My Year of Failure (While Building a Digital Writing Business)

Breaking success myths and online success-porn

I’ve had a year of failures. One after the other after another after another. I failed my kids and wife regularly. I failed in my business. I guarantee you…I failed our cat.

Many of us live in societies built upon bullshit notions of failure and success.

These have been schooled into all of us. Branded onto our skin and brains — like owned cattle.

The thing is… these are not binary opposites. They are not two opposing and balancing concepts. Yet, many use these terms as if they are.

Spend much time on social media and following ‘creator’ accounts and you are subjected to all forms of “Success Porn”.

The problem is that Failure and Success are simply points on a continuum called life. They are not Either/Or concepts.

• Do we call death — failure?

No.

Somewhere along the way these terms have become twisted and squeezed into bullshit facades far beyond their initial meanings. And as we move into another time of the year of ridiculous resolutions and proclamations… it’s darn important to pause, and critically engage in what’s happening.

A whole lot of asking “why?”

To get there, let’s unravel these terms a little.

Etymology (Roots) of “Success”

The word ‘success’ (in English) comes from the Latin ‘successus’ meaning “advance, coming up, a good result.”

The original meaning is more about a progression through things or the outcome of an effort. Think of things like “succession plans” in a workplace. This is about progression, movement, and ‘for-the-time-being’.

And, in past usage of the term, success could have dual meanings — as in:

“The good or bad outcome of an undertaking — as in: the good or ill success of their maritime enterprises.”

The ‘ill success’ — what a fascinating concept. Is this sort of like catching C-19 and then having immunity? (eg. the ill success of getting ill)

Etymology (Roots) of “Fail”

The origin of ‘failure’ is Latin ‘fallere’ meaning “to deceive, to disappoint”. the term initially focused more on the act of failing an expectation rather than an absence of success.

The term has evolved to signify a lack of success or deficiency in achieving a goal. However, it has some odd uses such as when a marriage ends, for example, and people say that “marriage failed”.

• But… what if it was an abusive relationship? (isn’t this a successfully ended marriage? A successful failure?)
• Or, neither people were happy and chose to move on? (another end of marriage success?)
• Or, what about when one partner dies — or both? (news flash: it happens to us all)?
• Is death a failure? For those ill for quite some time, death can be a success…

How About a Non-Binary View of Success and Failure?

Digging a little deeper into the essences of success and failure, it’s evident that these concepts are not binary or strictly opposites.

Instead, they are fluid points along a continuum of life’s journey.

The more important points, I find, are that they encompass learning, unlearning growth, and experience. This continuum perspective allows for a more nuanced and context-specific understanding of life’s ins-and-outs, processes, and in some cases… outcomes.

For example, what if we play with the idea of ‘failing forward’ or learning from setbacks, stepbacks, and blowbacks?

• Or, what about the concept of “lifting to failure” in weight training?
• Or, “running to failure” or “spinning to failure” as part of high-intensity interval training (HIIT)? (all the rage the last while).

The more we play and unpeel notions of failure, the more we can see it’s a critical part of success — not its antithesis.

An Example

We are avid skiers in our household. I didn’t start skiing until I was in my early 20s. Now some years later there’s not much I can’t ski. I’ve become certified at several levels of ski instructing and ski coaching. I find absolute joy in the sport.

However, I’ve also had some serious crashes and wipeouts — and thousands of minor ones. In my 20s I tore my groin on the first run of the day with new skis (and right under the chairlift). I got a ride in what is called the “meat wagon” — when ski patrollers strap you into a sled.

A few years later, I tore the meniscus in one knee — on the first run while visiting a friend at a ski resort he worked at.

These were classic fails.

• (Granted, my friend at the ski resort also had a pretty roommate and she took pity on me while I hobbled around on crutches. We dated for a little bit after that. A successful fail, some might say? — at least in my mind)

The time I have spent skiing — for the joy of it — but also to get better at it — was key in taking our teenage boys on an epic 5-day ski trip last year. We skied some intense, steep, endorphin-blasting terrain. 👇

Skiing this hike only skiing terrain — my knees were shaking — not just at the nerve-wracking terrain — but also trusting our boys could ski it without dying, or at least serious injury.

But we also talk about this prospect often — from skiing to intense mountain biking in the summers. 👇

In skiing — and we say this often in our household — if you’re not falling and wiping out occasionally, then you’re probably not skiing hard enough.

It’s not meant as some macho-ra-ra toxic masculinity statement… it’s encouragement to try with intention, to push comfort zones, and to learn.

Mountain biking also involves some falls — they just tend to hurt more and leave bigger marks.

We must fail often to learn.

In skiing, failing is often success.

And success is repeated failures.

What skiing and mountain biking can teach is knowing when ‘failure’ could be catastrophic (death-inducing). And, failure may mean some nasty bumps, bruises and maybe gouges requiring stitches.

Ill Successes

The concept of an ‘ill success,’ highlights the fluidity between success and failure. It reflects realities of what may initially appear as a setback can actually lead to unexpected benefits and outcomes.

Consider medical breakthroughs that have emerged from unintended research paths or the lessons businesses have learned from unsuccessful ventures, leading to more strategic future decisions.

Another angle to consider is the societal and personal interpretation of these concepts.

What one culture or individual might deem a failure, another may see as a success. This subjectivity further supports the idea that success and failure are not concrete, polar opposites but rather fluid and flexible states.

With these in mind — and in the spirit of reflection (looking backward), prospection (looking forward) — and maybe even a little introspection (looking inward) — let’s take a look at some goals I laid out this time last year (in a Medium article).

Retrospection

In mid-December one year ago, I posted these goals below in an article in Veronica Llorca-Smith’s A Smiling World publication. They related directly to building a digital writing business from scratch — and growing audiences on various platforms.

