Mama Maker: Esther from Virtual Assistant Internship

When Esther uprooted her life to move her son to Bali, “a very healing place,” she found solace within a community of entrepreneurs and expats.

“To have to leave my husband was really, really horrible. To have to leave America was really, really scary,” she says, describing the moment she distanced herself and her son from her husband’s dangerous mental breakdown, which was triggered by multiple head traumas in the military.

“Even when my personal life was totally falling apart, even when emotionally I was a complete wreck, you just keep going anyway,” she says. “You just get up the next day and do it again.”

The village of support that surrounds her in Bali has simultaneously allowed Esther’s virtual assistant business to flourish, while changing her perspective towards moments of fear and self-doubt.

Esther recognizes that “when you do the stuff that’s hard and scary, that’s what takes you to the next level.”

“If I’m feeling like ‘I can’t do this, I don’t know what I’m doing’…I now know I’m going through something,” she says.

“I’m up-leveling.”

In four years, she’s helped 100 women do the same through Virtual Assistant Internship, which gives them the tools to start their own lucrative businesses from anywhere in the world.

“It’s a very tangible way of changing someone’s life,” she says.

Women Helping Women Succeed

Esther’s journey began as a working mom and military wife whose husband worked night shifts and could be deployed within a moment’s notice, leaving her feeling “depressed and sad and stressed” she says.

“It was so hard because I loved my job,” she says, describing her corporate role in software product management that required her to travel frequently.

“But I also love my family and my son, and I was watching him having to be taken care of by all these relatives all the time, and neither of us were ever around,” she says.

“I was crying in my hotel room one night and I was like ‘that’s it’,” says Esther. “I felt like God was saying ‘trust me, I have something better for you — this isn’t how it’s supposed to be.’ ”

“Women aren’t supposed to be stressed out all the time and not see their kids,” she added.

The next day she quit her job and began scouting out a virtual assistant gig that would give her the flexibility to work from home and set her own hours.

After six months on the job, Esther kept getting asked about how it works, so she began mentoring others around top tasks for online business owners, like content repurposing, light email, and calendar management.

“I don’t understand why no military wives, none of my friends, nobody knows about this. This is insane,” she recalls feeling at the time.

Fast forward six years and her community of graduates ranges from women in the military to local moms in Bali who’ve started their own virtual assistant businesses and agencies.

“It’s really like this tribe we’ve created of women that are all hiring, helping, and mentoring with each other,” she says.

“I literally save messages from them telling me ‘Thank you so much, you changed my life.'”

When self-doubt creeps back in, she reads the notes, stored in her phone, to remind her why she should keep going.

“I really feel like it’s my purpose.”

It Takes a Village

Bali makes it easy for Esther to create the kind of village that every working mom needs in order to thrive.

“It’s much more community oriented than in the States and I think that surprises people,” says Esther.

She lives in a shared villa and has staff that helps with her son, delivers freshly prepared meals, and drives him to school.

Between her neighbors and other Balinese women she’s be-friended, Esther says she has plenty of people she can call in a moment’s notice to help with her son.

“He goes to this amazing ex-pat school, Montessori style, so they do an international curriculum in English until about noon, and then in the afternoon they go on field trips,” she says. “They go to the beach, They go on hikes through the rice fields.”

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While her son’s at school, Esther works side-by-side with fellow female business owners who run agencies or are influencers in their own right.

They all “meet up and co-work together” in one of their villas, a cafe or a co-working space.

Even in such a gorgeous setting, Esther says it’s very tempting to work around the clock, so they’ll bring in a massage therapist or taking a painting class to get the creative juices flowing.

They often finish the day together at the beach or watching the sunset.

And while she and her husband are working on their marriage and figuring out living arrangements, the supportive community in Bali is hard to beat.

“It just feels like home now.”

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Whether Esther is teaching the next batch of virtual assistants how to grow their business or helping entrepreneurs create online course content that sells itself, she believes in the legacy that comes with building community.

“Nobody knows what they’re doing,” she says. “You think all your other mom friends have it together or that person on YouTube. Nope. We’re all just making it up as we go.”

“It’s not about you. It’s about the tribe you’re creating.”

Mama Maker: Rachel from ParentSpark

As a parenting coach and mother of three boys, Rachel Goldman Sklar is chock full of creative ways to overcome the day-to-day challenges of raising young kids.

