We were lucky to catch up with Gretchen Bridgers recently and have shared our conversation below.

Hi Gretchen, thanks for joining us today. Talk to us about building your team? What was it like? What were some of the key challenges and what was your process like?

Always A Lesson was a one-man band for many years! In April of 2012, I start a blog where I shared what I was doing as a teacher in the classroom. Sharing lessons taught and lessons learned was my goal. I didn’t even care if anyone read the blog because it was cathartic enough for me to reflect and strategize with each post I wrote.

I also posted resources I used in my classroom on a website called “Teachers Pay Teachers” [TpT]. Besides tutoring children after school, this became my highest return side-hustle endeavor. Of course, it didn’t happen immediately. I posted lesson plans and activities inconsistently, varying in value and visual appeal. I collaborated with other TpT sellers to learn how to better market my products and create materials teachers needed before they knew they needed it. It was quite the learning curve going from an educator mind to a business mind.

Around this time, I learned that teachers didn’t have time to read blogs with their ever-increasing workload, I followed advice from other bloggers suggesting pivoting content to audio form. I never listened to a podcast (or even heard of it), but decided it was worth a start. In June of 2015, the “Empowering Educators” podcast was born!

Adding the podcast to the blog meant I had an official website now. I provided dual, relevant content via the blog and podcast for years. The relevancy and applicability of content attracted an audience of educators that allowed me to continue to grow my offerings. I started presenting professional development [PD] sessions virtually and in-person expanding upon the ideas I shared on the blog and podcast. Many of these sessions I later offered as downloadable bite-sized PD for purchase off my website.

My lawyer husband told me I better hurry and file an LLC to protect the Always A Lesson name and brand. By December 2015, I was official. I felt excited but also like a fraud. I didn’t have a deep understanding of how to run a business, especially the back-end requirements. But I followed the motto “Eat the elephant one bite at a time.” I trusted that I would figure it out as I went, just like I had with the blog, podcast, TpT materials and PD sessions. Always A Lesson grew inch by inch, offering by offering. At each milestone, I made mistakes and I learned lessons. But it was progress nonetheless.

At the same time that my business was expanding, I branched out professionally. I left the classroom so I could have a larger impact. Being an instructional coach to brand new teachers in grades K-12 enabled me to impact multiple classrooms of 30+ kids instead of just my own. I continued to blog, podcast, create resources and PD sessions centered around what I was learning in my coaching role.

However, I was running out of time and energy. I couldn’t do all that was required of me in my business. I heard about other solo entrepreneurs in education (coined Edu-preneuers) hiring virtual assistants [VA’s]. Many of the VA hires were overseas. I really wanted someone I could partner with without having to combat major time-zone and language barriers.

Scrolling on Instagram, I came across the sweetest profile of an educator who decided to stay home once becoming a mother. I asked her if she was interested in working a few hours here and there. She agreed. I didn’t have an interview, a plan of action, nor task outlines etc. We both went into the partnership blind.

As she completed tasks, I started writing down the steps – just like writing a lesson plan for a substitute teacher. We kept these files in google drive for easy reference and updated them as necessary.

She started a business Instagram page to help local moms in her area meet up and put on events for the children. Her page started to take off and she no longer had the additional hours to help me. She had to step away. I was devastated. I had zero plan. I could not create content AND do the back-end work of the business. I had grown too big to run the show on my own now.

My family had the most wonderful babysitter who was in college to become a teacher. I gifted her a basket full of goodies as she went into her first year of teaching, including my very first book “EDUC 101: What They Didn’t Teach you in College.” I knew the tips I shared would help her successfully navigate that hard first year.

She mentioned needing extra money a few months into her career. We talked a lot about what I did to earn extra money after school hours as a teacher (ie. tutoring, coaching soccer, babysitting etc.). I asked her if she wanted to virtually work for me as a VA. She said “yes.” Luckily, I had the beginnings of a system to manage task completion with the google docs we created. My edu-preneur buddies started using online programs to track tasks as well as the components of each task.

