Interviews → Renaissance Life / Josh Waggoner

Josh:

would you mind giving a short history of your creative journey and CD Baby?

Derek:

I wrote a little book, “ANYTHING YOU WANT”, you can get for like $5 and read in an hour. It tells the story better.

Josh:

When did you know you wanted to be a musician? What inspired you to learn music?

Derek:

I was 14 when I heard Iron Man by Black Sabbath. That did it for me.

I was required to practice music since I was a kid, with no great love for it, so by the time I loved it I was well-prepared.

Josh:

Can we talk about Kimo Williams? How did he influence you?

Derek:

See sive.rs/kimo

Josh:

Do you remember your first time performing in front of a crowd?

Derek:

I was terrified, of course, but now that I’ve performed over a thousand shows, I have extreme stage comfort.

Josh:

What are some memorable stories you recall from performing?

Derek:

Authenticity is inconsiderate. Don’t be yourself. Be generous. Perform. Give them a show.

Josh:

You are a super ambitious person. How do you decide what to focus on?

Derek:

The intersection of happy, smart, and useful:

Smart and useful (but not happy) = rational, but happiness is the oil in the machine. Without it, the friction kills the engine.

Happy and smart (but not useful) = self-help addict, or searching for “passive income”. You can’t actually pull yourself up by your bootstraps. Ultimately you must be lifted by those around you.

Happy and useful (but not smart) = over-educated charity volunteers, could be making $200/hr as a lawyer but instead they fly to Africa to carry water to villages. They’d help more if they stayed home, made more money, and used it to pay 100 local people to carry water to villages, if they really cared. Great intentions but lame strategies.

Just happy (not smart or useful) = parable of the Mexican fisherman. “Just be happy!” But you’ll regret thinking of nothing but today if you don’t prepare for tough times.

Josh:

Related: “More than anything, I want to make lots of stuff. I want to make articles, books, websites, music, companies, systems, apps, and especially new ideas.” This speaks to my core. How have you gone about optimizing your life for creativity and learning?

Derek:

Say no to the obstacles!

No to hanging out, watching shows, drinking, playing games.

Netflix is the enemy. Nintendo is the enemy.

Josh:

Do you have any advice/thoughts on people who are still hooked on money? Maybe they want to focus their life around creativity but still feel limited by the $$$. Any advice?

Derek:

No! Money is important! Make money! Save money!

Read “Mr. Money Mustache”. Reduce expenses. Get rid of everything you can. Sell the big house and rent a little apartment.

Refuse consumerism. Instead of $1000 iPhone get an old $100 Android. Put the $900 difference into savings. Notice that makes your phone less fun. That’s the point! Save money and reduce distractions.

Live way below your means. Save it all. Have a nest egg.

The unhappiest people I know are the ones who said money isn’t important.

Josh:

How do you go about learning something new? (What’s your learning process?)

Derek:

Find a good book and focus.

Shut off the phone, turn off the internet, and power through the initial learning curve.

Then multiple teaching sources. Video course, three different books. Different perspectives help you see something clearly.

Then deliberate practice.

Josh:

Do you think it’s possible to spend too much time learning and not enough time practicing/trying things out? (Ex/ Learning another new programming language instead of building with what you have)

Derek:

Think of it like physical sports or any physical skill.

Reading about it isn’t the learning. You have to apply what you learn.

Trying it is the learning. Doing it.

Josh:

Where did the idea of “hell yeah or no” come from? Was it from something you observed or experienced?

Derek:

I was over-commited. Said a half-ass yes to too many things.

I had to raise the bar, to say no to almost everything, and yes to almost nothing.

The beautiful ideal is to leave space, to have free time, so that when something worthy comes along, you can throw yourself into it entirely, and have a huge impact.

Better to do one thing and do it great, instead of half-assing many things.

Josh:

Would you mind talking about your philosophy around owning (material) things? How do we resolve this as creatives (and multidisciplinary’s) who generally have a lot of tools and things? (instruments, notebooks and paper, paint, sticky notes, booooooks :)

Derek:

What helps you?

