The Oval Table

Rusty Gaillard - What Does Success Look Like To You?


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Our guest today may very well challenge your definition of success.

Stanford MBA and Apple executive who held the Worldwide Director of Finance position, achieved a level of success that many would envy.

He had everything he thought he wanted. He held his dream job at Apple, had a home, a family, had graduated from one of the top colleges in the world.

He expected that this path would fulfill him but, ironically, he felt like a failure.

Constantly dreaming about retirement or fantasizing about becoming a mailman, Rusty had “checked all the boxes” but felt locked in the trap of being a success.

For years, Rusty struggled to escape the trap of success. Like so many A Players, he created meaning from pursuit and progress, but he had already accomplished everything he thought he would and it wasn’t enough. 

He says, “Staying at Apple until retirement felt like selling my life for a paycheck.” 

He knew that he wanted his work to have meaning and purpose, but it took years to find the path to happiness - but did so by becoming a coach. 

Now he is sharing the process with others.

Today, Rusty helps other A-Players escape the trap that chasing success has locked them in.

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The Oval TableBy Douglas Bowers and Carl Walsh