I Owe My Success As A Creative Entrepreneur To These 8 Questions I Ask Every Month

I Owe My Success As A Creative Entrepreneur To These 8 Questions I Ask Every Month

The only way to find the right answers is to ask the right questions.

There are eight I regularly ask myself about my business and creations and the answers always reveal ways I can improve my work and get closer to my goals.

I hope they help you as much as they’ve helped me…

1. If you had to stop doing 10% of what you’re doing, what would you abandon?

It’s easy to convince yourself something is too important to stop doing.

But this hypothetical question forces you to identify your least valuable activity.

And once you identify it, you’re a LOT more likely to abandon it.

2. Is this actually working?

It’s so easy to fall into the “because I’ve always done it” trap.

But when applied to an individual project or your entire approach to your business or creations, this question does a couple valuable things.

It forces you to define what it means for something to “work,” assess whether it is, and if it’s not consider how you may want to switch things up.

3. What would you do if you had to launch/finish X in Y days?

This question is a procrastination and perfectionism killer.

When you’ve struggled to get a project started or wrapped up, choose a hypothetical (and aggressive) deadline and consider how you’d approach it if you had to launch or finish in that time period.

The question forces you to consider ways to simplify or speed up the process and once you see them, it will often inspire you to make it happen.

4. What work did you most enjoy doing recently?

Whether it’s a particular type of client or something you created, consider what’s giving you the most satisfaction and success.

Then optimize to pursue more of that.

(Personally, the answer for me always seems to be my For The Interested newsletter.)

5. What work did you least enjoy doing recently?

This is the flipside of the question above and it’s every bit as valuable.

6. What have you learned to do well in the past year?

You’re always learning so it’s helpful to consider what you can do now that you couldn’t previously.

Besides being a boost to your ego, this question reveals ideas for content, products, and services you can offer.

Lots of people need to learn what you now know. 

And remember: Your ideal audience is often the person you used to be.

(Personally, after I develop an effective system to grow my audience and business I share it with others in my Skill Sessions.)

7. What would happen if you raised your prices?

I’ll tell you what will probably happen.

A small increase in price will have zero impact on the number of sales you generate — aside from earning you more money.

And a significant price increase may reduce your total sales, but it also might earn you more money overall and/or give you a business that better reflects what you want.

Think about it.

8. What would it look like if it were easy?

This question comes from Tim Ferriss.

Here’s a video that summarizes the concept:

Want more strategies to grow your business?

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