What hurts you?

The book you read helps you. The book you don’t, hurts you.

The tools you use help you. The tools you don’t, hurt you.

I had a bunch of musical instruments here, but I wasn’t playing them. They were hurting my psyche! I kept thinking I should play them. But I wasn’t. So I gave them away.

Also, many tools can equal one toolbox. If your collection of tools violates your self-image as a minimalist, put them in one neat container.

Josh:

What’s your writing process/philosophy?

Derek:

• Write all of my thoughts on a subject.
• Argue against those ideas.
• Explore different angles until I’m sick of it.
• Leave it for a few days or years, then repeat those steps.
• Hate how messy these thoughts have become.
• Reduce them to a tiny outline of the key points.
• Post the outline. Trash the rest.

Josh:

What (if any) do you think most writers get wrong?

Derek:

The only wrong thing is to not do it!

But also try imitating your heroes. You won’t sound exactly like them, so don’t worry about that.

Be a ruthless editor. Wait a week after you write something, then save a copy and chop everything possible out of that copy. Leave only what can’t be removed.

Josh:

What were some big takeaway from writing the book Anything You Want?

Derek:

I can write a book in 10 days.

Josh:

What’s your approach to writing multiple books at once? (Your Music and People / Hell Yeah or No / How to Live)

Derek:

No, I only write one at a time. I just haven’t released them yet. Soon.

Josh:

You recently experimented with doing a daily blog for 30 days, how was the overall experience for you? What did you like/dislike?

Derek:

I prefer the agreement with my audience where I only put out something that needs to be said - something worthy of their time.

Nobody likes the 300-page non-fiction book that could have been an article, because it’s inconsiderate to the reader. The author was pleasing the publisher’s expectations instead of the audience’s.

Nobody likes the dumb sequel to a movie that shouldn’t exist, but was just done for the money. It’s a waste of the audience’s time. We shouldn’t care that you had an obligation to the studio.

So, while having an obligation to yourself to write daily is good for creativity, it’s bad for the audience.

That said, I haven’t posted anything in months, and that’s bad for the audience, too. I need to find the balance.

Josh:

What character traits do you think makes a great creative (artist/musician, entrepreneur, tap-dancer, etc)?

Derek:

Art: surprise.

Entrepreneur? That’s different. Generosity.

Josh:

What are your thoughts on luck? Do you think it’s possible to improve your chances of being lucky by doing X Y Z?

Derek:

Being prepared is a given, (being good at what you do), then it’s frequency.

To roll six sixes, roll the dice as often as possible. Try something every day. Ideally every hour.

Josh:

How do you personally go about building and cultivating a thriving community of creative friends around you?

Derek:

Personally? I don’t. I choose solitary creation over a community.

Josh:

What advice would you give to someone pursuing creative work? Someone who is just starting out. Someone who has been at it for a while but is looking for that next level.

Derek:

Read my next book “YOUR MUSIC AND PEOPLE : creative and considerate fame”. It’s all about that. It’s to musicians but meant to be read metaphorically by any creative person.

Josh:

Who / What inspires your work? What do you look for inspiration? Alt: Who has influenced you on your creative journey so far?

Derek:

I get inspired by ideas : something that’s in-theory and I want to see if it’ll work in-practice.

I also get inspired by serving others. Whatever people are telling me they want or need, I will work ’til I drop to provide.

Josh:

Do you currently have any daily habits or routines? If so, how do you go about doing them while balancing your time and energy?

Derek:

Not at all. I throw myself entirely into one thing at a time.

Josh:

If you could master 3 skills instantly, what would they be and why?

Derek:

1. Fluent in every language on earth, because language itself is intrinsically interesting to me, and I’d also find it interesting to get to know and feel connected to people all around the world.

2. Mastering entrepreneurship would be fascinating. To create a useful, sustainable, profitable business every month? That’d be net-positive for the world!

3. Mastering willpower or discipline would mean i’d always do the right thing, no matter how I feel. That’d be healthy and considerate.

