Weekly Digest: June 5, 2021

by | Jun 5, 2021 | News

David Andrew Wiebe, May 2021For the most part, we don’t spend enough time thinking and reflecting in proportion to the amount of time we spend working and creating.

Creating is the fun part, to be sure. But if we want to create sustainable, profitable careers in our chosen fields, we can’t spend all our time, energy, and resources endlessly creating and tweaking what we’ve created, as is the artistic tendency.

The Road Less Stupid author Keith J. Cunningham argues that there are four hats business owners must wear to ensure success – Artist, Operator, Owner, and Board.

As an artist seeking success, you are a business owner whether you want to be or not, which I point out in case there’s any resistance to the notion of artistic entrepreneurship.

And your success will ultimately be determined by your ability to develop new skills in the areas you aren’t already strong in (Operator, Owner, and Board), and see the grand picture forming from a variety of angles. It’s not enough to see your career coming together through the eyes of the Artist, because the Artist will always want to create and tweak.

At minimal, you would need to seek out a mentor or coach, which is, incidentally, something someone wearing the Board hat would think to do.

We all know that Steve Jobs was an amazing artist/creator. But he nearly drove Apple into the ground the first go round. Developing his business and risk management acumen (Board hat) is what enabled him to lead the business into the Promised Land.


  • Which hat takes up most of your time and energy?
  • In what areas are your strong, and in which areas do you feel weak?
  • What new skills could you develop to gain a better vantage point for what you’re trying to create artistically and entrepreneurially?
  • Which hat is your favorite?
  • Which hat is your least favorite?
  • Which hat(s) do you think you need to spend more time wearing?

For more questions to ponder, refer to my least purchased but critically important book, Start Your Year the Right Way.

With that, here’s what I created for you this week:

David Andrew Wiebe

I publish daily to inspire creatives and creators just like you.

Here are the posts that went live this week:

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Music Entrepreneur HQ

At Music Entrepreneur HQ, I give modern music makers the tools and mental models they need to create the life they love through music, something I’ve been up to since 2009.

Here are the posts that went live on Music Entrepreneur HQ this week:

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News Break

I publish at least once per week on the topic of self-discovery.

Here’s what I shared on News Break this week:

As always, I appreciate the read, share, and follow.

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Random Things I Dig

I’m about six chapters into The Road Less Stupid and have been enjoying the read so far.

Featured Product

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.

>> Begin your personal development journey NOW

Final Thoughts

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