They went like this 👇

On Medium:

I passed the 100 Follower mark and the 1000 Follower mark by April. I failed to reach the $100/month marker until August.

On LinkedIn, which was one of my main focus areas at this time last year, I have failed to reach my goals. 👇

I recently went over 4,100 Connections. I’m nowhere close to 10,000.

Another fail.

On X (Twitter), things have been steady. And, I’m actually about bang on for my goals.

I just hit 1,000 today, the day I’m writing this article. And 1,0001 when I finished writing it. If I can hold for a week, I meet this goal.

On, Substack, I publish Box Cutter Co. and last week I sent out Free weekly issue №52. This was 52 weeks of free issues.

I am at almost 430 Subscribers (and currently 2 paying ones).

Another fail!

Regarding books and other products, I have yet to sell anything on Gumroad. 👇

I have not published any ebooks (granted some in the works). I have not published any ‘paid’ courses yet — but have published:

• Two Free 5-day Educational Email Courses focussed on Solopreneurship and
• Seven Free 5-day Educational Email Courses as part of our educational startup Humanity Academy.

Another fail!

Solopreneurship

In the spring of 2022, I walked cold turkey from a well-paying decade-long career. I’d climbed corporate ladders and nearly tripled my salary over that decade. But I also lost parts of my soul. So I walked.

I set out to build a digital writing business from scratch. Doing what I absolutely love doing: researching, synthesizing, and writing.

On the digital writing business front, I’m at about $2,000 for the year.

Fail!

However, on the Solopreneur front, this time last year, I had set some modest goals 👇

I’ve been fortunate on this front.

My services contracts (writing, research, ghostwriting, and non-profit development work) have ebbed and flowed between $9k — $15k per month (which I met by April 1)

The services side of my gig has kept this creative enterprise moving along nicely. And, my average hours working each month are down significantly from my employment years — especially in comparison to the years I was in healthcare admin during C-19.

A successful fail at employment!

A flailing success at Solopreneurship?

Planning to Successfully Fail into 2024

I plan to continue failing. Successfully Failing. Like a boss.

But…wait… I am the boss.

As a Solopreneur (and Co-founder with my wife of Humanity Academy), I am the boss. I’m also the Chief toilet cleaner and sometimes lead chef. I’m often Lead dog walker too.

And this is all by design.

Some might suggest I was a failure for walking away from a 6-figure salary, good benefits, pension contributions, bla bla bla. Actually, some do suggest this.

It was certainly a successful enterprise by the numbers — at least the $ ones. But it was an abject failure when it came to how I wanted to spend my limited time on the planet.

With a little retrospection and introspection, it’s clear that what we might often label as ‘failure’ are merely blips along fuzzy continuums. Our societal fixation on ‘success’ as a static destination, or ‘failure’ as some quantifiable easily identifiable thing, fails to recognize the complexity and necessity of the process.

That’s a bit cliché, yes. But necessary.

Engaging in a little Prospective Introspection

This past year, every apparent ‘failure’ in reaching my digital writing and digital writing business goals was an opportunity to learn, unlearn, grow, and refine my approach. And, maybe most importantly, adjust my goals and check in on how I’m feeling about things.

The ‘failures’ became fuel for more creativity and a foundation for resilience. For example, not everyone is going to agree with what you post — especially if you take a stand on things, call bullshit, or write your mind.

My multiple successful failures and failed successes were not endpoints or even points at all, but waypoints, guiding me along a better and deeper understanding of what it means to create, share, and impact others through my writing (and funnily enough, my elementary-level illustrations 👇).

Plus, interwoven through all of that are the impacts of my own Self. Writing, for me, and synthesizing is almost always a joy, a passion, and something I find deeply satisfying. It’s the type of thing I want to spend my limited time on the planet — doing.

And, if I can generate income from that… full bonus!

If I were to try and wrap this article in a little bow for you (in the xmas spirit) successfully failing and failing successfully over this past year has ingrained, (branded?) a few valuable tidbits:

• Avoid Comparison: Success is personal, not a race or even an event against others.
• Long View: Achievement unfolds over time, not overnight — and repeat #1.
• Genuine Truths: Find and use that unique voice. We are all independently unique and see things uniquely. Write from that perspective.
• Timeless Ideas: An unfruitful or dead-resonating idea today can bloom tomorrow, or maybe even next year.
• Ongoing Experiment: Each failure is a step towards growth — or maybe ungrowth — Learning or Unlearning — and that’s OK.
• Patience: Real sustainable progress demands time and persistence. I did not learn to ski double-black diamonds overnight.
• Impostor Syndrome: It’s real, a shared struggle, and not a personal flaw.

If possible, keep in mind success in the Creator Economy, in writing, and in life is not about hitting every mark — especially those imagined in a prior time, in a different context.

When I set those goals last year, for example, I hadn’t lost more family members, a friend, and a dog — to name a few of this past year’s events.

Life’s about navigating our unique paths — learning and unlearning from our past, being in the present, and pondering some of the future.

Success isn’t about rapid (or even slow) achievements. It’s a slippery, continuous, murky journey that often requires a bunch of patience and persistence.

And the Internet is full of far too much “success porn”. Those who fail are fine examples of how failure can be endured. They are also excellent people to talk to, for those who fear failure.

It’s a funny paradox really… freedom comes from the knowledge that we can get through the worst that life throws at us.

But do it with purpose-filled intention… and you’ve got a successfully failing formula for a fulfilling life.

• What are you planning on successfully failing this coming year?

David Loewen abandoned a well-paying career in 2022 and has built a mildly profitable digital writing business from scratch. He publishes a Free weekly newsletter sharing systems, processes, and experiences of being a Box Cutter Co.