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A Life of Failure

The Winner’s Circle

I’m such a loser. My whole life has been one failure after another and I’m sick of it.

How many times have you felt this way? More than once, I bet. Life, no matter how fortunate, throws periodic curves. This is not a character flaw; it’s life.

Hard times define you more than success. Success lulls you into a false sense of superiority. When things start to fall into place too well for too long you fall into the trap you are somehow better than you really are. Learning turns off and it’s unhealthy.

The good news is you can still learn from your wins and good fortune. You must be aware success is a poor teacher and be willing to challenge your inclination to think a win means you are right. Plenty of winners have been wrong throughout history. In driving they have a term called “dead right.” You might be right, but you’re still dead. It’s an important distinction!

Failure First

Edison didn’t invent a working light bulb the first try. Failure precedes success every time. EVERY TIME! There are no shortcuts.

Your reason for visiting this blog, kind reader, could be one of a legion of reasons. Maybe entertainment is all you seek. For the remainder of the crowd they are searching for answers. And answers mean you have tried and failed and are on a journey of discovery. Welcome.

Failure is the best thing that can happen to you early on. Lessons learned early provide a foundation to build on. Child actors provide ample proof early success breeds the illusion of being right. All too often it ends in tears. Sports stars by default enjoy early success followed by financial hardship a few years after their career ends.

Before we point and laugh at sports figures and child actors, we might want to look long and hard in the mirror.

Life has been beyond good for me lately. Business is good, investments are smoking hot (have you checked your index funds lately?), I’m adjusting to my newfound business growth and my writing has been honored with a nomination for two Plutus Awards. Life is great and I’m worried. Now is not the time to become complacent; now is not the time to become arrogant. There is no doubt I’m on a roll, but it is a matter of when, not if, newfound challenges will poke their head above the waterline.

You’ve experienced the same thing. Maybe a relationship is awesome. Maybe you found the job of your dreams or have reached your financial independence (FI) goal. Then life intervenes, or worse, you do something stupid. Don’t worry. We all do it. Bellying up to the bar of stupid is not an exclusive club. You are born with a membership and membership has its privileges.

And good thing!

If everything always turned up roses life would be boring and (sorry guys), but you’d be stupider than a box of dull thumbtacks.

Tragedy and Crisis

I’m writing this the night before this is published while sitting in a hotel dining area at FinCon. What an awesome opportunity! FinCon, that is. The people I get to reacquaint myself with is a great pleasure. New people grow my circle of relationships and influence.

Yet, things can go south fast. What if I don’t win the award I covet? I can feel proud of the winner and her success or I can act like an ass. Or I could hedge my bet and smile while secretly loathing. Only genuine pride for the winner is allowed. The other is the first salvo of the war against myself.

A busted beak is a tragedy and crisis.

Other tragedy can also rain on my parade. Illness, disease, or death of a loved one can mess up a sunny afternoon.

Not all problems are self-inflicted either. You can do everything right and still get crushed.

The real question is: What will you do if the big one hits? Most issues in life are minor inconveniences. However, what if the unthinkable happens and you lose it all?

Careful planning doesn’t prevent fraud or theft from destroying your best laid plans. Your business or side gig not only can fail, but a lawsuit could rob you of all you have worked so hard for decades to build. It can happen.

CNBC recently published an article where Richard Branson was asked what he’d do if he lost everything. His answer was revealing. Branson said he would review his notebooks for ideas he never had a chance to try and now try them.

What an attitude! He lost everything and his first impulse is to learn from the loss and go right back to building something important.

More important, most people probably missed the hidden message: you can’t try every idea!

Smart people know several streams of income are better than one. Successful people like Branson and Elon Must hedge their bet with the pursuit of several ideas. They also are smart enough to know some ideas, even good ones, are not realistic to attempt under the current workload.

The Winner’s Circle

Disaster is not the end unless you die. Death isn’t a bad end either. We all get it right the first time.

Failure is a grand opportunity to undertake ideas you couldn’t previously consider. There is no doubt in my mind every successful person will be right back where they are now, if you take all their stuff away, within a few years or a decade, at most. Winners know how to win! It’s like riding a bike.

