Jackie Dos Santos Siapno: Holding Space for Grief, Gratitude, and Motherhood
Jackie dos Santos Siapno opens up about motherhood, entrepreneurship, and learning to carry grief while staying present for the life she continues to build
There are seasons in life when joy and grief seem to arrive together—sometimes quietly, sometimes all at once. For Jacqueline “Jackie” Dos Santos Siapno, both have become part of everyday life.
As a dentist, entrepreneur, and mother of two, Jackie moves between many roles in a single day. She runs Happy Pilates and Happy Latte Cafe, raises daughters Bella and Maria, and continues to navigate the loss of her mother, Happy, who passed away unexpectedly three years ago.
It’s a life that feels full in every sense of the word—busy, beautiful, and sometimes heartbreakingly difficult.
Building something in honor of their mom
For Jackie and her sister, Tippy Dos Santos, opening Happy Pilates began with something simple: taking a class together.
“Honestly, it’s as crazy and as simple as this—my sister and I took a Pilates class one day, truly enjoyed it, and suddenly thought, ‘Why not open our own studio?’” Jackie shared. “There weren’t many Pilates studios along Marcos Highway at the time, so we saw an opportunity and decided to go for it.”
That first studio found its community quickly. This year, they opened a second branch in Alabang.
The café came naturally after.
“A lot of our clients would look for coffee or matcha before or after class. So when the space beside our studio became available, we immediately felt like it was the perfect opportunity,” she said. “Opening the café just made so much sense. It felt like the missing piece we didn’t know we needed.”
But beyond business, both spaces became something more personal.
“We wanted a meaningful way to honor our mom,” Jackie said. “For us, creating spaces where people can move, connect, rest, and genuinely feel happy felt like the best way to do that.”
Learning to live with loss
Three years after their mother’s passing, grief still feels present.
“My sister and I talk about it every single day—even up to now, the fact that our mom is gone still shocks us,” Jackie shared. “Navigating life without her has been, and continues to be, the most difficult thing we’ve ever had to go through.”
Some days feel heavier than others. And milestones—especially birthdays and Mother’s Day—still carry a weight that hasn’t disappeared with time.
“I often tell my family and friends that May is the most difficult month for me because it holds both Mother’s Day and, at the end of the month, my birthday,” she said. “Since my mom passed, I haven’t really been able to celebrate these occasions in the same way because the pain can feel overwhelming.”
But within that grief, she’s learning to hold space for gratitude, too.
“I’m slowly learning how to hold space for both grief and gratitude—for all that I am still blessed with in this life,” Jackie said. “The love I have for her is still very much present, even if she isn’t physically here.”
Motherhood in the middle of everything
In between managing her businesses and practicing dentistry, Jackie’s days revolve around her daughters.
“Raising two daughters has been both incredibly challenging and deeply fulfilling at the same time,” she said.
With Bella, she’s enjoying watching her personality unfold more each day.
“We’re able to bond over so many things now, which has been so special for me.”
With Maria, she’s been savoring the return to the baby stage.
“I truly missed it,” Jackie shared.
Both girls, she says, are clingy—and she loves that.
“I really make it a point to be as present and hands-on as possible. I bring Bella to play school three times a week, and Maria comes along with us too. On days we don’t have school, I prepare activities for them or take them out so we can spend quality time together.”
Like many mothers, Jackie knows presence isn’t always about having unlimited time. It’s about choosing to be fully there in the moments you do have.
Motherhood, she says, has expanded her in ways she didn’t expect.
“I’ve realized that the love you have for your children somehow allows you to keep giving, even when you feel like you’ve already reached your limit,” she said. “Every time I think I have nothing left to give, I somehow find more within me because of them.”
“Motherhood now, with two daughters, feels fuller, deeper, and even more purposeful. It’s chaotic at times, exhausting on some days, but also the most rewarding role I’ve ever had.”
The people who help her hold it all together
Jackie is quick to say she doesn’t do it alone.
She credits her husband, their household team, friends, and her sister Tippy as the people who make her version of motherhood possible.
“Tippy is such a present and hands-on aunt,” she said. “We see each other almost every day, so the girls are really able to spend a lot of time with her.”
Living in the same subdivision makes spontaneous visits easy—and meaningful.
“She’s incredibly busy with work, but despite that, she always makes time for them, which I really appreciate.”
Jackie hopes Bella and Maria grow up with a bond similar to the one she shares with her sister.
She’s equally grateful for the people at home she lovingly calls her “angels.”
“Without them, I truly wouldn’t be able to continue chasing my dreams while also being the kind of hands-on and present mother I want to be,” she said. “Sobrang swerte namin with our helpers. They really have genuine love and care for their alagas.”
What she hopes her daughters carry with them
If there’s one thing Jackie wants Bella and Maria to remember from childhood, it’s not perfection. It’s presence.
“My husband and I work on this every day,” she said. “We want them to grow up in a home where they feel deeply loved, where happiness is something they experience daily, and where they are truly given time—not just physically, but emotionally present time.”
It’s something she learned from her own parents—and something she hopes to pass on.
“Our parents blessed us with such a loving home, and that’s something we deeply value and want to recreate for our children always.”
“More than anything, we want them to feel secure in that love and to know that they are always seen, heard, and valued.”
And for those still grieving the loss of someone they love, Jackie offers the same reminder she continues to return to herself.
“Grief is not something you’re meant to carry alone,” she said. “There’s no right way to grieve, and no timeline for it either. But allowing yourself to be supported, instead of isolating yourself, is something I’ve learned is really important.”
Even in grief, there is room for love. Room for joy. Room to keep showing up.
And perhaps that’s what Jackie is practicing every day: holding space for what’s missing, while staying fully present for what remains.
Frequently Asked Questions
Jackie Dos Santos Siapno is a Filipina entrepreneur, dentist, and mother of two. She is the co-founder of Happy Pilates and Happy Latte Cafe, which she runs alongside her sister, singer and lawyer Tippy Dos Santos.
Jackie and Tippy opened Happy Pilates after discovering a shared love for Pilates and seeing an opportunity to create a wellness space in their community. They later opened Happy Latte Cafe beside the studio as a natural extension of that space for connection and rest.
Jackie shares that Happy Pilates and Happy Latte Cafe were created as meaningful ways to honor their mother, Happy. Through these spaces, she and Tippy hope to create environments where people can move, rest, connect, and feel happy.
Jackie says motherhood has taught her resilience, softness, and gratitude. Raising two daughters has also shown her how love can continue to expand even in the most exhausting seasons.
For Jackie, presence is one of the most important values she hopes to pass on to her children. She wants her daughters to grow up feeling deeply loved, emotionally supported, and secure at home.
More stories of grief and loss
Finding Love and Strength in Grief
How This Video Game Helped A Father Cope With Loss
Love Never Dies: Mothers’ Stories of Grief and Loss
