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5 Terrifying Things Successful Educator-Entrepreneurs Embrace

  • Lesley TaylorLesley Taylor

“Expect the unexpected I always say and the unexpected never happens”
The Whetherman in The Phantom Tollbooth

As Head Coach at Mirasee, I have watched thousands of entrepreneurs work through our programs.

Some are a lot more successful than others, and because I know you want to be in the Successful Group, I thought I’d take a few moments to tell you what separates those who succeed from those who do not.

Today we use the word “entrepreneur” fairly loosely to mean someone starting in business, but let’s unpack that term a little to help you better understand what you are about as an entrepreneur and how you might find that success you seek.

What It Means to Be an Entrepreneur, Literally

“Entrepreneur” is a word of French origin. Some say it was first used in the 16th century to refer to persons who led military expeditions. They would have been prepared to take risks and faced uncertain outcomes as a result of their efforts. And as part of their planning for surprises that might otherwise topple their victory, these action takers would have included planning with an expectation of the unexpected.

Apparently, two centuries passed before the term “entrepreneur” was applied to business folk including merchants, farmers, craftsmen, and other sole proprietors who all shared the common activity of buying at an uncertain price and selling at an uncertain price—risk taking again.

If you continue to hunt down references to this term you’ll find risk taking at the core of the entrepreneurial journey—plenty of evidence of using scant resources to make more but with much uncertainty around outcomes with only plausible outcomes as a guide.

Risk and uncertainty surround the term entrepreneur as does taking action, being an adventurer.

We encourage our students to embrace the very heart of entrepreneurship in their course building. Course building is full of uncertainty and it is an uncertainty with lots of moving pieces.

There is the uncertainty around self: “What can I give?”

There is the uncertainty around what the target audience are willing and able to invest in: “What does my audience want?”

Then, when those two things are figured out, there is the uncertainty around how to make the offer: “What message will resonate with my audience?”

In course building, there are so many whens and whys and wherefores. Like a ping pong ball, plausible answers are hit back and forth often in quick succession and things begin to look good. And then it’s an idea down when the ball goes into the net. And sometimes once that ball has rolled off the table, you can’t even be bothered to stoop to pick it up and get on with the game by trying another tactic or simply getting better at the first one.

Instead you quit before you either won or lost, thus sealing yourself as a loser for the game you began to win.

Other doubts flood in too.

Students are uncertain that they truly know more than those they want to teach, and if they do know more, then the question moves to, “what exactly is the more I know?”

Students are uncertain that they truly know which bit of the “how much” to teach, and if they know which bits to teach then the question moves to, “how much of it should I teach and what is the order I want to teach this in?”

Students are uncertain that they can find those they want to teach and if they think of a way to find the target group then the question becomes, “how do I overcome my fear and talk about what I am doing?”

Students are uncertain that those they want to teach actually want to invest the time needed to learn this stuff, and if they do want to invest the time in it, then the question becomes, “how much time do my students want to spend learning this and at what times of day?”

Students are uncertain that those they want to teach actually want to invest the money needed to learn this stuff, and if they do want to invest the money then the question becomes, “how much money and how do I decide?”

“Uncertainty is the risk at the heart of the entrepreneurial journey. ”

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And so the uncertainties flourish because uncertainty is the risk at the heart of the entrepreneurial journey and if you are just beginning to try this new path then you are an entrepreneur.

Every step of the entrepreneurial journey demands a bold move. It requires embracing things that would normally scare away less courageous souls.

Below are the five things that successful educator-entrepreneurs embrace, even though they’re terrifying.

“5 things successful educator-entrepreneurs embrace, even though they’re terrifying.”

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1. Fear and Doubt

Embrace fear and doubt as expected. This will empower you to boldly take action.

Fear and doubt are just part of your entrepreneurial journey and are best embraced. Yes, you’ll want to accept them and move through them rather than use them as excuses for inaction. I know, that sounds tough but keep reading.

Do you really think everyone else has it figured out? Do you really think everyone else feels confident and certain all the time?

The truth is, entrepreneurs are always stepping out into new territory and that is always somewhat scary. Typically the unfamiliar brings unfamiliar challenges that make us feel insecure. That’s normal and it presents you with an important choice, one you will face a lot on this journey into the unknown as an entrepreneur: “Will I let my fear and doubt stop me or will I lean into my fears and all the unknowns surrounding me in order to take action?”

Action taking is a must for entrepreneurs and it will help you build your entrepreneurial muscles along with your skill set.

Top Tip to Embrace Fear and Doubt:

When you feel too afraid to take the next step, pause, work out a way to be OK with whatever the outcome, and then take action. Just make a move.

