When asked what we regret in our careers or life to date, it can be difficult to formulate a response. Not only is it tenuous at best to try to pinpoint the exact moment where we should have pursued this direction instead of that, seized one opportunity over another, or taken a risk over a guarantee, but each decision – whether later deemed good or bad – has led us to where we are today.

Regrets may be futile, yet there is a particular variety of wisdom that can only be gained in hindsight. As we move through each decade and navigate changes and challenges in our career and personal life, we begin to identify our supposed missteps – big and small. We begin to understand how our own doubts, insecurities, self-limitations or expectations may have been getting in the way all along, and take such insight into the decades ahead of us.

Without such experience, it can be difficult to gain such clarity around what we might be doing wrong or what might be holding us back in our work, side projects, relationships or health. But sometimes the experiences of others can help speed us along.

In an attempt to gather the lessons we can only gain through time, we’ve asked several creatives – including Lisa Congdon, Debbie Millman, Tina Roth Eisenberg and Ken Done – to reflect on what they wish they knew at every decade.

I wish I knew in my twenties…

To 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

That there’s no rush…

“The pressure to do things quickly or have success happen right away is ingrained in our culture of instant-gratification, but really your real life is so long. There are so many things that you can do and there is no reason to panic when you are in your 20s. Sure, you only live once, but you also have this long life ahead of you.” – L.C.

You can create the world you want…

“I really wish I realized sooner that I needed to be an active participant in creating the world I wanted. I was floating and going with whatever came my way – I wasn’t very active about thinking about what type of person I wanted to be, or what environment I wanted to work in. My daughter was my biggest career catalyst, and I wish I had that wake-up call earlier. It never occurred to me that you could start companies sooner – when your life is so much easier and you have fewer responsibilities.” ­– Tina Roth Eisenberg, designer and founder of CreativeMornings and Tattly, New York City

That careers are never 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

No one has it all figured out…

“Acknowledge that no one has it all figured out – even your mentors, bosses, or design heroes – and that’s okay. The important thing to remember is to keep creating. Spend more time and energy on making your best work, and less on comparing yourself to others.” – B.W.

To stop being so hard on myself…

“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

Skills are more important than grades…

“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.” – Adam J. Kurtz, artist and author, New York City

Not to worry so much…

“Shit isn’t real yet when you’re in your 20s. Your early 20s problems will feel really insignificant soon. Try a bunch of stuff, be a little reckless, smoke weed one time, kiss someone nice, stop trying to be cool – it’s not working, it never works – and generally let yourself live.” – A.J.K.

Everything will be okay…

“I do wish I could tell my younger, confused, insecure, lost, and angsty twenty-something-self that everything will work out okay. I will meet the perfect person that I can share my life, passion, and work with, and that I will someday get to do something I love everyday with people that I love and respect, that I will get to create beautiful things that inspire people in their everyday lives.” – Angie Myung, co-founder of Poketo, Los Angeles

“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.” – Ted Vadakan, co-founder of Poketo, Los Angeles

It’s probably not the worst decision ever…

“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, Melbourne, Australia

I wish I knew in my thirties…

The difference between empathy and compassion…

“One of the biggest things that I did learn, is that there’s a fine line between empathy and compassion. In certain lines of work, you don’t want too much empathy. Like an emergency room worker for example. You want them to feel for the patient in one sense, but not so much that they can’t do their job. This isn’t to say at all that we face life or death experience, but understanding how we work as a business and as individuals has been a massive learning curve, as it’s the humanity in our line of work that give it it’s value.” J.W.

That mistakes always count for 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.” – J.W.

To take care of myself…

“I recently had spinal surgery for a herniated disc, and it was one of the most agonizing experiences I had ever been through, and while I was in the midst of the experience I was feeling lots of regret. Regret that I didn’t exercise enough, or eat right. That I sat too much at work or in the car. It took nearly two years to fully recover, but in that time I became so much stronger, and I now know my body on a whole new level.” – J.W.

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.” – L.C.

I wish I knew in my forties…

Aging is life affirming, not scary…

“It didn’t take me long to realize you know what, it’s actually affirming to turn forty. You’re always learning and that’s the key – it never ceases.” – T.V.

You can’t control everything, but you can adapt…

“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.” – T.V.

How to balance trust and being accountable…

“There was one instance with Poketo where we maybe put too much trust in a person and we didn’t get what we needed. While I always see the good side of people, at the same time you need to be accountable for whatever needs to get done and not just solely relying on someone else. To grow as a business, you need to find a balance between being the captain of your ship and being able to trust your crew.” – T.V.

Compromise, compromise, compromise…

“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.” – T.V.

I wish I knew in my fifties…

To savor…

“Savor every day. Savor every day. Keep experimenting. If you want to do something, do it.”– D.M.

20. You set your own rules…



“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.” – L.C.

I wish I knew in my sixties…

To have patience and perseverance…

“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, New York City

Wisdom takes time…

“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!” – M.K.

I wish I knew in my seventies…

Every age has highs and lows…

“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, Sydney, Australia

You can be 77-years-young…

“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.”– K.D.