How to Become a Teacher Business Owner with Lindsay Flood

This post contains affiliate links. If you click & make a purchase, I receive a commission at no additional cost to you! Thanks! As an Amazon Associate, I earn from qualifying purchases. Read my full disclosure here.

So many teachers desire to do something outside the classroom. Some want to pursue a side hustle, while others are looking for a more permanent. Yet, few teachers ever take the leap.

Fear is a strong emotion that guides MANY of our decisions. But that anxiety can be shifted into productivity to help you become a teacher business owner who flourishes if you know what to do.

In today’s episode my friend, Lindsay Flood, joins me to discuss how she has become a successful teacher business owner (to 2 unique businesses) while teaching full-time, learned to give herself grace, and allowed failure to be her greatest teacher.

Lindsay also spends time sharing encouraging words for you as well as tips to improve the amount of time you do have to devote to your business.

Hi, I’m Lindsay! I’m so honored Jennifer asked me to be part of her podcast. I love her mission & drive to help classroom teachers leave with a plan. I’m currently teaching art for the third year, but I previously taught ELA for 8 years. I live in the South with my husband Allen, my hilarious 7 year old son Noah, & our almost 2 year old Jack Russell Terrier named LucyAnna. I love creating, dreaming, & all things colorful & fun. You can find me on IG @ohheylindsayflood.

Important points from this episode

  • Lindsay’s TpT experience
  • How she juggles teaching full-time and two side hustles
  • Why failure has been an important part of her journey
  • How she deals with mom guilt
  • Thoughts on hiring others to help you

How to Become a Successful Teacher Business Owner

Lindsay’s background and TpT experience

I started TPT way back in 2011. I initially started it because my husband and I had moved to New Orleans and we were in the process of an adoption. At this point, my husband was in seminary full-time and I was the only one bringing in any money. 

So my mom told me about this site she had found called Teachers Pay Teachers. Of course, back then it wasn’t nearly like it is now. But, I decided to upload my first resource in December 2011 to help bring in funding for our life and our adoption. My first resource was Snowmen at Night and I’m so embarrassed because it just had random fonts and was created in Microsoft Word.

Yet at that point, I was so proud and thought I was so fancy. So I got my first check for $23.12 and we thought we were so uptown that we went and got ice cream to celebrate. I’m so glad I stuck with it because it has been a big part of my life and my husband’s life including when we adopted our son.

The truth is, teachers and pastors just don’t make that much money and the TpT income helped us tremendously. The Lord provided the funds we needed for living expenses as well as our adoption.

Our son Noah was born in September of 2014, and I’m a little crazy when it comes to money. But we needed a certain amount of money and I’d already taken every little penny that we had as 20 year olds. I had moved as much as I possibly could into our savings account, but we didn’t have enough. So my husband suggested that we take out a personal loan.

In September of 2014, I posted a resource on TPT that was featured in the October newsletter and we brought in the amount of money that was needed for his adoption. It was about $100 more than we needed for our personal loan so we paid it off immediately. So TpT has been a huge blessing in our family!

I’ve been in the classroom 12 years now, but when Noah was born, I decided to take 3 years off. I thought I would be the Pinterest mom, but that didn’t work out; I did what I could. So I worked on my TpT business full-time for 3 years and I really loved the flexibility.

My products have always been ELA-based because I taught reading for 9 years and it’s what I love to do. Three years ago, I just got tired of the state telling me how to teach my children when I knew what they really needed was not the curriculum handed down to me.

So my principal, who I love and still work for, asked me if I wanted the art position. Thankfully, I accepted that position three years ago and I’ve been teaching art ever since. The amazing thing about art is that I get to bring in as much ELA, writing, reading, and anything else I want to add as I want. 

So we still read a book every week, make graphic organizers, write about what we read, and we get to make a craft. I know the teachers who are blessed to have you as the art teacher love the fact that you really take art to a new level.

I am very blessed at my school that our enrichment team is a true enrichment team. We genuinely seek out ways to enrich the lives and the education of our students. We bring in the curriculum, and whatever the teachers are doing, in order to make it all work.

Do you have any other side hustles? 

