The Maestro Experience™

The Maestro Experience


A Journey Of Discovery & Growth For Creatives

Break Down Your Walls

Find your voice, break free from the status quo, and do the things that set you on fire!








Creative Professionals Community Austin Texas

Visionary Nonprofits

Purpose Driven CEOs

Social Entrepreneurs

Wellness Retailers


Community Builders

Applied Improv Firms

I've learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel

Get Seen > Speak Your Truth

Bob Olmstead Coach Creative Professionals Austin Texas


Experimental Art Director
Teacher/Coach For Creatives
Experience Design

Tiny Buddha Bob Olmstead Creative Coach
Positively Positive Bob Olmstead Creative Coach
Life As A Human Bob Olmstead Creative Coach
Instore Magazine Bob Olmstead Creative Coach
Best Life Coach For Creatives In Austin Texas

The process of finding your place in the world as a professional creative can be a complex process. How to make that happen? And what’s getting in the way?

The villain in this story is the status quo. That’s the problem. 

Until you break free, you’ll stay stuck. Safety nets. Peer pressure. Comfort zones. The sludge that traps you in the world of miserable but well behaved.

You don’t need to behave. You don’t need to conform. And rebelling against the status quo is good thing. It’s time to raise some hell! 

Three Indicators That You're Stuck

Best Coach For Authors Artists

Rabid Demons

Your demons are pounding on the door. What if one gets loose? That CAN’T happen! Then your self-doubt kicks in with vivid reminders of your failures and flaws. What if you’re an imposter? The noise is exhausting. 

Best Coach For Social Entrepreneurs USA

Intense Overwhelm

You’re talented. People compliment your work. They hire you. But you never get to the point where it all just works. Some problems never get fixed. It’s as though the world is speaking a language you’ll never understand.

Best Coach For Purpose Driven Brands

Endless Plateaus

Your creative work rocks! But why does it rock? Honestly, you don’t know. You kind of get what your value and talent is all about. But not enough to go to the next level. The lack of clarity and progress can be maddening!

All creatives struggle with these things on some level! The issue is never about “becoming” something. It’s about accepting who you REALLY are and growing from there. Fully embracing your humanity while unlocking your potential. 

As You Create, You Are Created


Creative and life coaching. Personal branding. Exploring beneath the surface to get to the real stuff. Finding the magic. Embracing imperfection. It’s a very human journey.

Best Life Coach For Authors

Module #1


The Hero’s Journey with you playing the lead role. What’s your backstory? What motivations inform you on a daily basis? What things move your narrative forward? This module gets to the very essence of your value as a human being and the wisdom you bring to the world.

Best Life Coach For Creatives

Module #2


Good self care. Priorities that serve rather than enslave. Feeling fully alive. What moments flow with meaning & connection? What activities set every fiber of your being on fire? And when is silence your friend? This module will help you get the fuel you need to thrive in all areas of your life. 

Best Life Coach For Artists

Module #3


Autopilot is not your friend. Nor is living from a place of reaction. It’s how you end up the mouse on the wheel. The key shift is to habitually take purpose-driven actions. In this module, you will align what you want with how you behave. 

Module #4


One of Walt Disney’s biggest moves was to bring his cartoons to life when he opened Disneyland. If there were no rules, what would your big move be? In this module, you will double down on the game changer that will take you to a whole new level. 

Best Coach For Health Food Retailers

Module #5


It’s time to start a wildfire! Your big move needs to be brought to life in the most vivid and powerful ways possible. Think about your audience. What would totally blow their mind? In this module, you will craft a few dynamic experiences that will deeply connect with the people you serve. 

Best Life Coach For Designers

Module #6


The person most likely to sabotage your success is the person in the mirror. How to stop getting in your own way? How to embrace success? In our final module, we zero in on honoring your brokenness and staying anchored no matter the storm. 

Jody Muniz Nutritional Designs

To call Bob our superhero is an understatement. His “Jedi” senses are wickedly accurate. With his guidance, we now offer the kind of customer experience that used to live only in our dreams.

