you can only connect the dots looking back

sometimes things that don’t make sense are the things most worth doing

Sep 04, 2026

Steve Jobs has this line I love:

“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future.”

It was from a commencement speech and he was talking about dropping out of a required class and taking a calligraphy class instead. He didn’t have any use for it at the time, but ten years later that calligraphy became the typography inside the first Macintosh. Every computer after it inherited the fonts.

The story seems like this miraculous tidy piece of destiny. But, I would venture to guess it was not tidy while he was living it.

It is a privilege to do things that don’t make immediate sense and wait for the payoff… But, to the extent that we have or can create that privilege, I think we should. Sometimes the only space we have to do things that “don’t make sense” is listening to the music we are drawn to while doing something else. I’d argue that space is worth making.

me in my polka dot dress in 2016 very unsure where life would take me and very unable to connect the dots looking forward

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forward and backward

Typically life runs forward and gets understood backward. You live forward, into fog. You understand backward, in daylight.

Sometimes, I think we take “the dots will connect” and turn it into a demand for right now. We stand in the fog and try to force the line into view right now.

but a baby dot does not know what it connects to. That knowledge lives downstream, in a version of you that has not yet happened. It would be an act of time travel or of quantum physics or something to create that connection.

So because we cannot yet make that connection, we stop placing dots that do not obviously fit. In the name of “focus” we prune the strange hobby, the odd interest, the opportunity we cannot logically defend. And, in so doing, we may be cutting the calligraphy class we are inexplicably drawn to every single time.

between seasons

My birthday is in August. August is a kind of “between the seasons” time of year. Maybe that is why I love living between seasons. I love transition. I love transformation. That liminal space where the old trail has ended and the new one has not yet declared itself.

I love placing dots into fog with no evidence they lead anywhere.

I am in one of those seasons right now.

I can tell you what the essay says about it: “Trust the shape you cannot see.” I believe it with my whole heart and I still wake up in the fog, tempted to prune every dot I cannot logically defend like a lawyer in court.

Trusting the dots seems so easy in the shiny commencement-speech version, after the dots have connected and someone is telling the story from the stage. But it feels a lot harder in the dark, with the outcome unknown.

If you are with me in the fog now, I am saying this as much for me as I am for you: nobody in the fog can see the line. our assignment is simply to keep placing dots.

I am holding a few goals in this season:

Place the dot before you can defend it. If a thing is alive and real for you, that is enough reason to do it.
Trust that the line is visible downstream. You are reading a book from inside chapter four and grading it for an ending it has not yet reached.
Let the strange dots stay. These are the ones that connect in miraculous ways the sensible dots never do.
Look back on purpose. Every so often, turn around. Read the dots you have already placed. You will find lines you did not know you were drawing.

You are living forward, into fog, the way everyone always has.

The dots you are placing today do not owe you their meaning yet.

Turn around in a few years.

There will be a line.

Offerings

FYI: I’ve been putting together a weekly newsletter called For People and Planet. It’s where I share stories about climate solutions and the people working on them. If you’d like to read along, you can find it here: forpeopleandpla.net