The Art of Failing: My Journey from $500K Flop to Foundational Success (Discounts on Lessons Learned Inside)

Box Cutter Co. Free Issue No. 61

Weaving failures into success

I have to be honest… I am failing!

I’m failing badly. And here’s why.

I launched my first paid course about 3 weeks ago and the silence is deafening.

👉 Learning Journals 101 (Shift your thinking, Change your life) is out.

And! — you most definitely should not take it.

Don’t look at it. Don’t even think about it. Pretend there is no link above.

Because it’s a failure. Simple. Straight-up, flop.

And who wants to be associated with failure? (Probably not you, right?)

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It only took me about 8 months to build the darn thing.

Well… actually… it took me multiple years and a doctorate in Education. So that’s like a 5 year and $60,000 investment.

But I couldn’t even have done that doctorate if I didn’t do the Masters degree specializing in Adult Education first (another $15,000 and two years or so).

But wait… I couldn’t have done the Master’s degree if I hadn’t first done the Bachelor's degree (another 4 years and $25,000 or so).

So really, in the spirit of transparency, that new 3 Module course I recently posted has cost me at least $100,000 and about 10 years to produce.

But Wait!

It would not be full transparency if I also didn’t add in the 20 months I have been a Solopreneur building digital writing businesses from scratch — and foregoing the almost $130,000 salary I walked away from.

• That’s almost $260,000 more to add to the cost of my course.

Then there’s the $60,000 or so that my wife and I used as a financial runway when I walked away from the corporate sector — cold turkey. No long-term plan.

And, Holy Shit, that $49 course I recently posted is now…. what?……..

• Almost $500,000 and about 12 years to produce!

At the current $49 offer price… well… I need over 10,000 people to take the course for me to get my investment back. And that doesn’t even include the subscription costs for Thinkific, Convertkit, Squarespace, interest on student loans, and so on.

SEEEE! That’s why I’m a failure.

And it’s also why you should steer at least 100 miles around that online course.

Seriously, who wants to spend $49 (or $24.50, because I offer a 50% discount to subscribers) — for some absurd three-module course that cost me about $500,000 and 12 years to make?

And, really, you shouldn’t enroll because I’m taking it down tomorrow. I’m quitting the Creator Economy.

I’m going back to a salary job at the bottom of the corporate ladder so I can do it all over again for the next 10 years.

Why not? — I still have over 15 years until retirement age approaches. It’s stable. It’s predictable.

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Context Matters

OK, if you’ve read Box Cutter Co. for a bit — you humoured yourself in continuing to read the above, recognizing I was being factitious.

If you’re new (welcome!), you can now see the fake gig from above is up.

I’m not quitting. (esp. because I plan to never return to corporately-driven toxic workplaces.)

Consider this for a moment. Think of a beautiful majestic bald eagle soaring above you. You can hear it calling “keeeee keee keee keee” (or however you spell eagle calls).

• Now think of that same beautiful bald eagle coming after your pet cat, or small dog. Dive bombing it, aggressive and hungry.

• Now think of it stuffed and in a museum.

• Now as an emblem on a flag or coat of arms.

Consider for a second how you felt in each of those situations.

As each situation changes (context), how you see it also changes. The significance of different things takes on different meanings.

As context shifts, contents in each context shift too. Some contexts can frequently become like a box. Think of cubicles in workplaces for example.

Has anyone ever taken a cubicle from a workplace and re-established the same thing in their home office? Did anyone do this during COVID lockdown?

Consider, for a moment, how much the context of ‘working from home’ has changed in recent years. How hand-shaking has shifted. Or, coughing in public.

Weaving Contexts

The ancient roots of the word context are directly connected to the word: text.

• “Con-” is a form of “Com-” meaning “with, together”.

• “Text” comes from the ancient root word*teks- "to weave," and "to fabricate."

And, so context, is the weaving together of “the circumstances that form the setting for an event, statement, or idea, and in terms of which it can be fully understood and assessed.”

That last part is the actual definition.

And the awesome thing about Contexts — is that, in many cases, each of us, individually, can author (or re-author) the contexts of a situation.

It’s also often called re-framing.

Or, as I heavily advocate for — “Thinking about Thinking”.

Metacognition, academics call it. For example:

• What am I feeling right now? Why?

• What’s the story connected to those feelings? Why?

• What emotions might those be? Why?

Those 3 prompts alone can open an entire world of self-exploration. Consider, this diagram I share often 👇

If you recall your first relationship break-up, it may have felt devastating at the time. The feelings in the moment were intense and all over the place.

