Over Promise, Under Deliver.

Expectations.

Your happiness is governed by the expectations you’ve set for yourself.

Read that again.

It’s something we discount, both in day-to-day life and the long-term.

It’s why for some people missing an ambitious morning alarm or running 15-minutes behind to an appointment can derail a whole day.

It’s also why your perpetually late friend shows up whenever they feel like and they seem to breeze through life, perfectly content.

The difference is just the expectations.

I’ve been thinking about this a bit lately. Not in any deep philosophical way, but in the every day moments that ultimately make up our entire lives. It’s like we play this weird game where the rules of life keep changing based on what we think should or shouldn’t happen.

Generally I’ve found the higher your expectations are, the easier it is to miss and feel disappointed.

That’s certainly true for vacations. The meticulously planned week-long European trip with color-coded itinerary and reservations booked months in advance can fall apart so easily with one rainy day or a missed flight. Versus a spontaneous weekend road trip that ends up in some quirky hole in the wall dive bar and a story you’ll retell for years.

The same plays out in our careers. A job that pays $75K plus benefits can feel like settling after graduating with a $250K degree. But the same position can feel like a dream come true for someone who never had college in the cards. The job hasn’t changed, only the story we told ourselves.

Once you land the job you realize success and failure have less to do with actual outcomes than with the expectations we set. Launch a project three months late when everyone thought it would take a year and you're the hero. Deliver two weeks late when people expected it yesterday and it’s time to update the resume.

I am not saying you shouldn’t set expectations. Or that you shouldn’t consider setting them high if you do – without crazy high personal expectations there would be no Kobe Bryant’s or Serena Williams’ or Steve Jobs’.

I am just saying expectations are a delicate thing, and there must be some balance. Feel free to shoot high, but give yourself grace when you inevitably land on the moon on your way to the stars.

I like to set guidelines for my big expectations; salary out of college, fundraising amount for my startup, number of times I’ll workout this month.

The key is to assume you will generally achieve 60% of whatever your goals are (maybe that’s generous). Call that 60% your “okay threshold” — the level at which you’d be okay with the results.

If that’s true and you’re willing to give yourself the grace, then you might choose to set your goals at roughly ~167% of whatever that okay threeshold is. So that way if you achieve 100% you’re extremely happy, and if you land at 60% you’re still okay (and if you hit 100%, reward yourself with some sort of prize to reinforce the win!)

Another simple hack is to give yourself a range vs. an exact outcome. This works especially well for deadlines, even little ones like giving an ETA of when you’ll arrive at a destination. If your maps app says you’ll get there at 7:15pm, it’s generally better for all involved to say you’ll show up between 7-7:30 than to say you’ll be there at 7:15 and show up at 7:20.

The famous saying to try and live by is “under promise and over deliver”. You should strive to do this with everything you do. Vacations, career goals, project timelines, exercise goals, giving an ETAs, whatever. Call it giving the extra 10% or going the extra mile, however you have to frame it.

The point is expectations are precious, and if you are conscious of how you set them – with grace and foresight – you can hack them to your benefit.

My favorite example of hacked expectations are birthday gifts and surprise parties. They’re the perfect encapsulation. Surprise parties are not inherently better than planned celebrations on paper – same cake, same friends, same bad singing. But they feel 10x more magical precisely because we weren't counting down the days, imagining every detail.

The gap between expectation (regular Tuesday) and reality (confetti!) is where the joy lives.

In short, it’s a balance. Maybe life with proper expectations is like jazz — structured enough to make sense, loose enough to delight.

Peace,
Ramsey