Our conversation couldn’t have come at a better time, as my nearly 3-year-old is still adjusting to life with a sibling and we’re constantly negotiating meals, trips to the potty, and bedtime.

While we typically resort to bribery, Rachel suggests a “first, then” technique instead.

“Children are so routine oriented and appreciate the autonomy that goes along with following order,” she says, describing how you might say “first you brush your teeth, then we read a book” as a series of steps instead of dangling the story like a carrot.

“First, then” is just one example from ParentSpark — the “chat bot” Rachel built with a fellow parent, Guy Rom, who brings engineering chops from Facebook and PayPal.

In one hour of feeding my newborn with one hand and chatting with ParentSpark’s virtual host “Heather” with the other, I learned a handful of techniques–and the research behind them–to try out with our testy toddler.

While convenient, ParentSpark is also designed to be more interactive than a parenting book. It features digestible content for the 140-character generation of parents who may not have the option or interest to read a book or attend a workshop.

“Books don’t really support you in an ongoing way,” she said. “They’re not there to nag you. They’re not there to remind you. They’re not there to help you reflect on how to tweak things for your own family.”

Rachel and I discussed how parenting books can also make you feel like you’re doing something wrong if it doesn’t work or that you should have started sooner (like my experience reading the 3-day potty training book).

Helping Families Succeed

Rachel’s initial exposure to parenting wasn’t easy. Prior to coaching, she worked in social services with child abuse investigations. She left to start her own family, and then found herself needing the kind of support she now provides.

“When it came time for me to go back to work–which was kind of driven by the fact that my children were challenging and I needed a break–I went back and trained to be a parenting coach, knowing that I would get my own coaching,” she says.

Rachel figured if it went well, she would turn it into a practice.

“And that’s exactly what happened,” she says. “I began to love parenting, I went ahead and had another baby, and I started my own practice.”

Rachel draws inspiration from all of these experiences to create the content for ParentSpark, and pays close attention to what she hears back from users.

“Every morning I come in and read what people’s takeaways are…and it’s really touching,” she says.

“We really want feedback,” says Rachel. “Every mom who uses it can help the next generation of moms who use it, because we’ll improve it based on all of our user feedback.”

Ultimately, she’d like to bring ParentSpark full circle and reduce the incidence of child maltreatment, through government grants and partnerships with social workers.

How this Mompreneur Makes it Work

Rachel keeps it real, and that’s part of her appeal. She’s created mantras like “At Your Wit’s End” and “Me Time” on Rock Your Inner Mama: Guidance for Mindful Parents. She makes sure to carve out time for her and her husband too.

“We go to Burning Man every year. That’s our one week of being completely disengaged from parenting,” she says.

As for the other 358 days of the year, Rachel navigates the highs and lows of running a startup, while juggling three boys with her husband, and continuing her coaching practice.

Her mornings start off on a strong foot. She’s mastered the art of keeping everyone in bed until 8:00 a.m. during the summer, and 7:00 a.m. during the school year. And she relishes in the solitude of her commute.

But like many of us, “evenings are fraught with chaos and kids fighting and us getting frustrated with each other,” she says.

“Feeding children is the hardest part of parenting for us,” says Rachel, as she describes the limited diet of her three boys, and behavioral issues triggered by blood sugar and gluten.

In similar fashion to the suggestions Rachel shares in ParentSpark, she had an epiphany.

“I was going to hire somebody to watch the kids in the afternoon so I could cook dinner, then I realized I should hire someone to cook dinner so I can watch the kids.”

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At the end of the day, Rachel values the balance that ParentSpark has provided her.

“I have the kind of job that affords me tremendous flexibility,” she says. “I’m really, really lucky that I have a really good blend of work and parenting.”

When Life Catches You By Surprise

Today is the original due date of our now 3.5-week old baby. His early arrival and the transition for our whole family have kept us on our toes ever since.

When I became a mother for the first time with my oldest, and then a working mother, life changed dramatically. Little did I know that baby number two would completely rock our world again, in his own unique ways.

Here’s what I did (and didn’t) expect while expecting, and what’s surprised us most now that he’s here:

The third trimester was faster and more intense the second time

Around the mid-point of my pregnancy, I started to sense that this baby might run ahead of schedule. He was measuring a week ahead at his 20-week anatomy scan and the technician and doctors all made comments about active he was, making it hard to measure him as he did flips and somersaults for the camera.