However, over time, those feelings and emotions flatten out.

The context has changed. And… TIME… is a critically important context (in so many ways).

Like the differences between:

• Reflection (looking back)

• Prospection (looking forward)

• Introspection (looking in)

The RPI framework I’ve come to call it. (I thought about RIP… but… that has other connotations in other contexts).

Granted, Looking Back and Looking In concurrently can have much different outcomes than Looking Forward and Looking In.

• Why do these matter in this context?

Because how each of us feels about our Failures can be critically important. And how each of us feels about Failure is also — frequently — context-specific.

For example, just this simple symbol can have huge implications for each of us individually:

❌

With the counter pressures of the feelings associated with this symbol:

✅

Schooling and Education systems have had, and continue to have, massive impacts on who each of us is individually, collectively, and how we navigate “failure”.

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Failure Contexts (And The Creator Economy)

I have worked in a lot of different sectors. Some folks have asked me (in interviews, for example) “How did a guy who did fisheries technician and forestry work become a senior healthcare administrator?”

“A long and winding road, deep curiosity, and a non-conforming approach to life”— is often the gist of my answer.

Based on a life lived purpose-fully, I’ve been in many different contexts — especially those that involve “failure”.

Several times, I’ve been on accident scenes where ‘failure’ most likely meant death.

One time, our forestry crew was the first on the scene of a backroads accident.

A fellow had flipped his vehicle beside a gravel road, and gone through the sunroof of his vehicle. He was alive and a mess (as you could well imagine). We were 2.5 hours from the nearest hospital.

That day, we saved his life… barely. His scalp was a mess from the glass he went through. One lung collapsed on the way to town — multiple shattered ribs had punctured it. He ended out with a busted pelvis and leg too.

The contexts of serious medical situations, are what author and researcher Amy Edmondson calls “variable contexts” for failures.

Failing Well

Edmondson has an excellent new book: Right Kind of Wrong: The Science of Failing Well (2023). I came across it recently at our local library, and dove in.

She highlights the Silicon Valley mantra of “Fail Fast, Fail Often.” It’s intended to celebrate failure — but it has also created a lot of confusion about failure.

For example, folks working on assembly lines making vehicles, are not ‘failing fast, and failing often’. Nor, we hope, are heart and brain surgeons or pilots of airliners.

She highlights 3 kinds of implications of Contexts for Failures.

1. Consistent Contexts — like assembly lines. Where the state of knowledge is well-developed, uncertainty is low, and the most common failure type is pretty basic.

2. Variable Contexts — like an operating room with surgeons, where there is well-developed knowledge, uncertainty is medium, but the situation is vulnerable to unexpected events, and failure can be complex.

3. Novel Contexts — like a scientific laboratory where the state of knowledge is often limited, uncertainty is high, and the most common failure type is Intelligent Failure.

This sort of matrix to better understand various contexts for failures can be quite helpful — especially as there are pretty deep-rooted emotional aversions to failure and confusion about contexts.

But probably most importantly, deep social and interpersonal fears connected to stigmas and fear of social rejection because of perceptions of failure.

Failure to Learn

A couple of central problems with Fear is that it pretty much shuts down our ability to learn. We are hardwired for ‘safety’ and fear takes up a lot of our brain resources. (Thanks evolution!)

Thus, to learn from failure is far easier to type and say… than it is to put into action personally (and societally).

Second (and Edmondson highlights this), fear shuts down our ability and desire to talk about it. This has become even more so in our social media-flooded world (over 4 billion people globally).

The flood of productivity and ‘success’ porn — simply does not lend well to talking about ‘failure’. Consider for a moment, in your experience navigating social media, how many posts have you come across that openly discuss FAILURE?

And, compare this against how many posts you see celebrating ‘wins’ and launches and follower counts and so on and so on.

Or, on LinkedIn, all the posts about “how honoured and privileged” folks feel about their new position at such-and-such organization — but then flame out because of toxicity and shitty workplace practices.

• Where are those posts? (Not so much).

It’s a bias (and probably not covered in the latest workplace unconscious bias training…)

Failures in “The Creator Economy”

The Creator Economy — by Edmondson’s framework — is in the Novel Contexts. It’s like a scientific laboratory. Creators are trying new things, posting new content, and developing new products.

• The state of knowledge is limited — or a least constantly changing and limited.

• Uncertainty is High.

And, the most common failure type should be Intelligent Failure.

