Chip Conley

People always ask “What number do I need to retire?”

Which really means “Do I have enough?” “Will I have enough?” “Can I survive?” “Will I be happy?”

But people aren’t retiring as much as they used to.

People are reinventing. They’re working longer. Or starting something new. They’re getting a second wind.

But that hasn’t stopped anyone from asking the retirement question. So I wanted to break it down.

See, when someone asks “What number do I need to retire?” they’re really asking, “What is financial freedom?”

And “Can I have it?”

I say “yes.”

Except, first I have to change the equation. It’s not x amount of dollars = happiness for the rest of your life.

It’s x dollars + virtual net worth = financial freedom.

Here’s how I broke it down on the podcast. I was talking to Chip Conley. He’s the Head of Hospitality for Airbnb and second time “James Altucher Show” guest.

He first came on my podcast a couple years ago. (When I was living in Airbnbs)

I got a call from my host. “Hey, the Head of Hospitality for Airbnb is staying in the apartment right below you. Do you want to meet him?”

“Yes.”

He came downstairs with a bottle of wine. (Classic hospitable move.) I opened my computer and recorded our conversation.

Now Chip has a new book out called “Wisdom at Work.” So I invited him to the studio.

He’s 58. And he’s not retired. He said he found a new “calling.”

People with jobs and careers want to retire.

People with callings don’t.

So one way to “retire” is to find your calling. That’s one option. There’s another option, which I’ll get back to.

First, I asked Chip how he found his calling. Here’s what I found out:

1. Mine Your Mastery

“I spent 26 years being a boutique hotel entrepreneur. In 2013, the three young founders of Airbnb approached me. They said, ‘We want to democratize hospitality, will you join us?’”

He said yes.

Now, I should say, of course this opportunity was rare. It’s not everyday or in every lifetime that some future billionaires will approach you and ask for your help.

Chip already built up his skillset.

He had spent the majority of his career disrupting the standard hotel industry.

Boutique hotels were unheard of when he first got started.

His foundation matched their future.

But let’s say you’re reading this and thinking, “No one’s going to approach me.”

That’s fine. Make a list. Write down all of your skills (the things you got really good at over the last 5, 10, 20 years). Then cross out all the ones you don’t like doing.

• That’s Step A: Mine your mastery.
• Step B: Make a list of things you’re curious about.

Now draw lines between them. Where can you see yourself? And listen to your gut. “There’s lots of physical effects that can happen in our life that sort of tell you you’re on the right path,” Chip said.

That’s step 2.

2. Get Clear

“Getting clear internally is probably one of the most important things for us to figure out in life,” Chip said. “Weirdly enough we don’t do a whole lot in people’s upbringing to help them get there.”

“Zero,” I said. “We don’t do anything to help people get there.”

“Yeah, thank you.”

“We just feed them facts they’re going to forget.”

And sometimes in the process of memorizing those facts, we forget to understand ourselves. Sometimes I even feel guilty when I try to get clear.

Like “Oh, no, I don’t have time to get clear with myself I have a spreadsheet to do.”

Here’s how I get clear: I go back to my 10 year old self. And I write down everything I loved back then.

That’s it. Don’t go any further. Don’t try to match it with job description. Don’t try to turn it into a company.

Just go to sleep.

Let your brain digest it.

And in the morning, I wake up less anxious. And more clear.

3. Forget Who You Think You Are

Chip thought he was going to be CEO, Brian Chesky’s mentor. He was wrong.

“Within the first couple weeks, I realized… I’m the intern.”

“I was twice the age of the average employee. I didn’t understand the language being spoken in the hallways. I didn’t have an Uber or Lyft app on my phone at that time. I had never heard of the sharing the economy. I had gone from being the pioneer as a boutique hotel entrepreneur in my mid 20’s to being the establishment by 52.”

He could’ve quit.

He had all the excuses. “I’m too old.” “I don’t belong.” “I thought I was going to be the mentor.” etc.

He stayed.

“I decided the only way I’d survive here is to be as much of a curious learner as I am the wise sage.”

He combined what he knew with what he didn’t know.

“And that’s what a modern elder is,” he said. “A modern elder is not the traditional elder that passed and is regarded with reverence. The modern elder is all about relevance.”

“OK, how do you become relevant?”

“By taking that timeless wisdom and applying it to modern problems.”

For example: when Chip was building boutique hotels, he already faced the skepticism from the market because the boutique hotels didn’t have the name “Hilton.” So he had to battle that.

And find a way to build trust.

So, when he got to Airbnb, he could help them meet consumer skepticism head-on.

He saw they had this “super host program.”

Which did two things: it reassured you that the host is good at what they do. And it incentivized the hosts to step it up.

When Chip started working at Airbnb, there were only 200 superhosts in the world. And Airbnb hadn’t added any new ones for over a year. They were even thinking about getting rid of the program.

Then Chip stepped in.

He knew this could help fight skepticism and encourage people traveling to trust their host and trust Airbnb.

And it worked.

Now, there are 700,000 superhosts around the world.

But if Chip held on to this idea of “No, I can’t be the intern. I have to be the mentor” he would’ve left. And he would’ve lost his chance to be the modern elder.

—–

OK, back to to retirement.

The second option: build your virtual net worth.

I’m 50. And I’ve gone broke more than once.

People tell me, “You don’t seem 50.”

And then I’m supposed to say, “Thank you.”

But I don’t. And I won’t.

Because I’m actually proud to be 50.

It’s part of my virtual net worth. 

I’ll explain.

Let’s just say you need $10 million to retire. (This is not a real example. I’m just giving numbers that are easy to follow.)

So you have $10 million. And let’s say it makes about 4% a year after taxes. Meaning, you can retire and live a great life with $400K a year.

But there’s the flip side…

If you love what you’re doing and you don’t have $10 million, but you’re making $400K a year through multiple streams of income, it’s as if, virtually, you have $10 million.

And instead of retiring, you have your calling. 

And you’re not worrying every morning at 6am “Do I have enough?” “Will I have enough?” “Can I survive?” “Will I be happy?”

Because you already are.

—

I didn’t have my calling at age 20 or 30 or 40. I have it 50.