47 Questions You Must Ask if You Want to Turn Pro

47 Questions You Must Ask if You Want to Turn Pro

These are great questions for every creative to ask themselves.

This self-diagnostic is especially helpful when you’re seriously considering investing in high-priced coaching and training programs.

When you finally find a coach, there’s a good chance they’re going to ask you (at least some of the same) questions outlined below, to ensure you’ve got a solid foundation to build on.

Ready to turn pro? Let’s find out…

Digital Marketing

A lot of artists like to think they have their digital marketing bases covered but don’t have all the ingredients necessary to get to where they want to go.

Here are the key questions you need to measure yourself against.

Do you have a dot com domain name?

That would be [artistname].com.

It only costs about $10 per year.

Have you built a website on that domain name?

Set up hosting with a company like SiteGround (we use and recommend them). Install WordPress and start familiarizing yourself with it (there are plenty of tutorials on YouTube).

Does your website contain all essential elements of a press kit?

That generally includes a bio, sample of your best art (or music), high quality photos (of you), social media, videos, testimonials and reviews, contact information, tech rider (if applicable), and tour or media schedule (if applicable).

Do you have a blog? Or do you publish any other type of content ongoingly (e.g., podcast, video series, etc.)?

Content creates trust with your audience. What ongoing publishing efforts have you committed to?

Do you have an email list?

The stats are out on this. When it comes to getting engagement and even selling to your audience, email is a more effective channel than social media by a long margin.

Yes, push notifications, SMS text messages, and even Messenger and other messaging apps are growing in popularity, but your foundation – and even your artist retirement plan – are built on your email list.

Create yours now at ConvertKit.

Do you send at least one email per week to your email list?

This is a matter of list hygiene. If you aren’t sending emails at a regular, predictable cadence, you’re going to see more unsubscribes when you finally get around to sending campaigns.

Err on the side of sending too many emails rather than too few.

Do you make at least one offer to your email list per month?

Train your audience to buy from you. Make an offer at least monthly.

Have you created a welcome sequence for your email list?

A welcome sequence is a series of four emails introducing yourself and your product to your new subscribers.

Check out ConvertKit’s template (PDF download) for ideas.

Do you have a lead magnet?

Have you given your audience a reason to give their email address to you?

Entice them with an irresistible offer.

Are you using social media to share and promote your work?

Do you have a presence on Facebook, Instagram, Twitter, and YouTube? If not, you’re missing the main traffic channels.

Have you registered your artist or group name with all social networks?

I know, there are many to think about.

But just in case, it would be wise to have your account set up on all channels (so you can claim your username). That’s setting yourself up for success!

Do you have a YouTube channel?

Video is a powerful way to connect with your audience and share your work.

Have you optimized your YouTube channel for maximum exposure, growth, and profit?

Most artist channels represent missed potential.

From the title to the description, to call to actions, their channels are generally lacking and aren’t maximizing their potential.

Have you identified your Dream 100?

Have you identified influencers in your niche, online and offline publications that have access to your audience, and people you’d ultimately like to work and collaborate with?

If you haven’t, you need to build your Dream 100.

Do you have an offer that converts?

An offer that converts forms the foundation of your income. If you don’t yet have this, make it your top priority. Create something people want, and make sure there’s a demand for it. Then you can start growing your business.

This is also called validation.

Do you have products ranging in price from 99 cents all the way up to (at least) $2,000?

If all you have are 99-cent singles, you shouldn’t expect to get rich any time soon.

You need mid-ticket and high-ticket offers too.

If you’re just starting, then I would recommend building your high-ticket offer first, and then rolling out your lower ticket ones later.

Are you clear on all income sources available to you?

Most artists aren’t. They are aware of about three to five income sources and haven’t so much as considered anything outside of that.

There are dozens, if not 100 or more income sources available to artists. You can’t pursue them all, but you should at least be aware of the opportunities available, don’t you think?

Goal Setting, Priority & Time Management

How do you manage your goals, your priorities, and your time?

Do you use your time well? Or do you tend to squander it?