YET! Even though we might know this — it doesn’t necessarily make it ‘easier’. Because our brains are wired to fear failure. (For example, how often are your dreams haunted by ‘failure’?)

It takes investment, time and energy to ‘teach’ our Self to challenge our hardwired emotional responses to failure. It’s actually a critically important skill to hone and continue to use.

There is a commonly-used quote attributed to Viktor Frankl (who survived Nazi concentration camps).

“Between stimulus and response, there is a space. In that space is our power to choose our response. In our response lies our growth and our freedom.”

Learning to fail well takes a lot of practice. It also takes re-wiring much of our social conditioning that was embedded in school systems.

• This is ✅

• This is ❌

One of the most powerful (and simple, in theory) things we can do is admit “I don’t know”.

When we choose learning over knowing an entirely different life opens up. A whole new set of contexts becomes possible.

Learning over Knowing

There is no secret recipe to this. Time and time again research demonstrates the same core components of developing these skills: Self-Awareness.

That is the space in which our ‘growth and freedom’ lies.

There is no shortage of experts, or tools, or recommendations to engage to begin the process of self-transformation. It can be mindset (Carol Dweck), it can be Frankl’s powerful memoir, it can be ‘Awakening the Giant within’ (Tony Robbins), transformative learning (Mezirow) and many more.

The basic shift — especially if you are active in The Creator Economy — is taking on a “Learning” mindset.

I am very discerning with who I follow in The Creator Economy. I despise all the success-porn and comparison-bullshit. The folks I most enjoy reading and listening to talk openly about how they failed — and, most importantly, what they learned from that.

It’s coming on two years this April, that I’ve been swimming in this new sea of being a ‘creator’ in The Creator Economy. And, I’m still just learning. I will most likely have several more ‘failed’ launches and ‘failure’ products like Learning Journals 101.

But then how full of shit would I be if I sold a course with the sub-title (Shift your thinking, Change your life) but didn’t engage that myself?

I’d be very full of it!

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Permitting Ourselves to Learn (and Unlearn)

I have been building online with more purpose and focus since December 2022 (last year). I take a multi-interest (screw the niche down) and multi-platform (f**k the one focus) approach.

Recently, I shifted the name of The Solopreneur Series to The Soul-preneur Series. I am darn committed to remaining an Business of One. This makes me the Chief Writer, Social Media Poster, Dog Walker and Toilet Cleaner.

As well as course designer and launcher.

In the first six months after leaving (cold turkey) from a six-figure role, I just wrote, posted, watched, researched, and learned. I did it daily. I also kept tracking it in Learning Journals.

When I turned the corner last December, a bit over a year ago, I was keen to not lose my Self in this work. This meant, keeping my Bullshit Meter on high for my own content and approaches.

As well as watching and listening for it in others.

Writing The Authentic Self

I’m keen and determined to keep my Authentic Self in this work — not fall into what some ‘guru’ or ‘success-porn’ proponent says I “should” be doing, or NOT doing. This means trying shit on for size.

This also means lots of shit fails. And will continue to.

I’m not flying jetliners here or delivering babies or dismantling bombs. I get to have a “whoops” every day (if need be).

Here’s three ways you can try this on for size:

1. Reflect on a Personal Failure.

Take a moment and reflect on a moment of failure in your personal or professional life. Consider what you might have learned from this experience and how it has shaped your approach to challenges and risk-taking. And, consider how your feelings and emotions have shifted from the time of the failure, until now.

2. Reframe a Recent Setback

Choose a recent setback and practice reframing it. Shift the contexts. Can you identify any positive outcomes or lessons learned from the situation? Are you able to shift the focus from loss to learning?

What happens if you pretend (or actually) not to give-a-shit about what other people think about it — how does this shift your view of it?

3. Consider Failure as Learning

Have you ever considered writing a letter to your Self from the ‘Failure’ and have it explain to you what it came to teach you? If this ‘failure’ was offering advice or suggestions for the future, what would it say?

If it was sharing with you how to navigate future challenges with resilience and curiosity — what would it say?

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Hold onto your hats, because I’ll probably be failing many more times over the next while. How about you?

• Do you have strategies you engage to navigate failure? Actual and perceived?

• Is there anything you’re curious about or wanting to learn more about?

That’s it for this week’s Box Cutter Co. Free Issue. The next Free issue of The Soul-preneur Series is out shortly.

Enjoy the read, please drop a ♥️. Maybe even re-stack this post, or share it on social media channels.

Topics you’d like me to explore or highlight? Strategies or lessons learned that you would like me to share? Drop a note in the comments.

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