Bailey and Blum
Yes folks, I admit it: I am a cross dresser. I read this wonderful expression in the book I recommended on Friday, Tom Kelley’s The Art of Innovation.
He describes a business cross dresser as having the following attributes:
- Someone who, for example, was a lawyer or engineer and fell in love with design and switched
- Someone self-educated (I fall under this category)
- Someone self-motivated and enthusiastic
- Or anyone whose energy, motivation and personality are their main qualifications to get the job done.
In our To do list this week, I’d like us to work on exploring our inner “cross dresser.”
If you are a designer, how can you become a planner?
Exercise:
- Start helping a close friend or family plan an upcoming event.
- Make a list of what you enjoyed most and what drove you crazy, or you found boring.
If you are a planner how can you become a designer?
Exercise:
- Design (from start to finish) a close friend’s or family member’s event. (Make this a small event.)
- Make a list of what you enjoyed most and also what you enjoyed less.
This To Do list task can apply to any artistic profession that intrigues you. (Of course, we do not want our doctors to be “cross dressers.” ) The beauty of being a “cross dresser” is that it allows us to to move forward in practicing any art form without fear. Like the Nike commercial says, “Just do it” and learn from your mistakes.
I’m wondering…are you a “cross dresser”? What other profession or art form intrigues you enough to want to try it? Also, what were you doing before your present occupation?


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George Bernard Shaw once said: “You see things and say, ‘Why?’ But I dream things that never were and say, ‘Why not?’” That quote embodies how Preston Bailey approaches every event.















Jolyn @ Nuance Occasions
June 21, 2010
Most definitely a cross dresser – I was first a registered nurse, and wanted a creative outlet – which led me into wedding planning over 9 years ago. And as those years passed, I evolved into more of a designer concerned about the details.
I love to dabble in other arts, I learn new skills and have better understandings of those art forms can enhance my events. Currently, I love playing around with graphic design and florals in my spare time.
Allison
June 21, 2010
Hi Preston,
I am definitely a cross dresser! My earlier education and career path was in the field of child psychology and social work. However, I have always had a affinity for flowers and party planning. I grew up in the household with a mother who was floral designer. I spent many weekends assisting her with weddings. After 10 years as a social worker, I couldn’t put it off my passion any longer.
Kisha
June 21, 2010
Haaaaa!! My name is Kisha and I’m a crossdresser. Lol! MBA & former accountant, who quit CPA track ed to design events that leave guests feeling wonderful (and not just from tossing back cocktails). Crazy? Yes! Insane? Hell yes! But, I’m finally doing what feels natural to me. I’m also love culinary and performing arts. I’m working on my mom’s 54th birthday party.
Kisha
June 21, 2010
*I’m also in love with
Amber
June 21, 2010
I went from being a public health researcher to a graphic/web designer to a stationery designer (new endeavor). I am in love with all things weddings and design. I went to design school to learn more about the technical skills to complement the natural talents I had in it. It is the perfect outlet. I do not look back for a moment at the public health research field!
Janet Mohapi-Banks
June 21, 2010
Hi Preston,
Before being a completely self-taught cake designer I used to be an Applications Developer having obtained a first class degree in Computer Science. It was due to having children and making my daughter a birthday cake that I realised that I loved and had a talent for cake design. Now it’s my business, and I have to say that things are going from good to great! So what do you think, cross dresser? You should check out my website; I’m pretty sure I’m not going to go back to my day job, wedding cakes are so much more fun!
Lindsey
June 21, 2010
floral designer by day- journalist, curator, and cook by night
Dawn Easter
June 21, 2010
I have a degree in Biology and Respiratory Therapy and loved working with my patients in the hospital. It was tough work but I enjoyed taking a small part in the healing process, especially with the children. After a couple of years, I realized my creative side was suffering terribly and dipped my toe into event planning. I’ve never been happier! Now, flower design is calling my name, my need for creative expression is growing. I’ve recently completed my first wedding as the floral designer but definitely need to learn more. Now if only I could find a wildly creative and successful designer to study with…hmmm;-)
Janice Celeste
June 21, 2010
Dancing inspires me! I can’t dance, but I don’t let it stop me baby!
Rachel
June 22, 2010
Preston – Thank you SO much for this post! I am currently a corporate risk manager / insurance broker and am not in love with what I do. I have a passion for event planning and have been toying around with the idea of pursuing it full-time. However, I don’t hear of many people that have gone from a professional (boring) job like mine to such a fun, creative industry. I was starting to wonder if I was crazy for wanting to do it! You helped me realize that there are several others out there that have taken the same journey that I want to take, and this post has inspired me more than you know – thank you!!
Martine Chery
June 22, 2010
I studied International Relations and Management and worked first as a Consular agent for an ambassy and then switched as a Technical Advisor for a bank doing corporate law and realized that I was not AT ALL a 9 to 5 person. Even, it’s a good experience and I had to go through that to become what I am today, but I felt so miserable. I searched for a long time what I really want to do and just officialised what I was doing all along since I was in High school for friends and family: wedding planning.
thanks for sharing!
June 30 will be my last day working for people, I gave my resignation letter because I decided that my time has come to work fully on my business and realize my dream. I just can’t wait to start fully living this adventure, life is just beautiful!
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June 25, 2010
Great information! I’ve been looking for something like this for a while now. Thanks!
pharmacy tech
July 3, 2010
Great site. A lot of useful information here. I’m sending it to some friends!
Doyin
October 20, 2010
I studied Economics and was a Financial Analyst for over 10years before switching to Event Plannning which used to be a hobby. Im loving to design events now, its really fun!
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October 21, 2010
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adefunke
April 7, 2011
I am not an event planner but I like anything to do with flowers like the flower teddybear in preston s portfolio. So I would like to learn how to make dolls with flowers and how to preserve the flowers