Photo by Yeshi Kangrang on Unsplash

#32 – The Courage to Fail


Few accept to walk the tight rope over an unknown and scary zone to get to success waiting on the other side

Have you ever heard of Philippe Petit? In 1974, he performed the illegal act of walking on a tight rope between the World Trade Center’s Twin Towers in New York City. His stunt received international coverage and was even made into a book, The Walk, and later a movie, Man on a Rope.

Philippe’s chances of failure were very high. In fact, he risked the ultimate thing one can: his own life. This was definitely an extreme example, but I wanted to illustrate the parallels that success often feels like walking on a tight rope.

Success is never quick nor easy. One must work hard for it. Yet some people are making massive mistakes in how they go about achieving success.

As a business coach, I regularly see a couple of worrisome behaviors that hold entrepreneurs back from success:

The Tsunami Fail

Kent has been a business owner for several years. He struggles, so he has a day job employed for someone. But his dream is to quit and succeed in his business.

Kent has a good dream, but his stubbornness is a problem. Kent is in denial. Kent believes he is right….about almost everything. He struggles and struggles yet he doesn’t often implement good advice. Anything that pushes him into new territory scares him, so he retreats to old tactics that don’t bring him new clients. So he does nothing.

“I’m just gonna stand there and watch you burn…” sang Rihanna in an Eminem song.

What would you do if your house were on fire? Or you are about to lose everything?

Would you continue watching your tv show or drinking your tea?

Unless you are nuts, no, you’d get the heck out of there, call for help, and get the fire hose to put out the fire, right??


Yet many entrepreneurs are like Kent. They watch passively as figuratively their businesses fail. Often, failure comes suddenly and brutally.

Sadly, instead of taking the RIGHT action, they focus their attention on “safe” things they feel are in their control yet don’t bring them sales, like spending time on social media, writing content, attending social events, or checking out their competitors.

What they aren’t doing is the key: Sales.

I have literally had failing entrepreneurs tell me in the same breath:

“It’s so slow right now if I don’t find new clients soon I don’t know what I’ll do. I am too busy right now to sell.”

WHAT?! Yes, this is literally what a business owner who had a discovery call with me said.

Or how about this one? “I am very tired. I think I’ll book a vacation.” Says someone who has no future income lined up. Crazy.

Don’t be like Kent and go down in flames. Be your own hero and put out that fire! The earlier you take the right action, the higher the chances you have to avoid a catastrophe.

The Keyboard Warrior Fail

This is a business owner who is operating figuratively alone in the jungle. He has left the trail and got lost in the bushes. Like a hermit who hasn’t seen other humans in quite a while, he becomes a bit anti-social, unrelatable, and “savage”.

Disconnected from their audience, the keyboard warrior spends most of his business time alone and isolated. You’ll recognize them based on 3 things:

1. They produce A LOT of content consistently that they are very proud of yet no one seems to buy. They don’t have a good call to action or a good sales process in place. Instead, they may say “Schedule a discovery call, DM me, reach out” but often, nothing at all.

2. They occasionally try to spam or cold call strangers to pitch their offers to download their free e-book or come to their free masterclass, etc. or set up a pitch meeting (1980s sales are a major turn-off).

3. They don’t have genuine relationships with their micro-niche, nor have any serious strategy in place to build them. Instead, they see clients as “followers” and expect them to be dazzled and chase them to buy (haha! They really are lost in the jungle). They rarely make enough effort to build likeability and trust because their efforts are always one-sided (me, me, me). When they do network, it almost never results in inquiries or conversions.

When these keyboard warriors discover me as a business coach, they always tell me the same thing: they can’t believe they don’t have more incoming clients. After all, in their minds, they are doing everything right…..The worst part is that they keep doing it wrong FOR YEARS.


The Scaredy Cat Fail

Certain people have an almost allergic reaction to try new things. They get all sorts of angry, fearful, frustrated, and generally appalled by it. Put them in a new and unfamiliar situation, and they will find any excuse to go back to their comfort zone. That would be fine if their comfort zone were getting them the results they want. But, of course, this isn’t happening, and they are trying to find a way forward…without actually having to leave the old and familiar. Mission impossible!

Are You Ready to Fail Your Way Forward to Success?

It will be hard, scary, and full of new adventurous challenges. But if you have true goals, maybe you will find it in your heart to brave the wild? Listen to my latest podcast episode of Take Back Monday’s podcast, #32: Are You Courageous Enough to Fail?, to learn the steps to move forward the right way.

Spoiler Alert: If you want to succeed, you’ll need to combine Goals + Strategy, in that order. If you are serious about success, start here.

Thank you for taking the time to read this article. It is part of my newsletter series, Take Back Mondays, where I help people love Mondays again. It has been twenty years since I entered the workforce, over which time I have worked both in larger SaaS companies and run a digital boutique agency. I have managed hundreds of people, both in-house and remotely, from multiple nationalities, ages, cultures, and languages. Today I work as a business coach to help people turn their skills and passions into online businesses. If you like this article, please consider subscribing!



Subscribe to Take Back Monday Podcast, the Nr. 1 Channel for Successful 6-Figure Digital CEOs and a Profitable Content Creators. We post weekly episodes on Business, Marketing, Money, and Mindset.

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