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My Win-Win Project Management Story

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Welcome back to Your Win-Win Teacher Business. In episode #3, I’m sharing the story of how I fell in love with supporting other teacher businesses behind the scenes and why it’s a win-win for my life today. This is my project management story.

I’ve Never Shared My Project Management Story Before

I know So Many Teacher Business Owners who struggle to make the paper planner they used as a teacher support their needs as a business owner. So it felt important to share my story about what worked for me in different stages of business (and what didn’t work).

The next time you feel the urge to burn down your business, pause, take a step back, and get curious if you might just need a planning tool that is a better fit for your needs. I hope that listening to my project management story gives you the reset you need in this season.

Please Note: I Had No Previous Project Management Experiences

Project management is a big scary word that I don’t remember hearing during the 7 years of college when I studied to be an educator. But that doesn’t mean teachers don’t have transferable skills that make them natural project managers. Have you ever managed multiple students working towards differentiated project deadlines? I bet your brain will love learning about project management once you dive into a course and learn more.

Becoming A Project Manager With No Experience

It was never my plan to become a project manager for other business owners. I started building custom project management solutions (still one of my absolute favorite ways to spend the day). When I work with teacherpreneurs to set up custom project management solutions we really deep dive into all of their business systems and top level strategy. Sometimes at the end of the experience they invite me to stay on the team and help keep the new systems humming along with all the team members that I’ve trained and met throughout our experience. Custom project management builds are just that – custom – so I try to stay flexible and curious about what each business member needs next and provide support however I can.

While I had no experience when I started, I build dozens of custom project management solutions in that first year alone. I’m so glad I took the leap to learn more and share what I learned with others. I’ve gotten to make business connections that wouldn’t have been possible without this new skill.

Project Management for Teachers

While I typically work with teacher business owners, many people use project management tools to manage life projects and there is no reason you can’t lean on an amazing free project management tool to support you as a classroom teacher or administrator. Here is a guest training that I did with Dani at Thyme is Honey if your brain is feeling curious about what that might look like.


–> I’d love to support your business

Learn more here

–> Do you have a win-win story to share with the teacher business community?

Apply to be a guest here

–> Let’s chat business on Instagram @teacherjaniceva

Reach out on Instagram here


Read the transcript:

Janice Cook 0:00 Welcome back to Your Win-Win Teacher Business. In episode number three, I’m sharing the story of how I fell in love with supporting other teacher businesses behind the scenes, and why it’s a win-win for my life today.

Janice Cook 0:14 You’re listening to Your Win-Win Teacher Business, a podcast for teacher authors who want to make a big impact in the world for teachers and students, and have fun doing it. I’m your host, Janice Cook, here with a pep talk to start your week off strong. Some seasons of running a business feel hard and sticky, but it shouldn’t feel like that all the time. Let’s make your business a win-win together.

Janice Cook 0:39 Hey, hey, teacher business bestie, I’m so grateful to be having this cozy chat today. My brain has always resonated with the concept of an A bucket and a B bucket, so you’ll hear me referencing that a lot during episode three. Teaching was my A bucket. It was my primary revenue stream. That was the money that I used to pay my bills and cover my living expenses. Teaching online was my B bucket. It was bonus money. It was extra. It was a fun adventure and hobby that I grew for myself. Knowing that my A bucket was a strong, stable foundation allowed me to take calculated risks and reinvest the profit that I made towards future growth efforts.

Janice Cook 1:25 When teaching online became my A bucket, Teachers Pay Teachers and YouTube became my new B buckets. The A bucket and B bucket mindset has always served me well.

Janice Cook 1:37 I learned a lot of skills along the way as I grew my Teachers Pay Teachers store. I met incredible friends, and one day, one of my TPT mastermind friends shared a hiring horror story. She shared the steps that she had taken to research and prepare to hire out email marketing. She did everything right, and that service provider simply did not deliver. I was devastated as I listened to how this was going to affect her business. The money that was spent to have those emails written was money she would never get back, and those emails were not going to be usable for her list. She spent time hiring, onboarding, and communicating with this service provider. And now she would be spending time writing those emails again herself. What a gut punch. We both used the same email software, shout out to Flodesk, and I knew a lot about her store, her brand and her customers, so I offered to write emails to her list while she looked for someone new to hire. I wrote those emails she liked them, and she never did end up looking for someone new to write her emails because she wanted me to keep writing them. She was my very first virtual support client, and I still write to her email list years later. The day she shared that story will always be one of my core memories, and I’ll be forever indebted to her for taking a risk and letting me write to customers who were not my own for the very first time. I loved using what I had learned running my own business to support someone else and help them make a larger impact on teachers and students. It made my heart so happy.

Janice Cook 3:29 The word of mouth machine stepped in, and other TPT sellers reached out, asking if I could write their emails too, and I quickly learned about how to build a virtual support provider arm for my business. A new B bucket was born.