Right at the start of the third trimester, the doctor confirmed he was already head down, which was no surprise to me. I was having strong Braxton Hicks, which I didn’t have until the very end of my first pregnancy.

(I also learned that if you’re dehydrated, contractions can quickly turn into something more serious. It still seems to be a little known secret of just how important drinking water is during pregnancy.)

I carried on, preparing at work for the countdown to my planned start of maternity leave, and enjoying our final moments in the family routines that we had become accustomed to. We took lots of evening walks and I savored bedtime snuggles with my toddler, anticipating those moments would be harder to come by after the baby’s arrival.

However, I was growing increasingly slow on those walks and often felt too tired to read more than a couple of books before bedtime. (I would liberally edit our big brother-in-training’s favorite “hospital book” aka Babies Don’t Eat Pizza: A Big Kids’ Book About Baby Brothers and Baby Sisters.)

At my 35-week appointment, I was already 3.5cm dilated and 80% effaced, so the doctor predicted a couple of more weeks at most.

Little did I know, I’d be back in L&D 9 days later with contractions, another 1.5 cm dilated, and no signs of stopping.

Just because we’ve done it before, doesn’t mean it’s easier this time

When we found out we were having another boy, my first thought after laughing at our luck, was that we had everything we needed so it would be easy. From clothes to baby gear, and eventually less hormonal teenage years, I felt like we were all set.

Then I delivered a “late pre-term” baby at 36 weeks + 4 days, and everything changed.

That morning I had taken our first born to school, feeling like it might be my last time for a while. I took one more conference call and then walked into the family birth center to get checked out. While sitting there chugging water, I went from 4.5 cm to 6 cm, at which point they decided to admit me.

The labor itself was about as comfortable and peaceful as you can get. I repeated the low-dose epidural that had worked well with my first delivery, and sat around waiting to progress.

Meanwhile, we started to wise up to what it might mean to have a baby almost a month early. Despite reassurance from nurses and doctors that had preemies of their own who are now thriving 20-somethings, we didn’t know what to expect other than the immediate goal of delivering a 5-pounder.

Well, our little guy arrived at 9:26 p.m. on May 31 at a whopping 7 pounds, with a head full of thick black hair. All over again, we were instantly in love and mesmerized to finally meet him after all this time.

He passed all the tests they run for things like breathing, blood sugar and temperature regulation. He was sleepy during feedings, so the nurses encouraged me to try hand-expressing — but I quickly turned to my old friend Medela and a syringe to make it easier.

We were released from the hospital on schedule, and made an appointment to return to the doctor 48 hours later to check for jaundice. The doctor’s main concern at that visit was his weight, which had dropped down to 6 lbs 6 oz, so my new goal was to make sure he was eating enough.

Out came my brand new pocket-sized breast pump, bottles that claimed to be the next best thing to mom and a whole lot of math to figure out how often to pump, how long the milk could stay at room temperature, and how long before I had to toss a bottle he had started. (All while sleep deprived, since he was eating every 1-2 hours around the clock.)

It wasn’t until 5 days later that our instincts told us that his coloring didn’t look right, so we requested a blood test. Our suspicions were confirmed with a phone call that I don’t wish upon anyone, telling us our 6-day-old newborn had to be re-admitted to the hospital. His bilirubin levels had spiked and he needed blue-light phototherapy to flush out the jaundice.

One of the hardest parts of that dizzying moment was fighting back tears while telling our toddler that we needed him to be a big boy, and get back in the car to head to the hospital, right after he had walked in the door from school. This is one of the many reasons we’re so grateful to live near his grandparents.

I grabbed all the bottles I had pumped and some basic necessities, and we rushed out the door. What followed were two days and two nights of sitting in a hospital room while our tiny, lethargic 6-pounder lay under a blue light with a mask on for hours at a time.

My mission during that hazy hospital stay was simple: get him to eat and fill as many diapers as possible. I bottle-fed him under the light, and passed the hours by scheduling out feedings, pumping, and hand-washing bottles and pump parts, over and over again. The nurses came in every hour or so to check how much he was eating and what his diapers weighed.

He passed his final blood test with flying colors, and we celebrated with our much more alert baby. We came home and started to settle back into what felt like the beginning of a new routine for our expanded family.

