Keeping Small Businesses Competitive through Sharing Best Practices of Global Leaders


Jay Calderin

Jay Calderin is the author of Form, Fit & Fashion, which the LA Times called, “a new fashion bible for designers, aspirers and the just plain curious, this tome contains all the secrets.” His new book is Fashion Design Essentials – One Hundred Principles of Fashion Design was recently released by Rockport Publishers. Calderin founded and serves as the Executive Director of Boston Fashion Week. He is also an instructor and the Director of Creative Marketing at the School of Fashion Design in Boston. His work as a fashion designer has graced the pages of Vogue, Elle, the Boston Globe and the Boston Globe Sunday Magazine. He recently held the position of Regional Director of the Fashion Group International of Boston and continues to work with the professional organization.

Learn more about Boston Fashion Week here:


1. Tell us about Boston Fashion Week and how you got involved.

Jay: I founded Boston Fashion Week with the intention of creating a platform for local fashion talent to be nurtured and celebrated. It is built upon a grassroots effort to provide the public with greater access to fashion designers and afford the designers an opportunity to build an audience for their work. In house initiatives for Boston Fashion Week are always centered on organizing the local community of fashion professionals, not producing events. In addition to the usual fare of fashion shows, special events, shopping and parties that take place during Boston Fashion Week, there is also a special focus on educational programming. I’ve served as Boston Fashion Week’s executive Director since it was established in 1995.


2. For most successful entrepreneurs, there is no typical day so give us a sample of your schedules from start to finish.

Jay:  My morning begins with a walk to Starbucks for my single cup of coffee for the day. This daily ritual gets me moving and is ‘quiet time’ for me, a time when I can get my bearings before addressing the demands of my day. When I get back I read emails, and catch up on Facebook and Twitter feeds. At this point each day takes a different path. I may be teaching a class or have a project meeting scheduled. It may be a block of time designated to writing or research. Or I might be focused on web updates or graphic design work. There could be a photo shoot that requires my attention or a special event that I need to attend. It’s never the same day twice.


3. What are your “can’t live without” apps on your desktop/cell phone?

Jay:  My iPhone has become the ultimate personal assistant. I’m sure I could live without it if I had to, but at this point I wouldn’t want to. Facebook, Twitter, Accuweather, Google Maps, Starbucks, Shazam, and Photoshop Express are daily touchstones. And of course there are the basics; my camera, calendar and email access.

4. What are your tricks for time management?


  • Buffers. I try to always give myself a minimum of 30 minutes between scheduled tasks and appointments. I strive to be at least 15 minutes early for appointments, to avoid feeling rushed. I also don’t usually wait longer than 20 minutes for anyone who is late for an appointment.
  • Documentation. I carry a notebook with me at all times, so that I’m able to write anything of importance down immediately. With so much going on, it’s easy to forget things.
  • Redundancy. In addition to hard copies, I make digital notes on my phone or computer. I also email myself backups and reminders.
  • Prioritization. It is important to assign values to the things that are most important, both professionally and personally.”


5. Best advice received when you started your career?

Jay:  Show up and do the work.


6. Given the current economic climate, how has your strategy for building awareness of your work changed for the short-term and long-term?

Jay:  It’s always about the long-term. Investments outweigh the reward of a quick fix every time. My strategy hasn’t really changed that much with regard to the work that I’m involved in. If anything, the state of the economy has been a blessing in disguise, because smart individuals and organizations are discovering a new respect for building strong supportive communities, and that’s how you spread messages. The value of authentic and reciprocal relationships is slowly but surely being recognized and appreciated as an integral part of doing business today. I believe that strategic partnerships are at the heart of surviving challenging economic times, not to mention remaining relevant and innovative.

7. What’s been your proudest achievement as such an immensely accomplished Entrepreneur?

Jay:  I get the biggest sense of accomplishment when any of the things I’ve worked on – teaching, writing, speaking, events, or bringing people together – sparks something new that takes on a life of it’s own. It makes me feel as though I’ve done my job and made the world a little better than how I found it.

8. What are some of the ways that you achieve balance in your life?

Jay:  Figuring out what is really important in your life is key, and I think that changes at different times in your life. I’m in my 40’s now – quality is infinitely more important than quantity. Downtime is very important – time for friends, family and yourself. Also, allowing yourself permission to indulge in the things in your life that recharge your spirit.

9. Your top 3 book recommendations for our readers (and why?)

Jay:  You mean besides my two books? Well if we put those aside I would recommend:

If you had an exceptional month and earned double of your average month, what (if anything) would you spend it on?

Books, music, films, and technology.

10. What are some of your most rewarding charitable involvements and why?

Jay:  I don’t really think of it as charity because it has become a natural extension of who I am, but my involvement with Big Brothers for over 10 years now has been easily one of the most rewarding experiences in my life.

11. Who has been the most influential person to you as you’ve advanced in your career?

Jay:  Mister Rogers.

12. What’s your advice to someone interested in starting their own business?

Jay:  Starting, maintaining, and succeeding at a new business is overwhelming work that demands a serious long-term commitment. Do it for the right reason – love of the work itself. Otherwise it’s just a job and you might as well be doing it for somebody else.

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