from 6-10 pm to account for freshening up, travel time and the possibility of traffic jams. This will also help you form a more realistic picture of the time commitment required for the event.

Looking ahead to a more intentional 2025

The Yes-Damn Effect boils down to overestimating who we’ll be (and how much time we’ll have) in the future. “Yes” often feels synonymous with ambition or team spirit. Yet a thoughtful “no” can be far more powerful. It protects your energy and ensures that when you do say “yes,” you can give it the focus and follow-through it deserves.

As we move into 2025, let’s aim to align our calendars with our real priorities, not our fantasy selves. Each time you consider a new commitment, pause and think: Is this truly worthwhile? If the answer is yes, then embrace it wholeheartedly. If not, let it go. Your future self – and your team – will thank you.