10 Career Questions for Creative Entrepreneurs (+ a Free Assessment)

As a creative entrepreneur, you have an endless number of career choices available to you today. These options can be a real blessing or a real curse.

They can be a blessing because you can tailor-fit your creative work to fit your passions, gifts, and interests. But they can also be a curse because it’s easy to get paralyzed by all these options.

Over the last couple of years, I’ve developed several small streams of income. These include book sales, writing podcast show notes, substitute teaching (which I’ve since abandoned), editing and formatting books, selling on Amazon (which was a bust), website development, and a few other things.

I’ve been truly grateful for every one of these income sources. But I’ve reached a point where I want to start being more intentional by focusing on the most fulfilling and sustainable streams of income.

Preparing for the future

I’m still a full-time college professor, and I don’t have any plans to leave that position. I truly enjoy my work at St. Louis Christian College. The school has been very generous in allowing me to develop courses in writing, film, and the creative arts. I probably wouldn’t have the opportunity to teach these courses at a larger school, where I would be locked into one specific department.

However, it’s naive to think that any single job opportunity will last forever. What if something happens to you? To the organization? To the position? That’s not a statement about my workplace; that’s a statement about employment in general. Sometimes things happen that are beyond our control, and we always need to be prepared.

In addition, we all understand the importance of paying off debt, building up savings, and creating a more secure financial future for our families.

So the question is this: As a creative entrepreneur, how do you decide what opportunities to focus on when trying to build a side income?

Clarifying your ideal creative work

I recently sat down to explore this question in my own life. To be honest, I have been pretty frustrated by my own lack of direction and clarity about creative opportunities. Should I focus on writing books? Freelancing? Online courses? Speaking? Teaching guitar? Coaching? Consulting? Helping other authors?

I have a pretty broad skill set and can do a lot of different things. That’s definitely good. But when you mix it with an indecisive personality like mine, it’s a deadly combination. You feel paralyzed, unable to pick a direction because you don’t want to make the wrong choice.

I cleared all of those concerns from my mind and thought about all the qualities I want to have in my ideal creative work. After a couple hours’ worth of thinking and revising, I landed on ten questions that represent the type of life I want to design.

These questions are a little dangerous because they will give you clarity about the work you are currently doing, as well as any work you are considering. Clarity can be a dangerous thing. Why? Because you might realize the life you are living is not the one you want to live.

I’ll list and explain these questions in just a moment. Then I’ll describe how to use these questions to evaluate what you’re currently doing, as well as the opportunities you have.

I’ve created a handy assessment tool you can use to evaluate your own creative opportunities. This tool will give you clarity on which opportunities you should pursue.

Click here to download the Creative Entrepreneur Career Assessment

One more thing: These are my questions. They don’t necessarily represent what is important to you in your creative work. I would encourage you to develop your own list of questions, using mine as a jumping-off point.

The 10 questions

1. Do I enjoy this type of work? Does it give me creative fulfillment?

Do you enjoy what you’re doing? Do you look forward to doing it? Does it make you happy or fulfilled? You only have one life, so why spend your time doing something you don’t enjoy?

2. Can I become a leader in this field with enough time and good work?

This is not important to everyone, but it’s important to me. I want to be seen as a competent leader in my field. I want to influence others and make an impact.

3. Is there unlimited income potential in this type of work?

This is the very reason why I stopped substitute teaching. Sure, it brought in a little bit of extra income, but there is a cap on how much you can earn as a sub (and it’s a very low cap).

Ideally, I want to engage in the type of work where there isn’t a limit on how much I can earn. I want my income to be related to the value I bring to others, not by trading hours for dollars.

I don’t necessarily need to be a multi-millionaire (not that there’s anything wrong with that). I just want to earn enough that I don’t need to worry about money.

4. Is there a future for me in this type of work? Is the market potential good?

This is an important question because market realities change over time. For example: my wife used to work at a large bookstore chain. Many bookstores have closed in the last decade because the market is changing.

The purpose of this question is to make you think about what you do, and whether you are in a market that is growing or declining.