You can have breakthroughs in your career just by optimizing your schedule, and even the most productive artists usually have room for improvement.

Here are some questions you can use to evaluate yourself in this category:

Do you make new to-do lists at least weekly?

Before leaving on vacation, most of us make to-do lists.

The question is, do you make one for your work and your life?

Weekly to-do lists are the bare minimum. For busier pros, daily is essential.

Do you have a calendar (desktop, notebook, or digital), and are your weekly commitments logged in your calendar?

I use a desktop calendar pad. It has served me well for several years.

Are your goals fully documented, with a “by when?”

What specifically are you looking to accomplish? When will you have it done by?

There aren’t any right or wrong answers here, as we all find ourselves behind at times. The key is to have a goal, to be working towards it, and to put a deadline on it.

Do you keep a journal?

Not a diary. A journal.

Have you heard of Vishen Lakhiani, CEO of Mindvalley? His friend, Patrick Grove, is always a step ahead of Lakhiani’s monumental success. How? He keeps a journal.

At first, Grove said he spent a lot of time just journaling about the things he didn’t like. And then he started journaling on how to get what he wanted in life. Eventually, he found himself mapping out entire plans (that worked in the real world!).

Check out his story here:

Do you use your journal to ask meaningful questions, map out ideas, or chart a course for your eventual success?

Also see description from previous question.


Financial stability in the artistic world may seem elusive. But if you have a shaky foundation, it can be incredibly difficult to level up your career.

Here are some questions to help you ensure you’ve got the right structures in place.

Do you have a no-fee checking account to manage business income and expenses?

A personal checking account works. A no-fee checking account is better. A business account is the least preferred option, as it often comes with inflated fees, minimum balances, limited transactions, and the like.

Separating out your business finances from your personal finances allows you to create more clarity around solvency and opportunities for reinvesting.

Have you set up your three buckets of savings (emergency fund, dream fund, and aggressive growth fund)?

Put six to 12 months of expenses in your emergency fund.

Once that’s complete, start saving inside your dream fund and make your dreams a reality – toys, cars, vacations, maybe even homes.

Once you’re well underway with your dream fund, start putting money into your aggressive growth fund. This money should be allocated to aggressive investing – meaning you wouldn’t miss this money your gambles didn’t pay off (because you’ve already built up the other two buckets).

Have you automated any aspect of your savings efforts?

In my case, about a third of my income automatically goes to savings and reliable investment vehicles.

Do you have an investment plan?

You may not have the money to invest now, which is fine. But long-term, do you have a plan for investing?

Don’t just look to stocks and bonds. Also look at cryptocurrency, whole life insurance plans, precious metals, and other investment vehicles.

Do you have a strategy for how you circulate your money (intentionally)?

Money likes to circulate.

When we plan and direct it where to go, it follows our direction.

But if we go on autopilot, money tends to circulate all by itself without our active participation.

What strategy do you have in place to ensure your money is moving to the right channels?

Are you reinvesting in your business?

Money you make in your business is the seed money you can use to grow it.

This doesn’t necessarily mean allocating 100% of your income to business growth.

But it does mean being clear on how much you can put back into your business – for tools, staffing, training, systems, advertising, and so on.

Personal Growth

Are you committed to your ongoing growth? Do you see yourself as a lifelong student?

If not, it’s no surprise that you should find yourself stuck in a rut.

The best thing you can invest in is your personal growth.

And now it’s thinking time.

Do you read books to further your career growth?

I’m not the fastest reader in the world. I’ve still read about 200 to 300 books to date (I also read 52 books – 104 total – in 2015 and 2016).

Do you listen to audiobooks and podcasts to further your career growth?

I listen to audiobooks and podcasts whenever I’m driving.

Do you watch videos and take courses to further your career growth?

My Exhaustive Self-Indulgent History page holds a register of the long list of courses I’ve taken (or am taking) so far.

Do you currently have a coach, mentor, or both?

Is there anyone guiding you on your journey that has the results you want?

Are you part of a mastermind group?

