A Word From Our Executive Director, Dr. Jacquelyn Wilson

Nothing tops being entrusted with a facility housing 380 residents to do a surprise holiday dinner for the less fortunate. Thank you, for allowing us to do what we do. It takes a village and we are the VILLAGE. Thank you to all of our sponsors, donors, chiefs; it’s because of you, that we were able to make a difference. We meet the people where they are…PERIOD!

With every ounce of sincerity, thank you all from the bottom of my heart for making this year’s Gift Giving Extravaganza, the most amazing day in the history of #SurpriseTheStruggling™ (A Hashtag Movement for Homeless Women.) From my key Chief Ambassadors,  Thamicha Isaac, Ebony C Johnson, and Charlene Stewart for breathing into me when I was second-guessing. My event planner, Vanessa E-El, The Event Strategist—who delivers every year faithfully! My cake supplier CAKES BY COLEY. I adore you, Coco! To my DJ, Ron Cee of Exodus Entertainment. I love you! To my CLO, Ruthe McDonald who makes it all happen.  My photo lady, Delilah Peach Williams, love you, babe!

To the Ladies and Gentlemen who cooked/served/delivered from SPBC, POYED by Velvette,  Robin Devonish, Aja Webster Barton, Paulette Bailey, Cynthia Juhans, and my brother & the Doc, Bryant Pearson; thank you! To the director of Starbright Family Residence, Ms. R, for entrusting us with your residents! Also, to my sister Wanda Edwards, to my love, Essence Bembry, and her boys, APWorld & Fear the Fro, Atlanta Hawks, for donating the bags and shirts. To my Accountability partner, Eloquent Essentials for sponsoring gifts. To Dr. Natacha Chloe and my day one ambassador, Keisha Christie, for sponsoring always! Althea Webber Bates, Shawn Headley, Iesha Sekou, and EVERYONE who sent a monetary donation…I LOVE YOU! 

Tanisha Smith Franks, Luck Da Barber💜, my children, my family, and my GOD—we did it!!!! ANYTHING IS POSSIBLE WITH A TEAM! Looking forward to an even greater 2018!!!! LET’S DO THIS!!!

Warmest Regards,

 Dr. Wilson 

We meet the people where they are…PERIOD.

Surprise The Struggling Receives Blessing Bags to Support Their Endeavors

December 9, 2017, New York—Surprise The Struggling was the honored recipient of over fifty Blessings Bags that was raised during a recent fundraiser.

Poyed By Velvette

Poyed By Velvette’s, B2BAB quarterly fundraiser chose Surprise The  Struggling for its winter fundraising initiative. Over forty women pledged to donate, purchase products, and raise funds to fill fifty large bags with items to help aid #STS mission in helping homeless women and teen girls globally. Among the many items donated to fill each bag was an array of toiletries, including items such as toothpaste, toothbrushes, sanitary and feminine products, lotions, soaps, body washes, socks, hair grooming and shaving kits, makeup bags, slippers, water, protein bars, detergent, flashlights, and a host of other items that would help those in need.


       Blessed 2 Be A Blessing 


Blessed to Be a Blessing “B2BAB” is a series of quarterly fundraiser initiatives by Poyed By Velvette, that support various causes by raising funds, collecting donated items and bringing awareness to issues that impact young girls, teenage girls, and women living in our communities.

The fifty bags donated to Surprise The Struggling enabled the organization to reach more homeless women and teen girls this Holiday season than anticipated. Immediately, #STS was able to reach out to some women in need, earlier than expected this Holiday season, due to the dedicated and philanthropic endeavors of Poyed by Velvette’s B2BAB initiative.

It’s A Surprise Holiday Dinner Party!

Thank you all for your continued support and dedication in aiding #SurpriseTheStruggling in making a change in the lives of so many people; especially those affected by Homelessness.

We are asking that you will help us to surprise about 100 families (380ppl) this Holiday Season with a special Suprise Holiday Dinner Party. A way to bring some happiness and kindness this Holiday season. To let them know they are not forgotten.

If there is any way you can assist us, please email us at, surprisethestruggling@gmail.com Make all Monetary donations at, http://bit.ly/STSHOLIDAYSURPRISEDINNER or on our Giving Back page.

No amount too small, no item turned away.

Please do us a favor, and pass along this Event. Share it on your page and in your communities. Let’s make a difference this holiday season. We can do this as a community!

A Surprise Holiday Dinner…Seeking Sponsors

December’s Women Awakening Women Tea Huddle to Feature Dr. Natacha Aurelien

First Wednesdays Women Awakening Women Tea Huddle


NEW YORK CITY, it’s going down!  Women Awakening Women Tea Huddle, sponsored by the Dr. Wilson Leadership Academy and The Tea Room in Brooklyn, is returning on December 6, 2017,  starting at 4 PM.  Our special guest speaker will be Doctor, CEO, and Author Chloe Natacha Aurelien.