It doesn’t mean you shouldn’t stay there. But it does mean that you need to position yourself to either be successful in that market by standing out from the competition, or transfer those skills to a different market that is growing.

That’s exactly what my wife did. A couple of years ago, she transitioned into an event planning role with a different organization. The skills she developed working at a bookstore have served her very well in her current role, although the two industries aren’t related.

5. Have other people already affirmed me in this type of work?

It’s important to stick with your strengths. If others have affirmed you in this field, or a related field, then you can capitalize on your past success and experience.

However, if you have zero experience in a field where you want to thrive, you have a lot of work ahead of you. It doesn’t mean you shouldn’t do it, but it does mean you are starting from scratch.

6. Is this type of work scalable? Can I do it once and get paid multiple times?

As I’ve already mentioned, not all of these questions will resonate with you. You might disagree with many of them. But they are important to me—especially this one.

Writers like Dan Miller, Michael Hyatt, Pat Flynn, and James Altucher have helped me understand the genius behind passive income and doing work that “scales.”

Most people look at work as “I spend X amount of time, and get paid X dollars.” But the idea behind passive income is that you create something once and get paid many times.

For example, when you substitute teach, you spend a day at school and get paid once. But if you write a book or build an online course, you create it once and can get paid an infinite amount of times. The same is true for many other types of creative content.

In other words, I want to take the lid off my potential to create income. The way to do this is by creating more assets. I highly recommend you check out this insightful article by Mark McGuinness: Forget the Career Ladder: Start Creating Assets.

7. Do I feel a sense of divine calling toward this type of work?

In an ideal world, I want to do creative work that provides for my needs and meshes with my gifts and talents. But that’s not all—I also want to fulfill God’s calling for my life.

When it comes to your divine calling, it’s important to have an inner sense of calling as well as external affirmation. If you are truly called to something, other mature people of faith will affirm you in that calling.

It’s not enough to make art or make money. You need to make a difference.

8. Do I have time freedom in this type of work? Can I set my own schedule?

My most valuable asset is my time, and I want as much control over it as possible.

I know it sounds like I hated substitute teaching, but I really didn’t. It was enjoyable most of the time. But if I have to choose between doing freelance work at home, or subbing, I’ll choose freelancing every time.

Why? Because I don’t want to be locked into someone else’s schedule.

Some people will think this sounds unrealistic or selfish. But all things being equal, wouldn’t you rather have more, not less, control over how you spend your time?

9. Does this type of work help grow my personal creative brand?

This is a tricky question because every time you do excellent work, it helps grow your reputation. But what I’m talking about here is the choice between doing freelance work that is not related to my industry (creativity and arts), and work that is related to it.

At this point in my journey, I am happy to do almost any type of freelance writing work that helps pay the bills. But as time goes on, I want to focus more and more on work that helps establish my expertise in my niche.

10. Does this type of work let me “make my own luck,” or am I at the mercy of others?

One of my favorite movies is The Dark Knight. The District Attorney Harvey Dent (who later becomes the villain Two-Face) carries around a two-headed coin. Whenever he flips it, the coin always lands heads up.

His motto? “I make my own luck.”

As a creative entrepreneur, you make your own luck. If you’ve ever worked for a bad client or mean-spirited employer, you know the stress of feeling like someone else is holding the reigns of your livelihood.

Unless you’re independently wealthy, you always depend on others for your income. But there is a difference between being in charge of your own destiny, and giving control to someone else who can drop you in a heartbeat.

I once had a client who was critical and demanding. I didn’t enjoy working for him. I kept at it because I needed the money, but I hated the constant feeling of being at his mercy.

All I’m saying is that ideally, you want to diversify your income in such as way that you’re not at the mercy of one employer or client. In a volatile economy such as ours, things can shift in a heartbeat and your income source can be cut off quickly.

I’m not saying that everyone should work for themselves or be an entrepreneur. I’m just saying that it seems like a smart approach to develop several income streams in case something happens to any given one.

How to use the free assessment

Now that you have a handle on these ten questions, let’s explore how to use them. Make sure to download the free assessment below:

Click here to download the Creative Entrepreneur Career Assessment

When you open the assessment, you’ll see this:

At the top, you’ll see the ten questions (condensed as statements) in yellow.

