The clink of silverware against plates suddenly stops, replaced by a stunned silence that surrounds the table. Heads turn, eyes widen, and the woman next to me nearly chokes on her coffee, her hand frozen midway to her mouth. It’s July 2024 and I’m sitting in a conference room in Victoria, Canada, eating a hot breakfast.

On my left is a ~40 year-old man named Toby who sold his business for $400m three years ago. I can’t believe the words that have just come out of his mouth. It feels like I’m in a movie. Is this guy a comedian? I lean in with intrigue, thinking that he’s about to tell me he’s joking. I wonder what he’s going to say next. 

But he repeats what he’s already said:

“Truly, I felt like a failure when we sold our company for $400m.”

I sit back in my chair, look at him squarely in the eyes, with a wry smile, observing his tone and body language, and then it hits me: he’s definitely not joking.

“If we had done a few things differently, within our control, we could have sold it for $600m.” 

In that moment I realised something that will stick with me for the rest of my life: People will judge us on what we’ve done; we will judge ourselves on what we know we could have done.

So often we place our own expectations for our lives onto others. But everyone has a different set of expectations. It’s futile to place your own on someone else. Or to expect someone else to want to live the way you do. The better choice is to try and understand their perspective deeply:

• What are their expectations?

• Why have they created those expectations for themselves? 

There is nothing more important than living in full alignment to the expectations that you set for yourself in life. When you’re 90 years old, this is what you’ll look back on to assess whether or not your life was a success. Everything else is noise. The great thing is: you get to choose your expectations. And you get to choose the areas of life those expectations fall in.

This reminds me of a powerful quote from the Gospel of Thomas:

"If you bring forth what is within you, what you bring forth will save you. If you do not bring forth what is within you, what you do not bring forth will destroy you."

Fulfilment comes not from meeting external standards, but from expressing our authentic selves and realising our latent potential.

Do not judge others for their expectations, and do not allow others to judge you for your own.