Darius Bashar asked Gary Vaynerchuk an interesting question at last night’s DemoCamp24: What questions did Gary ask himself? (Not quite answered, but it might’ve been hard to get the gist across.)

After the event, Darius posted some of the questions he uses to figure out more about passion.

I was thinking about the questions in my toolbox, and I realized that I approach things very differently from the way that many bloggers I’ve read (particularly those who push personal branding) approach this discovery process.

I do ask people about their passions when starting a conversation, but that’s an opener that’s there so that I can see if they light up. It gets them away from the name-occupation spiel. If people stumble and don’t have a clear passion, that’s okay.

Looking at the questions I see on these personal development blogs, I often feel that questions assume you need to have a clearly definable passion that you can easily differentiate from other things you think about. While many people respond to that challenge, others might feel even more discouraged.

Me, I like discovering my passions through small steps. I’m not looking for a huge flame I had been previously unaware of. I’m just looking for a spark I can cultivate. That often emerges when I focus on relentless improvement and on sharing, two of the categories I’ve listed here. Other questions help me clarify, develop, and expand that interest. Passion isn’t something I expect to spring full-formed (Athena from Zeus’ forehead?). It’s something I grow into.

Discovery is shaped by the questions you ask. Some questions are sheer rock faces that are hard to get a grip on. Some questions are paths already marked by others so you know where to go. Some questions give you a lot of holds so that you can work your way around tough parts. Some questions are the shortcut walking trail a sherpa points out to you. ;)

Maybe some of these big-picture questions might help you think about your interests and passions, and maybe some of the more tactical ones will help you think about other things you do. Here’s a Swiss Army toolkit of small questions I use to think about things, and I hope to add more as I learn!

• Questions
  • Improvement
    • What worked well?
    • How can I make this even better?
  • Vision
    • What difference do I want to make, and why does it matter?
    • What can I do?
    • What can I help other people do?
  • Planning – dreams
    • What do my ideal days look like? How can I get closer to that?
    • What doesn’t matter to me? What can I say no to?
    • What do I want to build, experience, or share?
    • What are the different ways I can make that happen?
  • Planning – Career
    • What kind of value do I want to create?
    • What does wild success look like?
    • What skills can I develop?
    • What do I need to take the next step and scale this up?
    • Who can I touch, reach out to, influence, or help?
  • Planning – long term
    • What’s the best case scenario?
    • What are the curveballs that I might deal with? Probabilities?
    • How can I make a safety net?
    • How can I increase my chances of a favourable outcome?
  • Planning – short term
    • What are my priority items?
    • How much time do I have? Will it fit?
    • What important things should I plan for?
    • How can I have fun, learn, and create value?
    • How can I make this easier, more efficient, more effective, or more fun for myself and others?
    • How can I share what I’ve learned?
  • Sharing
    • How much can I share with the world?
    • Who might find this useful?
    • How can I make this easy to find, especially for me?
  • Conversation
    • What are you passionate about?
    • What does wild success look like?
    • What could make you even happier?
    • What do you need to get there?
  • Delegation
    • What part of this can I delegate?
    • What do people need to do this?
    • What does good output look like?
    • What limits are there?
  • Presentation
    • Why does this matter?
    • What should people do or feel?
    • What do they come in with?
    • What’s my key message?
    • What stories and examples can I share?
    • How can I organize this?
    • What interaction can I build in? What questions should I expect?
    • How can I make this even shorter and clearer?
    • What do I want to learn from this?
  • Evaluating a presentation opportunity
    • Why does this matter to the audience? To the organizer? To me?
    • What can I say that is new, will make people think, and will make people act?
    • How can I scale this up before and after the event?
    • What’s the context?
  • Writing
    • What do I want to say? Why does it matter?
    • How can I illustrate it?
    • Can I make it clearer?
    • What am I missing?
    • What’s related to this?
  • Free time
    • How can I be present and enjoy life?
    • How can I express love?
    • How can I move my goals forward?
  • Figuring things out
    • What’s the end point?
      • What has to happen before that? (and so on)
    • Where are we now?
      • What can we do right now to move toward the goal?
    • Why? (at least five times)
  • Social media adoption
    • What’s the immediate personal benefit?
    • What’s the long-term personal benefit?
    • What’s the social benefit?
    • How can we enable the social benefit with minimum
      effort?
    • What are the challenges? How do we address them?
    • Who are out there?
  • Finding people
    • What are the details of the request?
    • What communities are relevant?
    • What keywords can I search for?
    • Who else do I know?