I followed suit and placed all of our standard operating procedures [SOP’s] into Asana- a digital tool that can set due dates, designate owners of the task, outline each step of the task, etc. We also used an app called Voxer to communicate walkie-talkie style. This allowed for more in-depth discussion when needed instead of clogging up the Asana chat channels. Hearing each other’s voice built relationship among us and a personalized response ensured I met the varying needs of my VA’s. Sadly, this VA became overwhelmed as a classroom teacher and soccer coach. She was even planning a wedding! The writing was on the wall, and we parted ways a few months later.

I was on the hunt again for a VA, but this time I was armed with perspective. I created an online form so I could gather potential interest in being my VA. Those applicants who’s answer seem aligned to the vision and mission of Always A Lesson was invited to complete a hiring exercise. They had to design images, draft newsletters and edit a podcast episode. These tasks let me know the skill level of each applicant. Due to increased profits, I was able to hire two incredible former teachers working part-time for me as VA’s. They jumped into Asana with ease and each had their designated weekly tasks. It was a well-oiled machine.

I was proud of the systems I created. Clarity in assignment and actionable feedback allowed my VA’s to meet my expectations for years. Sadly, they both ended up moving on to their next chapters months apart from each other – one to help out at her church and one to start her own edu-preneur business. I went from two VA’s to zero.

Always A Lesson was thriving financially and I was desperate for help behind-the-scenes. I needed someone committed for the long-term, so I didn’t have to keep starting over. My prayers were answered when my very first VA reached back out to me. She paused her Instagram page endeavor and wanted to jump back in. Because of her familiarity with my business and the thorough systems I had created, it was a seamless transition.

An additional VA was recommended to me in my hometown by a colleague I trusted. I had her complete the hiring exercises I previously designed and she passed with flying colors. I added her to the team. A three-member team seemed to be the key for the volume of work I produced, and the support needed behind-the-scenes.

I learned that you need more than a vision to run a successful business. You need to track what you’re doing so you can improve it, especially as you share ownership with others in the task completion process. How you hire sends a message to the applicant about your expectations of them as a potential employee. Spend time designing a thorough hiring and onboarding system to set the tone for the quality of work you require. Systems save time, money and energy- precious commodities to a business owner!

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

I am an educator. My bachelor’s degree is in Psychology and Special Education. I taught third grade a handful of years before my district offered to pay for my master’s degree in Curriculum & Supervision as long as I taught an additional 5 years in the district. I fulfilled my commitment teaching second, third and fifth grades. I even earned my National Board certification.

Throughout my eight years as a teacher, I mentored new colleagues and student teachers. All of the advice I shared with those mentees, I shared on my blog, podcast, PD sessions and in instructional resources I created. When I left the classroom, I became an instructional coach to new teachers in grades K-12 in my large, urban school district.

After five years, I got married. My husband and I decided to start our family and I left my coaching position. I loved the work I did and realized I would have more freedom and flexibility if I worked for myself. I solely provided virtual and in-person PD, spoke at conferences and coached cohorts of instructional coaches each semester. I was no longer limited to who I could work with and where I could work with them. This allowed me to increase profits and impact!

I have written three books for educators. “EDUC 101: What They Didn’t Teach You in College” is for new and aspiring teachers. It provides practical tips not covered in traditional course work (ie. how to manage the large amounts of paperwork). I had the opportunity to co-write “Educators Who Know What to Do: Experts in Education.” I contributed a chapter on effective mentorship and teacher coaching practices. Recently, I released “Always A Lesson: Teacher Essentials for Classroom and Career Success” to help teachers increase their effectiveness in the classroom. It covers lesson design, classroom management, student engagement and student ownership.

Those I work with describe me as intentional, focused, and empowering. I have learned how to best help someone grow their skillset by getting clear on who they want to become. Together, we create the roadmap for how to get there. Being realistic with timeframe and work output, alongside my gentle accountability, those I work with experience tremendous growth.

