The Working Experience: Plan and be Flexible

M. Francis Enright
5 min readJun 1, 2020
Photo by Cathryn Lavery on Unsplash

Matty Kerr is co-creator and cohost with John Brancaccio of The Working Experience podcast which can be found on iTunes, Anchor, Spotify and our website: theworkingexperience.com. Find us also on Twitter, Linked In, Instagram and Facebook.

As we were wrapping up he said, “Yeah, and she tried to have him killed.”

“Wait, she what?”

It’s hard to plan creativity; it sounds like an oxymoron. Often it comes without warning, in flashes of inspiration that can only occur during the creative process itself. As the author writes or the artist paints or the architect designs, new ideas are revealed.

But it helps to have a plan.

In the process of creating a film pre-production, the planning stage leading up to the actual shoot, is crucial to the film’s successful completion. It is essential that each day is meticulously planned with a schedule of the scenes to be shot, a list of the props that will be needed, instructions for the actors’ wardrobe, hair and make-up etc. If the planning is not in place the film has little chance of being completed. Time and money will be wasted.

However, the director, the cast and crew, need to be flexible. Ideas are often generated spontaneously when everyone is in the same creative space that cannot be planned. One actor will come up with a new line in response to what another actor says or does; the director will re-think the physical actions of the characters; the cinematographer will have a better vision of how to shoot the scene, maybe from a different angle. It is impossible to plan those moments and everyone needs to be open to that collective creative energy and use it.

Planning is essential but so is flexibility.

I always send questions to guests a few days before they come on the podcast. I want to give them a chance to prepare their thoughts and feel comfortable but I also want to make sure I can keep the conversation going. With certain guests the conversation will flow naturally but I can’t always count on that. So I make sure I have the questions to fall back on. The episode can become dead in the water if I don’t.

However, the conversation can be awkward and stilted if I am just asking questions and the guests are answering. I let the guests know that the questions are to serve as talking points to guide our conversation. I need to make sure I am listening carefully to the guest and not just waiting to ask the next question. Quite often a guest will say something interesting that is not an answer to a question but it leads to another area of discussion so I make sure I take notes so I can go back to it.

When speaking with Tom O’Neill, the author of Chaos, I was asking him about his research methods and he got to telling me about dealing with the CIA and the Freedom of Information Act, which he said is a joke because when he requested information about a particular person he would either receive documents that were so heavily redacted that they were useless or would get the standard CIA response of, “We can neither confirm or deny that that person works or had worked for this agency.”

That kind of stuff is fascinating to me and I would never have thought to ask that specific question; it came out in the course of our conversation.

It is one of the reasons I love doing the podcast.

Then there are times during an interview when the guests says something off-hand and I say, “Wait, what was that?”

I was doing an interview with a friend of mine, Matt H. who works for a large insurance company in Massachusetts. He said he had some pretty good stories to share; since we know each other well I hadn’t sent him the usual questions.

He started by telling me about some of the general inanity that went on in the office: endless meetings, clashes at the copier, a snafu regarding a Tupperware container, a lunch being stolen etc.

Then he told me about another coworker who is obsessed with reality TV shows. Not only does he love watching them, it is his life’s ambition to be on one of the shows. He sends in audition videos and all that. Survivor is the gold standard for him but he would be on any show that would have him.

To give the guy’s life some context, Matt mentioned that his wife would call him every day at 4pm and if he is still at his desk she starts berating him for not already being on his way home. Matt and his friend wondered why the guy didn’t just leave and not pick up the phone but they figured it was just part of the psychodrama that these two played out.

As we were wrapping up he said, “Yeah, and she tried to have him killed.”

“Wait, she what?”

That is the funny and exciting thing about interviewing people; they drop a bomb like that and I need to hear more.

We did another episode to cover the case of attempted murder. The guy and his wife had taken a vacation on a houseboat in Texas and he had returned with a broken jaw, missing teeth and other injuries. The details are murky but it seems as though the wife may have slipped something into his drink and then whacked him with an oar and knocked him into the lake. He woke up in the water and managed to swim to the boat.

When they got home to Massachuetts she asked someone to find a hitman she could hire to finish the job. The guy went to the cops and she was arrested by the FBI. You can look up the details online.

Matt only remembered this amazing story because we were having an unscripted conversation; one point led to another and eventually we got to the attempted murder.

I couldn’t plan that.

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M. Francis Enright

Co-creator and cohost of The Working Experience Podcast. We explore what people do for work, how they do it and how they feel about it. Twice a week!