BONUS: Get Success Mindset Reimagined!

2. Failure


Embrace failure for what it teaches. This will empower you to perceptively learn.

“Embrace failure for what it teaches. This will empower you to perceptively learn.”

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It is just fine to meet with failure on your entrepreneurial journey. Most successful people have failed more often than most unsuccessful people for the very reason that they have pushed harder and more often at the edges of their competency.

You may not have any control over the number of times you succeed but you can increase your chances of that success. To succeed more often, you’ll want to try more often. And you have control over the number of times you try. So it works best if you do choose to try a lot and become inspired rather than deflated with any failures.

“At Mirasee we encourage our student entrepreneurs to go after failure and here’s why.”

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It may seem strange, but at Mirasee we encourage our student entrepreneurs to go after failure and here’s why. Failure demonstrates that you’re reaching out into new territory, into places where you have more to learn. At the end of each day we want you to ask, “What have I tried and failed at today?”

While you’re not in control of how your choices land for others and whether your attempts are “successful” or not, you’re always in control of what you choose to try to do. Keep trying because what we do know is that the more times you try at something the more likely you are to see success. It is just statistics.

Top Tip to Embrace Failure:

When you feel discouraged by failure, remind yourself that there are lessons to be uncovered and that you’ll want to expend your energy noticing the lessons learned so that you can try again. Just go spot the lessons.

3. Flagging the Problem as Your Own

Embrace flagging the problem as your own, which empowers you to be responsible to find a next-step solution.

The entrepreneurial journey is one that provides a place for the growth of your entrepreneurial muscle. So while you may have lots of people around you to support you, you’ll want to own your own problems because that gives you the space to solve them!

Avoid creating a situation in which you become dependent on blaming others or your convenient circumstances for your lack of success. Until you own your challenges you can’t be the one to fix them. Learn how to succeed as an entrepreneur in the long term, not just in the here and now.

Top Tip to Embrace Flagging the Problem as Your Own:

When you are tempted to see yourself as a victim, remember that you’ll need to see yourself as the “victor in training” if you want to empower yourself to have a chance at fixing things. Just grab the challenge.

4. Fortitude


Embrace fortitude as the cloak you wear. This empowers you to generate the energy you need to keep trying.

Dogged hard work is unavoidable. While conversations around you are all about working smarter not harder, do not underestimate what it does take to get going as an entrepreneur. It’s like pushing a car: once it’s moving it might be easier to keep it moving but to start with it’s just a lot of effort.

Successful people typically work harder than unsuccessful people to reach their goals. So find the extra effort you need for the adventure.

Top Tip to Embrace Fortitude:

When you are tempted to quit because things have got tougher than expected, remember there is more in you that you can find to push on—that is simply put—just push on. Just do it.

5. Fabricating a Future

Embrace fabricating a future that matters. This empowers you to craft a big enough vision to stay motivated to complete the task at hand.

You’ll want a big why for your journey. You want to have a reason bigger than yourself as the motivation for your success.

Dan Pink, in his book, Drive: The Surprising Truth About What Motivates Us, talks about three things. Two of those are learning new things and being in control, which are covered in points 2 and 3 above. The third factor Pink mentions is serving a purpose bigger than yourself. You all know of amazing feats of courage and success accomplished because a Mom was rescuing her child.

This is your time to find that purpose for your message going out to the world. What makes it important enough to move you? Be sure to get that big reason why for this adventure. Your fabricated future vision needs to be big enough that you will take all the moves and risks necessary to grasp it and make it real.

Top Tip to Embrace Fabricating a Future:

Make a plaque in which you have drawn those things you are going after, a plaque you can look at every day to sear your purpose into your subconscious daily.

“Freedom lies in being bold.” -Robert Frost

“Here are the bold moves you need to make to succeed as an education entrepreneur:”

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Here are the bold moves you need to make to succeed as an education entrepreneur:

  • Welcome fear as the trigger for adrenaline to flow for action taking.
  • Welcome failure as the trigger to learn about all the ways that don’t work so you can find the ones that do.
  • Welcome owning the messes that come from your action taking as your trigger to find a better way and become a stronger person along the way.
  • Welcome the struggles when you feel you don’t have the energy to do another thing and push on because you know that fortitude is what separates the successful from the simply brave.
  • Welcome the future vision that makes this matter as your trigger.

When you are tempted to quit on your dreams remember that while you might have to adapt the plans and find a better way, you’ll want to hang on to your dreams.

Successful educator-entrepreneurs behave like successful entrepreneurs and do the things others refuse to do, believing that is just what it takes.