Josh:

What are the best lessons your closest friends have taught you? (Or siblings)

Derek:

One friend is a role model of empathy.

One friend is a role model of discipline.

One friend is a role model of seeing the big picture.

It’s not specific lessons. It’s ongoing inspiration and guidance.

Josh:

What has the experience of becoming a dad taught you about life / the world so far?

Derek:

Parenting, for me, is like meditation.

It works best if I let go of my own thoughts, let go of plans, time-frames, and expectations, and just be present with him.

To enter his world by letting go of my own.

Josh:

What are some decisions you’ve made that have made you into who you are today?

Derek:

ALL of them. If I would have stayed in my home town with my high school sweetheart, and my pot-smoking friends, I would have been a very very different person.

If I would have kept doing gigs instead of starting CD Baby, I’d be in a very very different place, with different values.

Our situation determines our values. And tiny decisions change our situation.

Josh:

What are some unconventional philosophies you live by?

Derek:

Whatever scares you, go do it.

Josh:

Have you experienced any big setbacks or failures? How did you get through it? Alt: Can we talk about 2007?

Derek:

Of course!

Focus on the process, not the outcome.

A bad decision that leads to a good outcome is still a bad decision.

A good decision that had a bad outcome is still a good decision.

Focus on improving your decisions, and see the outcomes as just feedback.

Josh:

Have you changed your perspective on anything in the last year or so?

Derek:

Every week! Ideally every day!

I’ll tell you yesterday’s change of perspective.

While listening to an audio course on linguistics, teaching some cool things about Cantonese and the Bantu languages of East Africa, I got sad that I wasn’t travelling.

Then I questioned that and realized that much of travelling makes you think you’re learning and expanding, but is really low-reward.

Booking activities, booking travel, booking lodging, sitting on transportation, dealing with logistics.

Then even walking around a place: yes you’re seeing people in a bustling marketplace, or seeing people riding camels, or harvesting rice, but you could have seen that in a video.

It’s happy visceral fun to be in it, yes, but is it personal growth? Remove the stories you tell yourself and others, like, “I’ve been to Myanmar.” That’s not amazing in itself. Any idiot can go somewhere.

So what really changes you, in travel?

It’s learning about a place.

And most importantly: talking with people there.

What would be a better learning-growing experience?

#1: spending 8 hours planning, 12 hours traveling, and 20 hours walking around looking at things?

OR

#2: spending 8 hours reading about a place, 12 hours studying the language, then 20 hours having phone conversations with people there?

And objectively, not flying around the world is better for the environment.

So maybe all-in-all travelling your mind instead of your body is objectively better.

So that was yesterday’s change of perspective.

Hopefully I’ll have another one today and every day.

Josh:

Are there any books that you reread or catch yourself thinking about often?

Derek:

I almost never re-read a book because i take notes the first time i read it, and extract its ideas.

Then i don’t care about the book, but yes i reflect on its ideas, and apply them to my life.

Go to sive.rs/book to see all of my extracted ideas from over 250 books.

Josh:

Are you a fan of fiction?

Derek:

No. For fiction, I prefer films.

Josh:

What songs do you sing when you are alone (in the car, shower, on a walk, etc)? And what new bands are you digging recently?

Derek:

Amber Rubarth’s song “You Will Love This Song”

I’ve never been into bands. I’m listening to Debussy and a classic Pakistani singer from the 70s called Avita Parveen.

Josh:

In one word, how would your best friend describe you?

Derek:

Derek.

There is such a thing as over-simplification. Reducing a person to a word or even a sentence is creating error not truth.

Josh:

What’s one question you would recommend someone listen to ask themselves. A parting or takeaway question you want to impart.

Derek:

Take something you think of as true - like I did with “I want to travel” - and see how it could be wrong.

Find the opposite point of view.

Good luck doing that with politics.

Josh:

And what’s one action you want to recommend? An action step or challenge you would recommend for those listening to try out.

Derek:

Email me and introduce yourself.

Go to sive.rs - click CONTACT - and say hello.