In the green column on the left-hand side, list everything you are currently doing, or think you might do, to make money.

Here are some of the things I listed, in no particular order:

• Podcast show notes
• Writing non-fiction
• Writing fiction
• Preaching
• Leading worship
• Freelance writing (in my field)
• Freelance writing for businesses
• Ghostwriting books
• Website development
• Editing
• College teaching
• College adjunct
• Online courses, webinars, workshops
• Podcast / audioblog coaching
• Personal creative coaching
• Live speaking / workshops / training
• Book formatting
• Author coaching
• Graphic design
• Podcast / audiobook production
• Voiceover work
• Making music / playing guitar
• Teaching guitar (lessons or courses)
• Social media consulting

When you have listed all of the things you are doing, or could possibly do, to make money, then rate each one according to the ten questions. Give each column a number from 0 (low) to 5 (high).

For example, take “Editing.” For Question #1 (“I enjoy this type of work”), I would give it a “1” because I don’t really enjoy editing. But for Question #8 (“There is time freedom”), I would give it a “5” because I can do it on my own time.

When you have rated every type of work from 0-5, for all ten questions, you have a raw score out of 50 pts. The second-to-last column doubles this score so you have a more traditional “grade” out of 100 points.

Then, the final column automatically assigns a letter grade.

Here’s why this assessment is worth your time: you will be surprised at the results. When I completed the assessment the first time, I was shocked. I received a D or F on several types of work I’ve been doing. But I also received an A or B on several types of work where I haven’t been focusing enough attention.

The point? I’ve been spending time focusing on some things that aren’t truly important to me, and I’ve been ignoring some things that are truly important to me. Going through this process has been a real gut-check.

Two quick tips

Here are a couple of quick tips to make this process more valuable:

1. When you’re completing the assessment, don’t over-analyze your responses.

Don’t answer in a way that you think is “correct.” Be brutally honest with yourself, or the process will be meaningless.

For example, I can preach, but I honestly don’t enjoy it that much. My undergrad degree was in preaching, and I’ve preached countless times over the years. But I don’t get a lot of fulfillment out of it. So I rated that type of work as a “1” under Question #1 (“I enjoy this type of work”).

And by the way–please hear me on this–just because you rate something low doesn’t mean it has low value, or that it’s not important. Preaching is very, very important. But it’s not something I personally enjoy doing that much.

Don’t confuse the value of a particular type of work with your enjoyment of it. They are two completely different things.

2. Have a trusted friend look over your assessment results.

When I completed my assessment, I sent it to a very good friend who challenged me in a couple of areas. He pointed out how I could easily make money by using a talent I already have. I hadn’t thought about the opportunity he mentioned, but it was brilliant, so I’ve adjusted my plans to include his suggestion.

A trusted friend can alert you to possibilities you haven’t seen. They can give you much-needed perspective on your goals, gifts, and strengths.

Is this approach inherently selfish?

As you look through the ten questions I’ve outlined in the assessment, it might seem like this approach is inherently selfish. After all, these questions are about “me.” Shouldn’t it all be about serving other people?

Yes, it absolutely is all about serving others. But it’s hard to serve with excellence if you’re constantly worried about money. It’s hard to serve with excellence if you’re constantly shifting gears between different types of freelance jobs. It’s hard to serve with excellence if you’re doing work that you don’t enjoy.

I work on the assumption that I will do my best work when I am relaxed, happy, focused, and operating in my gifts. I also assume that God will not call me to a type of work for which I’m not gifted, and for which I have no passion.

(That being said … we have to balance this with the fact that we all have to “grow” into our calling to some degree. And many times, our passion grows simply from working hard at something. So we need to maintain a balance in our thinking.)

No, this approach isn’t selfish at all. In fact, it’s the opposite—when we are healthy, happy, and operating within our gifts, we can give and serve more from a life that is overflowing with joy and abundance.

This has been a long post, but I hope that these ten questions, as well as the assessment, are helpful to you. Feel free to ask any questions in the comments, or let me know if I can help in any way.

What other questions would you add to this list?