Women Entrepreneurs: Jesse Lee Gray

Ladies and gentlemen, please welcome the incredibly smart and talented Jesse Lee Gray. I had the pleasure of meeting Jesse Lee at an Alexandra Franzen workshop and I was immediately struck by this cool, interesting chick. So, I had to interview her.

Take it away, Jesse Lee!



1.     What is the name of your business and what do you tell other people you do? (such as author, teacher, designer)

I’m currently using my name: Jesse Lee Gray.  I’m kicking around some ideas for a business name, but haven’t settled on anything yet.  To keep it simple in a social context, I say “freelance writer.”  However if I’m networking, I say I’m an “organizational consultant with a writing focus.”  I help businesses get organized for scale, without losing the authentic something special that made them successful in the first place.

2.     How long have you been self-employed? What convinced you to become an entrepreneur?

I’ve been self-employed exclusively as a freelance writer for a little over a year.  Before that I owned a triple-bottom-line, residential cleaning company for 8 and a half years. 

Entrepreneurship provides me the freedom to decide how I do things and talk to people. I also get bored with a lot of repetition so the ever-changing challenges of self-employment keep my attention focused and my imagination firing at full tilt.

3.     Entrepreneurs rarely stay in one place. How many careers have you had?

Hmmm.  Student, teacher (briefly), house cleaner, cleaning service owner, freelance writer.  That’s 5.  If you count wife (which should totally count), it’s 6 :)

4.     What are some of the aspects of your current job that people don’t see? For example, most people don’t understand how much marketing is done by the authors themselves instead of a publisher.

Lots of flexibility and emotional intelligence are required.  My process can’t be exactly the same with every person or business: I have to adjust my communication style/ mode to fit each client’s needs. I have to *get* them quickly so I can understand them and get to work! When you’re good at adjusting nimbly, people don’t necessarily notice because the process seems organic.

5.     Who and what inspires you on those inevitable rough days?

Ash Ambirge of The MiddleFinger Project.  She highlights and provides sage advice about the challenges of business ownership and never fails to make me smile with her irreverent and humorous anecdotes.

6.     Name a few of your current projects. For example, conferences, publicity, design process, what you have for sale.

•        Orange PoppySkincare: I’ve been doing guest blog reviews of their spa services.  It’s been really fun to pamper myself with facials “for work.”

•        Online classes.  In April I took a class through the Freelance Writers Den on writing White Papers and am currently working through the Six AppealProcess in order to revamp my website to have more emotional appeal.

•        The Garden: a neighborhood farmhouse.  This organization is going through a rebranding and restructuring process as they switch from a for-profit restaurant to a non-profit, food-centered neighborhood resource, education and event center.  I helped them organize New Member information into a 2-part Welcome Guide and will likely continue to help them streamline their communications.

•        TheUnreasonable Institute: I have a long-term, part-time gig as their Scale Systems Maverick.  To achieve their mission to tackle the world’s biggest problems through entrepreneurship, they need a lot more locations than they currently have. To set new locations up for success, they needed a training package that encapsulates who they are and how they do their thing for each their programs.  A big piece has been codifying the curriculum that each location teaches to entrepreneurs. 

•        Final edits and finishing touches on two collections of my poetry. 

•        Go Should Yourself (hat tip to Ms. Mercury for pushing me to do this one)

•        Sand in My Teeth

7.     What are your recommendations for women who are interested in pursuing self-employment?

It’s a big jump, especially if it’s your first time, but don’t overthink it.  Listen to your gut, your heart, or whatever body part (that’s not your head) talks to you.  If it says “Do it,” then start making serious strides toward the big jump.  No matter how much research you do, you’ll never be ready for everything a freelance life will throw you.  But if you’re brave enough to take the plunge, trust that you’ll also be smart enough to figure things out as you go and nimble enough to adjust what’s not working.