What are you honestly prepared to give and take for your entrepreneurial success? Of the five things mentioned above, which one do you find most frightening? What’s your strategy to embrace it?

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29 thoughts on 5 Terrifying Things Successful Educator-Entrepreneurs Embrace


What are you honestly prepared to give and take for your entrepreneurial success? Of the five things mentioned above, which one do you find most frightening? What’s your strategy to embrace it?

I am not prepared for anything, but I embrace the unknown and accept the challenge leading to my entrepreneurial success. What I find most frightening is #5: Fabricating a Future. I will embrace the fact that the only way I will achieve the life I want in how I will serve others is do the work and why not enjoy it too!

Christy Sharafinski

Thanks, Lesley, for mining the meaning behind “entrepreneur.”

Though I’m naturally entrepreneurial, I generally consider “risk” to be an icky four-letter word. You & CBL are helping me reframe “risk” as natural, normal and even desirable, especially when surrounded by a safe, strong group of mentors and coaches. These trusted resources are a safety net, making risk seem much safer. Plus, I’m gaining a vision of the steps AFTER risk…whether the initial leap was successful or not. A “plan” is another positive four-letter word!


Hey Christy
Yes, ‘entrepreneur’ is a very interesting word when unpacked!
Yes, there is much in our lives that we can change with a simple reframe! Reframing changes how we think about something and then newly empowered actions follow.
Yes, Course Builders Laboratory is a great place to learn and test things out and then implement business ideas.
I look forward to seeing your successes!

Steve Ventola

Thank you Lesley for this essential article!!! I think everyone in the course would do well to read and consider your words. It seems you and others with CBL already know what those who are beginning the program will experience. You have set a foundation to light our path! Thank you again.


Hey Steve
Glad you found this useful. Yes, I have guided a lot of students wanting to begin entrepreneurial businesses. I’ve seen a lot!


What a great post!
Such timely advice for so many of us just embarking on this journey with CBL.
There have been many times over the last three years of my entrepreneurial roller coaster where I’ve just felt like yelling, “Let me off!” But…reading your post helps me remember that I have that “grit” required to be successful. (A reminder I need from time to time!)
Thank you!


Hey Angie
As long as you have that grit – stay encouraged and keep taking action. I like to remind myself that it is easier to steer a moving bicycle than one that is going nowhere because it is motionless. Easier to stay on for the ride too!


Hi Lesley!
Thank you for the great post! For me it would be fear and doubt. Reminding myself that it is very natural to have fear and doubt every once in a while is very helpful and then to keep reminding myself when fear and doubt rear their heads to acknowledge it is there, feeling it…and then moving on despite of it. Yes, that is very empowering.
When it comes to failure, I love the Montessori approach where the kids use materials that show them what works and what doesn’t, it is self-explanatory and nobody has to tell them what is right or wrong. This way it is an experience they make no matter the outcome and they stay motivated. Also a very empowering approach to life and very similar to what you write about…


Hey Tina
Thanks for your comments.
Yes, being bold enough to try things out, have a go is an essential part of learning new things.

Jayne Pugh

Great post, full of deep wisdom to help you push through when things get tough. And I know they do! For me it is fear and doubt. I push past this by having an audacious vision and by having the realisation that I have something to give to help others become their best. (I do still have the odd wobble though, I think we all do!) I have found the teachings of J C Maxwell useful on this subject. His book Failing Forward, very much mirrors the teachings of Mirasee. It is all about learning and understanding what positive behaviours you should use more and what negative behaviours you should drop. I also believe having a true sense of purpose or intention really helps people to push through and would recommend people define their WHY and vision to be a daily anchor to encourage you through the hard-stuff.


Audacious visions are great to have and to hold!
I like Maxwell’s work.
Thanks for the great reminders here.


Thankyou Lesley for this wonderfully broad, insightful perspective on what it takes to realise my big dream …. particularly being given the opportunity to prepare in advance for the struggles I will encounter and to devise some strategies now!!
That has been SO useful!
And because I DON’T KNOW what I’ll encounter, I want to embrace this NOT KNOWING too ….
and embrace being a LEARNER – adopt a beginners mind…. have a mindset of being playful and experimenting in order to find out.
Let go of being attached to specific outcomes/results …. just take another action …and see what happens! Let the whole process be fun!!!
BE committed to the journey! Its more than about me ….its about helping others!


Hey Meg
I am so glad you found this useful – having worked with hundreds of students around the world I see those things that are making the difference that makes the difference for those who are finding the path to success.

