A few years ago, I built a company called PopPD. (Some of you even helped me build it!)
It was truly a labor of love. For two years, I poured everything into it because I believed so deeply in the mission. My original vision actually came from this community (yes, from you all!) and from the members I'd been working with for years inside Teacher Hustle University.
I wanted to help educators discover more flexible ways to earn income by teaching professional development classes online and sharing their expertise in new ways. Sounds good, right?! (I was pumped!)
We built the platform, grew the vision, and even raised money from investors to bring it to life.
One of the many highlights of this experience... winning an award for Top 200 Edtech startups globally!
And then… the landscape totally flipped (in what felt like almost overnight).
With the rise of AI, Edtech shifted incredibly fast. Faster than we could realistically keep up with as a small startup. Eventually, we ran out of funding before we could make meaningful enough progress to raise another round.
We had to shut our doors.
It broke my heart. (And I'll be the first to admit, I tried to keep it going for a little too long.)
For a long time, I carried around this feeling that I had failed. Failed at another business. Failed the people who believed in me. Failed the community we were building.
But looking back now, I see it differently.
I see the growth.
The resilience.
The lessons.
The people I met.
The skills I built.
The clarity I gained about what actually matters to me now.
And maybe most importantly… I can see how every single part of that journey led me exactly to where I am today.
These days, I don’t believe success has to look flashy or exhausting. Success can look like flexibility, peace, meaningful work, and making enough income to breathe easier.
That’s the version of success I care about, and the one I want to help you build, too. (Because I'll never, ever stop believing that teachers have an incredible skillset that spans a variety of options for extra income, fufilment, and designing a path that works best for you.)
{Listen to the full story and my completely vulnerable take on perfecting the pivot on the Seriously Connected podcast. Recorded a few years back while PopPD was still around and I was trying desperatey to make it work, so we talk a lot about the importance of failing faster by letting go of what isn't working as quickly as possible. All of the advice still rings true today!}
Listen to the Podcast Episode: Perfecting the Pivot
The Opportunity
One thing I’ve been thinking about lately:
A lot of us are sitting on OLD ideas.
An old TpT store.
An Instagram account.
A half-finished course.
An Etsy shop.
A tutoring idea.
A business they stopped talking about years ago.
And I think many of us carry shame around those things.
Like if it didn’t become a full-time business… it somehow “failed”.
The reality?
Businesses are experiments.
Some experiments teach us:
✨ what we loved
✨ what drained us
✨ what people wanted
✨ what season of life we were in
✨ what kind of work actually fits us
That’s valuable information.
You do NOT need to revive something just because you already invested time into it.
And you also don’t need to throw away something that still sparks something in you.
You’re allowed to:
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pivot
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simplify
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reimagine
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scale down
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start over
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return to an old idea differently
Say it with me: "We can evaluate old ideas without the guilt."
We've got this.
The Shift
One of the biggest mindset shifts for me lately has been this:
A business does not need to consume your life to be worthwhile.
Back in 2020–2022, online business culture was all about:
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scaling fast
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posting constantly
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building huge audiences
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working nonstop
But in 2026?
Things feel different.
AI tools can speed up work big-time.
Tiny niche audiences can sustain businesses.
Simple offers can generate meaningful income.
A small income stream that:
✨ pays for vacations
✨ gives your family breathing room
✨ supports a hobby
✨ creates flexibility
✨ helps you work from home
✨ or simply makes you feel more like YOU again
…is still so stinkin' valuable.
THE TOOL
I created something this week that I’m really excited to share with you!
The Side-Income Workbook for Teachers
A workbook designed to help educators think through:
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whether to revive an old idea
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whether to start fresh
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what kinds of income streams fit their life NOW
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what sounds energizing vs draining
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and what’s realistically doable in this season
Inside are 8 different pathways including:
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digital products
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freelancing
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memberships
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tutoring
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content creation
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online teaching
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local hobby businesses
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coaching/consulting
Each one includes:
✔ startup difficulty
✔ income potential
✔ time commitment
✔ how AI can make it easier
✔ reflection questions
✔ tiny first steps
My favorite part? It’s not designed to pressure anyone into becoming a full-time entrepreneur.
It’s designed to help you think clearly about your options.
Download the workbook! (It's free right now for Monday Mixtape readers!)
Download the Side Income Workbook
A no-fluff workbook that walks you through eight real ways to earn outside the classroom.
- Eight side-income paths, each broken down (with my totally honest take)
- Difficulty, income potential, and time-to-first-dollar at a glance
- Reflection prompts plus a 30-day action plan
Teacher Moves
Teachers are building the COOLEST little “micro businesses.”
Not giant empires.
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One of my teacher friends lists her clothes on Poshmark
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Another sells sourdough at the farmer’s market (soooo yummy!)
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One tutors 2 nights a week (She's saving for her next Disney trip!)
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One handpaints banners for birthday parties because she loves to paint
I love this era for us.
Tiny Challenge
This week, make a list of:
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every business idea
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side hustle
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account
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shop
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course
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offer
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or “thing” you’ve tried in the past
Then next to each one, write:
✨ revive
✨ rework
✨ release
No shame.
No guilt.
You’re learning what fits you now.
-Alissa
PS: Don't forget to check your inbox again next Monday for more inspo, tips, and stupid SIMPLE strategies to help you rethink your business and/or career journey. Hoping this becomes one of your fave Monday-morning notifications!
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