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Long Overdue Newsletter - June 2020

Quote of the Month

"It can be difficult to see the whole picture when you're still inside the frame."
Tim Cook, Apple CEO

Recording your Stories: Moving from an Idea to a Product

By: Chris O'Brien, Co-Founder

It was December 3rd, 2019. The final day of my 20s.

I was heading into my 30th birthday with a mixed bag of life. The bad: I'd lost my job right before Thanksgiving. And I didn't really have a plan for what was next.

The good: The side business (Long Overdue) was off to a great start. We'd just published David Ovitt's children's book, Cecil the Centipede. Kimberly and I completed Here or There, And Omar was finishing interviews on our first biography. It was an exciting first chapter, a year that also included Joy M. Lilley's Strawberry Moon and David Warden's Don't Be That Guy.

Still, I remember sitting down on the couch, heart pounding, stomach tied in knots. How do you tell your wife you've been laid off? Do you just casually mention it at dinner? Send it on the way home via text? I didn't know what to expect, or how she'd react, but I've got a writer's imagination so I was preparing for the worst.

Whatever I was anticipating, it wasn't the moment of grace I received. Same thing from my parents.

I've failed plenty of times before, but losing a job feels like the holy grail of fail. To experience this and realize, "Wait, life goes on?" was strangely an awesome experience.

Back to December 3rd. Omar and I had meetings arranged with two of our mentors. Both are leaders in Chicago who we deeply respect and who've turned ideas into successful products multiple times.

We meet our first mentor at a Thai restaurant. We catch up, hear what's new with him, and start talking about our idea to help families record their stories. He meets everything with a "Yes And" and quickly moves the idea into something tangible.

"What if it's a box and inside you have a book of story prompts, or a deck of cards, something with all of the story prompts listed out. Then you have a tripod where the person can set their phone and just talk."

And maybe it comes with instructions written on the box or a printout.

Step 1: Record your stories.

Step 2: Upload the file.

Step 3: Long Overdue helps turn these stories into a book and/or create a digital library of stories.

This felt like the perfect starting point. I could picture someone sitting down at the table with their mom or dad, grandma or grandpa, going through our story prompts. Who was your best friend in fourth grade? What was a hard time in your life that you learned a lot from? What advice would you give your great-grandson on their 30th birthday?

And of course, all of the "How" questions started to roll in. How do you make a custom deck of cards? How do you design a box? How do I try and balance this with a day job again?

Time for the next meeting.

We went to a bar over by Jellyvision in Lincoln Park. Our mentor shows up and this time we don't really talk about Long Overdue. It's all catchup. Reconnecting. She talks about life and work. Omar shares about his year traveling the world with his fiance, Elizabeth. I ate a greasy pizza like a 14-year-old boy after basketball practice.

Toward the end of the dinner, I shared an update on my job situation. I didn't want to hijack the conversation but, at the same time, I was hoping for some of her wisdom. Two times before I'd come with a problem and she'd delivered advice that completely reframed how I was looking at things. In one instance, I believe it saved a friend's life. So, feeling discouraged (and a little bit whiny), I shared how I only wanted to work on Long Overdue. I wanted to give 10-12 hours a day to it. Go all in. But how that wasn't realistic yet. Still have to pay the bills.

I don't know what I was expec