Our whole family is changing, together

The four of us are operating on little sleep, so we can instantly go from happy to sad or angry in a flash. We’re all being challenged and pushing up against each others’ boundaries.

The stressful moments have been peppered in with plenty of happy times too, like visits from the grandparents, starting out weekends crowded together in bed, and sitting at the kitchen table enjoying daddy’s new dinner creations.

Some of what we’ve experienced has been pretty textbook, including the potty training regression and acting out by our toddler to get attention.

What I didn’t expect was being hit by a ton of bricks when I couldn’t be available to my first born for routine things like helping him get dressed or putting him to bed. I was a puddle of tears the first night home, but now my heart swells watching father-son bonding take its place.

While we’ve dedicated so much time and attention to helping our newborn gain weight and keep the jaundice at bay, our now 2 3/4 year old is blossoming before our eyes.

His vocabulary has doubled again, as he uses full sentences, asks questions and energetically narrates what we’re all doing. He’s obsessed with how things work, and can use his age-appropriate screwdriver surprisingly well.

Friends told me he would seem like a giant next to his tiny little brother — which is exactly what he looked like when he came to the hospital to meet him — but what I didn’t expect is how quickly he would take to his newfound independence. He loves to be a helper, too.

We’re learning, all over again, to prioritize what’s best for the moment

The first time around, it took me a lot longer to surrender to the changes brought on by parenthood. We basically added a child to the lifestyle we had created in an urban setting, and I attempted to keep my foot on the gas pedal at work.

It wasn’t until I realized I was putting too much pressure on myself to be super mom, right around the same time that we began house hunting in the burbs, that we realized how much change was inevitable.

This time, just under a month of two kids under our belt, we are turning everything upside to create the life that’s best for right now. We’re even flirting with the idea of getting a minivan.

Through more doctors appointments and lab visits than seem possible in 27 days’ time, we’ve learned to advocate for our family when something doesn’t feel right, even when we’re told otherwise. We’re mama bear and papa bear on steroids.

And while I’m looking forward to reconnecting with working mamas and mompreneurs to tell their stories, I’m currently in awe of moms who stay home full-time.

(The prospect of being outnumbered for more than a few minutes at a time was terrifying at first, until I reminded myself of what I’m capable of managing in the workplace.)

I’m so grateful for the village of parents who’ve been through this before us, and amazed by those who’ve dealt with much more.

In hindsight, finding diapers and clothes that fit (a la Chrissy Teigen) and pumping around the clock are the least of our worries.

Thankfully, the couple of hours that we get to enjoy “wake time” with our sleepy little guy are growing in number each day.

Even though this month is a blur, we’re living this new life one moment at a time.

Mama Maker: Karli from Unlisted Market

Karli’s longtime dream of owning a boutique was suddenly in reach when she found out Rachel, owner of Unlisted in South Denver, was also expecting. The two mamas-to-be eventually had their boys just 2 weeks apart.

“Once you find someone in your tribe…that bond, as most moms know, is incredibly strong because you can share all of life’s trials and tribulations,” she says.

The two had first met when Karli started selling vintage goods at Unlisted, during the final 4 years of her 15-year tenure in PR & marketing.

“I just knew in my heart that it was the right time for me to make the move to step away,” says Karli, describing how she spent her pregnancy “building my brand outside of my corporate life.”

Fast forward to 2017: Karli was running a freelance PR business, selling her wares at Unlisted and raising her 10-month-old, when Rachel approached her about becoming a partner.

“As a single business owner, she was doing it all by herself. She was literally maxed out on her time,” says Karli.

“I feel like it was such a blessing,” she says. “I always dreamed of having a brick and mortar. I didn’t know I was going to be lucky enough to find something that already existed that I could just walk in as a co-owner.”

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Karli and Rachel offer fellow dreamers “the chance to step out, try retail on their own while having their overhead taken care of, and a very competent, trustworthy staff there everyday.”

“We’re constantly asking ourselves ‘what will bring in more traffic?’ and ‘how can we help our more than 100 vendors be successful?’ however they define it,” says Karli.

Recently, this meant setting up a cafe featuring locally roasted coffee and tea in a highly trafficked booth after one of their former vendors ventured out on their own.

“This to me is the dream. This is why we do what we do,” says Karli, beaming with pride that one of their vendors had become successful enough at Unlisted to open their own store.

Women Helping Women Succeed

While the 9000+ square foot space features male and female makers alike, it works particularly well for anyone who requires a flexible schedule.

