Creative People Share What They Wish They’d Known at Every Age

When thinking about life and career, it's often easy to reflect back and think, “I wish I'd known then….” With age brings wisdom, as experience helps you navigate the ups and downs of a creative career, for as we all know, there's no better school than life.

So just what are the important lessons that well-known creatives wish they could go back in time and tell their younger selves? 99U has gathered an impressive list of artistic minds, including Lisa Congdon, Debbie Millman, Tina Roth Eisenberg, and Ken Done, to reflect on what they wish they'd known during every decade of life.

Here are a few tips from age 20 to 70, and you can read the full list of advice on 99U.

Designers and creatives give their advice on what they wish they'd known about their careers during different decades of their lives.

In their 20s

Stop worrying about other people

“We spend a lot of time in our twenties trying to please other people or worrying if we are doing the right thing. There is something about getting older that just makes you think to hell with that, I’m going to do what I want to do because what have I got to lose? That was definitely my experience – I quit my job to be an artist, and I owed it to myself to try.” – Lisa Congdon, illustrator and author, Portland, Oregon

Careers aren't linear

“I used to think my career would be very linear, but even in the almost eight years since I graduated, I’ve worked at a branding studio, done illustration and product design, worked in-house for several large brands, and now as a freelancer. And I don’t necessarily want to be a graphic designer forever.” – Ben Wagner, independent designer and art director, New York City

Don't be so hard on yourself

“I wish I knew not to be so hard on myself and not to beat myself up so much. I wish I knew not to take everything so seriously in terms of my worth and my value. I wish I had spoken up more and stuck up for myself.” – Debbie Millman, writer, educator, designer and host of Design Matters, New York City


In their 30s

Mistakes are always worth something

“I could talk for hours about our failures trying to expand into new areas by solving problems that we only imagined existed, or disasters hiring the wrong type of employee or not putting aside money for tax, but those are lessons you have to directly experience to really learn from, as each business is so unique. At the end of the day, the business itself is your biggest teacher.” – Jeremy Wortsman, Director of Jacky Winter, Melbourne, Australia

No experience is wasted

“I had a career in education before I turned to art, so I thought I was throwing all this experience away to go do this other thing. But the good news is if you are going to change careers later in life or do something new, anything you’ve done before is going to contribute to you doing a better job at that new thing because you have all this life and work experience.” – Lisa Congdon

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Jessica Stewart

Jessica Stewart is a Staff Editor and Digital Media Specialist for My Modern Met, as well as a curator and art historian. Since 2020, she is also one of the co-hosts of the My Modern Met Top Artist Podcast. She earned her MA in Renaissance Studies from University College London and now lives in Rome, Italy. She cultivated expertise in street art which led to the purchase of her photographic archive by the Treccani Italian Encyclopedia in 2014. When she’s not spending time with her three dogs, she also manages the studio of a successful street artist. In 2013, she authored the book 'Street Art Stories Roma' and most recently contributed to 'Crossroads: A Glimpse Into the Life of Alice Pasquini'. You can follow her adventures online at @romephotoblog.
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