This art position that I’ve been given has really allowed me to delve into my creative side. My mom was very creative and after being a teacher for 33 years, if anyone needed anything crafty or cutesy…they went to her!

I have this chance to teach art in a different way. In other words, we look at the purpose behind why we’re coloring or painting this way. I know it has allowed me to be creative in ways that I never thought I would have a chance to do. 

If I was sitting in the classroom as a full-time ELA teacher disaggregating data all the time, this would not be my reality. So I can’t negate the fact that this was a blessing that is outside of the norm for a certified teacher. 

So as far as my creative side, I’ve always thought about creating and designing things but not like French Runway…just cute teacher stuff because I love teachers and their passion.

That’s where I came up with the idea for a boutique of things that teachers would want and could afford that were also designed and made by teachers.

My first big launch from the Hey Pretty Pieces Boutique was in May 2021. I spent pretty much every day that summer working on my boutique, but it didn’t feel like work because I loved it! I loved designing and creating the collection, I loved finding the teachers that I was going to feature in my store. Honestly, it has just been so  stinking fun.

Ultimately, I would love to do that full-time since I have all of these ideas; I would love to make this boutique work. And because I have my TpT income, I can actually do another little side hustle which is where the boutique came from.

When we were children, we dreamed about big things. Yet as adults we stifle those dreams that we had as children. And while we may not want the exact same things as we did when we were kids, it’s important to recognize how important our dreams are and how achievable they can be.

We are all multifaceted individuals with a variety of interests. Therefore, we should tap into those things as we think about potential side businesses because those are the things that won’t feel like work.

I am friends with Amanda Richardson from Mrs. Richardson’s Class and she is an amazing and inspirational human being. But I was talking with her in the winter of 2020 about this boutique model and I was sharing my fears about nobody buying from me and the fact that my boutique was different from everyone else’s.

She told me something that really stuck with me. She said, “There is plenty of room for everyone at the table. What you are sharing is Lindsay’s, and those people who are meant to find you will find you.”  

But when you speak it out, that dream you have, and you take that first step to buy $200 worth of inventory…it is scary! It takes willingness and courage to step outside of the norm. And the generational differences with my mom, who taught in the same school for 33 years, and my grandmother, who taught in the same district for 45 years, are astounding.

While there is nothing wrong with staying in the same job until retirement, that just isn’t how my path has been laid out. But if you look at the world around us, people go to college, get their degree, and then they stay somewhere for a little bit before transitioning to something else.

For our generation, this is odd because it wasn’t what was modeled to us. Stepping outside of those lines and realizing that it’s okay NOT to stay in the same job for 25 years and it’s okay to pursue something else is more difficult for those of us in this particular generation.

We observed that grandma was successful doing this and mom was successful doing this. Therefore, it stands to reason that if I follow the path I’ll be successful, too. But our society has transitioned so much and it is so important to acknowledge that while there’s comfort in sameness…continuing on the same path isn’t always the best choice. 

There has been a huge transition in our profession over the last two years and people who originally had the mindset of “I plan to keep teaching until I die or retire,” are taking a step back and seeking other opportunities. Recognizing that there are other paths out there and giving teachers permission to look for alternative careers is important.

Why failure is important as a teacher business owner

It takes a lot of courage to choose a different path than the one that’s laid out before you and it’s okay to fail. When I first reached out to Stephanie, my amazing polymer clay earring designer, I had no idea what I was doing. I told her I didn’t know what I was doing, but I wondered if she might be interested in selling earrings in my online boutique.

She said she didn’t know either but we could learn together. Then she gave me a very wise piece of advice. She said, “You have to leave room for mistakes. That’s what I do for myself.”  It’s ok to make a mistake, so just leave room for it and give yourself grace when it happens.

It’s just like we tell our kids at school, “God gave us erasers so we can fix our mistakes!”  So now I’m going to take my leftover lanyards and give them as Christmas gifts to my son’s teachers over the next several years. I’m taking my mistake and providing lanyards to teachers who need or want them as gifts!!

Being ok with making mistakes is difficult for many of us as teachers, but it is so important that we are willing to “put ourselves out there” in order to try something new. Understanding that I am going to make mistakes and I’m going to mess up, helps me be ok with mistakes because I can learn along the way.

