HSHSP Ep 177: Becoming a Mompreneur, Interview with Cheryl Pitt

A Production of the Ultimate Homeschool Podcast Network.

This week on HSHSP Ep 177: Becoming a Mompreneur, Interview with Cheryl Pitt.

HSHSP Ep 177: Becoming a Mompreneur, Interview with Cheryl Pitt. Homeschooling and family business go well together. Join us for this encouraging interview on becoming a mompreneur, with Cheryl Pitt of 2 to 1 Conference. #HomeschoolHighSchoolPodcast #2to1Conf #Mompreneur #HomeschoolFamilyBusiness #MomEntrepreneur


HSHSP Ep 177: Becoming a Mompreneur, Interview with Cheryl Pitt

Homeschooling and family business go well together. Join Vicki and Kym for this encouraging interview on becoming a mompreneur, with Cheryl Pitt of 2 to 1 Conference. We are so excited that on this episode we have the opportunity to interview our good friend, Cheryl Pitt! Cheryl is a true mom entrepreneur: a Mompreneur!

Cheryl is a homeschool mom and serial entrepreneur. She and her husband have 4 kids ages 23-4. She and her husband also raised his youngest brothers and are caregivers for their grandfather.

Cheryl has had to make lots of adjustments while being a business woman, wife, caregiver and homeschool mom. One of her priorities has always been her family’s homeschooling. She prioritizes watching her kids to understand their strengths, interests and needs. For instance:

  • Her oldest liked checklists and workbooks
  • Her husband brother (the older one) liked checklists and workbooks, also
  • His youngest brother had ADHD and auditory processing issues, so his homeschooling needs were completely different
  • With her younger set of kids, Cheryl has noticed:
  • Her 11 year old has some auditory processing issues but is very creative
  • Her young daughter is very creative but is a perfectionist
  • Her 4 year old is a tactile learner and quite busy

What is Cheryl’s advice for helping teens find their strengths and interests towards their future careers?

Hold onto the freedom of sticking to the way God created your children! Don’t try to restrict them OR to plan their future for them.

  • Leverage their interests, gifts and skills.
  • Let them explore on their own.
  • When doing career exploration, do a LOT of exploring. Some kids come out of the womb knowing what they want to do, but most don’t .
  • We never outgrow growing, even as moms. Kids don’t know their whole futures, it takes exploring!
    • Cheryl and her husband have a security business. Her oldest son explored staying with the family business but after helping out for 5 years, he went into farming. That was the right fit for him!
    • Need some Career Exploration curriculum to get your homeschool high schoolers started? Download 7SistersHomeschool’s popular Career Exploration Bundle.

Cheryl’s advice for homeschool families that want to make the best of work/life balance while helping kids discover their gifts and interests:

  • Have lots of experiences, not just book education
  • Do as much traveling as you can
  • Give them exposure to people with different interests and disabilities
  • Spend family time whenever the family can be together

Mompreneurs wear lots of hats!Juggle those hats! Choose which hat to drop! None of us can do it all. When monkeys take the hats, find creative ways to get them back...or let the monkeys have them. Cheryl Pitt 2to1 Conference

Speaking of Cheryl’s serial entrepreneurism, Cheryl has so many hats, she reminds us of the children’s book: Caps for Sale. Her hats blow off and she has to catch them and put them back on!

Cheryl is founder and hostess of 2:1 Conference for Christian homeschool mom entrepreneurs: Mompreneurs. (You should come to 2:1 Conference if you are a homeschool mom and business woman or homeschool blogger. Kym, Sabrina and Vicki go every year and love all that they learn and all the friends that they make!)

  • Enterprise Security Systems (helps governmental agencies with security).
  • HS Mompreneur (a subscription box for Christian homeschool mom box of goodies that will bless your heart, your homeschool and your business). Vicki and Kym raved about their sample boxes Cheryl gave out at the last 2:1 Conference: SUCH a cool stapler was in it, besides all kinds of other cool stuff.)
  • Vicki pointed out that Cheryl, while being successful, is not an intimidating presence.
  • She started blogging in 2008, when homeschool journals online. Some bloggers were being to montetize> Cheryl wemnt to Blissdom and she loved it but wanted to offer something like that for her people; the online homeschool mom. The dream grew over time. Worked with close friends. Cherly feels like she’s not an intimidating presence, a reingleader because the conference is God’s.

Cheryl’s advice for upcoming mompreneurs.

  • Watch out for fear! It all boils down to trust. Seek God, if it’s his idea, it will work. It will be hard but it will work!
  • Lay down pride: In business, we are serving people, not just making money, not just running businesses!
  • Take baby steps…and keep on taking baby steps!
  • If you’re faithful with what God gives you, it will grow.
    • But remember: Success is not linear. We don’t start a business and have continuous upward growth.
    • We go forward, hit bumps, adapt, grow, hit lulls, adapt, grow.
    • Growth isn’t the litmus test of success. There are seasons of growth and times of rest. Keep faith

Kym has an analogy that being a mompreneur is like cars driving down road. There are lots of twists and turns, sometimes a bumpy road. But when you can stay on the road, you’ll arrive!

