How to go from Teacher to Successful Entrepreneur with Lauren Denny

As a former teacher, you possess so many unique entrepreneurial skills and qualities. And while starting a business may be enticing to some people, it can also be a scary thought. A multitude of questions swirl around in your mind including…

• Can I actually start a business of my own?
• Will I be successful?
• How will I know what to do?
• Where will I get customers?

These are all valid questions, but ones that can ultimately, paralyze you to the point you stay frozen with fear. Unless they don’t and you allow the grit and determination you have in your soul to move you toward your goal.

Today on the podcast, Lauren Denny from Simply Stained Shop is sharing her journey from teacher to successful entrepreneur. And as with most former teachers turned entrepreneurs, she didn’t start out with a plan to leave the classroom.

But her story is unique in that she has not only created a successful business with her husband, she now employs her mom, dad, and others, has a podcast, and runs a ranch! Learn why she chose to leave the classroom, how determination and support pushed her farther than she thought possible, and what she has learned along the way.

Teacher to Successful Entrepreneur

Lauren’s classroom experience & side hustle turned a full-time job

I’ve always had a passion for making our classroom feel like home.  And since my husband is a carpenter, I asked him to teach me how to use all of the scary woodworking tools in order to create things for my classroom.  

At that point, I had no confidence because I felt like only the people who had carpentry skills could create these things.  But once my husband took me under his wing and allowed me to work alongside him to build things, I ended up with a hobby creating things from our woodshop.  

Then when I started seeing classroom stages pop up all over Instagram, I asked my husband if he would help me build one for my classroom.  While they were cute, I really wanted a stage for my classroom because…

• I was always afraid of speaking in front of the class when I was a student and I wanted to give my students a place where they could shine. 
• I also realized when you were singing or performing on stage you could become a different person and I wanted my students to develop better confidence.
• Also, I’m short, so it allowed me to be able to write the date on the top of my whiteboard!

When we moved that stage into my classroom, the rest is history.  We now own a company called Simply Stained Shop!

How did you go from building a stage to building a company?

It happened simultaneously while I was still in the classroom and it did not start as a business.  In fact, I never intended to leave the classroom and I’ve been very fortunate to have had the opportunity to leave the classroom.

It started out as a hobby.  My husband got me a Cricut because I just knew it would save me so much time cutting out all the letters for bulletin boards.  Then when my teaching partner’s birthday rolled around, I wanted to make her something.

So I used my Cricut to make her a little wooden sign using scraps from our woodshop and that’s how it slowly started to become something bigger.  I decided to make hall passes for my classroom because I needed something more sustainable than a little flimsy piece of paper.

Then slowly people started coming to my room and saying things like, “Oh that’s really cute!  Can I get one?”  And at first I was like, “Yeah sure. Here I’ll make it for free.”  Then I realized I could actually seel these things and I remember looking at my husband one day and saying, “Oh my gosh, Ben!  I just made $15!!”

And then I started to make more and more.  

For the first two years of building this company, I was still teaching.  And at the time, I didn’t really think of it as a company.  It wasn’t until I shifted from treating it as a hobby to realizing I was actually building a business that my mindset changed.

Taking my business more seriously and giving myself permission to move from teacher to successful entrepreneur allowed me to go from a hobby and a passion mindset into something that could actually sustain my family…which is where we’re at today.

So many of us are afraid to bet on ourselves.  It is easier to take the safe road and stay doing what we’re doing because we’ve always done that than it is to genuinely “go all in” making our hobbies into legit businesses.  

At what point did your mindset shift?

I don’t have an entrepreneurial mindset.  My husband has built multiple businesses and he loves to try new things while I like to stay in my lane. 

I went to school for five years to become a teacher and I already knew my road.  So it really wasn’t until I was matching my income that I realized, “This isn’t going to go away!”

Sometimes I still feel like, “Is this too good to be true?” But I came to see that if I was matching the same income from a job I was doing with a degree that had to mean something.  I was determined to take myself more seriously because if my principal expected it of me when I was in the classroom I should expect it of myself now.

But it is sometimes easier to have a boss than it is to be your own boss.  You have to believe in yourself and I’m starting to learn to give myself grace.  And the truth is, you’re way more awesome than you give yourself credit for.

What fears did you encounter when you finally decided to leave the classroom?

I was on social media at that time sharing my 4th grade classroom journey and creating Teachers Pay Teachers products under the name Cursive and Crayons.  Then I created another platform called Simply Stained Shop to share all of the decor.

