Sandy Dempsey of The Dreaming Cafe: Launching A Dream


December is about launching a dream, for me. And to help me celebrate, I have asked other amazing individuals to share their journey of launching their own dream. Please welcome Sandy Dempsey of the Dreaming Cafe as she shares her story and nuggets of wisdom from following her dream.


Hi Sandy! Thank you so much for being here at Dirty Footprints Studio to share your story about launching your dream. I’m very proud to say that I’ve had the opportunity to meet you in person at the Creative Dig Workshop this year, and to have spent some time hanging out with you personally. I think you are an amazing chica. I deeply admire that your big Creative Juicy dream in life is to actually help others reach their own dreams as well.

Sandy, how did you know it was the right time to quit your “regular job” and leap into your dream full time?

This question was harder than I thought it would be. I’ve re-written my answer about six times so far.

I think it was hard because there were so many small steps leading up to the point that when a series of events occurred in both my personal and professional life I had choices, I had options. I didn’t have to stay in a bad situation. I could resign.

It started with a burning desire to work for myself, to write and to create every day, to teach and to help others.

The Dreaming Café fed the flame of this desire until I had no choice but to figure how I could do it; how could I go out on my own.

So, I started to plan. I cut back my spending, paid off my car loan early and began to save. I also spent every single day off ‘pretending’ I was already self-employed. I invested in workshops and seminars that fed this desire and committed to building authentic, supportive relationships with other writers, artists, and entrepreneurs.

I also began teaching. In August, while still working full-time I taught my first online Journaling for Self-Discovery workshop. I have since taught the workshop four more times, each time with more and more students.

The positive feedback from my students bolstered my self-confidence and affirmed that I was on the right path. It wasn’t just about making money. It was about sharing something I was passionate about and helping others.

I had originally planned to resign from my corporate position sometime after the first of the year, but when a particular ugly situation evolved at work in late October it was the final straw that broke the camels back.

Crying all the way home from work and sitting in traffic for an hour every night is no way to live. That night my husband finally saw what was going on. He wanted me to quit on the spot. He told me it was time to get out and it was time to start following my own dreams.

I resigned a few days later.

What type of support and/or resources did you find helpful in making this transition?

My husband is my number one supporter. He doesn’t understand everything I do or why, but he supports me none-the-less.

It was also important to me begin meeting and getting to know other writers, artists and entrepreneurs and people living a creative life. It didn’t matter if they pursued their dream full-time or part-time, just hanging out with people who ‘got-it’ made a big difference. It opened my eyes to possibilities I never knew existed.

I found these people in books, online and in person. Books and blogs were two big resources that have helped me make the transition. I love to read and learn and to follow other people’s journeys.

And, like I said, I made it a priority to attend workshops and seminars so that I could hang out with and learn from others.

I stay in contact with many of the people I’ve met this way and talk frequently via email and phone.

Once I was sitting in my office at work, Tweeting away when my cell phone rang. When I answered it, it was a woman I’d met on Twitter and Facebook. She’d seen that I was online, knew we had a lot in common and called me. (My phone number is provided to my subscribers.) It was great having a conversation in the middle of the work day. Connecting with people like this happens more and more now.

What type of support and/or resources do you find helpful now that you are working on getting The Dreaming Cafe up and running full time?

I have taken the time to build a circle of support from people I have met at seminars and workshops and from my online community. We stay in touch via social media, email and phone.

I also take the time to connect with every new Dreaming Café newsletter subscriber. I have met some inspiring people doing great things. I love it when my readers email me back and share their story, what they are working on and their dreams and goals.

To create an offline support network I am considering joining a local woman’s business organization that has two educational / networking meetings a month. Joining the local chamber of commerce is another option and I am in the process of putting together a woman’s entrepreneur mastermind group. If this works out I’ll have the opportunity to meet with, brainstorm with, find support and support with other woman on a weekly basis.

I have discovered that I can’t sit around and wait for someone to reach out to me. If I need support I need to ask for it. And, if something doesn’t exist, like a meet-up group, then I need to create it.

