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Connecting to Your Work

David Sherry
2 min read


This past week I was in Mexico City for the Founders Summit. I lead a workshop on planning and vision for Remote founders.

This week I’m back to it before 2 weeks in Northern California (Mendicino area) spent writing mid-month!

When you’re working on something important, it’s normal to go through many phases with it.

We think everything is a straight line, from idea to execution to joy.

In an ideal world, our flow isn’t interrupted….

We have an idea we’re excited by, and we simply execute it.

The truth is much messier. We go through a variety of phases with it.

What’s important is that with our revisions, and phases we get closer to what it is that we want instead of further away.

Many times it’s the opposite: we give in to obligation, fear, or trying to simply please others rather than creating something fresh from our own experience.

Preparing for this talk, I started out very much with a “lecture” format. This means writing a speech and delivering it.

This format was “safe.” I could control all of the variables, and I simply had to write a compelling talk to give.

But with each iteration, I stripped back the “talk” aspect of things and moved more into an unknown territory of a workshop.

Rather than filling time with me talking, I shaped my talk into a workshop where it was mostly about the conversation with the group. This means taking a leap into the unknown. It meant having enough to go off of, but not the safety of a perfectly controlled outcome.

There were about 50 founders there, would people participate?

And, could I shape my “talk” and workshop in real-time, in response to how the group interacted with one another.

This meant being there, present with the group. No slides to fall back on.
This meant being open to taking things in a different direction as it emerged.

Connecting with your work is the most important thing for keeping momentum with your work.

We lost interest because we disconnect from what we thought was interesting.

I was disinterested in convincing anyone in the group of anything – rather I wanted to give each person the experience of what coaching might be like, right there in the workshop.

I wanted light bulbs to turn on, and spontaneity to be there. That was exciting to me.

And so the “work” was to keep uncovering what a talk would look like that could do something like that.

I’m happy to say the feedback was great, but more than that, it was the workshop that I wanted to give, not the workshop that I was “supposed to give.”

The tightrope here is that we can’t forget other people as we focus on the work we want.

I would say more than half of my time preparing was spent considering the audience, how they would relate to the information, how they would feel.

After all, the talk was in service to them, not to me.

But I need to feel it first.

Committing to Your Work