Today's question: What kind of external affirmation do you need, in order to know that you've been successful?

It's prompted by the story of Gordon Sondland, the U.S. ambassador to the European Union, who spent 10 hours Thursday testifying before Congress as part of the impeachment proceedings.

We're not going to get too deep into the politics here. Let's just say that this is likely not what Sondland, a successful business leader and philanthropist, expected when he was sworn in as an ambassador last year.

Most press accounts suggest Sondland wound up President Trump's pick for EU ambassador after donating $1 million to Trump's inauguration committee in late 2016.

On the surface, he and Trump have a lot in common:

  • Both are very wealthy Republican businessmen.
  • Both made their money in real estate and hotels.
  • Neither had ever held a full-time job in government until 2017 and 2018 respectively.

But his donation came late. He had a relationship with President George W. Bush, and supported his brother, Florida Gov. Jeb Bush for president in 2016.

When Bush dropped out, Sondland backed Sen. Marco Rubio. It was only then that he pivoted to Trump. 

One reason why, a friend told The Washington Post recently, was that he greatly coveted an ambassadorship.

There's nothing strange about wealthy donors becoming ambassadors. It happened in the Obama administration, and it's happened in the Trump administration. Total business as usual in Washington.

But with Sondland, it feels a bit tragic, especially in light of his compelling personal story:

  • First member of his family born in the United States; in fact, he's the son of Jewish parents who survived the Holocaust, but who were separated from each other for years in the process. 
  • Sondland's mother -- pregnant at the time with his older sister -- escaped Nazi Germany because she had a Russian passport through her father,. Eventually, she made her way to Uruguay.
  • With no foreign passport, his father hid on a ship, made it to France, enlisted in the French Foreign Legion, was captured, wound up in a "concentration camp in North Africa" in Sondland's words, was liberated by the British, and then joined the British army.

(That last bullet point alone is an entire book, right? I'd read it.)

Sondland's parents stayed in touch via Red Cross refugee letters, and they reunited six years later in in Seattle. They ran a dry cleaning business, raised Sondland's sister, and then had him.

His childhood, he said in an interview was, "lower middle class to middle class." He tried college, got involved in commercial real estate, and ultimately became wealthy building and running hotels.

He and his wife, Katherine Durant, ran their business and donated to charities.

It wasn't enough, apparently.

As the Post reported, his "ambition was clear, as was his fondness for the trappings of the job" of an ambassador. 

Now, he's been sucked into the potential impeachment of the president. There's even a move to boycott his hotels.

All of which might lead a reasonable person to ask: Who needs the trouble?

It's funny. I've gotten to know a lot of wealthy and successful business leaders, mostly as a result of my writing. Some are truly great people.

But others are all too human. They crave external validation.

A few years after I wrote my 2010 book about Harvard Business School, a billionaire who has to remain nameless offered to pay me an insane amount of money to ghostwrite a book for him -- but only with a 100 percent guarantee that it would be a New York Times bestseller.

He wanted that title: New York Times bestselling author. It was clear that this was about him finally getting the respect he thought he deserved.

(I turned down the offer. Without giving away the tricks of the trade, I can write a great book and I can guarantee some key metrics of success, but making the Times list isn't one of them.)

If you're a business owner (or hope to become one), it all leads to that key question: How you'll know when you'll truly feel successful?

Are you willing to cede that validation to something external? Or do you make the call yourself?

I grant you: "Ambassador Murphy" has a nice ring to it. And I wouldn't mind if one of my own books (finally) made the New York Times bestseller list.

But that can't be the measure. Because, if you're looking for external validation, I suspect that no matter how much you get, it will never be enough.