The Tea Huddle is a safe space for sacred conversations over tea and a light meal for less fortunate and homeless women in our communities. If you would like to be a blessing and donate, no amount is too small, please visit our Giving Back page for the donate button. Or you may email surprisethestruggling@gmail.com We meet the people where they are…PERIOD!

Resiliency Moving Beyond the Baggage: Women of Color Empowerment Conference

Come out and meet Dr. Jacquelyn Wilson, Surprise The Struggling, Inc. Executive Director, at this year’s Women of Color Empowerment Conference at Rawson Elementary School. 260 Holcomb Street, Hartford, Connecticut 06112 1PM-6PM November 4, 2017.

There will be a live panel featuring Entrepreneurial women from different backgrounds, who are all making a difference and giving back to their communities in various ways.

Resiliency Moving Beyond the Baggage: Women of Color Empowerment Conference

First Wednesdays Women Awakening Women Tea Huddle

What can be more invigorating than being able to come together for inspiration, encouragement, and fellowship? Not much!

Surprise The Struggling Inc. and Dr. Wilson Leadership Academy’s inaugural First Wednesday Tea Huddle is happening tomorrow night, November 1, 2017, 4PM-7PM, at The Tea Room located at 452 Pine Street (between Belmont & Pitkin), Brooklyn, New York.  All women are invited to come out and hear an inspiring word from dynamic speakers, while gathering with other women, sharing the same struggles, triumphs, and dreams—over a cup of tea.

First Wednesdays Women Awakening Women Tea Huddle

First Wednesdays Women Awakening Women Tea Huddle is a joint venture between Suprise The Struggling Inc. and Dr. Wilson Leadership Academy to bring assistance, awareness, and advice to less fortunate and homeless women and teen girls. You are invited to join Executive Director, Dr. Jacquelyn Wilson tomorrow night for sacred conversation, empowerment, inspiration, and support over a cup of tea and a warm meal.

Sponsored Dr. Wilson Leadership Academy and The Tea Room, #STSGlobal will be catering to the less fortunate and homeless women in the community. All in attendance will receive a blessing bag filled with essential items to help take care of the bare personal hygienic needs.  Joining the festivities for the inaugural First Wednesday are two dynamic speakers: Minister Wanda Edwards of Colors of Survival and Minister LaTonya Smiley of Eve’s Roses.

To DONATE, click on the donate button on the Giving Back Page or go here: http://bit.ly/STSWAWW

If you would like to contribute material items, such as food, toiletries, blessing bags, or a  check or money order; or if you need further information on becoming a SPONSOR of one or more Wednesdays, please email: Rue McDonald at, rue@surprisethestruggling.org.

No amount is too small. We’re blessed to be a blessing. We Meet The People Where They’re At…PERIOD!

Looking Forward To Seeing You!

Upcoming Bags & Breast Cancer Awareness Lunch


Bags & Breast Cancer Awareness Brunch


Our very own, Founder and Executive Director, Dr. Jacquelyn Wilson will be a special speaker at this year’s Bags & Breast Cancer Awareness Lunch. 

On Saturday, April 29th, 2017 from 12:00 noon until 3:00 PM, guests will enjoy a beautiful afternoon of activities that include brunch and drinks, and special speakers for the afternoon. In addition to Dr. Wilson, guest will be honored with another special speaker, LaTonya Smiley, Founder and CEO of Eve’s Roses http://2liveunbroken.com

The event will take place in South Amboy, New Jersey, hosted by the lovely Miss Tracey Hamilton.

Guests are encouraged to R.S.V.P as soon as possible to, Blessintra@yahoo.com/347.295.8970. If you cannot attend, but still would like to donate, please visit our Giving Back page and click on the link to make a donation. No amount is too small.

Looking forward to seeing you!

Celebrating Women’s History Month…Nichole Bailey!




Bonus! We have a few more ladies we want to acknowledge this March, as we are celebrating Women’s History Month. #SurpriseTheStruggling’s thirty-second highlight this month is the encouraging and inspirational Nichole Bailey—#SurpriseTheStruggling’s benevolent and kindhearted supporter and Ambassador with a heart of gold. Nichole has lent of voice and given her support to our organization in so many ways. The love in her heart for what we are doing is just a testament to her faith, who she is, and what she believes.

