As almost any entrepreneur or creative will tell you, unexpected problems are to be expected. Below, you’ll hear some incredible stories that highlight and illustrate the kinds of issues and problems entrepreneurs and creatives are dealing with everyday. It’s not easy, but the silver lining is that dealing with unexpected problems is one of the best ways to develop antifragility.

Audrey Tjahjono

One of the most unexpected problems I’ve faced in my creative journey happened during a session where everything seemed fine on set, but once I delivered the previews, the client came back with concerns I genuinely didn’t see coming. She felt the expressions weren’t quite right, noticed uneven skin tones that looked like bruising, and wasn’t fully happy with how she appeared in several shots. Read More>>

Greg Gandolfo

“When people ask about unexpected challenges in reopening Gandolfo Family Market & Deli, the biggest surprise wasn’t the work itself—it was discovering how selective and inconsistent Santa Barbara County can be. Our family has owned the building since 1983, but the deli and market have been there long before us. The original deli opened in 1978, in a building constructed in 1976. Read More>>

Madeline Pierce

One of the things nobody warns you about when you first get into photography is how social the profession can end up being. We tend to think of artists as introverts who would rather spend time alone with their craft than with other people, but everybody fails to mention just how important (and difficult) networking is. Read More>>

Justin Brown

The biggest challenge we’ve faced in making our own tattoo ink has been getting artists to actually try it. At the end of the day, ink is the permanent part of a tattooer’s job. If an artist isn’t sure whether an ink is reliable, the safest move is to stick with what they already trust. And “good” ink isn’t just about how it heals. Read More>>

Casey Cheuvront

I have a nickname: ‘One-speed Casey’. That means I tend to go full-bore at everything, until I stop dead (one speed, or no speed, I guess.) That can work for you – or against you. Read More>>

Nia Smith

In my life I have five major titles, a follower of Jesus, a mom, a wife, a business owner, and soldier. All of these take effort, time and sacrifice and sometimes you have to give everything you have to get where you want to be. Read More>>