Geoff Coughlin

Hi Lesley,

Just about completed the Foundation Module after signing up to the CBL a couple of days ago – wow! What a great introduction to get into the right mindset and get highly motivated to start and build my pilot in Module 1. I love your positive and practical thinking and the importance of embracing failure and disappointment and taking responsibility for it so that you can review what happened and most importantly make the changes needed and move forward.

I’ve been a trainer/educator for over 20 years and going the on-line route is completely new to me and I feel so supported and know that support will be there when I need it (and I haven’t had contact with my coach yet! I know that will come soon). Thanks for this great start to the programme – and to Danny, Jim and Co! Best, Geoff


Hey Geoff
I love the enthusiasm with which you are embracing both the Course Builders Laboratory – the lab where you are going to be learning how to best create an online course that is wanted by your target group – and entrepreneurship. If you can embrace the tough stuff and keep moving forward you are on track to be among our successes, and on track for creating the sustainable business that you want to craft around a message that really counts for something remarkable.

Annette Pang

Hi Lesley, Thank you for helping me get on board. I skipped the entire Foundation section and now
listening to it before entry to Modules. I love the section on emotional change. I will keep on plowing through this weekend. Will keep you posted, Annette


Hey Annette
Glad to help. Feedback is always welcome – let me know what you choose to embrace that makes the biggest difference to your success.


Love the post Lesley! If I were to focus on one of the five, it would be fear and doubt, definitely.

Thanks for re-framing that idea!


Glad you liked this post Darla
Yes, re-framing is a very useful way to move forward through what otherwise might be blockages because it allows for other possibilities – how can I look at this in a way that empowers me to act?
I use re-framing questions in every context in which I have students, both in business and academia. Of course, fear and doubt are never ‘all gone away’ for the educator-entrepreneur because there is always the need for movement into learning something new and trying something out which = taking risk. But we can re-frame and realize that when fear and doubt are the names on the door, we can still choose to go through the door.

Carol Tice | Small Blog Big Income

Great post, Lesley — as a reporter with 20 years covering startups, I wish more freelancers would adopt the entrepreneurial mindset and learn to get out there and ‘fail fast’ — try many things to see what sticks — rather than timidly sitting by worrying about making one wrong misstep.

Entrepreneurs know that failing fast is the only way to quickly identify the right path. Name a great company — Amazon is a terrific example — and research their history, and you’ll find so many missteps, often costly ones, before they figured out their USP and the innovations that would make them stand out from competitors.


Agree completely Carol – thanks for taking the time to post these comments. ‘Fail fast and learn and grow’ is the way to go.

Amar kumar

Hey Lesley,

Glad to read your interesting post! Fear and doubt are two words which always involve in entrepreneurial journey. Every business owner always try innovative strategies and new strategies makes them scary about results. Success is always built upon risk, change, and personal development. The journey teaches us to cope with failure. We learn to get up anyway, and to push onward towards your dreams. Many start their journey with pie-in-the-sky, smooth-road ideals, yet, success is rarely, if ever, that type of journey.

Every successful person travels a painful journey. Suffering is an integral and essential part of any real pursuit of success. You may as well accept suffering as a traveling companion, rather than resist it and create more struggle. See each day as a day that you are blessed with new chances and opportunities to start from the place you find yourself. Success takes a tremendous amount of effort and sacrifice. Eventually, thanks for sharing your experience with us.

With best wishes,

Amar kumar


Hey Amar
Thanks for you comments. I agree with much of what you have shared but would prefer to replace the word ‘suffering’ with ‘struggle’ as for me it has a better energy for taking control and making something happen out of it. What are your thoughts?


1. Failure

2. Fortitude. I strive though, you know everyone perform their best within their ability and the yield might be poor or fair.
Thus, this is where smart work comes at play because that’s what matter.
You can achieve better with less activity but before you can finally crack it, you’ve to sacrifice.
And that’s the spirit, to push on


Hey Kunle
You make a good point about working smarter not just harder but in terms of success it is important to remember that working smarter not harder is about achieving more with the effort you put in not simply about doing less. Does that make sense?


I liked the distinction ” the succcessful” vs the “simply brave”, separated by fortitude Stamina. I’ be been plenty brave, time to get successful:((!


Hey Siglinde

Glad you liked that distinction and that it has empowered you with with new ideas around success. Go get that success this time and let me know how you get on. 😀


Great post Lesley!
I love the way you framed failure as just a way to get smarter and better prepared for future success! So true.
Excellent advice!


Thanks Lizzie!
Glad you liked the post. We can’t choose all the outcomes but we can always choose how we think about something, and how we think about something impacts EVERYTHING else. 😀

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