Ivanka Trump, no. 33 on this year's 40 Under 40 list, is reshaping how we think about the modern workplace.
Photograph by Ben Baker for Fortune; Grid Photo: Neilson Barnard—Getty Images
By Michael Casey
October 9, 2014

Hindsight, as they say, is always 20/20.

Each year when we select the new class of our 40 Under 40, we get them talking about their business, sure, but we also go deeper. We ask them about their best de-stress tactic, how they manage their time, where they like to travel, and even about their favorite room in their home. We ask them about the best advice they ever got. This year, we tweaked that and asked: what advice would you give to your 20-year-old self? Here are some of their best answers.


Ivanka Trump, EVP, Development and Acquisitions, Trump Organization (no. 33)

Ask questions and listen more than you talk. You can’t be an expert at everything—and at 20 you’re more likely to be an expert at nothing! That said, with inexperience comes fresh perspective.


Nick Woodman, Founder and CEO, GoPro (no. 12)

It was the same advice that I gave myself when I was 20, which is, any time you have a difficult decision, imagine yourself as a 90-year-old looking back at this moment. What decision would you wish that you would have made? Go forward and look backward.


Michael Patterson, Partner, Highbridge Principal Strategies (no. 38)

Construct your own definition of success, don’t let the world do it for you. Just because someone puts a carrot in front of you doesn’t mean you have to chase after it.


Sophia Amoruso, Founder and CEO, Nasty Gal (no. 30)

Shave your legs.


Vijaya Gadde, General Counsel, Twitter (no. 28)

Vijaya Gadde, general counsel for Twitter Inc., stands for a photograph at the company's headquarters in San Francisco, California, U.S., on Wednesday, Jan. 15, 2014. Vijaya Gadde, who became Twitter's general counsel in August 2013, helped lead the company through its initial public offering and its largest acquisition. She is the highest-ranking woman executive at the company. Photographer: David Paul Morris/Bloomberg via Getty Images

I would tell myself that life is going to be really, really unexpected and not to be easily discouraged about whether or not I picked the right class. You never know where you’ll end up and just have to keep moving forward.


Sarah Kauss, Founder and CEO, S'well (no. 36)

Sarah Kauss, founder and CEO of S'well

I would tell myself to buy real estate next to the High Line in NYC! I’d also tell young Sarah to be more patient with my career and to realize that good things will happen with hard work and time.


Tristan Walker, Founder and CEO, Walker & Co. (no. 35)

David Paul Morris—Getty Images

Keep up that relentless determination but couple that with some faith. You’ll find that you spend less time managing your anxiety and fears and more time getting things done.


Kevin Chou, Co-founder and CEO, Kabam (no. 25)

Photograph by Robyn Twomey for Fortune; Grid Photo: Courtesy of KABAM

When pursuing your first job, focus on working with great people, and not the job with the highest paycheck.


Anthony Watson, CIO, Nike (no. 19)

Courtesy of Nike

I would tell myself that tackling and overcoming the challenges of growing up as a member of the LGBT community will make you a resilient, authentic, compassionate, perceptive and powerful leader one day. Hang in there, you will have many amazing people walk along side you and bring out the best in you.


Nate Morris, CEO, Rubicon Global (no. 34)

Joe Harrison, JH Photography Inc.

Visit your mother more often.


Alexa von Tobel, Founder and CEO, LearnVest (no. 37)

Mandel Ngan—AFP/Getty Images; Grid Photo: Vivien Killilea—Getty Images

Get up, dress up, show up. I think of it as my motto—get up with the energy to tackle every day, dress the part, and show up with your best A+ attitude. 




Josh Tetrick, Founder and CEO, Hampton Creek (no. 22)

There are too many urgent needs in this world—whether in food, education, health, campaign finance reform—for you not to focus your energy on them. They’re too urgent, and the irony about focusing on what the world needs the most is that there’s actually a lot of happiness that flows in engaging something higher than yourself.

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