“I do think our model–in the way that doesn’t require them to work in the store–is conducive to people who are trying to balance family life and their own creative passions,” says Karli.

Among the women-led businesses featured at Unlisted are Prairie Rose and The Shabby Chandelier.

How this Mompreneur Makes it Work

Karli takes her now almost 2-year-old son to daycare while she juggles various roles at the store, including running the cash register, stocking and doing social media.

“I learned very quickly that he will thrive and I will thrive and our family will be happier,” she says, while noting that some days are easier than others.

“I think mom guilt is so real,” she says. “You try to justify all of your decisions. And you know what? We’re all doing the very best we can with what we have at that moment. I’m not going to judge anybody who does anything different.”

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Just like she found Rachel, Karli believes that finding a tribe of “like-minded moms” who support your decisions is key.

“When you find someone who’s in that same path, it feels really, really good,” says Karli.

Mama Shaker: Dr. Sharon Somekh of Raiseology

When her oldest daughter started middle school, pediatrician Sharon Somekh decided it was time to re-orient her career around what she loved most about her profession: working with parents.

In March, she left her practice and launched Raiseology, so she could build “more meaningful relationships” with parents virtually from her home office while being an “accountability partner” for her 11-year-old.

“I help anxious parents go from feeling like a deer in headlights to feeling like they can really do this… to the point where they can stop being so anxious about the day-to-day and really enjoy what they have in front of them–which is their kids.”

“We all love our kids and want what’s best for them,” she says.

Women Helping Women Succeed

As a mother of four daughters, ranging from 3 years and up, Sharon has personally navigated through multiple stages of working motherhood. For her, it was actually easier to get through 80 hour weeks as a resident when her first two were very young.

“One of my mentors said something to me that I’ve since told many, many moms,” says Sharon. “When your children are young is when you will feel better working more. A lot of moms think when their kids grow up, they’ll go back to work. You don’t realize that that’s when it’s hard to go back.”

She says feeling secure in your childcare arrangement and getting help are key to making it through the early years–I couldn’t agree more.

“Whether it’s emotional help, coaching help, physical help, outsourcing certain things you don’t enjoy doing at home–it will make your life much easier and it’s worth every investment in yourself to do that,” says Sharon.

Part of that support has come from moms who pitched in for preschool pick up and drop off. Her then 3-year-old started to notice and at one point told Sharon she wanted to be a stay-at-home mom when she grows up.

“Nothing hurts more than that,” she said. “But when she asked me ‘why do you work?’ I gave her a very honest answer. I think we underestimate what our kids understand and we need to have real conversations–that are age appropriate–with them.”

“Every mom has mom guilt,” she says. “They may have guilt about different things, but they still feel guilty.”

She says knowing your limitations benefits both you and your children.

“I think the example we set for our kids is really important. I like that they see that I’m a driven person and I value what I have to offer and think it’s important enough to put it out into the world.”

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How this Mompreneur Makes it Work

“If you’re asking how I manage four kids, I don’t,” Sharon says pointing to the independence that she’s fostered in each of her children.

She described a recent parent-teacher event where another mother she was volunteering with called her 11-year-old three times to make sure she was getting ready for school.

“I did not have a doubt in the world that my daughter was waiting for the school bus,” says Sharon.

Her 8-year-old makes her own lunch for school, and Sharon and her husband are currently training their 5-year-old to get herself dressed with the help of routines and checklists.

“It takes effort in the beginning, but it definitely has amazing payoff…and it’s great for the kids because one day they’re not going to be living in your house.”

You can learn more about Sharon’s “system of empowerment and independence” on her blog. In addition to her group program for parents of toddlers to school-age kids, she also consults parents of infants one-on-one, and she’s launching a podcast this summer.

Mama Maker: Christelle from Cooking with Kids and Wine

Christelle manages a team of business analysts at a systems integration firm, where she’s affectionately known as “mama bear.” Despite her technical role, a 90-minute commute, and the tightly packed schedule of a working mother, she’s found a way to cook dinner with her kids four nights a week.

“It’s not gourmet, it’s not something I’d serve at a restaurant, but it tastes good,” she says.

With her two sous chefs, Christelle manages to get dinner on the table between daycare pick-up at 6:00 p.m. and a bedtime routine that starts around 7:15 pm (and ends just after 8:00 pm with a glass of wine).