Janice Cook 3:44 And as a side note, I was never able to shake the big feelings I had about that hiring horror story. I became so passionate about helping other teacher business owners have positive hiring experiences that I created a comprehensive guide about hiring help in a teacher business and I offer that guide for free. You can grab your copy at cookfamilyresources.com/hiring-guide.

Janice Cook 4:13 My client roster grew quickly and providing support to other teacher business owners quickly became my A bucket. My own TPT store became my B bucket, and I was making a higher hourly wage supporting clients than I was teaching online, so I slowly phased out online teaching entirely. When the online teaching industry collapsed, many concerned friends and family members reached out to inquire what I would do now having suddenly lost my job. Would I return to teaching in person again? But I never had all of my eggs in that basket, and I was already off of the online teaching ship before it sank.

Janice Cook 4:55 How was I keeping track of all of the moving pieces for my business and the businesses of others? In an Erin Condren Life Planner. How was that working? Not well, but it’s all I knew. I had always used a paper planner as a student to keep track of my assignments. And as a classroom teacher, and as a mom, my paper planner held it all together for my brain. So as my life ebbed and flowed, I tried to keep up with the plans and the details using my paper planner – the only tool I knew about at the time. Maybe you can relate. You know the saying you don’t know what you don’t know? Today, it makes sense to my brain that Steve Jobs and Jeff Bezos were likely not running their successful companies using a paper planner. There are, and always were, better tools suited for the task of running a business. It took me a while to find out about those tools, and that’s okay, that’s just the reality of this accidental entrepreneur journey.

Janice Cook 6:04 Another online business owner was raving about Asana as a digital project management tool. I didn’t get what all the fuss was about. I had a Google Calendar. It wasn’t really changing my life. I still leaned on my paper planner to run the show, and it was working okay, and getting the job done. I didn’t see the point of learning another tech tool, and I wasn’t sure what problem it could even solve for me, because I didn’t know if I even had any problems with my current systems. But she convinced me to check out a mini course about Asana to learn more, and I decided to take the leap. It was called Creating Your CEO hub, and it was by Tasha Booth. I’ve never met Tasha, and that’s the only course I ever took with her in my business journey, but she delivered a big dose of light bulb moments about how businesses should be run and should be organized, and why that was the path forward for every business owner.

Janice Cook 7:07 My eyes were open to the world of project management, and there was no way I was keeping this knowledge to myself. I needed to share with all of my TPT seller friends and help them get a proper project management tool in place for their business. After Tasha’s small course about Asana, I took a very large course about Asana from Louise Henry. I learned about big dreams in that course and how a project management tool turns dreams into action. I learned a whole lot about running a business. That course reached far beyond Asana. I built an Asana workspace for myself, and others started to ask me to build custom workspaces for them too.

Janice Cook 7:52 Before I dove into the adventure of building project management solutions for other businesses, I decided to take the official training that Asana provides, get the official badge, and sleep at night knowing I fully understood all of the paid and free features of that tool, not just the ones I needed inside my business. The word of mouth machine continued to work its magic, and I started building project management tools for other teacher business owners. I decided to make the art of supporting teacher business owners an A bucket that felt like home. It felt like what I was meant to do all along, and I look forward to stepping into the office each and every day.

Janice Cook 8:36 Why am I sharing this story today? This is your business. You get to decide how many eggs to put in your A basket and how many eggs to put in your B basket. You get to design what your ideal work week looks and feels like. You have so much flexibility that likely isn’t being tapped into. So as you tune into this podcast every Monday, I want you to remember that your business belongs to you.

Janice Cook 9:08 Let’s celebrate the parts of your business that are working and double down to do more of what has proven to be effective. Let’s get curious about the parts of business that feel sticky. Let’s get brave and take messy action together, because you deserve for business to feel like a win-win again.

Janice Cook 9:28 I’m so grateful you’re here. I can’t wait to share guest conversations and maybe even share your story here on the podcast. I love the world of education. Supporting students was such a fun chapter, but hearing about what feels sticky inside your business and helping you make small tweaks so that it feels like a win-win. That’s the A bucket for me. Thanks for letting me share my story. In episode number four I’ll be sharing some tough love on the topic of CEO tasks.

Janice Cook 10:06 Thanks for making this podcast part of your day. I’d love to help you find clarity with your next step in business. Go to cookfamilyresources.com/hiring-guide. I’ll also leave that link in the show notes for you. This guide is packed with good news for those days when you feel like you can’t possibly do it all. It might be time for you to invest in paid support, but the truth is, there are a lot of free steps to explore first. After you dive into that guide, I’ll be in your inbox every Monday morning with more actionable tips to help you enjoy running your business again. See you in the next episode.

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