Round Table

Do you have any professional regrets?

Dear Design Student
Dear Design Student
4 min readSep 4, 2015

Daily micro-regrets

“Yes I must, what are they though? Everyday I have one micro regret about something I said to someone at work. I’m an extremely impatient person who loves working at big, old company. People are crazy and they treat each other like garbage. Try not to.” — Renda Morton, design manager

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Shoulda, Coulda, Woulda

There are too many times I care to admit that I didn’t take that step forward — I didn’t take that risk — because I felt like I didn’t know enough. I grew up in a small, rural town, so anyone from fifty miles away was automatically thought of as smarter and much more experienced. This ideology was a part of my childhood, had an impact on my confidence, and it weighed heavily on me until I moved more than fifty miles away.

It took awhile — about ten years — but eventually I learned the people who are successful are the ones who don’t wait until they feel they know it all before taking a risk. Part of the journey is learning along the way. With the benefit of hindsight, I know that I should have — could have — taken those risks, made bigger moves, and I would have done just fine: Shoulda, coulda, woulda. — Greg Storey, designer

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“Catching Up” isn’t a real thing

I was 26 when I started developing, coming from a financial services background. I looked around and saw my peers being much younger and more experienced than I was, so I thought I had to catch up. In doing so, I nearly worked myself to death. Literally. 100 hours of work a week isn’t a badge of honor; it’s a death march. I wasn’t able to actually give my clients the service they needed because I was too busy trying to do everything, all the time, for everyone. — Andrew Norcross, developer

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No, I Insist

I’m a passive person by nature. It’s taken a long time for me to realize that, and even longer for me to try to counteract it. I’ve had to get comfortable with asking for things clearly, and refusing things firmly. In the process I’ve realized that most of the bad experiences I’ve had I could have avoided, had I been louder about what I thought or what I felt.

So many bad ideas that could have been salvaged. So many wasted hours that could have been put to better use. Speaking up can be painful, but silence can hurt worse. Liam Campbell, developer

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Non, je ne regrette rien

Of course I have the thousand daily agonies. Conversations I bungled, bad situations that festered too long before I took action, chances I should have seized sooner. Learnings!

Overall, I am pretty pleased with where I am today, while far from finished. So, when I look back on the key choices I made in my career, I can see that while some were annoying in the short term, they all proved to be useful. So what I regret the most is any time I’ve spent consumed in rumination rather than fixing my mistakes and moving forward.— Erika Hall, designer

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An appreciation of Larry Bowa, who worked hard at hitting a baseball and fell short a lot

There’s an old baseball adage that goes something like “Natural hitters make lousy teachers.” I believe that. Natural hitters don’t have to think about it. They can just do it. It’s a reflex. And that’s why when they get in a slump there’s almost nothing you can do to get them out of it. They don’t study their mechanics, they don’t watch film. Instead, they tend to do things like think back to the socks they were wearing before their slump and start wearing those every day.

I am not a natural at anything. Almost everything I am good at, I’ve worked very hard at being good at. Design, relationships, interacting with people, knowing when to stop talking, etc. All of this has taken years of work, and sadly a trail of bloody regrets. Along with the appropriate apologies, which is also a learned skill.

Looking back on all of the situations you’ve handled badly in the past is important, because the key to handling them better in the future is contained within them. As long as you also have the desire to handle them better.

And then there was that time I made Andy, the designer with a nose ring, make a header full of nose rings for an article about regrets. — Mike Monteiro, designer

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Written by Dear Design Student

Advice on design from people who work for a living.

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