Working Moms: Entrepreneur & Mother of Three

Meet Madeline, a working mom - A Well Crafted Party

Meet Madeline, a working mom! Her story is part of a blog series of stories of working moms. I’m excited to share 13 stories from real working mothers. I also really would like to hear YOUR story and I’d love to hear it. Keep the conversation going in the comments & on social media using #wellcraftedworkingmoms. A huge thank you to the women who volunteered to share their stories, Mary Boyden of Mamma Bear Magazine for her photography and Madeline Roosevelt for hair and makeup!


I met Madeline at one of the many blogger meet-ups that she and I have both attended. She is fantastic at connecting with people and networking. When I first put out the notice for volunteers for this project Madeline was one of the first people to message me. She volunteered her amazing hair and makeup services to help make the working moms feel great in their photos. It was such a huge, kind offer. Of course, there was no way I was going to have her do all that work and NOT ask her to be interviewed as well. She has a great story and I’m excited to share it.

Meet Madeline, a working mom


Madeline Roosevelt is the mother to three kids—two boys and one girl—aged 11, 8 and 6 years old. Madeline worked as a freelance hair and makeup specialist before, during and after pregnancy. She had her first child when she was thirty years old. Madeline was partnered with the children’s father for seven years and is now a single parent.  Her children live with her every other week.

She has worked in her field of hair and makeup for the past fifteen years. She currently works on commercial photo shoots, weddings, and special occasions. She has worked for Nike, Adidas and Reebok among other companies. In addition to her freelance work she does cuts and colors at a local salon as well as runs the salon’s social media accounts.


Meet Madeline, a working mom - A Well Crafted Party


I had a hard time really nailing down a title for Madeline because she does SO MUCH. Beyond her hair and makeup and social media work Madeline runs a blog and social media accounts promoting her business, as well as serving as an Oregon ambassador for Single Moms Planet. Entrepreneur seemed to fit the bill. While her hours differ from week to week and it may not always be full-time hours photo shoots can be incredibly long days and can cause some weeks to be well-over full time and other weeks can be more like part-time hours.

One google search of her hair and makeup work will quickly show you how talented she is!



A typical work day in the life of an entrepreneur and mother of three


A typical work day for Madeline begins at 6:30 AM when she gets her kids ready for the day and drops them off at school. She then goes home to get ready for her day. She will work different schedules throughout the week depending on what jobs she has at the time. She picks up her children after school, and then often has to attend a meeting or work in the evenings.


When my kids are adults and look back at their childhood, I want them to know…

“Sometimes they get frustrated that I’m not there, ” Madeline explains of how her children sometimes react to her working.

“They say, ‘Oh, you have to work again,” she explained, “and I say that I have to work to pay for food and a place to stay.”

Even though it can be hard sometimes Madeline said that she feels that it is important that she and her kids have a good relationship and that when they look back they know that she was there for them.

“[Having a good relationship], that’s the most important thing,” Madeline said. She continued to say that she changed her schedule because she doesn’t feel that working all the time was good for her relationship with her kids and now having a flexible schedule helps.


Maternity Leave, Childcare & Mom Guilt… oh MY!


I absolutely had to ask a few questions about some of the topics that often come up for the working mom such as maternity leave, childcare, and the challenges & joys of working. I love the answers so much that I felt it was best to just put it in their own words. Read on to learn about the ups, downs, ins and outs of Erin’s working mom experience!



When did you go back to work after having your children? 

“I took maybe a month off,” Madeline said.

I was a little shocked to hear how quickly she returned and asked her if it was her choice or something that she had to do while wishing to stay home.

She answered after a bit of deliberation, “I was fine. I was used to it. So, I don’t know any other way. I was fine going back to work right away.”


What type of childcare solutions do you use in order to work?

Madeline’s parents are local and have provided child care throughout the kid’s lives. She now has school to help with childcare needs day to day.


What challenges do you have as a working mother?

