This is the story of how two people found meaning through asking each other questions.

We documented the whole process in the eBook, the 30-Day Question Challenge: Download it now for free here

It started back in 2019 when I was recently unemployed and talking to anyone. For those of you who have had a stable thing ripped away, you know that feeling: filling the days infusing empty hope into every message, note, and phone call.

I was feeling down and was calling old connections. To my luck, Alycia Angle picked up and I happened to catch her on a long lonely drive. I put on my fake upbeat attitude and she shared some of the career anxiety she was feeling as she was growing out of her current role. It was cathartic for both of us and I started to feel some genuine confidence chipping away at my false optimism. We agreed in that March of 2019, that we’d keep each other on track...somehow.

Fast forward three months when Alycia came to Boston for a conference and crashed at my place. We talked in our Season 1 trailer about how this formed the foundation for the 20/20 Perspective, but it transformed a casual conversation of being professional vague accountabilibuddies into a collaborator relationship on a concrete new venture: A podcast. About failure.

As we were recording our first few episodes, that initial energy that perennial starters have and struggling finishers lose was starting to fade. We were going to become another failed podcast statistic: two episodes and nothing more.

We needed a reset, or a boost, or something that could motivate us to keep going.

It was Alycia who suggested the 30-Day Question Challenge. Her background in Industrial and Organizational Psychology meant that she’s seen the transformative power that self-reflection can hold.

While I certainly love a good time capsule, I don’t really do the regular self-reflection stuff on my own even though I know what kind of positive change it can drive. I’m not good at showing up for myself…but with a buddy? Hell yes.

The process we followed was pretty simple:

1. I would generate a question of the day and text it to Alycia. It would be the kind of question that spurred creative self reflection, like “What is your spiritual center?” and “Who do you aspire to be?”

2. We both would individually record ourselves talking through our answer to the question.

3. We would sync up and share our insights on what we said and what it could mean.

We had something to help us with all this self-reflection: several decades of experience! We would do exercises like this with teams and organizations but rarely as participants.

There was something special about subjecting ourselves to our own medicine. Having a trusted peer hear and provide an equally qualified perspective on your own personal feelings was a rare treat. We learned all kinds of things from the experience:

• How our strengths are hiding our worries and fears

• Passions and interests that we mute because they’re not typical corporate topics

• Justifying assumptions and overturning others

30 days later we finished and learned something else: we had to do this thing again.

It took about ten more months and two podcast seasons before we looped back to the 30-Day Question Challenge. It’s an annual year-end activity that’s way more transformative than a performance review, a way of realigning and washing away the dirt from the past year to see what’s changed. 

We collected our best practices, did some more research on how to effectively architect programs like this, and turned it into the 30-Day Question Challenge eBook. Some of the key features of the book:

• Creating a north star to personally motivate yourself

• The mechanics of how to effectively create and review an audio diary

• Strategies to identify observations in your own responses

• Detailed techniques to process through observations to find insight

• Dumb stuff we said during our own 30-Day challenge

If you too want to find clarity like we did/continue to do, then download the eBook here for free. And even better, if you’re reading the book and feeling like it’s too much work to handle on your own, there’s resources in there so you can connect directly with Alycia and I to help you find what you seek.

Keep questioning, friends.