Episode 003

Getting Stuff Done vs
Dreaming Stuff Up

with Charlie Gilkey and Ishita Gupta

Jeffrey’s Premise:

The most influential and fulfilled entrepreneurs and artists can toggle between getting stuff done and dreaming stuff up so they can experience those moments of opening that keep them lit up with meaning.

No doubt you’ve had the experience of being busy all day, yet getting absolutely nothing done. You work through the easy tasks on your to-do list, avoiding the ones that are truly important—because those projects scare you to death! How could you learn to focus on the things that actually matter? To create your own productivity systems that eliminate distractions and hold you accountable for creating value? To find the necessary balance between contemplation and action?

Jeffrey is joined by speaker and business consultant Ishita Gupta of Fear.less Magazine and business growth strategist, speaker and author Charlie Gilkey of Productive Flourishing to discuss the formative experiences that led to the productivity systems they use today. Ishita shares her take on the need for a personal connection in any innovation, and Charlie explains why it’s better to focus on being useful rather than trying to do something new and different. They riff on the process of determining what is really important and eliminating tasks that don’t create value. Listen in and learn how Ishita and Charlie approach contemplation and the significance of finding that quiet time to connect with yourself.

Our Guests:

Charlie Gilkey

Charlie Gilkey is an in-demand trainer, speaker, and business growth advisor who helps small businesses start finishing the stuff that matters. Focusing on strategy, planning, execution, and leadership development, he’s regularly featured on Inc.com, BNET, and MSNBC. His mission is to help people thrive by using their creativity and energy in ways that help themselves, those around them, and the world at large. Charlie’s book The Small Business Life Cycle is an Amazon bestseller.

» ProductiveFlourishing.com

Twitter: @CharlieGilkey


Ishita Gupta

Entrepreneur, speaker, and business breakthrough strategist Ishita offers training programs to help business owners thrive. She founded Fear.less, a digital magazine that profiles hundreds of authors, entrepreneurs and thought leaders on how they’ve overcome fear. A sampling of the publications featuring her work include Huffington Post, AmEx Open, Forbes, and Inc.

» IshitaGupta.com

Twitter: @ishitagupta

Key Takeaways

[2:18] Charlie’s young genius

  • MacGyver, creative with limited resources
  • Fortune of misfortune: resourcefulness, adaptability

[6:42] Ishita’s young genius

  • Super-curious, questioned being told what to do
  • Desire to do extraordinary things
  • Bounce back from embarrassment

[11:15] Ishita’s impetus for developing systems

  • All-nighters in college (hated compromising herself)
  • Missed opportunities from sitting in indecision
  • Needs systems, accountability to stay afloat

[15:46] How Charlie came to develop systems for productivity

  • Pursuing master’s in philosophy, Army officer at same time
  • Read about others’ productivity systems
  • Changed what didn’t work, became documentarian of process

[19:47] Ishita’s take on why innovation must be personal

  • Forced to confront own fear (Seth Godin’s altMBA)
  • Interviews around overcoming fear, turned into magazine
  • Solve your own problem first

[25:46] Charlie’s take on innovation

  • Focus on being useful
  • Start by assimilating others’ work, find your 5% difference

[32:43] Charlie’s approach to getting the right stuff done

  • Tendency to be afraid of important to-dos
  • Focus on fewer things that really matter

[35:22] Ishita’s advice around getting the right stuff done

  • Accountable to someone else
  • Repeat long-term goals daily
  • Eliminate distractions

[38:35] Ishita’s take on dreaming

  • Direct correlation between desire and opportunity

[42:40] Charlie’s insight around the significance of contemplation

  • Contemplation added to morning routine
  • Society has lost ability to sit with selves

[46:22] How Ishita gets into a contemplative space

  • Dance party
  • Get into world (i.e.: outdoors)
  • Engage with others

[51:08] Charlie’s advice for getting into a contemplative space

  • Disconnect from internet
  • Implement ‘inbox perspective’
  • Tea ritual

A special thanks to the early supporters of the Tracking Wonder Podcast. Your enthusiasm, feedback, and support helped make this possible. Thank you.

A few very special early supporters:
Patti Shade, J.R. Schumaker, Madeline Danaher, Marty Neumeier, Lyn Henderson, Lucas Dodd, Carol Delmonico, Megan Eberhardt, Leigh Marz, Tricia Chitwood, Emily Seay, Dana Andersen, Kristal Pooler, Mandy Marshall, Julie Sperring, Stargazer Li


Each week brings you in-depth conversations with leaders, stories from change-makers, and provocative ideas from artists and scientists – all designed to inspire you to shape your best work with more possibility, impact, and – yes – wonder.