We had the good fortune of connecting with Jaime Derringer and we’ve shared our conversation below.

Hi Jaime, how do you think about risk?
Taking risks is critical in my life and career. I took a risk when I quit my day job to run my business full-time, I took a risk moving across the country to California, and took many business risks—some that failed, some that succeeded. However, as the saying goes, you miss 100% of the shots you don’t take! As an entrepreneur, I had to get over my fear of failure rather quickly, and now I thrive in taking risks and experimenting… I treat it more like a game, making it a lot more enjoyable.

Let’s talk shop? Tell us more about your career, what can you share with our community?
Sometimes in life we get really comfortable, so comfortable that it becomes counterproductive to growth. While my business was continuing to grow, I realized that personally, I was stuck. The year I turned 40 was a transformative year for me in which everything changed. I took a risk and sold my business in order to remove obstacles from my life, and present me with more future opportunities. Simultaneously, I began focusing more on myself. You can choose to be either active or passive and the more I dig deeper into this, the more I realize that I have greater control over my life than I ever imagined. This it not an easy process—it can be painful, frustrating, and it takes time. The biggest lesson that I have learned over the past two years is to keep my eyes open, always question everything and be open to possibilities.

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
I tell everyone when they visit to hike Torrey Pines, grab a burrito and eat it by the ocean (Roberto’s Del Mar, perhaps?), then for dinner, eat a meal in Little Italy (Barbusa is a favorite) and then walk down by the harbor with a big cup of gelato in hand.

Who else deserves some credit and recognition?
I just read The Power of Now by Eckhart Tolle and I don’t know what took me so long but I’d like to read it 100 more times. I highly recommend it. My husband has been the most supportive force in my life, supporting me while I took risks, offering advice when I needed it and being there for me no matter the outcome. Also, I have to acknowledge the design community, who let some random girl with no background or knowledge of design into their space, schooled her, embraced her voice and allowed her to expand the conversation about design to a greater audience.

Website: http://design-milk.com and http://cleverpodcast.com
Instagram: @designmilk @jaimederringer @cleverpodcast
Twitter: @designmilk @jaimederringer
Facebook: http://facebook.com/designmilk
Youtube: http://youtube.com/user/designmilk

Image Credits
Portrait of Jaime Derringer by Jenny Siegwart
All artwork (c) Jaime Derringer

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