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The Empathy Edge

Jason Silver: How to Enjoy Your Work More

Feb 25, 2025
55:29

Work can be one of the biggest drivers of positivity in your life, but no one ever really explains how to be successful without sacrificing everything outside of the office. When you enjoy your work, you’re more successful and any joy you feel on the job spills over into the rest of your life as well. Kind of like practicing empathy at work and bringing that skill home with you!


My guest today is Jason Silver, author of Your Grass is Greener: Use What You Have, Get What You Want. At Work and in Life. We discuss why leaning into values matters, what he learned about people-centric leadership at AirBnB, and how he carried that into his other successful endeavors. He shares 9 of the most common workplace challenges, why the term "best practice” is dangerous, and the difference between intention and purpose.   He shares powerful habits to find more enjoyment at work - which he says is not the fluff but the fuel  - and he tells you exactly how to ask your boss to allow you to do your work in ways you enjoy more! Finally, we discuss why it’s easy for leaders to attribute cost but less easy to attribute exponential benefits when you focus on enjoyment and people first.

 

To access the episode transcript, please search for the episode title at www.TheEmpathyEdge.com


Key Takeaways:

  • Take care of your people first and they will take care of any problem your business runs into. 
  • The earlier you start, the more you can bake the values of the organization into the company and team members, which makes it easier to make every decision based on those values. 
  • It is not a waste of time to reflect and learn from our weeks. If we don’t know where we were unintentionally pulled sideways or intentionally set other things aside, we won’t know what we need to focus on going forward. 
  • You are not going to find every aspect of your job fun or enjoyable, but it doesn’t have to be constant fun for you to find overall enjoyment in your career.

 


"Enjoyment isn't the fluff. Enjoyment is the fuel. The more you're enjoying your work, the more likely it is that you accomplish bigger and bigger things." —  Jason Silver



From Our Partner:

SparkEffect partners with organizations to unlock the full potential of their greatest asset: their people. Through their tailored assessments and expert coaching at every level, SparkEffect helps organizations manage change, sustain growth, and chart a path to a brighter future.


Go to sparkeffect.com/edge now and download your complimentary Professional and Organizational Alignment Review today.


About Jason Silver, Founder and author of Your Grass is Greener

Jason Silver is a multi-time founder of kids and a multi-time founder of companies.He gets his biggest thrill helping modern employees and their teams unlock a better way to work—surfing is a close second. He was an early employee at Airbnb and helped build an AI company from the ground up back before AI was the cool thing to do. Today, he as a self-professed "Startup Personal Trainer", advises a startup portfolio valued in the billions on how to build great, lasting companies that people actually enjoy working for. He’s a sought-after public speaker, instructor, and advisor on how to transform work into one of the biggest drivers of positivity in your life. When he’s not busy helping people solve their hardest workplace challenges, Jason’s kids are busy reminding him just how much of a work in progress he still is too.


Connect with Jason Silver:

Website: thejasonsilver.com

Book: Your Grass is Greener: Use What You Have. Get What You Want. At Work and In Life

LinkedIn: linkedin.com/in/silverjay


Connect with Maria:

Get Maria's books on empathy: Red-Slice.com/books

Learn more about Maria's work: Red-Slice.com

Hire Maria to speak: Red-Slice.com/Speaker-Maria-Ross

Take the LinkedIn Learning Course! Leading with Empathy

LinkedIn: Maria Ross

Instagram: @redslicemaria

Facebook: Red Slice

Threads: @redslicemaria


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