Mystery Gift Box #037 | 40+ Questions to Help You Become More Creative

Hey friends,

The five enemies of questioning.

Fear. Knowledge. Bias. Pride. Time. We all know the importance of asking thoughtful questions at the right time in order to make the best decisions. Yet we are never taught how to be a better questioner…

The Book of Beautiful Questions provide over 200+ questions in the area of decision-making, creativity, connectivity, and leadership. Here are some key questions that you can ask yourself to ignite your inner creativity:

Stop asking these self-limiting beliefs Questions

1. Am I creative?

2. How creative am I?

3. Where will I ever find an original idea?

4. Where will I find the time to create?

5. How can I come up with an idea that will make money?

6. Where do I begin?

Questions to find your big idea

1. What interests me?

2. What bugs me?

3. What’s missing?

4. What do I keep coming back to?

5. What is ripe for reinvention?

Questions to see the world differently

1. What might I notice if I were encountering this for the first time?

2. What if I stand on the desk?

3. What is in the background?

4. What here would fascinate a five-year old?

5. What would Seinfeld (comic observer’s eye) be amused by?

6. What would Steve Jobs (innovator’s eye) be frustrated by?

Questions to ask before committing to an idea

1. Can I own this problem?

2. What can I bring to this that others can’t?

3. Will I still love this problem tomorrow?

4. What is the potential upside?

Questions to understand any problem

1. Why does this problem matter?

2. Why does the problem exist?

3. Why hasn’t it been solved already?

4. Why might that change now?

Questions to find time to be creative

1. If I began to see my attention as a precious resource, how might I better protect it?

2. How can I shift from a “manager’s schedule” (schedules of meetings)to a “maker’s schedule” (uninterrupted multi-hour blocks)?

3. Am I covering too many projects?

4. What if I trade the morning news for the “morning muse” (thinking)?

Questions to get started with creative projects

1. Am I chasing butterflies (keep jumping to new projects)?

2. Who will hold me accountable?

3. Am I rearranging the bookshelves (“preparing to create”)?

4. How can I lower the bar?

5. What if I begin anywhere?

6. Can I make a prototype?

Questions to get honest constructive feedbacks

1. Am I coming across?

2. What do you like least about this?

3. And what else?

4. What would you suggest I try?

Questions to prevent your creative work from getting stale

1. How can I keep moving away from what I know?

2. Is it time to be a jackhammer (deep dive in one area)? or a hummingbird (explore new places)?

3. What am I willing to abandon?

4. Where can I safely explore and experiment?

⛰ 4-4-4 Exploration Project

January 2023: Writing and Storytelling (Subject) ✅

February 2023: KURIOS – Cabinet of Curiosities (Cirque Du Soleil — Experience) ✅

March 2023: 28 Days of Cold Exposure (Subject and Experience) ✅

April 2023: Complete Growth / Product Marketing Course (Subject) 🟥

May 2023: LL project (Skill + Subject) 🟧

📚 This week, I finished reading…

Didn’t finish any books 🤓

Have interesting gems you want to share with me and others? Share it by replying to this email and I will include it in the next gift box :)

With love,

Ryan O. 🎮

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