Good Woman: Cara Jackson

How do I possibly sum up what this woman means to me in a couple of paragraphs? For our final Good Woman feature, I am honored to introduce you to my business manager and dear friend Cara Jackson. Cara has tirelessly worked with me behind-the-scenes here at Goodwin since its inception, jumping right in to help me craft the business plan. She is the yin to my yang. Her intellect, experience and powerful clarity has brought my dreams and visions into sharper focus. I always joke that I’d be in a ditch on the side of the road without her, but I definitely believe that’s true (and know that she secretly does too, haha). Cara has been by my side through all of the ups and downs of small business, and has continually filled in the gaps for me in so many areas. She keeps me grounded, logical and always finds a rational approach to my creative work.
Not only does she do this for me, but for several other incredible small businesses. She is a strong, inspiring boss lady who I have been so fortunate to work with over the last few years. The time has come for me to begin a new adventure, but I will forever hold this chapter in a special place in my heart. And as Cara would say… “now we can just be friends!”
Read on for an interview with Cara Jackson. Special thanks to our dear friend Chelsea O’Leary for capturing these memories on camera.


What is a good woman to you?

To me, a good woman is kind at her core. Thoughtful. Steady. Her words and actions align, and she shows up for herself and for other people.

What qualities do you find good about yourself?

I think I am empathetic, a good listener and a calming presence.

You were the girl most likely to do what when you were young?

Spell everything correctly. It seems like another lifetime ago, but I competed in the Scripps Howard National Spelling Bee on 3 separate occasions, in the 5th, 6th and 8th grades. It’s funny to think about the sheer number of ridiculous words I learned to spell as a child that I will never ever use in everyday conversation or probably ever again, for that matter.

Where are you the happiest?

Anywhere with good people, good food and good conversation.

What is the best risk you've ever taken?

My initial reaction to this question was to say starting my own business. But actually, I think the best risk I’ve ever taken was going to law school in New York. I didn’t visit the school or even know that much about it before committing, I had been to New York once (and only for a day), and I didn’t know a soul there. I didn’t even want to be a lawyer. But I wanted the education, and I wanted to be in a city that held opportunities I couldn’t find anywhere else. Law school was really damn hard, and it left me with a bewildering amount of student loan debt. But it kickstarted my life in New York and opened the door to some incredible job opportunities and life experiences. I grew up in that city and cannot imagine having done anything differently.

What would you do if you had more hours in the day?

Read more and definitely sleep more.

What are you going to do next? Do you feel like you're doing what you were meant to do?

I’m incredibly content doing what I’m doing now, which is working with creative entrepreneurs to help them manage and grow their businesses. But I always want to be learning and growing and seeking out opportunities that make me stretch and make me a little uncomfortable, because I believe that’s where the real growth happens.