What advice does Cheryl have for mompreneurs with so many hats to  juggle?

  • There’s no such thing as balance. So don’t waste your time trying for perfect balance!
  • Daily prioritization. Prayerfully decide what’s important to do first each day. Remembering you are a:
    • Daughter of Christ
    • Your husband’s wife
    • Your children’s mother
    • Then a business owner
  • Beware of the tyranny of the urgent. Sometimes urgency IS the priority. Prayer will clarify whether urgency is a distraction or the priority!
  • Routines are important to get the day-to-day necessities done.
  • Juggle those hats! Choose which hat to drop! None of us can do it all.
    • When monkeys take the hats, find creative ways to get them back…or let the monkeys have them.
  • Whatever God has put on your heart! Don’t sit on it, start taking baby steps!
  • Life happens, you’ll have challenges. Keep those baby steps going!!

Get in touch with Cheryl at:

For more encouragement, listen to this episode of Homeschool Sanity Podcast with our friend, Melanie Wilson about getting organized. She is the expert, organized mompreneur!

You’ll be so encouraged by this interview with Cheryl Pitt!

HSHSP Ep 177: Becoming a Mompreneur, Interview with Cheryl Pitt

How to Choose the Right Work from Home Opportunity for You

A Production of the Ultimate Homeschool Podcast Network.

How to choose the right work from home opportunity for you starts with determining what will work for your family, personality, and budget. There are so many options. Pick one and start today! FREE Podcast.

Announcement: Starting in May, Mommy Jammies will be a once weekly show! We’ll no longer be “live” but, we’ll have some fun and exciting things for you! Keep up with us!

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Today’s Mommy Jammies podcast is with special guest, Lindsey Stomberg, from TalkingMom2Mom.com.

Subscribe to Mommy Jammies here: https://itunes.apple.com/us/podcast/mommy-jammies/id781633557

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Scroll down to player to listen to the podcast with Lindsey Stomberg from Talking Mom 2 Mom.

Topic: How to choose the right work from home opportunity for you.

How to choose the right work from home opportunity for you



Show References:

Work from Home as a Medical Transcriptionist (also includes the link to the free one hour webinar).

TalkingMom2Mom.com Articles on Home Businesses

Big Sisters Boutique – the start-up business of Lindsey Stomberg with her daughters.

FREE Guide to Raising Tiny Entrepreneurs 

VIP Kids

Elite Blogging Academy

Different options for making money from home.

  • Handcrafted items and selling online/ Etsy/ local vendor events (great to do as a family)
  • Not talented enough to do crafts? Options online to design and sell your own tShirts/ mugs/ etc. and you don’t even have to keep any inventory. (Teespring/ Cafepress just to name 2)
  • Multi-Level Marketing (not for everyone but if you have an outgoing personality and a lot of supportive friends/ family these can be super successful)
  • Blogging for profit (Elite Blog Academy)
  • VIPKid (must have a four year degree for this one but pays $14-$22 an hour for teaching English language online)
  • Medical Transcription (Deb Burns – free one hour webinar offer)

How do you know what is right for your situation and budget needs?

  • All work from home opportunities come with risk, some more than others.
  • To some degree all work from home opportunities have start up costs and require extra time devoted to the building of its foundation.
  • Some things require skill immediately and others require just a passion to begin. All will require effort and attention to grow and sustain.
  • It is important to sit down with your spouse and discuss the following:
    • What job will work best for your personality and skill set?
    • What job do you see as being something you can potentially stick with and continue building long term?
    • Are there any budget concerns that need to be addressed when it pertains to start up costs with one vs. another?
    • What is the end goal of your pursuing this? Is this meant to be a hobby or a legitimate income source? How much are you expected to bring in per month and what is the expectation for hours worked?

Choosing to work from home can be very satisfying on many levels. For my personality, I need something that feels like mine separate from homemaking and homeschooling. I pour my creative energy into what I do and it is therapeutic. It also fulfills a need for us financially and that is important too.

Meet Lindsey

Lindsey is a stay at home, work from home mom to six children ten years and younger. She homeschools and enjoys large family living. When Lindsey is not changing diapers, cleaning house and cooking meals, she enjoys binge-watching shows on Netflix with her husband … because let’s get real, who has energy after 8PM when you have this many kids?

As her husband would say, Lindsey is a chronic hobbyist. She is always learning a new skill whether that be graphic design, making cloth diapers, or streamlining a start up business with her 9 year old daughter. Lindsey likes to DIY her way around the home, explore natural remedies, and create new and exciting recipes in her Instant Pot during her downtime.

Lindsey is the author of The ABC’s for Godly Children Bible Curriculum. She is the co-author of It’s the Heart Not the Hemline: A Biblical Unit Study on ModestyThe Five Solas: Signs to Follow on the Narrow Path, and Filling Hearts while Cleaning Homes: Five Minute Devotions for Families.

Contact Info

For all questions, comments, and/ or advertising requests please contact us at info@talkingmom2mom.com

You can contact Lindsey individually at lindsey@talkingmom2mom.com