Ever had an “aha” moment from a single question? An instant when something about your business comes into focus? It’s like putting on glasses you didn’t know you needed.

That’s the power of asking the right questions.

This week, we’re diving into self-reflection for solopreneurs. We’ll explore transformative questions for your business — ones you may not have considered, or have been avoiding.

First, meet our 3rd book winner!

Many more readers answered the 3 quick questions to help me know you better. From all responses, I selected one more person to receive a copy of Seth Godin’s new strategy book, arriving in late October.

Our third book winner (out of five) is:

⭐️ Bob Lopez, a real estate consultant for buyers, sellers, and investors. Congrats, Bob!
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If you’d like a chance at one of the books, here are the questions, or scroll down for details on participation.

Now, ready to unlock your solo business potential? Read on to dive in and start asking the right questions.

Why we avoid self-questioning

Let’s first address the elephant in the room: why don’t we ask ourselves these pivotal questions more often?

✅ Fear of the answers​
Sometimes we avoid asking because we fear what we might discover.

✅ Comfort in the familiar​
Sticking with what we know is easier than challenging our assumptions.

✅ Lack of time​
Reflection often gets neglected in the hustle of running a business.

​Research published in the Harvard Business Review found that a habit of reflection can separate extraordinary professionals from mediocre ones.

Ask yourself these 7 breakthrough questions

Over the years, I’ve collected dozens of self-reflection questions that unlock my thinking. Here are 7 of my favorites.

❓ If I had to restart my business from scratch, what would I do differently?​
This encourages a fresh perspective on your current operations and highlights areas for improvement or innovation.

❓ What’s the one skill I need to develop that would impact my business the most?​
This pushes you to identify key areas for personal or professional growth that correlate with business success.

❓ What’s the biggest assumption I’m making about my clients, and how can I test it?​
This encourages you to challenge your preconceptions and gather real data about your target market.

❓ What untracked metrics could provide valuable insights into my business performance?​
This gets you thinking about the numbers that really matter and helps you make smarter choices for your business.

❓ What will my field look like in 3 years, and how can I position myself to become and remain a leader?​
This pushes you to peek into the future, anticipate industry trends, and map out ways to become an expert in your niche.

❓ What 3 solo business owners do I admire most, and how can I adapt their strategies to fit my solo business?​
This encourages you to learn from successful peers in your field, helping you identify and adapt proven strategies to your unique situation.

❓ What would I do if I wasn’t afraid of failure?​
This question challenges you to think beyond your comfort zone and envision bold moves for your business.

Each of these questions can lead to “aha” moments and reveal important self-insights. Which one resonates most with you?

Jumpstart your self-reflection journey

Ready to craft your own powerful questions and make self-reflection a habit? Let’s get started.

1️⃣ Curate your own “question bank”​
Keep a running list of powerful questions. Add to it whenever you find a thought-provoking query.

2️⃣ Create a “Question of the Week” challenge ​
Choose one powerful question each week and dedicate time to explore it. Journal your thoughts, brainstorm ideas, and commit to taking one concrete action based on your reflections.

3️⃣ Find an accountability partner
Share your reflections with another solopreneur. Verbalizing our thoughts can lead to new insights.

What powerful question will you ask yourself this week? Hit reply and let me know — I’d love to hear your insights and discoveries.

Until next week, keep questioning and growing!

❤️ My favorite visual delights

Here are this week’s gems from around the Web for all types of visual thinkers and solopreneurs:

🔈 BBC Sound Library now free to use​
The BBC has open-sourced its vast sound library, making around 33,000 sound files free to access, modify, or distribute for non-commercial uses. If your next project, social media video, or podcast needs sound effects — rare birds, clock sounds, street noises, music, or other audio elements — here’s a great new free resource. Plus, it’s fun just browsing.

🤝 Influence: The unseen key behind powerful persuasion​
Robert Cialdini literally wrote the book on the science of persuasion, his 1984 classic, Influence: The Psychology of Persuasion. This article, based on an interview with Cialdini (now 79), updates his key principles for the digital age. It’s a quick read that provides an overview of his work, whether you’ve never encountered it or need a refresher.

✏️ How yellow pencils teach a branding lesson​
With a new school year comes fresh notebooks and pencils, many in bright yellow. Discover how color transformed a generic item into a luxury good, and consider how you might put this historic branding lesson to work in your solo business.

🍀 3 questions, 2 minutes, 2 more chances to win Seth Godin’s new book!

I mentioned above that I’ve put together 3 questions to understand the SOLO readership better. It takes about 2 minutes to fill it out and share your thoughts.

The goal? To help me create the content and resources you want, and avoid clogging your inbox with off-target material.

Dozens of SOLO readers have responded (thank you!), and I’m learning a lot. We have such a diverse reader community. There are writers, futurists, app developers, artists and designers, online course creators, coaches and consultants, a “reluctant marketing guy,” and many more solo business founders.

Your thoughtful responses will guide me (as they have with this issue) in helping you grow your solo business, on your terms.

⭐️ As an incentive (always nice), I’m giving away a copy of Seth Godin’s new book, This Is Strategy, releasing in late October, to five SOLO readers who respond.

Whether you’re just starting out or have been working solo for a while, there’s still time to participate (and 2 more books to give away). 3 questions, 2 minutes, 2 more opportunities to win a book.

So if you missed the first two rounds, here’s your chance to take part:

If you’ve already responded, thanks again. You’ll be included in the drawing pool and have two more opportunities to win a book.

Psst... did you get your free Solo Business Canvas yet?

If you haven’t downloaded your copy of this one-page, interactive visual framework to help you grow your solo business, what are you waiting for?

The Solo Business Canvas is my labor of love, nearly a year in the making, to help solopreneurs sort out the key components of their business. It will help you:

• Get clear on what you offer
• Spot new ways to make money
• Identify your ideal customers
• Map the resources you need
• Know your exact next steps

After completing the Canvas, you’ll have an easy-to-follow roadmap for creating a successful solo company. Download your copy and put it to work in your business.

Did you miss these?

Catch up on some recent popular issues of SOLO you may have missed.

✅ Can You Spot the Invisible Drag Forces on Your Solo Business?​

✅ How to Stand Out When You’d Rather Hide​

✅ Meet the Solo Business Canvas​​​​​​​​​​​​​

Want to check out other past issues? Visit the SOLO Newsletter archive.​

Thanks again for being a SOLO reader and coming along on this journey with me.
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Know someone who wants to unlock their solo business with powerful questions? Share this issue!

And if you received this issue from a friend, I invite you to subscribe.​

See you next week,