Why belonging should never require you to split yourself in two
Working moms are often told they cannot give enough to their children. Homeschool moms are often told they should give everything to their children.
So what happens when you are both?
For years, working homeschool moms have lived in the space between two communities that were never designed to overlap. When they talk about struggling at work, they are told to quit. When they talk about struggling with homeschooling, they are told to put their children in school. The advice may be well-intentioned, but the underlying message is clear: You cannot keep both.
In this episode of Find Your Freaks, Tonya Kubo sits down with Jen Mackinnon, founder of Practical by Default and the Working Homeschool Mom Club, to talk about what it takes to build a life that does not fit neatly into one category.
Jen began homeschooling reluctantly because it was the right fit for her oldest child. When financial circumstances required her to return to work outside the home, she found herself surrounded by people who could understand one part of her life but not the other. She did not need someone to tell her which responsibility to abandon. She needed people who understood what it meant to carry both.
That search eventually led her to create a community that now supports more than 30,000 working homeschool moms around the world.
Together, Tonya and Jen explore the judgment these moms face, the practical systems that make an unconventional life more sustainable, and why belonging does not require you to divide yourself into pieces other people find easier to understand.
Episode Highlights
- [01:30] Meet Jen Mackinnon and the working homeschool moms who are her kind of freaks
- [09:50] Why judgment doubles when moms work and homeschool
- [15:50] Realizing this was not just one mom’s problem
- [20:00] What makes a system practical and sustainable
- [24:50] The buffer block and why leaving space in your week matters
- [30:50] Rethinking what community can look like for working moms
- [38:00] Why making mistakes does not mean you are failing your children
When Your Identities Are Not Supposed to Overlap
Jen did not set out to become a homeschooling advocate. She was a reluctant homeschooler who made the choice because it was right for her oldest child. She later returned to full-time work outside the home because her family needed the income.
Neither choice felt optional, and neither community seemed to understand that.
When Jen shared a difficult day at work with homeschooling friends, their solution was to quit her job. When she shared a homeschooling struggle with coworkers, their solution was to put her children on the bus. She could find people who understood working motherhood and people who understood homeschooling, but few who understood what it meant to do both.
This is what happens when communities are organized around only one part of a person’s identity. People are welcomed as long as they fit the established story. The moment their life becomes more complicated than that story allows, they are treated like the complication is the problem.
Jen did not need to choose which part of her life mattered more. She needed a community where both parts could exist at the same time.
“I couldn’t get advice that wasn’t telling me to either quit my job or put my kids in school.” —Jen Mackinnon Share on X
When Advice Asks You to Abandon Your Values
Most people offering advice believe they are being helpful. They see someone struggling, identify what appears to be the most obvious source of stress, and suggest removing it.
The problem is that the obvious solution may require someone to abandon a choice they made intentionally. A mom may work because her family needs the income, because she loves her career, or both. She may homeschool because it is the best fit for her child, even if it makes life more complicated.
Telling her to give up either one does not solve the problem she brought to you. It changes the subject entirely.
As Tonya points out in the conversation, advice feels like judgment when it asks someone to go against their values. A more supportive response begins with curiosity. Instead of assuming work or homeschooling is the problem, listen for the actual point of friction. It may be a lack of time, childcare, space, support, or a system that no longer fits.
Sometimes the most useful thing you can say is simply, “That sounds really difficult.” Listening without judgment may not provide an instant solution, but it gives the other person room to identify what kind of help would actually make a difference.
“When the advice is to go against your values and your choices, it feels like judgment.” —Tonya Kubo Share on X
Practical Systems Should Support Your Life
Jen’s business is called Practical by Default because she believes tools and systems should make real life easier. A planner may look beautiful, but it is not useful if it does not have room for your work, homeschool responsibilities, appointments, and family life. A meal plan is only effective if it accounts for your schedule, energy, budget, and dietary needs.
The goal is not to follow someone else’s system perfectly. It is to create a framework that supports the life you actually have.
One of the systems Jen taught Tonya is the buffer block: a portion of the week intentionally left open. It might be a full day, half a day, one hour, or even 30 minutes. When an appointment changes, a child gets sick, or a deadline moves, the buffer block gives you somewhere to put what no longer fits.
If everything goes according to plan, that time can become rest, connection, or space to catch up without panic.