Do you have weekly, bi-weekly, or monthly calls with other like-minded, ambitious people who can contribute to you?

Are you part of an online community?

Are you part of a forum, Facebook Group, or membership where like-minded, ambitious people gather and discuss relevant issues?


Success is available to anyone, and it doesn’t have anything to do with talent or smarts.

But there are some roadblocks that can stop even the bravest artists and creatives dead in their tracks.

Here are some valuable questions to ask:

On a scale of one to 10, how teachable are you?

This tends to shift from moment to moment. So, become present to how you feel now. Are you committed to being teachable, even when you don’t feel like it?

On a scale of one to 10, how open minded are you?

Again, this can change from moment to moment. Assess based on how you feel now.

The more open minded you are, the faster the change you can ultimately cause.

On a scale of one to 10, how willing are you to accept change?

As we ask new questions, have new conversations, and take new actions, it’s only natural that there will be new occurrences in our lives. And the new can be uncomfortable. It can even appear wrong.

How willing are you to accept change on the way to getting what you want?

On a scale of one to 10, how willing are you to accept the coaching of another?

We all say we’re willing at first, but then when we’re burdened with difficult questions, or saddled with unfamiliar and seemingly difficult tasks, sometimes we hide away, don’t act, or give up entirely.

How willing are you to accept the coaching and direction of another?

Health & Recreation

Your well-being is crucial to your ultimate success. Without you, there is no business.

Here are some questions worth asking in this area:

Do you have a support group? Family or like-minded friends who can lift you up when you’re feeling down?

As an artist or creative, it’s critical that you develop your inner circle of people you trust and rely on (and know what you can count on each of them for).

The journey isn’t always easy.

Do you get out into nature at least two hours per week?

Change of pace and change of environment are crucial to maintaining inspiration, which leads to innovation and breakthroughs in your business.

Getting outside is important for your well-being in the fast-paced world of creativity and business.

Do you have a hobby you can engage in (preferably something physical, outdoors) daily?

My business coach surfs daily. I try to get out for walks, hikes, and fishing as much as I can.

Is there something physical you can engage in on the regular?

Do you have a refreshment routine?

What refreshes you?

Can you meditate, read a book, go for a brisk walk, or do something else to recharge your battery throughout the day?

Have you scheduled your vacation time?

This should go first in your calendar.

If you’re always going at a breakneck pace, you need a week or two away every three months.

If you’re going at an intense pace, you still need two weeks every six months.

And if you’re working hard but not intensely, three to four weeks per year are recommended.

If you’re working 25 hours per week or less, you probably have a very sustainable schedule already.


Your mission is at the heart of your activity.

Yes, we all do a lot of things for the same, basic human drives.

But there is something magical about developing your “why.” When you know your “why,” all other decisions in life and your career seem to come with ease, including which social networks to be on, who to collaborate with, where to put your energy, and more.

Let’s get to those questions.

Are you clear on the results you want to achieve?

Have you thought about what it would look like to create the life you want? Have you envisioned it vividly in your mind’s eye? What is the impact and legacy you want to leave?

Sometimes, our mission only becomes clearer as we move further and further down our individual path. But best to your ability, I recommend getting clear on the future you’re unfolding.

How much would you be willing to spend to get that result?

We often say we want things, but when the rubber meats the road, we find ourselves balking at $97 courses, $900 weekend programs, and $2,000 masterminds.

What price are you willing to pay for your dream? It doesn’t matter how much money you have right now. What matters is that you’re willing to go the distance.

How much would you be willing to sacrifice to get that result?

The idea that we can get everything we want in life without some sacrifice is beyond misguided.

Most of us would do well to focus on three to five things and see them to completion before we add anything else.

What would you be willing to sacrifice, short- and long-term, to create focus and get the results you’re looking for?

What is your mission? Can you articulate it in one to three succinct sentences?

Your mission is also your brand, which makes it critical to develop.

Starbucks’ mission is this:

To inspire and nurture the human spirit – one person, one cup and one neighborhood at a time.

I bet you didn’t know that!

