Powerful Questions That Lead to Progress

In reviewing the 20+ pages of notes from my business retreat last week, I was struck by how many questions I had written down.

Questions, when used in business planning, are more powerful than statements because they make us think and formulate our own answers. They encourage us to consider our situation, environment, abilities, and resources.

See if any of these serve you at the moment.


Questions for Low Mojo

What do I need to do more of?
What do I need to do less of?
Where am I not making my best effort?

Questions for Mismanaged Self-Management

If I make this choice, how will it serve me 3 months from now? 1 year from now? 5 years from now?
What if I pass on this opportunity? What if I agree to it?
What's the worst that could happen? The best? Which is easier to live with?
What 1 thing on my task list will have the biggest impact on my success?
What is my motive for doing this?
What's the best use of my time at this moment?

Questions for Sluggish Marketing

Who needs to know about this event/exhibition/product?
Who haven't I been in touch with lately?
Have I outgrown this space/exhibition/event?
Who needs to know about my art?

Questions for Negative Mindset

Who can I send a Thank You card to today?
What are my blessings?
What do I need to do to fill the creative well?
What am I tolerating?
Who can I help today?

Questions for Challenging Actions

What obstacles will I need to overcome?
Where am I playing it too safe?
What makes me uncomfortable, and how might my business expand if I overcome that discomfort?
By when can I make that happen?
Where is there opportunity that I'm ignoring?
Am I all in?

Which questions can you use right now to revitalize a less-than-desirable situation?


Share this post

Your mailing list is your #1 marketing asset.

Your Artist Mailing List report

A transcript with the 3 lists every artist should have + a 3-page assessment for understanding the health of your list. FREE with opt-in.

29 thoughts on “Powerful Questions That Lead to Progress”

  1. I grow my art life by writing down questions and answers.
    I do out reach to my art people by snail mail.
    I send out career updates,it lets people know what I am working on.
    My career updates have resulted in 43 sales in the past few months.
    Three of the updates got three of my works placed in a children’s hospital.
    Solid business practice wins.

  2. Victoria Pendragon

    Fabulous questions… every one of ’em.
    Printing out for future – frequent – reference!

  3. Thankyou for this post today. I have printed them oout too. It has really helped me to focus on where I am right now and know where I should go.
    Thank you Alison for helping me a while ago to make art when I have sick kids and holidays. I am doing it now !!!!!! No more excuses just time in the studio (balanced of course with my children’s needs ๐Ÿ™‚ )
    Thank you

  4. Hi Alyson,
    These ARE amazing questions and I am going to do the same when I have access to printer. Thank you for all that you share!!
    Lyna Lou

  5. Wow! This is exactly what I needed to hear when I needed to hear it – thank you so much for this post! I’m just starting my art career and I’m feeling more than a little overwhelmed. Despite the fact that I’ve had several of my own businesses (one of which is a Marketing business!), the avenues for marketing art seem so much different – maybe because my art is so personal to me. You’ve helped me to snap out of my fog and realize that the same things that made my other business successful will make my art career successful: dedication, perseverance, organization and a passion for what I do. Thank you again!!
    Btw, Bob, I would love to see a copy of what you send to your clients, if you wouldn’t mind sharing!

  6. Analysing those problems to generate those tough questions is almost as hard as answering them.
    Just perhaps get out into the studio and paint for yourself and not worry about the saleability of the outcome or worry about will it fit the ‘in colour for home decor’ might be the simplest of all answers.
    One day you will be too old and to frail to paint perhaps be unable to see what you are painting clearly…trust me it comes to us all one day. And you probably will still be struggling with those answers.
    Meanwhile that body of art you have created while ignoring those answers will be your lasting legacy to the world?

    1. Phil: Sometimes – really – people can’t “just paint.” Something real is getting in the way. And someone asking just 1 simple question might help unblock.

    2. Hi Alyson: for me it’s just the body letting me down…big time! Got an unused spare anyone?

  7. Here’s a super quick way to turn your blog post into a handout, Alyson:
    Just paste the URL of the post in the box. Click ‘make print friendly’ and then hit the PDF button. You can now download your post as a PDF complete with images and share it with whoever you want ๐Ÿ™‚

  8. There’s another useful question you can ask yourself at times of “low mojo”, etc:
    What’s my pay-off for engaging in this negative behavior or situation that I *say* I want to change?
    Sometimes that hidden benefit can lie very deep, but until you confront it and consciously decide whether it’s worth it, it will remain a stumbling block.

  9. Possibly the best and most useful blog post I’ve ever seen on this site. Thank you for an excellent and provocative list of questions.

  10. Sandra Cherry Jones

    Those are all thought provoking questions. I keep going back to the one of What if I pass on this opportunity? I normally do only small local farmer’s market shows but I have the opportunity of having booths at much larger shows that have a much larger group of people attending. The booth fees are much larger also. I can’t decide whether to pass because of the cost or to take a chance and just go for it. Decisions, Decisions,Decisions. What would you all do?

    1. Yes is a bigger word than No!
      So always say Yes to any offer that will advance your profitable art career.
      And No to those that don’t.

  11. Great posting today Alyson. Thanks
    Just the stuff I need right now to get back in the saddle as a painter not a viewer.
    This is definitely a printable reminder notice. Done!

  12. I don’t have a mailing list and am a little concerned about where I might cultivate it. Using a Facebook list I’m not sure is the right one, Having spent this last year caring for my Mom, my artwork has taken a back seat. But, I’m very excited about building up a body of work and finding the best way to keep others informed about my progress. So I will definitely take a serious look at these questions. They will really take some thought, but if a sale happens from doing something that originated from one of these questions, I’m all in.

    1. Hi Ann perhaps consider adding your art to every place online to link anyone browsing there towards your personal website?

    2. Ann: Phil’s suggestion is good. I also think it’s incredibly important to exhibit in live venues. That’s where you’ll find your best best prospects.

Leave a Comment

Your email address will not be published. Required fields are marked *

Scroll to Top

Your Artist Mailing List: Rethinking + Assessing

Get a transcript of episode 182 of The Art Biz (Rethinking Mailing Lists for Artists) followed by a 3-page worksheet to evaluate the overall health and usage of the 3 types of artist lists.

Where can we send it?ย 

To ensure delivery, please triple check your email address.

You’ll also receive my regular news for your art business.

Privacy + Terms

You're invited!


  • More than 7 strategies for growing your list lists, and why 1 shines above all.
  • How to redirect your energy for better results.
  • How a gratitude practice can help you shift your mindset.

I’ll also give you a peek behind the scenes at our classes and community.

This event is coming up soon. Will you come?