This kind of structure does not take away freedom. It creates freedom by reducing the energy spent wondering what has been forgotten or how everything will fit. A strong system provides enough structure to hold your responsibilities without packing your life so tightly that one unexpected event causes the entire week to collapse.
“The purpose of planning is to create a framework with enough flexibility to work with your life.” —Jen Mackinnon Share on X
Community Has to Fit Real Life Too
Traditional mom communities are often built around gathering in person during the day. There are park dates, homeschool co-ops, coffee meetups, and activities where children play while parents connect.
Those options are not always available to working homeschool moms. Jen and Tonya both experienced homeschool activities scheduled during standing work meetings or prime working hours. Participating would have required them to neglect one responsibility to support the other.
For working moms, community often requires more flexibility and creativity. It may look like a quick coffee date, a Zoom call with someone in another time zone, voice messages exchanged through Voxer, or a WhatsApp conversation that pauses for several days before picking up exactly where it left off.
These connections may not resemble traditional community, but they are not less meaningful. They work because the people involved stop measuring connection by frequency or format and start building around what their lives can realistically hold.
The question is not whether you are connecting in the “right” way. It is whether you have people who understand your life and are willing to meet you inside it.
“Take the idea of community and ask, ‘How can I make this work for my life?’ Then give yourself the freedom to do that.” —Jen Mackinnon Share on X
Your Best Is Not the Problem
Working homeschool moms carry a tremendous amount of pressure to get everything right. When a child struggles with a subject or the schedule falls apart, it is easy to treat the difficult moment as evidence that the entire decision is failing.
Jen offers a different perspective. Making mistakes and learning alongside your children is part of the process. Her own family went through multiple math programs before finding one that helped her daughter understand fractions. That same child, who once hated math, now works in cash balancing and loves her job.
One difficult lesson does not predict a child’s future. One exhausting week does not mean the family made the wrong choice.
The goal of home education is not to know everything or execute every lesson perfectly. It is to help children understand how they learn, how to find information, and how to keep going when the first approach does not work.
That lesson matters for adults too. You can change the curriculum, adjust the routine, move the buffer block, or ask someone else to teach fractions. Adaptation is not failure. It is part of building something that works.
“Your best is exactly what your children need. Making mistakes and learning with them is part of the process.” —Jen Mackinnon Share on X
Freak Flags Fly
Each episode ends with five quick questions. Here’s how Jen flies her flag:
- You’re my kind of freak if… You make the choice that is right for you and your family, whether that means homeschooling, public school, or something else entirely.
- Something you love that your friends just don’t get: Making sourdough. Buying it from the store is not the same.
- A community you would infiltrate just to understand it better: The homesteading community.
- A tool, ritual, or practice that helps you stay connected to your people: A daily routine of checking in with her communities, beginning with her morning coffee and Facebook group before moving to Voxer and other platforms.
- Someone doing freakishly good work who deserves a bigger stage: Lisa from The Canadian Homeschooler, who helps Canadian families find homeschool resources created for their educational systems, currency, and experiences.
Meet Our Guest
Jen Mackinnon is the founder of Practical by Default, where she helps working homeschool moms balance their careers, their children’s education, and everyday life with confidence. After struggling to find advice that did not tell her to quit working or stop homeschooling, Jen created the Working Homeschool Mom Club to connect with other moms making both work.
What began as a small Facebook group has grown into a worldwide community of more than 30,000 members. Through practical resources, flexible planning tools, and honest conversations, Jen helps working homeschool moms create systems that support their real lives.
Meet Your Host
Tonya Kubo is a community strategist, writer, and rebel with a cause: helping people find the place where they truly belong. She’s spent nearly two decades building online spaces that feel more like chosen family than comment sections, and she’s not afraid to call out the fluff in favor of real connection.
As the founder of Find Your Freaks, Tonya brings together unconventional thinkers, builders, and bridge-makers who believe that “normal” was never the point. When she’s not hosting the show, she’s raising two daughters, leading client communities, and making meaning out of the mess.
Episode Transcript
Get the full transcript from Episode 030.
Resources & Mentions
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Let’s Stay Freaky
What’s Next
Since recording this conversation with Jen, Tonya has started homeschooling her twelve-year-old again, this time with more experience and a different perspective. Next episode, she explores a question that keeps becoming more important online: When everyone sounds like an expert, who do you trust?
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