Jobs and the Future of Work

If you want to wind up successful and happy, look at your boss and ask one question

A worker arrives at his office in the Canary Wharf business district in London, Britain February 26, 2014.      REUTERS/Eddie Keogh/File Photo                GLOBAL BUSINESS WEEK AHEAD PACKAGE Ð SEARCH ÒBUSINESS WEEK AHEAD 5 SEPTEMBERÓ FOR ALL IMAGES - S1AETZLIYFAB

Spencer Rascoff, CEO of Zillow, says this is what you should consider when looking to someone as a role model. Image: REUTERS/Eddie Keogh

Alyson Shontell
Editor in Chief, Business Insider U.S.
Shana Lebowitz
Strategy Reporter, Business Insider
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It's easy to look at somebody powerful and say to yourself, I want that life. I want to be COO of a tech company and make millions of dollars a year and spend it on a fancy car and a personal trainer.

It's not as easy to look at the full picture and realize said executive also works 80-hour weeks and never sees his or her family.

Which is why Spencer Rascoff, CEO of real-estate website and app Zillow, has always been careful about choosing career role models.

Before cofounding Zillow, which is now a $7 billion company, Rascoff cofounded the travel website Hotwire, which was bought by Expedia in 2003.

On an episode of Business Insider's podcast, "Success! How I Did It," Rascoff told US editor-in-chief, Alyson Shontell, a trick that's made him so successful:

"I've always looked 10 years my senior and tried to find somebody at my company to think about if I want that person's life, their whole life."

Rascoff said this is basically the opposite of what most people do:

"Usually, younger people, earlier in their career people, look at a senior person and they look at their compensation, and I'm advising not to do that. So you're an associate in the marketing department, look at the VP of marketing and say, 'Do I want her or his work-life balance, respect in the community, intellectual stimulation of their job, title, sure, compensation, yes, but sort of the whole package?' That's the path you're on."

Rascoff's advice dovetails nicely with an insight from former ReWork CEO Nathaniel Koloc. Koloc told the Harvard Business Review that instead of asking yourself what job you want next, you should be asking yourself, "What life to do I want?" As in: Where do I want to be five, 10, or 20 years down the line? Any decisions you make about your immediate future should reflect those longer-term career goals.

In other words, taking a job just for the high salary might be a good decision in the short term. But it's worth thinking about how this job will help you build the overall life you aspire to in the long run.

Rascoff said, "You could wake up in the blink of an eye and end up in [your role model's] world. And if you don't like that trajectory, then find some other path."

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