When you are beginning a business, organization, or a job, you have a burning in your heart and spirit to do something in a way that no one else has. It is imperative to have a level of faith and a circle of support and encouragement that are not afraid to lift you up and pray for you and your success from a clear and pure heart—no strings attached.

Nichole Bailey, Change Agent, Bits of Faith

Nichole has given this to us. Her words and support have encouraged us and enabled us to push through any negativity and doubtful times. To know, that someone we had just met would go so far to be of help and assistance to us, means more to us and our organization than she will ever know.

#STSGlobal is not just an organization but also a family. We are a family that cares about our staff, volunteers, and Ambassadors, and our consumers. It is important to us always to represent our faith and to convey that hope to those we meet. When we think of Nichole, she embodies this same principles and beliefs. She is a reflection of our mission and is not afraid to meet the people where they are at, and not only meet their physical needs but also their spiritual needs.

We are profoundly grateful to Nichole for choosing to be a part of the #STSGlobal family. To assist, encourage, and support in so many different ways. Her spirit shines brightly and her legacy that she is creating is phenomenal. She is blessed, and we are profoundly blessed for knowing her.

Nichole Bailey—Wife, Mother, Change Agent, Motivator, Writer, Server—is the founder and creator of Bits of Faith, a place where positive affirmations serve as a catalyst for your growth and healing. Bits of Faith provide its visitors and readers with a regimen of inspiration, motivation, and encouragement. Visit the website to learn more,  http://bitsoffaith.net/ Follow on FB and IG,  https://www.facebook.com/Bits-Of-Faith-778903188893879/  https://www.instagram.com/bitsoffaith1/

We salute you, Nichole Bailey! Thank you for being a constant source of encouragement and a reminder to have faith! We stand with a heart full of love and gratitude, having you as part of the #SurpriseTheStruggling Family!

Celebrating Women’s History Month…Nicole DeRosa!




Continuing our celebration of  Women’s History Month, #SurpriseTheStruggling’s thirty-first highlight this month is the courageous and inspiring Nicole DeRosa aka Cakes by Coley—#SurpriseTheStruggling’s day one supporter, and friend, and our very own Cake Genius! Nicole has been a supporter beginning with our sister organization, The Stop Bullying Project®. Even through difficult times, Nicole has been a constant support to our organization. Her dedication and courage to continue to push past every obstacle in her path have inspired us.

We believe that you are a reflection of those you surround yourself. It is an honor to know and be friends with Nicole. Her strength is an encouragement never to give up on your dreams and your passion. Her courage in the face of adversity reminds us that not every day will be the greatest but if you are willing to push ahead, you will get to where you want and need to be.

Nicole DeRosa, Cakes by Coley, Cake Artist

Nicole embodies the essence and heart of the #STSGlobal mission. Her support and friendship have been invaluable to both of our organizations. We honor her today as a woman making history because she is creating a legacy that goes beyond beautiful and delicious cakes. (Believe us, her cakes are divine and her decorating skills above par!) A legacy comprised of her determination, strength, and courage. Nicole could have given up after two devastating losses and setbacks but she moved forward, even though it seemed impossible. Her determination is infectious and her heart and compassion are awe—inspiring.

We are so grateful to have met this beautiful woman and have the opportunity to be inspired by her story. Nicole’s character speaks for itself. Her workmanship, artistry, and work ethic are evident in every cake she creates, and every interaction she has with a longtime customer or someone new. You will always receive the best.

Experience the passion and love that Nicole pours into her work. Become acquainted with Cakes by Coley, and you will understand the woman and heart behind the brand and taste the love in every bite.

Nicole “Coley” DeRosa—Survivor, Fighter, Entrepreneur, Businesswoman, Cake Artist, Baker Extraordinaire, Champion—is the proud owner and creator of Cakes by Coley LLC, a custom cake company located in Brooklyn, NY, specializing in amazing, delicious and one-of-a-kind creations for any and every occasion. Their mission is to provide beautiful works of edible art that are just as tasty as they are breathtaking. They pride themselves on providing outstanding service, focusing on superb attention to detail, and practicing expert artisanship with every one of their creations, no matter the size or price. They work hard continuously to exceed the expectations of all of their customers.

To experience the awesomeness that we have for the past few years, visit Cakes by Coley http://www.cakesbycoley.com/ Visit the FB and IG pages also. Be certain to check out the galleries on all three sites. https://www.facebook.com/CakesByColey/   https://www.instagram.com/cakesbycoley/

We salute you, Nicole “Coley” DeRosa! Thank you for being an example of strength, courage, and example of how to overcome obstacles with grace! You inspire us every single day! We stand with a heart full of love and happiness, proud to have you as part of the #SurpriseTheStruggling and The Stop Bullying Project® Family!