5 Lessons I Wish I Knew Before Starting My Teaching Business

As the new year approaches and I step into my fifth year of entrepreneurship, it feels like a good time to reflect on the lessons that have shaped my journey so far.

So grab a snack and lean in because these 5 insights weren't left neatly giftwrapped under the tree.

They came through trial, error, and enough missteps to make Santa double-check his naughty list.

My hope is that these lessons will fast-track your progress—or at least help you sidestep a few of the bumps I’ve hit along the way ??.

Ready to dive in? Let’s go!

1. The Power of a Map (and a Guide)

Wandering aimlessly is exhausting.

In my first year of building a teaching business, I wasted so much time doing the wrong things.

I didn’t know where to start, so I just started everywhere.

The breakthrough came when I stopped trying to figure it out alone.

I found a mentor—someone with a good track record of helping teachers and values that aligned with my own.

He gave me a roadmap, and for the first time, I had clarity about the steps to take.

As an independent teacher, success often comes down to following specific steps in the right order.

Think of it as building a house.

You wouldn’t start with the roof before laying a solid foundation, right?

• Before you can teach groups, you need a reliable way to consistently attract enough students for 1:1 coaching.
• Before you can scale to selling digital products, you need an exceptional coaching program that delivers real results.

And before any of that, there’s one step that everything else hinges on:

Identifying your niche.

If you’re stuck, start by answering these three questions:

• Are you PASSIONATE about helping these people?
• Do they have a strong DESIRE for the service you provide?
• Do they have the MEANS to pay you what you want to earn?

If the answer is a solid “yes” to all three, you're off to a great start.

Extra tip: Your niche may go through several iterations before you really find the sweet spot. Mine did!

Don't let the initial uncertainty hold you back and stop you taking action.

Your niche isn’t a soulmate—it’s a first date. Test, iterate, and see where it leads.

The sweet spot isn’t the perfect start. Sometimes, you just need to begin and adjust as you go.

2. A Huge 'Why'

Why do you want to build your own teaching business?

Forget the surface-level reasons.

What’s the deeper motivation that drives you?

• Is it to make a bigger impact on the world?
• To enjoy the freedom of being your own boss?
• To work from anywhere?

For me, it was a combination of all 3.

My 'Why' became the anchor I needed when things got tough—because let’s be real, challenges are inevitable.

Having a strong 'why' won't make the bumps on the road disappear, but it will give you the grit to keep going.

And that leads us perfectly into the next lesson...

3. The Power of a Growth Mindset

Being an entrepreneur means putting on your learner hat again—and keeping it there.

In my experience, three skills, more than anything else, are tied to success as an independent teacher.

Let's call them the "income-generating' skills".

1. Coaching - You could be a marketing genius, but if your service doesn’t deliver, clients won’t stick around.
2. Marketing - You can’t help people if they don’t know you exist. Marketing is how you attract the right audience.
3. Sales - Yes, I know—this one can be intimidating (it definitely was for me at first!). But here’s the good news: At its core, sales is about listening and communicating—two things I’m willing to bet you’re already great at as a teacher.

Every session you teach, every post you write, every discovery call you have—it’s all building these skills.

Embrace the challenge of levelling up in these areas, and KNOW each day as you improve, your results will too.

I've been on this journey for years, and I still have SO much to learn.

And that's ok.

Actually, it's exciting.

Every day I get to sharpen skills that will help me have a more successful business and provide more value to others.

That's pretty cool!

5. Consistency: The Unsung Hero

It really is the key to getting results in anything.

Here's the truth about motivation:

It's a feeling. And feelings? They come and go.

You don't need me to tell you that there are going to be hard days.

Even when you love what you do, there are still going to be mornings when opening your laptop feels like climbing Everest.

I've had my fair share of those!

But if we wait until we feel motivated to work, we'll just never get enough done.

Anyone can show up one time.

It's the people who show up even when they aren't 'feeling it', who inevitably reap the rewards.

Consistency turns effort into momentum, and that momentum leads to results.

6. Managing Expectations

One thing I’ve learned about progress: it doesn’t follow a clean, upward trajectory.

You might put in X hours of work today and not see Y results tomorrow.

Progress in entrepreneurship is more like boiling a pot of water.

At first, there’s nothing—no bubbles, no steam, just stillness.

But even though you don’t see the changes, that doesn’t mean nothing is happening.

I’ve been down that road...

Stretches of time, study, energy, and effort without any tangible rewards.

Optimism fades and doubts creep in.

It's tempting to question everything.

Here’s what I wish someone told me during those moments:

Every day you show up, you’re adding heat to the pot.

No bubbles yet? Don’t be fooled.

Things are changing.

Energy is building.

And every ounce of your effort cranks up the heat just a bit more.

Remember, every journey has its own rhythm.

Stay true to your purpose and keep doing the right things.

Your pot will boil in time.

One final thing...

Be kind to yourself.

You WILL make mistakes and you WILL mess up.

Know this and own this. It's all part of the process.

Mistakes do not make you a failure.

There's always a lesson to be learned.

Extract it, draw a line under it, and move on.

Do this, and each mistake starts moving you closer to your goal, not further away.

Alrighty, time to wrap this one up (Christmas pun intended ??).

I hope you found something of value here.

Robbie :)

P.S. Looking for a little extra support? Here are some free resources and training I’ve put together to help you on your journey:

?? Social Media Marketing Training for Teachers Learn simple, actionable strategies to attract students and promote your services on social media without feeling sleazy.

?? Video Marketing for Teachers Discover how to create video content that attracts attention and builds your online presence.

?? Webinar Training Step-by-step guidance on using webinars to build trust, engage your audience, and make sales.

?? Free No-Prep Business English Lesson For teachers looking to serve professional clients without spending hours on lesson prep.

?? Follow My TPT Store Get access to over 100 ready-made ESL lessons and curriculums—plus plenty of freebies to save you time and effort.