Learning to Ask Questions (Copy)

For me, the idea of consulting began with questions. The questions I asked out loud and the questions that tugged quietly in the background while I was running my gallery. Some questions I could name clearly. Others I didn’t yet know enough to articulate. And often, I wasn’t sure who to ask, or where to look for guidance.

Looking back, I realize I couldn’t have been alone in that. Artists, gallery owners, creative entrepreneurs, we share many of the same uncertainties, just from different angles. If I had questions about running a retail art gallery, it’s likely that others do too.

The search for answers applies to artists as well. After college, who was I going to ask?

That’s why I’m writing. Not because I have every answer, but because I’ve lived the questions and learned from them along the way.

When I was preparing to open my gallery, I signed up for every business start-up class the community college offered. If there’s a small business development center near you, seek them out. They’re often free, practical, and genuinely helpful. I filled notebooks with information and referred back to those notes for years.

But even with all that preparation, there were pieces that didn’t click right away.

For example:

I sat through multiple workshops on business finances and still didn’t fully understand how vital knowing what my cash flow was. I thought, “As long as money is coming in, I’ll be fine.” That’s not how it works, of course, not when rent, payroll, and artist payments are due on specific timelines, even when sales slow to a crawl after the holidays. Eventually, I learned. But sometimes the learning curve was steep.

I also believed that the consignment model was the perfect solution for my retail gallery. If I didn’t have to purchase inventory, I would avoid risk. Or so I thought. What I didn’t know to ask was: What are the advantages of having wholesale items in the gallery mix? I didn’t realize that wholesale pieces could have helped balance margins and create more predictable profits.

And then there was advertising. Every business needs to advertise, right? But how much of my budget should be spent on advertising? I tried everything free - listings, flyers, community calendars - and some of that reached potential customers. But I also spent money on ads that didn’t bring customers in the door. When those ads didn’t work, I felt foolish, like I should have known better.

Looking back, the problem wasn’t that I made mistakes. We all make mistakes.

The problem was that I didn’t know how to ask the strategic questions that mattered most. I didn’t yet know how to observe my business with curiosity before making decisions. I didn’t yet know how to recognize which advice applied to my gallery and which didn’t.

No one knows all the right questions at the beginning. We learn some of the questions to ask through running the business. By watching what works and what doesn’t. By asking, sometimes too late “What should I have been paying attention to here?”

If you’re in the early stages, or even years in, and you feel like you should know more by now, please know that you are not behind. You are learning in real time.

The key is not to assume you should already know the answers but to stay open, curious, and willing to ask the next question. That’s where the growth is.

And over time, the questions themselves become a compass of sorts, pointing you towards what matters most.