How has this transition changed your Creative Juicy Life on other levels other than just work?

I was really surprised out how leaving my job affected my husband and my Mom. They laugh and smile more often. They seem lighter and happier like a burden has been lifted from their shoulders I never realized how much my stress and unhappiness was hurting them.

From my own perspective, I am more creative. I am more in love with writing. I’ve rediscovered things I love to do. I have more ideas than I know what to do with. And, I am happier and more peaceful than I ever remember being.

Now that you are actually living your dream, what pleasant surprises have you discovered about being self-employed?

Reading about and ‘pretending’ to be self-employed and actually being self-employed are two very different things.

The surprise is that as green as I thought the grass was on the other side…it’s even greener.

The sun shines warm and bright, the sky is blue, and flowers of every imaginable shape and size grace the landscape in a dizzying array of color.

Yes, there are storms, too. But, I am learning to work through them with the faith that my dreams will carry me through until the sun shines again.

One more thing, it’s scary, but not in a bad way, if that makes sense.

What surprise challenges have you encountered so far as well?

Not having a routine or people to talk to on a daily basis has been a real adjustment.

Also, just learning to relax is totally new. Having time to myself that is unscheduled and unstructured is taking some getting used to. I used to be on the go from four or five in the morning until nine or ten a night. I never stopped. Now that I can stop and slow down, I am not really sure how. It’s a learning curve. I have to let go of old patterns and limiting beliefs that say I have to be busy and producing all the time.

How can The Dreaming Cafe help others on their Creative Juicy Life journey?

Imagine never feeling alone again and connecting with people who ‘get’ who you are.

That is what the Dreaming Café is. It is a growing community of creative individuals dedicated to a life of self-expression, lifelong learning and personal growth. It is a safe, supportive, creative environment online (and soon to be offline) where you can come, hang out, relax, learn, grow and have fun with people who understand and ‘get’ who you are, who you want to be, what you want to do and what you are doing now.

I am passionate about sharing information and helping people to grow and to learn and to build a creative life based on their own unique vision.

The Dreaming Café provides an abundance of free information on my website, blog and newsletter. (Check out the “Free Stuff”)

I also teach an online journaling for self-discovery workshop and next year will be presenting an entire series of workshops and teleseminars that will focus on living a creative life, personal growth and self-discovery and working for yourself. These workshops will be taught not just by me, but several guest teachers, writers, artist and entrepreneurs, from around the country.

2010 is going to be an exciting year for all of us. The possibilities for living a Creative Juicy Life are endless. You just have to take the first step and embrace the journey.

Where and how can the readers of Dirty Footprints Studio reach you?

Your readers can visit my blog at

They can also sign up for a weekly dose of inspiration and information by subscribing to the Dreaming Café’s newsletter.

My email address is: sandy@thedreamingcafe (and I love getting emails.)

They can find me on Twitter:

and Facebook:

Or send me snail mail at: Sandy Dempsey, PO Box 171, Sewell, NJ 08080

Thank you so much, Sandy, for sharing your journey with us and your generous offer (see below). You are a huge inspiration. And—thank you for spreading such LOVE in the world by beginning to help other kindred souls live the Creative Juicy Life of their dreams! Best of luck and happiness in the new year! Big hugs!

Thank you, Connie for this wonderful opportunity to share the Dreaming Café and my journey with your readers.

You have been a true inspiration to me this year and have helped me discover new ways to express myself and to embrace my inner artist. I am grateful for having found you and honored to call you a friend.

Peace, love and hugs,



Sandy is generously giving away two free gifts to a lucky Dirty Footprints Studio reader in celebration of launching a dream!!! If you would like to be entered to win a copy of Steven Pressfield’s “The War of Art: Break Through the Blocks and Win Your Inner Creative Battles”, and a Dreaming Café bookmarker leave a comment on this post. The winner will be chosen this Saturday!

Peace & Love.

Join The Paint Wisdom Newsletter!

My weekly newsletter is filled with studio updates,
announcements,& short musings intended to nourish your Artist Soul.