Your mission need not be complicated. But it should be defined, and it should be clear.

Can you articulate what your mission is in one to three sentences, such that anyone could “get” it?

Final Thoughts

Ready to take the next step?

Then sign up for your first-time coaching session with me!

Weekly Digest: September 11, 2021

Weekly Digest: September 11, 2021

David Andrew Wiebe: July 2021What are you working on right now?

What are you forcing yourself to work on?

And what do you actually want to be working on?

These are innocuous sounding questions, but as I’ve been discovering, what lies beneath the surface level answers might just surprise you.

This week, I engaged in the creation of multiple videos – some talking head, but mostly guitar shorts / memes.

I also ended up releasing a 15-minute guided meditation (which will be available on all online music stores and streaming platforms on September 24!).

With all the blogging I’ve been doing, and predominantly informational content I’ve been creating, you may have assumed that I’ve been working on exactly what I want to be working on. But the truth is, most of this represents things I’ve been forcing myself to do. And it took some looking for me to understand this.

Do you know how long I’ve been thinking about making meditation audios or guitar videos? Probably years!

So, there’s all this pent-up energy that’s finally starting to burst and find its expression. And it has basically meant thinking differently about daily blogging and content creation in general. Because I realized most projects, I want to be working on fit nicely into this schedule.

If you think you know David Andrew Wiebe, well… you’re really just beginning to see all that he’s about.

I don’t know how long I’ve been bottling up my own expression. But it has been too long.

Don’t let your mind rule your creativity. Let your heart lead too.

Don’t let your mind rule your creativity. Let your heart lead too. Click To Tweet

New Value-Packed Blog Posts & Podcast Episodes

Here’s what I created for you this week. Click on the headlines that pique your interest.

Music Entrepreneur HQ on Social Media

Here’s a unique, value-adding piece we shared on social media this week:

David Andrew Wiebe quote

Must-Have Resource

There’s a personal development program I’ve been through three times, and each time I go through it, I learn more about myself and what matters most to me. I’ve also been able to improve my health, grow my business, and challenge myself intellectually.

The name of the program is The Gold Within.

Any artist looking to get clear on the impact and difference they want to make in the world (their brand) should go through The Gold Within program at least once.

The Gold Within

Final Thoughts

Thank you for your creativity and generosity. I’m rooting for you.

Why Support the Education of Underprivileged Children in South America?

Why Support the Education of Underprivileged Children in South America?

Here’s why:

My late father and grandparents (my father’s parents) were all great supporters of the cause.

As of this year (2021), all of them have passed. My dad, specifically, passed in a motorcycle accident when I was 13. I will remember my father and grandparents fondly.

So, I wanted to do something in their memory. Which is why my current efforts include raising funds for the education of underprivileged children in South America.

What We Were Able to Accomplish Last Quarter (June to August 2021)

Here is our donation receipt from last quarter:

Donations from last quarter

In total, we were able to raise just a little under $300 through anonymous donations, custom commissioned portraits, and infoproduct sales through our funnels.

The “Make a Difference Campaign”

Our goal this quarter (September to November) is to raise $1,500. That’s why you’re seeing the “Make a Difference” campaign on my blog, on Music Entrepreneur HQ, and on Content Marketing Musician.

Make a difference: Content Marketing Musician

Between now and November 19, 2021, we will be donating 50% of the proceeds from all products on Content Marketing Musician to support the cause.

What Charitable Organization Are We Giving to?

Last quarter, we sought to get a support statement from the organization we’re supporting but did not hear back. That means we can’t use their organization name in any of our marketing efforts.

If you would like to have a private conversation around what organization we’re supporting (and why), you can contact me directly.

How Can I Help?

If you’re a musician or creative seeking resources to help you get results in your career, then making a purchase on Content Marketing Musician will help support the cause (we will be donating 50% of the proceeds).

Secondarily, you can:

Thank You!

Thank you for reading and for your generosity in supporting our efforts to create more opportunities for underprivileged children in South America (and related inter-world development projects). Here’s wishing you all the best in your creative efforts!