It’s normal to have regrets at some point in your life, be they about a personal relationship damaged, a professional career that could have been, or that super cute puppy you walked away from at the adoption fair. And while most people will tell you that regrets are nothing but a waste of time, that doesn’t mean we can’t learn from the moments that we wish we could do over.

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Like the creatives interviewed here, you can also channel your own regrets into advice for younger souls, and hope to spare someone else the pain of what might have been.

Photo Credit: Giphy

So let’s take a look at what these artists wish they would have known during each decade of their lives. Maybe their wise words can help you identify and avoid some pitfalls. Or, if you’re already feeling in a rut, maybe this is the inspiration you need get your two feet back under you and start making some changes.

In Their 20’s:

“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.” (Illustrator and Author Lisa Congdon)

“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.” (Independent Designer and Art Director Ben Wagner)

“At least as a creative, the skills you acquire in school are more valuable than the grades. I wish I tried to learn more while I still had access to those resources in a safe and nurturing space.” (Artist and Author Adam J. Kurtz)

Photo Credit: Twitter, @adamjk

“If I were to see myself in my twenties, I might say hey, things are going to be okay. Do what you love, work hard. Know that creativity is everything in life. Even in business, creativity is the driver. It’s really what makes you whole, in that inspiration and that creativity.” (Co-founder of Poketo Ted Vadakan)

Photo Credit: Instagram @poketo

“When I left New York to come to Australia [after falling in love with Melbourne], I think there was a lot of fear in that. When I was retouching images of dog food or working as a kitchen hand, I definitely felt I had made the worst decision ever, but it’s so hard to be in touch with those feelings now, when I couldn’t imagine life any other way! All will be revealed in the fullness of time.” (Jeremy Wortsman, Director of Jacky Winter)

Photo Credit: Instagram, @jwortsman


In Their 30’s:

“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)

Photo Credit: Instagram, @jwortsman

“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)

In Their 40’s:

“You can’t control everything. My uncle used to say to me, that we are like grass; it bends, but it doesn’t break. Even in turbulent times or uncertain times, it’s good for people to adapt, to embrace spontaneity and go with the flow and bend like grass, but not break. Be open to change and accept it with grace.” (Ted Vadakan)

Photo Credit: Instagram, @poketo

“For Angie and me, Poketo is like our baby. It’s something that we’ve been doing since we first started dating and there are difficulties in growing something together. There will always be disagreements, but what we’ve learned is to talk it out and come to a compromise. We need to be in sync to execute something new, so it’s never one-sided.” (Ted Vadakan)

Photo Credit: Instagram, @poketo


In Their 50’s:

“Savor every day. Savor every day. Keep experimenting. If you want to do something, do it.” (Writer, educator, designer, and host of Design Matters, Debbie Millman)

“Now I’m approaching my fifties, I wish I knew earlier that you set your own rules. Part of why I worked so hard for so many years was this pressure to keep up. But I realized that was a pressure I was putting on myself – no one else was telling me that I had to work that hard or take on that many projects at once. We invent our own rules and we have control, which is pretty cool if you can orient yourself to it in a healthy way. (Lisa Congdon)


In Their 60’s:

“Even the things I’m unhappy about in my life have allowed me to persevere and to be patient. I now know that things will take a lot longer than you think they will to achieve. If you don’t have patience or perseverance, you’re not going to be able to work.” (Maira Kalman, Illustrator and Artist)

“Things get murky and confusing at any age. But you can’t have the kind of perceptions at twenty-five that you have at sixty-five, and I don’t think it would even be good to have that kind of wisdom – it might prevent you from doing all the stupid things that you should be doing!” (Maria Kalman)


In Their 70’s:

“There are hills and valleys, some deeper than others, some higher than others. In your mid-twenties you’re convinced that you know everything. By your 30s and 40s you’re beginning to understand that this may not be so. For me, the 40s, 50s, 60s, and 70s have been filled with the desire to become a better artist.” (Ken Done, Painter and Designer)

“I’m surprised to find myself with the chronological age of 77 when really I feel as if I’m still somewhere between the ages of fourteen and twenty-eight. The key to feeling young is keeping your eyes open and trying as best as possible to get the most out of every day.” (Ken Done)


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