This podcast was a big step for me because it required me to reach out to teachers, who have no idea who I am, and say, ”I don’t even have a podcast started yet, but would you like to be a guest whenever I figure out what the heck I’m doing?”  But I didn’t let the fear of the unknown and those fearful thoughts bouncing around in my mind, dictate my path.

If we can simply recognize that a mistake does not equate failure, we will be so much better off. A mistake is simply a mistake, and now you know what NOT to do the next time. That is where giving yourself grace comes into the picture because you just need to get up and try again.

And the truth is, most people don’t know what our vision was to begin with so they don’t even realize we have made what we think is a mistake. 

Want a Free one-on-one

Discovery Call?

Understanding where you are currently and how to get to the next level is crucial if you plan to leave the classroom. Let me give you personalized insight into your next best steps!

How do you balance a full-time teaching job, 2 side hustles, & a family?

I’m going to be really honest when I answer this question. I struggle with high-functioning anxiety like a lot of teachers do. And while I believe that Jesus will give me the peace I need to make it through the day, I am on medication.

This past summer, I focused on building my audience and interacting with my audience on Instagram which has been so fun. But right as school was starting back, I had a “come apart” session. I was struggling with the idea that I was only one person and no one was putting any pressure on me, but me.

So my mom, my husband, and my doctor told me to eliminate something because I just couldn’t do it all. I couldn’t be a good art teacher and run my TpT business while running, organizing, designing, and mailing all of these things for the boutique business.

I called my earring designer and just told her I couldn’t do it. She immediately said, “I completely understand. You can’t do all those things!”  So it’s choosing and moving around the things that are most important to you.

Understanding that if you don’t do all of it, you’re not a failure has been so important in my journey. I’m called to care for children as my job, but above that I have a husband and a son at home. So I can’t dump everything out and then expect to be anything but exhausted.

That’s why balance is really hard for me; rest is really hard for me. Anyone like me deals with the same struggle because we want to be so great at all the things. But if you’re trying to be great at all the things, you can’t be great at any of them.

So I had to step back and realize it’s okay that I don’t do all of those things perfectly. I’m looking towards the near future and thinking about stepping out of the classroom again and giving my boutique the attention it needs to thrive.

I have to be very certain of the path that I’m taking but I also have to remember that it’s ok if I don’t complete every little thing, every single day because I can’t do it…nobody can.

This is so much easier said than done. My philosophy is always do everything as unto the Lord, and I want to always do everything to the very best of my ability. But as I’ve gotten older, I finally started understanding more about how important it is to say no.

This means sometimes saying no to good and great things because I only have so much time in my life for all the things. I have to make sure that every yes I’m giving is honestly my very best yes and if you’ve never read The Best Yes by Lysa TerKeurst you need to get it right now!

In this book, Lysa talks about how every yes we give means we’re automatically saying no to something else. That is why we have to be mindful of both the yes we are giving and the no that will be required.

So many times when we think about balance, we think of a scale with equal weight on either side. But the truth is, our lives require constant readjustment as priorities change and as different seasons arise.

We have to take a step back sometimes and realize that certain seasons are just busier than others. In my own life, my boys both play high school baseball and golf. So during baseball and golf season, we spend a lot of time going to matches, games, and tournaments.

Therefore, I look at my calendar ahead of time in order to determine when our schedule is going to get a lot more hectic. Then I decide if there is any way I can allow some space or some margin in my schedule for those times.

Again, it’s about readjusting each season, each year, or even each week and being flexible.

Do you ever struggle with mom guilt as a teacher business owner?

I struggle with guilt in all areas of my life! If I haven’t done things well enough, I struggle and that’s what led up to my little mini meltdown.

The weekend before our students were to come back to school, we were decorating our 3rd through 5th grade hallway or wing. We were doing a Lego theme and in my head, I wanted it to be like Disney World.

I didn’t have anything ready in my art room because I was so focused on making everything perfect in the hallway. At one point, one of my teacher friends said, “Lindsay, you need to quit working in the hallway and work in your room. The wing looks fine like it is! Don’t worry about it. We’ll just build it as we go.”