One of my biggest fears was the social side of things.  I was afraid of what other teachers would say things about me like, “She’s just a sell-out. She’s using teachers. She’s just going to get out of the classroom and she doesn’t understand teachers anymore.”  So I was afraid about explaining where my heart was. 

But once I was able to match my income, it was getting really hard to give 100% to my classroom as well as my business.  So we took a step back and looked at where we wanted our lives to go and we decided to follow a passion for learning how to farm and ranch and that’s how you found me on Instagram!

We’ve accumulated all these animals including Rupert, a baby doll sheep who is quite an Instagram favorite. He’s very small, but he has a smile and a larger than life personality that truly does make everybody smile!

So now we’re learning how to grow food, raise chickens, and eat fresh eggs in the morning. 

Simply Stained Shop has given me the opportunity thankfully to make a choice between staying in the classroom or having the opportunity to work with my husband, employ my father, my mom, and today we have multiple employees as well.

But it was to the point where I realized I couldn’t fulfill my big dreams if I stayed in the classroom and worked 7 to 5 p.m. every day.  And because I loved teaching and I loved being a part of the classroom, it was very scary for me to make that jump.

• I was afraid of how people on social media would respond because so much of our business is social media.  I knew that I wanted to be transparent with the people who are supporting our dreams.
• I was also afraid I wouldn’t be completely fulfilled.
• I wondered if I would be a failure and end up having to close down our business. 

So I held onto doing both things for such a long time because I was so afraid.

If you knew then that you would be successful, would you’ve left sooner?

I don’t think so because I think it gave me the ability to push forward through the times that were really hard. 

There would be multiple times where I would get up before school to do the work that I was building with Simply Stained Shop, change, go to school, teach, do community events as needed, and then when my contract hours were over (and I was done with all of my grading), I would come home, do all the things, put my kids to bed, and my husband and I would stay up until 1 a.m. doing more Simply Stained Shop work.

So I don’t think I would have appreciated the hard work if I didn’t do both things for as long as I did.  I just think it put a lot of determination within me and allowed me to see how badly I really wanted this.  I think if I had shortened my time, I wouldn’t have been able to get that.

As much as we hate those hard times, it’s in those when you just have to just get scrappy and do what needs to be done.  You also begin to realize that you have a lot more ability and desire in your heart for something than you might have originally thought you had.

It also reminds you that when times get tough, you can figure it out.  And I think that does something for your confidence that learning any other way can not do.

What would you say to someone who’s struggling with hearing a lot of negativity?

I have learned now that the people who are on your side are going to be on your side regardless. The people who have stuck with me from the very beginning enjoy watching a journey and they’re cheering us on.  

The naysayers that I was afraid of and that I thought was going to be the majority are really not.  Now I’m happily saying that I was wrong and I did not give the community of teachers the benefit of the doubt. 

We still have an amazing community within our business and I’ve noticed that most people want to be around things that are positive and see others succeed.

I would say that sometimes those voices you are hearing are fears within your own mind and not so much the reality of things.  

Can you describe the virtual field trips to Simply Country Ranch?

During the pandemic of 2020 when all of the kids went home and the teachers were like, “We don’t have lesson plans” I worked with Jesse from Cooties and Cuties and she helped me put together a virtual field trip.

We created a free digital download with a video on our YouTube page.  Then I started reaching out to our Instagram followers and saying,  “Hey I have 10 spots today or this week if you’re interested.”  I would jump on a Zoom call for 20 minutes and the kids would have a private event with me and our farm animals where I answered questions related to the topic they were currently studying like reproduction, DNA, or life cycles.

This was a way for us to reach our audience of teachers where they were at and gave us a way to meet what they needed from our business.  

How to go from teacher to successful entrepreneur

I love that your podcast is all about exit strategies and helping teachers see what the possibilities are outside of the classroom.  There are so many different options for teachers that we aren’t able to unlock unless we are really looking at it.

We’re all authors!  Think about it, we teach our kids to be authors every day.  

Want to write a children’s book?  You can self-publish like we did.  You can put it out even without having to have your hard copy in the form of digital books that you can make on Amazon and Barnes and Noble.  There are so many options.

Teachers carry with them so many skills that not everybody is blessed with.  If you are listening to this podcast, you need to understand that even if you don’t see it in yourself, you bring so much to the table.  While classroom teaching is absolutely one perfect avenue for some people, it is not the correct lane for every single person for their entire life.

We are giving you permission to take a step back and consider if you should pursue something else.  Allow yourself to dream and determine if choosing a different career path is the right decision for you.

How important was the support of your husband and family?

Having a support system is extremely helpful and I hope teachers have a support system in place while they are teaching because it is such a grueling career.  