The only difference between a phoenix rising from the ashes and the current superstar is the area they will excel in. Elon Musk started with PayPal and morphed into Tesla, Solar City and (who would have thought) The Boring Company. The path is different, but the path still leads to the top. Once again, winners win.

The same applies to you! Your prior losses are only learning experiences. You know what doesn’t work! People who never try don’t even know that.

Business failure is common. Some of my business ideas turned into painful lessons. I’m NOT exempt!

When Branson says he would review his old notes for new ideas he means it. He knows some of those ideas could splatter upon contact. He also knows many ideas, executed properly, are winners.

The winner’s circle is littered with people who understand the value of multiple streams of income. They also know Warren Buffet wasn’t tax on all of his billions of net worth. Most of it is unrealized gains.

What you will not find in the winner’s circle are people who never tried or people who try every idea which poked from the inside of their temples (jack of all trade, master of none). Winners understand balance.

Action Plan

The top of the food chain loves to share their story. They know there is no real competition. Your blog doesn’t compete with mine. Your tax office (even if across the street) doesn’t compete with mine. You are your own competition. Don’t screw it up!

You must work on multiple streams of income, but you don’t have to bust tail on every revenue source! Dividends, interest and rents are income streams you don’t need to handhold daily.

It’s never too late to have a plan. When I was In Costa Rica these monkeys had an awesome plan to steal our food and won often, too.

A business or side gig can contain several revenue streams within the corpus of the main business. Think of your friendly accountant. My tax practice earns revenue from tax preparation, plus bookkeeping, consulting, payroll (most of that was sold for a different revenue stream) and this blog and all its sources of revenue.

Failure WILL happen! And thank the gods that be it does. Life would suck without value lessons. Imagine how boring this blog would be if I told you story after story of all the glorious things happening in my life with nary a hic cup. First, you wouldn’t believe me and second, you wouldn’t have read this far into this post. Crap happens and it makes life worth living.

The good news is most crises are minor bumps in the rearview mirror. You can come back and relive the thrill of starting all over again, this time with a boatload of experience. It may never happen, but if it does, what a grand opportunity to try all those ideas you couldn’t shoehorn into your busy schedule.

And that is why you should, like Branson, keep a notebook of your ideas. You never know when you might need it.


Here are my working notes on this post. The idea was born weeks ago and finally breaths life. Writers might find value in where I started my writing process on this post and where it all ended up. Enjoy.


For a life of success to happen you must first expect a life of failure. Many ideas will fail even with the greatest of care taken when planning.

Richard Branson recently said in an interview, if he lost all his money he would review his notebooks for ideas he never had a chance at trying. Successful people try a lot of things and frequently fail. They also work multiple ideas at once so when one falters there are more in process to work on. It’s a lifelong commitment trying many things.

You need multiple streams of income. You WILL fail. A lot. You only need a few a few hits to do well; one home run is a life changer!

Therefore, the most optimistic thing you can do is embrace a life of failure.


Friday 27th of October 2017

In a world of participation trophies and everyone gets prizes, we don't get as many opportunities to learn from mistakes and failures. Failures made me a better athlete, student, husband, father, coach, teacher,etc. Self destruction finds weak points in ourselves and we can grow much faster by knowing our flaws. We can then fix them or outsource them. Either way we are moving forward, and value is created. Great article.


Friday 27th of October 2017

Thanks for sharing. I agree about the importance of failure. Most of us have some aversion to risk and therefore fail less than we would if we optimized every decision. I’m certenly an example of that. While many businesses fail, the most well off among us include many business owners.

Ms. Frugal Asian Finance

Friday 27th of October 2017

Thank you for the honest post! I used to feel like a failure almost every day when I was in school. But now that I have a job and a family, that thought doesn't creep into my mind that much (fortunately). I think when I'm placed in a competitive environment, I tend to compare myself to others and feel like I'm not good enough. It can be demoralizing!

Tom @ Dividends Diversify

Friday 27th of October 2017

Couldn't' agree more with the underlying premise of the post. A few old adages apply to sum up my thoughts. Don't sweat the small stuff and when one door closes another opens. Easier said than done, but still universal truths. Tom