Jody & Sunday Muniz
Nutritional Designs
Award Winning Nutritionists & Business Owners 

Kareem Badr Improvisor GM Hideout Theater

Bob did an amazing job of rapidly getting to our challenges. The result of our first meeting was the focus and inspiration that would motivate and fuel everything we do. I couldn’t recommend working with him enough.

Kareem Badr
The Hideout Theater
Award Winning Improvisor & Business Owner


It’s not about an egocentric guru holding you accountable, it’s about a shared experience that will impact every area of your life. 

It’s about the stories you want to tell, the wisdom you want to share, and the projects you want to make happen. 

It’s about owning your authentic voice without apology: personally, professionally, and creatively. 

It’s unleashing the full might of your creative process & potential, whatever that looks like, wherever that takes you.

It’s looking directly into the face of your brokenness and saying– I’m here. Let’s figure this out together.

Be You Without Apology


Best for soloists & small firms
$ 475 Monthly
  • One (90) Minute Discovery Call To Kick Off The Process
  • Two (60) Minute Phone Coaching Sessions Per Month
  • (2-4) Deep Dive Worksheets Per Month
  • One "Big Moment Experience" Per Module
  • Ongoing Online Collaboration To Sustain Your Progress
  • (15) Minute Emergency Triage Calls


Best for established creatives & brands
$ 950 Monthly
  • Two (2) House Discovery Calls To Kick Off The Process
  • Two (90) Minute Phone Coaching Sessions Per Month
  • (2-4) Deep Dive Worksheets Per Month
  • One "Big Moment Experience" Per Module
  • Ongoing Online Collaboration To Sustain Your Progress
  • (15) Minute Emergency Triage Calls
Dr. Allison Chase Psychologist

Bob seems to “get” human behavior, which makes it safer to deal with the down and dirty stuff that creates road blocks. It was his ability to take me, as a frustrated “worker bee”, and move me into my role as an "owner" that has made the difference.

Dr. Allison Chase
Eating Recovery Center

Karim Currey Social Entrepreneur Digital Artist

Bob knows how creative minds think, and he knows the ins and outs of business. I am a very passionate driven being and I am known to jump from one thing to another on raw passion. Bob was able to quickly reel me in, point it out and sort it out. I am grateful for Bob’s coaching.

Karim Currey
Gifted Multimedia
Social Entrepreneur

Frequently Asked Questions

You listed creative and life coaching but The Maestro Experience™ doesn’t sound like coaching? 

Coaching is but one of many tools I use to guide you on this incredible adventure. And that’s what it is, an adventure. An unconventional adventure of discovery and growth. But it’s also about many other things, personal and professional. Buckle up! You’re in for one heck of a ride.

Deep Dive Worksheets? What are those? 

Your best discoveries, your greatest breakthroughs, will come from the journey itself. I am but your guide. The Deep Dive Worksheets play a very important role to that end. They facilitate the kind of “aha” moments that lead to powerful realizations and open new doors. 

What is a Big Moment Experience? 

Big breakthroughs almost never happen in a vacuum or randomly. They happen, usually, as a result of well fertilized the soil. Big Moment Experiences are designed to do just that, fertilize the soil. There are only six of them, one per module. And they will always be at the backend of a module. Their purpose is to get you out of your comfort zones and into taking meaningful action.  

Online collaboration– how does that work?

Online collaboration is a cloud based, private space where we can chat, share files, assign tasks, and keep the fires of momentum burning. It’s also a great space for asking questions, such as when you’re stuck on a worksheet. Or to get additional support, when you’re feeling a little overwhelmed. 

How long does it take to complete the program?

That varies greatly based upon any number of factors. The typical range is (6-18) months, with the average being about nine months. Honestly, most people don’t want to rush the experience. They end up getting so much from it that whatever it takes, it takes and they are ok with that reality.

Do I have to sign any contracts?

Yes, I have a standard Letter Of Agreement that must be signed to engage my services. That said, my LOA will not obligate you (financially) to pay for the full term of my program. That’s not how I do business. Meaning, once your monthly or quarterly fee is paid, you are under no contractual obligation to continue.

What happens if we’re not a fit? 

There are two reasons I offer a free Rapid Clarity Call. First, to give you chance to benefit from my expertise free of charge. The second is to determine if we’re a good fit. Personality issues popping up after joining the program are extremely rare.

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