There are a lot of things you can do while you’re still teaching and seeking out your passion but having a support system really gave me the confidence to keep going.  Obviously, having my husband teaching me and standing alongside me allowed me to make fewer mistakes than I would have if I’d just started something on my own. 

Finding a community and making sure you have a solid support system is so important.  Others, who are going through similar experiences, can provide support, but all of your support doesn’t have to come from other teachers. 

If you don’t have a support system in real life, be sure to find a community online and plug into it.

What is your podcast about?

We have a podcast called The Simply Country Podcast and it’s basically just Q and A style where average people who want to learn more about a certain topic ask us questions.  So we’ve been interviewing people who want to know more about how to… 

• raise chickens
• get started with a dairy cow
• begin raising goats 
• live a more sustainable lifestyle

These folks are just getting their feet wet and diving into homesteading a little bit.  We just meet them where they are and share the things we have learned.  

Do you have suggestions for transitioning from teacher to successful entrepreneur?

I would say discipline is needed.  I learned that I was scrolling a lot more than I had really intended each day and putting my phone down allowed me to reclaim a few more minutes.  

Getting up a little bit earlier each day instead of pressing the snooze button a bazillion times helped me practice discipline.  I just decided “I’m getting up now and I’m going to start my day.”  That put me in the right headspace.

Having a cheer force behind you, whether that is a friend constantly checking in with you or a great support system that is really helpful.  But putting my phone down was the biggest game-changer.

I started making a to-do list of my top three.  I love following Hustle Sanely with Jess Massey on social media because she talks about “your top three” or those tasks that you want to accomplish each day.  This has helped me understand that if I do nothing else productive today, I was successful because these were the three most important things I wanted to get done.

There is even a tracker on our phones that allows us to see how much time we are actually wasting on social media scrolling.  And while we don’t like to admit it, that reality can be the kick in the pants we need to realize we have more hours in our day than we think. 

Then if we actually applied that to something productive, we could make so much forward progress towards those big goals and dreams we have.

Creating deadlines is super-important as well.  When we were writing our children’s book, we knew we wanted to have it out by a certain date so that meant we needed to have all of the writing done by this date.

If you are a procrastinator, this could be a really meaningful practice.  Set deadlines and then chunk the required tasks up into shorter deadlines by looking at your big picture and then working backwards.

If you want to transition from teacher to successful entrepreneur, you have to have deadlines so you can complete essential tasks in a timely manner whether that means announcing things on social media or just writing it on your calendar.  

When you’re teaching, you have a principal or another administrator that expects you to meet specific deadlines, but once you become your own boss, this can be a lot more difficult because you let things slide a lot longer than you should.

Final thoughts for someone who wants to shift from teacher to successful entrepreneur

I would probably say that you have the permission to change.  For a long time, I felt like I didn’t have the permission to be anybody else other than the person who graduated college to enter into my teaching career with an elementary degree. 

I felt like I wasn’t allowed to be anybody but that person. Over the time, I realized that I’ve grown and changed and you can still hold on to a lot of those pieces and parts, but maybe it’s time to go to a different school or a different grade level, or just to leave teaching entirely.

We’ve all realized over the last couple of years that life is very short, it’s fragile, and we are not guaranteed anything.  So it’s okay to try something out without feeling like it’s your “end all be all.”   You’re allowed to maneuver and change and grow and follow your passion.  

Start by learning and understand that if you go in another direction, it can just be something that adds a little extra joy back into your day.  You might find that joy spills into other areas in your life and gives you joy back into the classroom.

If you’re looking for an extra income, use this podcast, the community members, and Jennifer’s coaching program to give you ideas of what kind of talents you possess and how to best use those.

Speaking for myself, it was more about the permission to go after something when for so long I told myself I wasn’t able to.  I resigned myself to the fact that I had chosen a lane and I had to stick with it for the 30 years that I signed up for when I accepted the job.

But what I’ve realized since then is that I was looking at what was traditionally accepted as a teacher and yet I’m a teacher in so many ways whether it’s…

• teaching other teachers how to design a beautiful classroom space
• creating a virtual field trip to a farm 
• writing a children’s book 

Once a teacher, always a teacher and that will never change…even if you decide to shift from classroom teacher to successful entrepreneur.

Be sure to follow Lauren on IG @simplystainedshop & check out her website SimplyStainedShop.com and use the code HTM10 for 10% off your total!! Also make sure to share any of your takeaways from this episode by tagging me on IG @classroom_exit_strategies. I’d love to celebrate with you.