“Juggling. Finding balance. I restrained my schedule because sometimes my job requires me work all day and then I have to scramble finding someone to pick my kids up. So that is like the only challenge I have right now.”

Meet Madeline, a working mom - A Well Crafted Party - photos by

What joys do you have as a working mother?


“I get to see my kids grow up. I get to see them grow and evolve. From the time that they are a baby to now. It’s nice to see them being self-sufficient. They know how to take care of themselves, for their age, so that’s good.”


Meet Madeline, a working mom - A Well Crafted Party - photos by

How do you fulfill the other needs in your life (going back to school, working on a dream business, seeing friends, being creative, etc.) while working and being a mom?


“Gosh, sometimes I do [work on personal projects] late at night or when [the kids] are at school. It’s always a juggle,” she said.

“I’ve been learning to have a schedule. A calendar. I’m putting it in so I know what day I need to do it so I’m not needing to fit it in on a random day.”

“I think it’s good to have a community of moms to talk to if you’re facing any challenges,” Madeline said, “Because I feel that being a mom is sometimes stressful. It’s a lot of work…It’s a lot—especially emotionally, because sometimes you’re having a bad day with your kids and you sometimes wanna run away or go on vacation.”

Madeline fulfills her need of community by being an ambassador for a local chapter of Single Moms Planet. Single Moms Planet is an online (and sometimes in person) community of support for single mothers.


How do you prioritize your family and children as a working mom?


“It’s really hard. Because, being a single mom, I have to take the work as it comes because it always goes up and down. Sometimes I see them and sometimes I don’t.”

Madeline has her children every other week and said that the schedule is good for them.

“When I don’t have them thats when I try to cram in everything that I need to do, then when I have my kids I try to spend as much time with them as possible.”


Read more from Madeline:

Check out Madi’s blog at Up Close with Madi!


Thank you! A huge thank you to Madeline for sharing her story as a working mom and participating in this series. Does her story resonate with you? Share in the comments below or on social media with #wellcraftedworkingmoms !

Check out Momma Bear Magazine for more articles on motherhood and to check out the great momma swag!

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Jenni is a freelance writer and media assistant based in Portland, OR. A Well Crafted Party is a blog about all the little things to celebrate in life. Follow Jenni or A Well Crafted Party with BlogLovin, RSS feed, Twitter, Facebook, Instagram, or Pinterest.

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  1. Reply

    So nice that Madeline shared her story and talents for this series!

    • Pech
    • April 25, 2016

    Another wonderful profile showing how unique but yet so similar moms are, and Madeline having to roll with the work punches when it comes from different sources and ebbs and really flows sounds like a lot to track of, she sounds amazing having to track and be so flexible all the time!

  2. Reply

    I can’t image life as a single, working mom. I have so much respect for the Ladies that wear all of the hats. Happy Mother’s Day, Madeline!
    Brettni Brumfield recently posted…The Time My Friends Hijacked My Earth Day PartyMy Profile

  3. Another amazing mom juggling it all! I’ve been loving all the looks from this series, Madeline has done a great job on the hair and makeup!
    Erin @ Platings and Pairings recently posted…Harissa Hummus + A Vitamix Giveaway!My Profile

    • Mary
    • April 25, 2016

    Wow! Madeline sounds like a rock star. She’s juggling so much and seems so level headed about it all. It’s gotta be stressful being an entrepreneur and solo bread winner. The lack of steady consistent work I’m sure can be so stressful. She seems to be taking everything in stride! What a great role model for her kids.
    Mary recently posted…Weekend Wine Love – Wines of the WeekMy Profile

  4. Yes! Self-sufficiency is important to me as a mom, too. I want my kids to depend on me for some things—security, love—but am thrilled to see them try new things and become independent on their own!
    Catherine @ Ten Thousand Hour Mama recently posted…Happy Mother’s Day to Me: A series to celebrate ourselvesMy Profile

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