It was during her drive home one day that she came up with the idea to share some of her family recipes–old and new–by starting a blog, Cooking with Kids and Wine.

“Part of me is cooking. It’s definitely in my blood,” she says, describing the passion that sparked in her own childhood.

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“My grandmother and I used to love cooking together,” says Christelle. “My favorite cooking memories are with her. She was amazing at coming up with recipes and we just had so much fun together.”

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Christelle embraces the mess that comes along with bringing young children into the kitchen, and takes pride in blogging with photos that aren’t professionally styled. That doesn’t mean she shies away from complex recipes.

“My heritage is French, Irish and Mexican, so lots of different flavors.”

In fact, she recently recreated the French Financiers reminiscent of trips to patisseries in France while visiting her grandparents.

How this Mama Makes it Work

Her advice for parents who aspire to do the same?

“Introduce it as early as possible. I was giving my kids salmon and hummus when they were 10 months old.” (Much to the surprise of their daycare providers.)

Christelle counts Stuffed Squash among their staples, and often creates recipes based on what’s in the fridge.

“We don’t have hot dogs in the house,” she says. “I do have chicken nuggets in the freezer for desperate days, but they don’t think to ask for those things because it’s not offered to them.”

In her tips for bringing kids into the kitchen for the first time, Christelle recommends having all your ingredients handy and making a game out of it.

“I would have them smell the spices when I was cooking. They were always involved, and I think that’s part of why they enjoy it,” she says.

She also gives her kids the space to decide when they want to join her in the kitchen, and admits “sometimes they’re not in the mood to help.”

Christelle blogged about a recent weeknight when her daughter helped pull together Sloppy Joe-Styled Sausage and Peppers, complete with freshly picked basil, while her son opted to play with legos instead.

When I asked if she sees her kids developing their own passion for cooking, she said it’s too soon to tell. For now, she’ll enjoy creating those memories that would otherwise be elusive on busy weeknights.

“There are times when they ask to cook with me and that makes my heart happy.”

Mama Shaker: Jennifer Sydeski Hurd

While conferences and after-hours networking play such a big role in start-up life, toddler mom Jennifer didn’t want to make the trade-off. So she set out to weave motherhood and entrepreneurship together, by asking a long overdue question.

Why not offer childcare at events?

“I sat in the very back and waited until all the biology-related questions had come up,” she says, describing how she got up the courage to pose the question, with her kid in tow, in front of an audience of conference attendees.

“The person I asked it directly to was like ‘uh, I’m not really sure,’ but the person next to her was like ‘yes please!'”

“It was really helpful to have a person in leadership drop in and say this is important to someone else too.”

As an adjunct professor of technology, juggling her son between daycare, grandparents and babysitters, Jennifer’s start-up “Connect Wolf” is driven by her desire to “know where he is and if his heart is beating.”

“Not only are moms interested in this for personal use, they’d like to see it in various businesses where they take their children,” she says, while at the same time “they’d really like it not to feel like they’re lo-jacking their baby.”

Together with her co-founder, she’s found “really great workshops and seminars by experienced entrepreneurs in the same area that can really help you take your idea and refine it.”

For Jennifer, being in a highly specialized wearables space, “it’s really important to do all those things to be competitive when you’re looking for money for development.”

It Takes a Village

Jennifer’s husband travels during the week, so she’s responsible for piecing together childcare for her son, in between her commitments at the University and with her start-up.

“Even in my more flexible situation, it means picking him up by 5:30 and then getting him to a sitter’s, and then running out the door to get somewhere by 6:00.”

The same rush happens before and after events, despite the fact that “those minutes are important for making connections and understanding what’s going on,” according to Jennifer, who knows she’s not alone in the struggle.

“As I’m running out the door at the end of something, and everyone else is getting their cheap wine and snacks, I see three other people running down the steps.”

Jennifer and her 3-year-old understandably “don’t want to be separated when we’ve been separated all day,” so having time in the car together traveling to and from the event is priceless.

Then there’s the toll it takes on her wallet.

“I’m looking at hundreds of extra dollars a month and thousands of dollars a year beyond his standard $14,000 a year in childcare.”

In her pursuit to remove these barriers, Jennifer has started connecting local event organizers with Flexable, a Pittsburgh-based provider of certified “pop-up childcare” founded by mompreneurs Jessica Strong and Priya Amin (author of Make the Leap: A Guide to Reaching Your Goals).

