Monday Seven No. 033

On celebrating wins, expectation vs. reality, and procrastination

Apr 13, 2021

Welcome to the latest edition of Monday Seven — actionable ideas and frameworks for those of us who seek more out of life and work.

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Hi friends,

I spent the weekend celebrating a life goal.

We bought a five-acre property on a rural island in the Pacific Northwest. I’ve been working towards this goal for the past two years.

At the start of the year, I shared this publicly in my annual review:

We’re also planning to buy 5+ acres and build a compound on a little island in the Pacific Northwest. Besides inviting family and friends to stay, we want to use the land as a place to make new friends and invite entrepreneurs, creators, and artists we admire to stay with us.

Turns out we found land with a compound already built. An income-generating cottage on the property made it possible to afford this sooner than we expected.

It all happened in 36 hours. The next morning, I woke up at 3 am and again at 6 am. Each time adding to an ever-growing to-do list. When daylight finally broke, I decided to prioritize celebrating the win by sharing the news with family and friends.

Sorry if this is how you’re finding out. I guess the downside of writing a newsletter is that I don’t always have time to update everyone I care about personally before sharing publicly.

I consider myself highly task-oriented. The benefit is that I tend to get a lot done. But, I’ve had to learn to slow down sometimes and enjoy the process. In an effort to do so, I’m being more deliberate about taking time to celebrate wins.

This week, we dive into a framework for celebrating wins, the gap between expectations and reality, how self-love helps us avoid procrastination.

Let’s get into it.

No. 033

Celebrating wins

I used to believe the way to get what you want was to put your head down, stay focused, and just execute. Celebrating wins was a distraction for the weak.

A younger foolish self would say something like, “while they’re out celebrating, I’m getting ahead.” In the illusionary race of my mind, the tortoise lost precious time by stopping for one too many celebratory drinks from the pond, while I, the hare, zipped by undistracted by the temptation of vast carrot fields.

That kind of mindset left me miserable, burnt out, and alone.

Celebrating wins amplifies the energy we need to navigate the choppy waters ahead. It’s equally important to share wins with people that will celebrate in the way you need.

After sharing wins, the reactions we receive are personified by four characters:

The Quiet Critic
The Investigator
The Cheerleader
The Super Fan

The Quiet Critic’s silence is deafening. It seems like they just don't care enough to show the faintest pulse. It might be that they live in a zero-sum world and see anyone else’s win as their loss. It’s just as likely that they’re too busy. But a true friend shows up to your parade. The 20-something-year-old me with more “friends” had a few of these rotten apples in the basket. I said goodbye long ago and recommend the same.

The Investigator gives a warm, “Congrats!” But, in nearly the same breath starts lobbing the questions. It can be genuine curiosity and care. But it can also come across as them sizing up your garden rake. Unfortunately, sometimes these people are engaged in comparative lifestyle studies. Either way, they fail to show up how you need them to. They’re feeding selfish curiosity rather than celebrating with you. I think most people are well-intentioned, but we measure the outcome and not the intent.

If you’re lucky, most people in your life are the Cheerleader. They go beyond sending the usual-suspect emoji response. The Cheerleader takes time to send a few thoughtful words. They make you feel great.

The Super Fan, however, is a special breed. They win our hearts. We feel like they’re on the court winning with us side-by-side. How do they do it? By reflecting our feelings back to us and making us feel seen. The Super Fan is a rare person. I found one way to attract Super Fans is to be one. We’re memetic creatures. If we surround ourselves with present people, inevitably, those around us start to become Super Fans as well.

There’s also a hidden benefit: when we show up as a Super Fan, we gain energy from other people’s wins. A friend’s win becomes our win. It’s a force multiplier.

The gap between expectation and reality

Most of the suffering in life stems from the gap between expectations and reality.

Perhaps the greatest gap between expectation and reality is in the world of politics. Politicians are masters at setting great expectations. But, it seems they are as ineffective as us mere mortals at improving reality. The political life cycle goes something like this: promise the world, get elected, fail to meet expectations, get replaced by a politician promising more, and so on.

Any time we expect life to be a certain way and are not willing to accept reality, we suffer. Freedom asks us to radically accept the reality that is happening around us.

The beauty of life is that it challenges us to look within and observe with attention. Life can be the greatest teacher if we show up with curiosity and humility.

Self-love and procrastination

A rhetorical question I ask myself when I procrastinate is “Do you love yourself?"

Of course, I do. But I find that when I think about it this way, I take action because procrastination just leads to more pain. Since I love myself, I don't want to cause pain.

Most people delay taking action because they hope to avoid pain. But some pain is always inevitable. The paradox of procrastination is that we avoid immediate pain but in the process, we choose prolonged pain delivered in a slow torturous drip.

I think the answer to avoiding the procrastination tarp is as simple as self-love.

One question for you –

What are you avoiding because you know it's painful?

Music of the week –

La Fiesta by Chick Corea (Spotify, Apple, Youtube)

Quote of the week –

Pain is inevitable. Suffering is optional.
—Haruki Murakami from What I Talk About When I Talk About Running

Thanks for reading. Long-time readers will notice this week’s format was different than the rest. I didn’t include numbers and didn’t stick to the usual seven.

Leave a comment below and let me know what you think