How to Earn an Oversized Income From Your Foolish Mistakes

Hint: There is no such thing as a “foolish mistake.”

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At some point you are going to get desperate. During your desperation, you will get smart. As you get smart, you will subconsciously create opportunities to problem-solve and, ultimately, excel.

Personal growth is, in large part, a matter of making mistakes and learning from them. Overcoming obstacles is dependent on enacting specific strategies, now that you know better, so you never again have to stare down the rabbit hole of negative repercussions.

But … if you are not motivated, such success will elude you.

For as long as you are human, mistakes are inevitable. I do not mean to pander with that statement; consider the words a reminder. It is how you act upon those mistakes once you smarten up, however, that will make the difference between falling further and enlightenment. Whether you are financially unstable, having difficulty keeping a family together, or you simply have writer’s block, channeling your mistakes as building blocks to a thriving future is one of our greatest natural tools.


“I wish I did things differently back then.” — You cannot take back time.

“If only I knew then what I know now.” — You cannot take back time.

“I can’t believe I was so stupid.” — You cannot take back time.

“Regret” — You cannot take back time.

See a pattern here?


During a particularly dry period as a writer a close friend had little choice but to search for outside work. He was married, and his wife was out of work due to a baby on the way. My friend took a job as a real estate broker, which he later admitted was “the single biggest mistake I had ever made.”

He had developed a close friendship with the company’s three owners, who rewarded him with his own office and the finest leads. My friend, however, was not skilled in the real estate arena, and he soon found himself in massive debt to the tune of $200,000. The job was commission only, and though my friend was a good opener, he was not a closer. The company owners did not care; they had told him that he was building new leads that would soon pay off. Unlike my friend’s wife, who had saved substantial money but nonetheless had been burning through it due to the pending arrival of their first child, my friend had no such savings, preferring to live the life of an “on the edge novelist.” He did not believe in being comfortable, a situation of which I knew all too well.

When he finally quit, my friend realized that he could not collect unemployment as he was not fired. The baby was due in a month and the couple was by now out of money. He pawned his more valuable and valued wares at a local pawn shop, which was enough to keep their mortgage paid for three months.

Three months came and went. My friend’s wife had no one she could ask for money, as she was estranged from her only relative, her brother, and so my friend began borrowing. Their debt ballooned to $250,000. He deliberately made payment arrangements he knew he could not keep to hold off his creditors. His credit tanked, and as she was a co-signer on the house deed his wife’s did as well.

The couple separated, and eventually they lost the house. My friend’s wife reconciled with her brother, and my friend lived on the street for three months with no child visitation rights.

He pleaded with his wife and her brother to give him “one more chance.” My friend explained that the pressure to find a job led him to the wrong place of employment, and his well-intentioned loyality — as his bosses treated him with respect — kept him there. He swore he would never be so “stupid” again and would only look for work that suited his skills.

His wife did not accept his pleas, considering them little more than “cheap talk.”

And then … my friend got smart.


My friend first contemplated why he was such a loyal employee, who did not leave when he could have, and then switched his thinking to “My loyalty is a virtue.” He realized he was loyal to his wife, and his new child, and he would not allow his mistakes to be anything other than an opportunity.

That was the first step.

He no longer fought his wife when she brought up “no child visitation for six months.” He took the opportunity to find a new job — working at a credit repair company of which he would also be a client. He performed due diligence on the company first, then set his interview. He was far more motivated to earn a substantial income this time around than to bemoan the fact that he had to find a job outside of his passion.

And so he did. He wrote early in the morning and at night, though, using his work as samples and attaining two projects in the process by answering Craigslist ads.

He then hired a financial advisor, and 10% of his income was invested each pay period.

At the end of the six months, he sent his wife a pdf of his bank statement, along with an email spelling out his plans for the future and how he truly learned from his mistakes.

They have since reconciled, and are in business together. He still works at the credit repair company, but he and his wife now travel around the country on his vacation time, with their now 11-year-old boy, discussing their inspirational story and helping others in the process.


My friend did not create an “oversized income” despite making mistakes. He created an oversized income by becoming smart because of his mistakes. He was motivated. We can all play a game of hypotheticals: If he did not have a child on the way or if he was single, perhaps he would not have been motivated to find a job while commencing what has become a now-thriving writing career.

One cannot live in hypotheticals, however.

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Joel Eisenberg is an award-winning author, screenwriter, and producer. The Oscar in the profile pic isn’t his but he’s scheming. WGA and Pen America member.

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