You need to surround yourself with people who will speak truth to you. And although I have said it 100 times, just give yourself grace. You are you and that is exactly who you are designed to be. Everybody has a unique journey.

I made $23 the first month I was on TpT, but there are people who make four, five, or six figures their first month. I still don’t know how they do it; it’s like magic. But for my mental state, I cannot sit here and compare  myself to those people.

If you were to scroll back on my Instagram page in 2020, you will find that I hardly posted because I would get on there and see all these people doing all these things and it overwhelmed me so much. Only follow people who are encouraging, authentic, and real.

What is tricky about the big names in our industry is we think they’re doing everything solo when in actuality, they have entire teams of full-time employees working to help them do all of the things. This isn’t the beginning of their journey.

In all likelihood, these individuals started out much like us, but since then, they’ve been able to scale their business and grow the way they have because they hired 10-15 full-time employees to help them run their business.

We all only have 24 hours in a day and at some point even the people who seem like they can do everything are going to need help or they will burn themselves out completely.

Do you have anyone who helps you with your businesses?

With my TpT shop, I’ve always been the control freak. I haven’t been able to let go of any of those responsibilities. However, my husband does keep up my website.

For my boutique business, I hired someone because I couldn’t make all of the physical products that I was going to sell. I wanted to make earrings, but I had no idea how to do that. I started out printing all of my stickers with my Cricut, but I quickly discovered that wasn’t going to work.

So my friend Amanda said, “You have to spend money to make money.”  And I realized that she was right, so I decided to start paying to have my stickers made which sounds so silly and simple but it was a huge step for me. It was tough to spend a couple hundred dollars on stickers that might (or might not) sell.

Then I decided not to learn to make earrings because that would have been a waste of my time and the people that would have gotten the earrings would not have enjoyed them. I saw art teachers, who I follow on Instagram, with the gorgeous earrings and that is how I found Stephanie, my earring designer.

For my boutique business, yes I pay people to make the things. They send them to me and then I ship them out. I design the t-shirts, but another company actually prints them for me. The idea is that all of the people who create products I sell in my boutique are teachers.

One of these days, I might be able to let go of the TpT shop, but for now, I can only let go of one thing at a time.

The truth is, our businesses are our babies and it’s hard for us to pass them off to someone else. But it’s also important to remember that if you want to scale your business you eventually have to hire someone to help.

So when you begin, hire people to do those tasks you don’t enjoy or you don’t want to do. This is a great way to let go of the reins a bit while also learning how to delegate.

What is your best productivity tip?

So I have 2 things I’d like to mention.

First of all,I am a big picture person, which means I tend to see the end before I see all the little pieces that come into play. So I use my iPad and Apple pencil to sketch out what that looks like. It might be color schemes, patterns, or just whatever I want a new lauch to look like and include.

Then I label everything and color code it so that I can keep it all organized. Once I have my big picture, I can go back and add all of the little pieces.

My husband is the complete opposite. He likes to have all of the little pieces figured out before putting it together into the big picture. But for me, having the big picture helps me make all of my smaller decisions much more easily. 

The important thing to remember is to do what works for you as a teacher business owner. There are a million different ways you can do things, but unless it works for you, it is pointless. Comparison is the thief of joy! Your people are going to find you.

Secondly, don’t let the opinion of one person sway you away from what your gut tells you is the right thing to do. Be open to constructive criticism, but you don’t need to change everything as a result of one person’s opinion.

Go with what has worked for you in the past. Then if or when it stops working, you can reassess. Remember, you aren’t going to please everyone; your ideas are unique to you and other people like you because you’re you!

Do what you love and what you have a passion to do! My passion is to encourage teachers with things they love and can afford to buy. That’s why my boutique is so meaningful to me. But also know that anything you are building from the ground up is going to take time (and patience) to become profitable.

You cannot do everything, all the time perfectly. Just do what you love and your people will find you!

Be sure to follow Lindsay on IG @ohheylindsayflood, and then hop over to my IG @classroom_exit_strategies & share any takeaways from this episode.

I’d love to celebrate with you and help you find success as your own teacher business owner. If you think you would like to find out more about how I can help you be successful outside of the classroom, sign up for a FREE 30 minute Zoom call with me.