enwaken

Goalposts · in Logbook

“I'll feel good once…”

Everyone has a sentence like that. Most people have one that starts “I'm worried about…” too. Goalposts writes yours down, asks how good you expect life to be, and then asks again in three months, in a year, and every year after. Eventually you can see how often you were right.

Write your first goalpostFree. Takes two minutes. Works in any browser; no app needed.

Three of mine

I didn't have Goalposts for these. I wish I had. Each one is from an essay, in my own words at the time.

  1. I'll feel good once…

    I'm rich. By my late twenties I had a house in San Diego, a BMW in the driveway and a salary over $200k a year.

    “And yet, I was deeply insecure.”

    Becoming A Success First Meant Losing All My Money →

  2. I'm worried about…

    Losing it all. At 30 the business imploded, I declared bankruptcy, and my marriage ended.

    “It was the most painful chapter of my life. But it was also the most important.”

    Becoming A Success First Meant Losing All My Money →

  3. I'll feel good once…

    I can afford anything I want. Years later I could: a McLaren, a Rolex, the occasional private jet.

    “I sold my McLaren. My wife wears the Rolex. … I've had wealth. But I've gotten over it.”

    My Quest to Get the Coveted American Express Black Centurion Card →

How it works

  1. Write it down

    A goal (“I'll feel good once I'm out of debt”) or a worry (“I'm worried about AI taking my job”). Say how good life is now, and how good you expect it to be once it happens.

  2. Get asked again

    Three months later, a year later, and every year after, an email asks how good life actually is. One tap to answer.

  3. See the pattern

    Your predictions next to what happened, side by side. Most people find the good things lifted them less than they expected, and the bad things sank them less.

Why bother

Psychologists have a name for this: impact bias. We overestimate how much a good thing will lift us and how much a bad thing will hurt, and for how long. Knowing that changes very little. Seeing it in your own words, about your own life, changes a lot more.

That's what took me decades and a bankruptcy to learn. Goalposts is the shortcut I didn't have.

Who's asking

I'm Sanjay Singhal.

I built and sold Audiobooks.com, went bankrupt at 30 and rebuilt, was diagnosed with bipolar disorder, had a heart attack before my wedding, and spent twenty years in therapy. I invest in startups and fund mental health research.

I write about all of it, the money, the becoming and what came after, in a book that's still being written. Goalposts is part of Logbook, the tool I built for the middle part.

Read the book →More about Logbook →

What are you sure of?

Write it down. Find out in a year.

Write your first goalpost