Learning from other people’s mistakes is so much better than making them yourself. But this is one mistake we all make from time to time: We get too ambitious and bite off more than we can chew.

Let me tell you a story that I wish was less icky.

We had a month before the workshop. Usually this is plenty of lead time.

For me, when I conduct my own workshops. Which is 99% of the time.

But every so often, another company who needs a specialist in data visualization will hire me to co-lead a workshop with them.

Collaboration takes six times longer than doing it yourself.

I wish this wasn’t true. I wish the world was ruled less by time and more about the quality of the output.

But the workshop date was already booked by my collaborators with one of their big, household-name clients. I wasn’t in charge.

Even though we had collaborated on the workshop before, during the pandemic my collaborators shifted their platforms from Microsoft to Google. The transition meant our PowerPoint had to be remade in Google Slides.

What’s more, my collaborators updated their brand during that dark time, so the design of every single slide needed to be revised.

Can I add one more wrench into these gears?

The usual suspect I traditionally co-presented with was pulled for another assignment, so they swapped in a well-intentioned substitute who had never seen the content before. No script, no prep, not even a finished slide deck to work from.

Are you feeling uncomfortable yet?

A team of 5-6 of us met for hours each week, trying to get the slides in shape while also customizing the agenda for the client and learning new material. Building the plane as we fly it, as the saying goes.

The closer we got to the workshop date, the more we were saying “we are just going to have to call it good right here” aka we started compromising the level of quality that lived in our hearts because we were up against a deadline.

I hate being in that place.

I’ve seen a version of this go down countless times as ad hoc teams wait until the last minute to pull their conference presentation together.

So, of course, the answer is Start Earlier.

Easier said than done.

One approach I often use: I list out all the tasks that have to be done to complete a project, along with a generous estimate of time needed for each task. (The less experience you have doing similar projects, the more time you should estimate for each task.)

Then I plot the expected end date on my calendar and schedule the tasks backwards from there.

At that point I can usually see, within the context of the rest of the events on my calendar, whether it’s realistic for me to get this project done on time, with the level of quality I want.

I’ve conducted so many workshops at this point in my life that I already know the schedule. It takes me about 2 months, given all of my other life events, to get a workshop together.

This means that way back at the stage where a potential client and I are doing the negotiation dance, I can start managing expectations. If they want a workshop next month, I have a very quick and easy answer.

Because I’ve been there. I’ve bitten off more than I can chew. More than once. The anxiety it gives me isn’t worth the income.

When was the last time you bit off more than you can chew? Did it give you anxiety? Or make you hustle harder? What did you do about it? Write back and let me know.