I am most proud of the example I set for those I work with. It’s one thing to say “set a goal and take action,” but when I can give concrete examples of how I have grown as an educator and business owner, they respect me and value my perspective. I live what I preach and I preach what I live. People want to learn from someone who is where they want to be and gets the intensity of the process to reach that place.

At Always A Lesson, educators receive personalized guidance to reach a goal- from start to finish. I am invested in the growth of educators because it impacts generations of our nation’s kids.

How do you keep in touch with clients and foster brand loyalty?

Writing a newsletter is a task designated to only myself. No one can replicate my thoughts and suggest potential next steps like I can because I am the only one living my own story. I have attempted in the past to have my VA’s write a newsletter to my email followers, but it lacked authenticity in my opinion. The content was great. The writing was artistry. But something was missing – me. I had to be part of the process.

Many of my edu-preneur buddies exclusively sold to their email list. I didn’t enjoy the marketing and selling side of the business. Instead, I loved teaching, supporting, and coaching. I’d love customers to buy from me, but I detested asking them to buy from me. That is why my profits started off slow because I didn’t have the guts or the strategy to sell well to my email list.

It took years for me to perfect my newsletter writing. I wrote inconsistently and ineffectively. It was awkward at first, learning to add value while also selling a product or service. Had I made email writing a priority, I would have gotten more practice. But I put off what I wasn’t good at … yet. As a result, it took me longer to get good at it and certainly delayed profits.

Now I can proudly say I LOVE writing to my email list. I am transparent with them, connecting my real life with my professional life. I share just enough detail to be relatable. I want readers to see how similar we are because they will trust my advice, products and services when they see themselves in me and my story. I spend the majority of my emails sharing a story. I am known for taking normal events happening in my life and relating it to the world of education. I share the lesson learned and clear action steps to apply the lesson in a variety of roles in education. Then, and only then, I’ll share purchase links for relevant products at the close of my email.

I no longer lose tens to hundreds of email subscribers for poorly selling to them. Instead, readers stay around for a while (and they actually read the content and click on links in the email) and new readers join weekly.

Growing my email list has been an intentional passion project. I had to practice consistently to find my voice and develop my style. Now my email list accounts for a large portion of profit instead of a loss in my business model. It all comes down to authentic relationships, in education and business.

Any stories or insights that might help us understand how you’ve built such a strong reputation?

I happened to be an instructional coach when the position was rather new in the education realm. Many schools created the instructional coaching position without a clear job description or designated duties list. This left many instructional coaches looking for professional development and resources to find clarity and confidence in their role.

Because I had been coaching teachers for years and selling downloadable coaching resources, I was invited to speak at a virtual instructional coaching summit. The way I presented PD and my level of knowledge on the subject was well received and I was invited back year after year. Because of this, I made a name for myself in the instructional coaching space.

Instructional coaches needed more than just PD and downloadable resources. They themselves needed ongoing coaching. So, I created a service to meet their need- the Teacher Leader Mastermind. A cohort of under 10 members met every other week over Zoom for a single semester. Through introspection, goal setting, and feedback each member designed their personalized growth pathway. Each time we met together, we discussed the progress towards the goal, actionable steps to take over the next week, celebrated milestones, swapped stories and strategies and grew close together in community.

My product and service offerings (ie. blog, podcast, downloadable resources, PD for purchase and Teacher Leader Mastermind) continue to build my reputation in the instructional coaching and teacher support market.

Contact Info:

• Website: https://www.alwaysalesson.com
• Instagram: https://www.instagram.com/always.a.lesson/
• Facebook: https://www.facebook.com/AlwaysALesson/
• Linkedin: https://www.linkedin.com/in/gretchenschultekbridgers/
• Twitter: https://x.com/gschultek
• Youtube: https://www.youtube.com/channel/UCY7FCBzm0vfTYV1YMjq51kA
• Other: Online PD: https://alwaysalesson.teachable.com/

Image Credits

Courtney Helton Photography
Brooke Bryand Collective