3 life lessons I learned from one of the world’s best executive coaches

Nobody gets to the Olympics without a coach, the saying goes. The concept clearly applies to business leaders and entrepreneurs, whose performance influences dozens, or even thousands, of people. 

Marshall Goldsmith is among the most prominent of these executive coaches. I knew him through his cleverly titled book, What Got You Here Won’t Get You There. In his latest book, The Earned Life, Goldsmith and his co-author Mark Reiter investigate the principles of crafting a life beyond success; one of fulfillment and free of regret. 

I sat down with Marshall to discuss The Earned Life, and how to apply the book’s principles to an entrepreneur’s career.

Stop looking for a path without tradeoffs

One of the most common themes of entrepreneurial wisdom is to seek asymmetry; to find opportunities with a lot of potential reward, and little potential risk. While this is certainly a good principle to aim at, extending it too far can leave a person feeling paralyzed. The path with certainty, reward, and a happy ending is a fairy tale.

“Any path you pick has trade offs. Make peace,” Goldsmith tells me. “See, you keep looking for a path that doesn’t have trade offs…. There’s no such path. The Great Western disease is—although you’re in Hong Kong, your questions are very Western—the Great Western disease is, “I will be happy when.” When. 

“As if there’s a “when,” as if there’s some place you’re going to go. Once you get to this place, you’re going to be happy for eternity. Right?”

Goldsmith says, “Now there’s one book that always has the same ending, “…and they lived happily ever after.” That book is called a fairy tale. That’s not the real world. In the real world, we’re constantly restarting life. There is no “happily ever after” story. There’s no place you go. Again, that’s the Great Western myth. I will be happy when.” 

I can’t help but wonder if that’s true of business case studies as well; life bears little resemblance to a challenge-solution-outcome situation, unless the outcomes all become new challenges. In one sense, it’s just an endless experience of problems. Life is empty without it.

Ask simple questions to weigh the tradeoffs

I was chatting with one of my readers a few weeks ago, when he mentioned a creative block; it felt like he was at a crossroads with two signposts, though he couldn’t see what it said on the signs. In situations like this, it’s difficult to even know where to begin.

In The Earned Life, Goldsmith shares some advice on clarifying between ambiguity, or difficult decisions. Questions like, “What do I want to do for the rest of my life?” “What can I do that’s meaningful?” “What would make me happy?” take years—decades—to find answers to. There’s no way trying to answer a question like that, on the fly, would be possible. 

Instead, he writes, “Begin with a basic question.” This includes questions like: 

  • “Do you love him?”
  • “Who’s your customer?”
  • “Will this work?”
  • “Can we afford this?”
  • “Where did we go wrong?”
  • “Are you serious?”
  • “What are you running away from?”
  • “What are you running toward?”

Goldsmith writes, “Any question simply phrased that demands a deep, soulful examination of the facts and your abilities and intentions—i.e., that elicits the hard truth—qualifies as a basic question. The most common question I pose when I’m advising people on their next big life move is as basic as it gets: “Where do you want to live?” It’s so basic that people rarely pose it to themselves. But since we all hold an image in our mind of the ideal place for us, we answer with little hesitation. Then the real thinking begins about our future: What do we imagine doing all day in this ideal place? Can we find meaningful work there? How would the people we love feel about this move? If we have children or grandchildren, could we tolerate living far apart from them?”

One simple, important, modification I found was to pick the highest priority question. For example, “Can we afford this?” might be more important than, “Where did we go wrong?” in the present moment; when I wrote a book a couple of years ago, the opposite was the case.

Start with the end in mind

Near the end of our conversation, I ask Goldsmith if he has anything to add. Goldsmith says, “Here’s my advice: Take a deep breath. Imagine you’re 95 years old and you’re just getting ready to die. You’re on a deathbed. Here comes your last breath. Right before you take that last breath, you’re given a beautiful gift, the ability to go back in time and talk to the person who’s listening to me right now. To help that person be a better professional, more important, help that person have a better life. What advice would the wise old 95 year old you who knows what mattered in life and what didn’t, what was important and what was not, have for the you that’s listening to me right now? 

“Breathe. Whatever you’re thinking now, do that. In terms of a performance appraisal, that is the only one that will ever matter. That old person says, ‘You did the right thing,’ you did the right thing. That old person says, ‘You made a mistake,’ you made a mistake. You do not have to impress anyone else.”

He emphasizes, “In case you’re still on the fence: “Final advice: go for it. World’s changing. Industries change. You do what you think is right, and may not when least you try. Old people, we sell them regret the risks we take and fail. We usually regret the risk we’ve failed to take.”

Originally posted at Fast Company.

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