“People are receptive to it when it’s brought to their attention,” she says. “I think it’s just a matter of getting it to be a thought during budgeting and planning.”

Helping Women Succeed

“A lot of this comes down to awareness that this is a hurdle for women entering entrepreneurship,” says Jennifer.

“I’ve actually had really good luck talking to 24-year-old guys that just got out of school. People who are entering the workforce right now have been taught about inclusiveness and how important it is to find the problems.”

She believes solving the childcare conundrum for start-ups can also benefit corporate culture, and “that leap where we see so many people falling off between middle management and executive leadership, where there’s such under-representation of women.”

In academia, the topic has been explored in a recent paper by the Working Group of Mothers in Science and in Mary Ann Mason’s book Do Babies Matter?: Gender and Family in the Ivory Tower.

“I’m really excited to see more of this done and surprised that I’m the person who’s like ‘excuse me’ tapping on their shoulders.”

Mama Shaker: Tash, from Coastermatic to Corporate Life

For first-time mom Tash, the birth of her son seemed like the right time to pass the torch to another mompreneur-in-the-making. Within days of welcoming his arrival, Tash signed over her other “baby” Coastermatic to its new owner Megan, and began settling into her next chapter.

“With Remi coming, it was becoming clear that I needed to move on from Coastermatic and let it go,” she says.

Timing was everything, as she had been working on projects with Megan, a mom of two “bitten by the entrepreneurial bug” who “already knows the business intimately and loves it.”

“It’s really exciting that something I made can give someone that opportunity, and that I can pass this thing on, that I loved really dearly, to somebody who’s really excited about it, and can use it to expand her skillset and grow,” Tash says.

Transitions have been a way of life for Tash since she left grad school where Coastermatic was incubated with a friend, and became a product designer at a large tech company two years ago.

“At this stage in my career it’s a really good fit and a good spot. It’s really nice to have maternity leave and health insurance,” she adds.

Tash has found the lessons she learned from running her own business and “thinking about everything that goes into making a product and bringing it to market” to be “hugely beneficial” working in the tech world.

“I have much greater empathy for all the other people I work with, and understanding the roles that they have and their responsibilities,” she says.

Tash believes “going back to into a corporate workplace with a more holistic toolset” makes her better at her job, and wouldn’t have happened without the experience she developed in grad school and while running her own business.

Transitioning into Motherhood

As for motherhood, Tash has eased into it with the same pragmatism she applied in her evolution from entrepreneurship to corporate life.

“I’d heard from friends that there’s not a lot of getting things done once the baby comes,” she says. “That was helpful to hear since I’m definitely a to-do list person. It’s been kind of nice to take the pressure off and not worry about all the things that need to get done.”

While Tash admits it took a few weeks to “relax into it,” she now feels like she and Remi are “getting into a groove.”

“Sleeping would be good,” she adds.

Whether she’s being peppered with questions from inquiring friends considering their own journey into parenthood, or speaking to aspiring entrepreneurs, her insights could easily apply to both.

“We didn’t know answers to any of these questions the day before he was born,” she says.

Fortunately for Tash, her start-up experience is coming in handy in more ways than one.

Why Breaking All the Rules is Best for the Moment

While I’ve become accustomed to my weekend ritual of writing about a Mama Maker or Mama Shaker during nap time, this was one of those weekends where life had other plans — in the best way possible.

Life with our 2.5 year old is giving us the full colors of the rainbow. One minute he’s falling into a puddle of tears and resistance, the next he’s all hugs and I love you’s. It is both the hardest time and the most wonderful time, all in one.

I started the weekend with full determination to psych myself up for potty training. But after reading one book that felt like too much pressure, and another that felt just right, we carved out our own little rhythm.

After a little bit of potty talk over coffee and lego videos, we continued on with our Saturday morning music class, complete with full drum set encore, and walk to the grocery store afterwards. Inside, the ordinary became the extraordinary in the eyes of my fire truck-loving toddler.

We spotted three “real life firefighters” who my son admired from a couple of feet away. They pointed out that his yellow rain boots were the same color as their truck outside, and he lit up with anticipation. Afterwards, one of the firefighters chased after us to hand my son a sticker. Day officially made.

