“There are no stupid questions.”

We know this to be true. (At least, we’ve heard it enough to hope it’s true).

But what nobody talks about is: what does it mean if you don’t even know what question to ask?

Sometimes, in times of great conflict and confusion, I feel like a cartoon character: a great big question mark over my head. In this state of mind, I feel like sticking my head in the sand and throwing a little pity party.

When I’m in way over my head (as I now seem to be most of the time) things come up that are so perplexing that formulating a clarifying question (even a “stupid” one) seems hard.

A great example is an area of business that many entrepreneurs struggle with: Finance.

From the internal (bookkeeping and records) to the external (fundraising and pitching) there is a TON of new information to absorb. It is literally like another world, with another language — and I had no clue where to start.

Unlike making and selling the product (tangible, accessible — and fun), finances are not always intuitive and can often seem “not that important” in the scheme of a start-up. I remember saying things like, “Why stress out about tracking sales right now? We’re only selling a few thousand dollars worth of product a month — I can practically track it in my head!”

Once we felt the need to get our act together for tax time, I dutifully punched numbers into Quickbooks — then relied on our financial advisors and Accountant to process the information for me. When there wasn’t much feedback on our numbers, I was relieved — that meant our numbers were fine! No need to stress or investigate further…. Keep punching numbers.

The same on the legal end of things. After we formed our company and got a fat binder of documents from our lawyers, I didn’t think too deeply about what sort of company we were (Partnership, LLC, C-Corp… whatever!). I kept on sampling product at stores and doing all the “real” work on the front end.

Honestly, I thought that our accountants and lawyers would be like new Wild Friends team members — they would call out an alert if something wasn’t good, let me know if my numbers were wrong, tell me what to do and when to do it.

It turned out that’s not what accountants and lawyers are for — they are there to answer your questions, not question your methods or decisions.

I wasn’t asking enough questions.

I didn’t even know what questions to ask.

It took our company’s first outside fundraising round for me to look up and realize that I needed to really, actively, engage — to take responsibility for good bookkeeping, solid legal understanding, and excellent future projections.

After all, the future existence of our company depends on these things just as much as on a good product and growing sales. If we can’t prove our company’s worth to investors, we won’t get outside capital — and that’s when growth stops, even (especially) in the fastest-growing, most successful companies.

So, I had a fire lit under me! I really wanted to learn. But, I STILL didn’t have any real, specific questions — just that big question mark hanging over my head.

I started with basic self-education: I read this book, and this one (both highly recommended). I gained a greater understanding of finances and company formations! This was exciting.

Even better: With all this new information came TONS of new questions.

At first, this made me feel a little overwhelmed, but in hindsight, this is GREAT.

This is when advisors, accountants and lawyers really start to come in handy. They are fountains of information — once you know what to ask, the advice and information will come to you.

Usually this information will bring with it a whole new set of questions — but this is how learning happens.

Truth: it’s scary and hard to find and ask the right questions… but not nearly as scary and hard as it is to live with your head in the sand.