The rest of the day consisted of mutual naps, lots of potty “reminders,” bribery, and hovering near tile and hardwood. My germaphobe self had to confront the realities of a very natural thing in the eyes of a curious toddler. We put in a few good hours of practice, and then ultimately gave ourselves “the night off,” breaking all the rules of potty training books.

(Here are the Potty Training Essentials that helped us through it.)

Dinner out as the three of us felt extra special, even though it ran a lot later than we intended. Seeing your toddler through the eyes of admiring strangers saying how well behaved he is definitely made us feel like there’s light at the end of this very tiring tunnel.

Mac & cheese, french fries and cheeseburgers never tasted so good after 8 p.m. We were treated to our own live performance on the ride home, as my son sang B-I-N-G-O and Itsy Bitsy Spider at an hour that would normally be reserved for bedtime.

My third trimester’s sleep was not surprisingly interrupted and I lay awake thinking about the logistics of the road ahead with our new baby. It feels like his older brother is well aware of his impending independence by putting on his own pants for the first time or climbing up on a step stool to help himself to a banana.

Our little firecracker continued on with his showering of affection and big boy behavior at my parents’ house, and told us all how he loved us over his second or third peanut butter and jelly sandwich of the day.

I felt pampered myself by resting my growing belly while listening to inspiring sound bites from a future Mama Shaker, getting a surprise Facetime call from my college besties and their babies, followed by a sunny patio visit with two of my longest-running local girlfriends.

The weekend wrapped with a quick walk with my overly fluffy labradoodle in pre-sunset light, more hugs from my energetic toddler for myself and the baby, and a cobbling together of dinner amidst the chaos of a very messy house. Knowing full well that tomorrow morning I will get back on the train, and have a moment of working mama independence, I wanted to soak up all that life.

Mama Maker: Veronica of Maia Moda

Trying to nurse her 5-month-old in a dress, while attending a wedding, inspired management consultant Veronica to do something she had always wanted to do, and start her own business.

“Once you have a child, it really zeros in on what’s important in life. What do I want my legacy to be and what do I want to spend my time on?” she says, describing what ultimately led her to bring the idea to fruition when her son was one year old.

“You go through so many changes as a new mom,” said Veronica. “One of the things you want to keep is some of yourself. Part of that is your ‘pre-mommyhood’ style. You don’t want to have it give it up, and why should you?”

“In today’s world, we have innovation all over the place. There’s no reason your nursing clothes shouldn’t have the look you want,” she says.

Veronica is tapping into virtual mom’s groups, along with NYC’s Garment District and burgeoning community of women entrepreneurs, to help propel her line of American-made breastfeeding-friendly apparel, Maia Moda.

She’s even been accepted into the 2018 class of Project Entrepreneur, started by Rent the Runway co-founders Jennifer Hyman and Jenny Fleiss, in partnership with UBS.

How This Mompreneur Makes it Work

For Veronica, it’s the blend of motherhood and running her own business that makes it all possible. She says her holistic approach now leads to more open and passionate conversations.

“I never used to talk to people that much about my work because it was very separate,” she says. “Now I feel like the two worlds collide a lot more. Because of my business, I’m super excited about it so I’m happy to talk about it.”

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As a mom of two now, Veronica has figured out a schedule that allows her to spend part of her week on the business, supported by a nanny for her baby and daycare for her oldest. She appreciates having dedicated days of the week for focusing on Maia Moda.

Women Helping Women Succeed

Veronica is encouraged by the changes she’s seeing around the culture of breastfeeding with “celebrities showing off their bumps and looking fabulous” and people posting “brealfies” (aka breastfeeding selfies).

“Women are feeling much more comfortable breastfeeding in public. We’re here to support that and to make that lifestyle work a little better through the clothes you wear.”

This also means Maia Moda clothes are washable, stain-resistant, wrinkle-free and “classic, but in line with the trends of today,” says Veronica.

“We want you to be really happy because there are enough things on your mind,” she says, noting she can be reached anytime, and welcomes feedback and requests.

While you can shop directly on the Maia Moda Web site, I decided to do so on Amazon so I could test-drive the Maia Top on my 7-months-pregnant belly.

As you can see, the flowing style can work all the way from baby bump to breastfeeding:

To read about more mompreneurs who are passionate about changing the culture of breastfeeding, check out Mama Maker: Sascha from Mamava and Mama Shaker: Jennifer Jordan from Aeroflow Healthcare.