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5 Inevitable Obstacles to Success You Must Handle Wisely.

Preye Raymond is a leading content writer who enjoys a blend of pragmatism in his self-help topics.


A 10-year-old Canadian kid knew he was destined for more than just performing as a family jester. In 1972 he wrote a letter to one of his idols -Carol Burnett (host of the Carol Burnett show) to ask her for a guest appearance so that he could perform his ‘one hundred and fifty voice impressions’ on her show.

The young lad received a letter back from Burnett saying;

Unfortunately, at this time we aren't hiring children, ...Just grown-ups. But stay in school, study hard, and keep watching our show. Yours truly, Carol Burnett.'’

However, the bad news and heart-breaks were just beginning for this lad. During his pre-teen years, his father lost his job and things became extremely difficult. While in high school, the youngster and his siblings started working in a factory to support the family. His family couldn't afford rent so they eventually started living in a Volkswagen van and also in a tent.

He could no longer cope with both school and working for the factory with his family, so at age 15, he decided to drop out of school. The youngster also decided to pursue his dreams as a comedian, and he started to job-hunt for open-mic shows with the support of his father.

His first gig was at the Yuk Yuk comedy club in downtown Toronto, where he started performing his impressions. But he didn't get a good review. Even the club owner-Mark Breslin, had this to say about the young man's performance;

I can only call it ‘Bad Rich Little,’ and when the audience started to boo him, I had to put the hook around his neck and give it a yank...”

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He left the club but returned at the age of 18 with a more polished act. His stand-up performances started gaining positive attention, and soon he went from open-mic-nights at the Yuk Yuk to regular paid shows.

In 1980, he decided to take his career further by auditioning for NBC's Saturday Night Live, but he failed to pass the audition and the role was given to someone much older. After his rejection, from SNL, he took a voice-acting job on The All-Night Show and was booked as the opening act for the rock band Goddo at The Roxy Theatre in Barrie for two shows consecutively. But he failed to impress the crowd with his act and they booed him offstage. Feeling embarrassed, he refused to return for the second show.

But his failures didn't derail him from his career path. His performances at the Yuk Yuk club still brought in some positive reviews. His outstanding impression of Sammy Davis Jr at the club, earned him a front-page story on the Toronto Star magazine(two weeks after he was booed offstage) and an appraisal in the Barrie Examiner. This was the first time the young comedian received meaningful mainstream media content with praise and merit.

These top Canadian magazines further increased his fame, and he started landing huge roles in shows, televised programs, and series. In 1983, he moved to Hollywood where he began performing at The Comedy Store, landed a major role at The Duck Factory, debuted his impressionist act in The Tonight Show Starring Johnny Carson, and made several guests appearances on other popular TV shows and sitcoms.

His career and fame grew stronger that he became the first highest-paid comedian to play a lead role in the 1994 hit movie - Ace Ventura: Pet Detective. This young man’s name was Jim Carrey.

Behind every successful artist, entrepreneur, and business magnate there is always a story filled with struggle, failure, and shame.

However, most people still find it difficult to deal with the conflicts and obstacles that cross their path on their journey to success. That's why they easily give up! And think that the likes of Carrey, Bill Gates, Bezos, and so on...always had it easy because of how appealing their existing wealth and status decorate their individual lifestyle.

It is true and nearly inevitable, that everyone has their own rough patches. You have yours, I have mine. But, the critical question is-how have you utilized your challenges wisely in improving your lifestyle and choices to get you to where you actually want to be? Or have you allowed your rough beginnings to wriggle you away from your purpose? These questions creates a clear-cut distinction between a lifetime of success and a lifetime of failure.

It is not always easy to completely deal with obstacles and challenges. But it can be properly handled if we choose to accept their inevitability. There are several unpredictable obstacles life throws at us, but I found these five to be the most common;

I) The One-Man Stigma

This is always the first on the obstacle list. When starting, working alone can be a drag on your work-life balance. The ‘one-man stigma’ is inevitable and you ought to expect it and work with it till you can master your art, and acquire enough resources to build your team, employees, or fan base.

Some people pride themselves on working alone, but that's always their first mistake. People who claim they like working alone make such assertions solely because of three main reasons:

  • Not enough capital to sustain a team or hire employees.
  • The difficulty in managing people and trying to ensure they do the job properly.
  • The issue of trust, betrayal, and so on...carried out by an employee, colleague, or a business partner.

These reasons are typical and expected- You won't have enough money to hire a team of experts in your first 2-5 years of business, even those who would likely work with you might mess things up and you may have to do the extra work of teaching them more about the business. Finally, those you have trained or partnered with might eventually stab you in the back.

It is not insensitive to say that these are the natural order of things. It is perfectly normal and you need to accept it so you can handle it rationally when it happens. It is all part of the one-man stigma. But don't allow such stigma to permanently alter your mindset to think that you prefer working alone, rather than to work with people. It may not be a healthy decision in the long run.

2) Social Conditioning

Social conditioning used in this context is simply society fighting your dreams, goals, and aspirations. Honestly, handling societal forces and obstacles is one of the most difficult to handle. Breslin called Jim Carrey's impressionist debut at the Yuk Yuk a “Bad Rich Little” because, at the time, the club's audience only found jokes relating to drugs, sex, and rock stars funnier than just mere impressions.

It is always a hard sell trying to convince a group or faction of people to accept an idea that they are not used to, especially if such idea deviates from common beliefs, norms, and behavior, excluding laws (nobody should be involved in ideas that goes against the law).

You can't completely eliminate the complexness associated with social conditioning (you may die trying), but you can use it to your advantage. For example, using what the public enjoys the most- ‘Propaganda’. I discussed more on social conditioning and the use of propaganda in this post.

3) Emotional Anchors

These are the naysayers for your ideas. They quench your enthusiasm and passion for a new project or a new business by feeding your emotions with a thousand reasons why your idea will suck!

Emotional anchors don't come from society or the general public, but from your inner circle (family and friends). We can be fortunate enough to have one or two supportive partners, friends, and family members, but the majority of people we relate with will always play the black sheep, especially if you are the social and friendly type.

The best and only way to handle emotional anchors is to distance yourself from them.But not in a toxic or obvious manner, but a mature manner. If it is difficult distancing yourself from them because of how close and dear they are to you, then another reasonable option is to stop telling them about your plans or ideas. Always keep them wondering.

4) Depression from Delayed Gratification

This is the period of shame, struggle, and pain. For those who are not familiar with the concept, delayed gratification is simply: putting off something fun or pleasurable now, to gain something more rewarding or beneficial in the long term.

As humans, we are naturally drawn to things that are pleasurable or mildly exciting. But on the road to success, engaging in numerous pleasurable activities can distract and mislead your decisions and choices, that is why delayed gratification is normally employed as a form of self-discipline to help us stay on the right track.

Delayed gratification is not the constraint to be wary of, it is the depression that comes with it. Self-control on pleasure and ‘fun’, can be quite boring, and it comes with a bunch of frustrations, particularly when you keep trying and failing, or getting little results.

This is the stage where most people get depressed, relapse, or quit with the hopes of doing something more fun or interesting than what they are currently doing. But the sad news is-nothing is fun, every aspect of life requires working hard and working smart to succeed.

Even being a criminal or drug lord is not easy. Criminologists and experts who study, and research criminal cases are often amazed by the intelligence and strategies most criminals utilize in pulling off a master plan. The most wanted fugitives sometimes take years to come up with a grand plan to carry out a criminal act and to evade the law.

The only way to deal with the depression that comes with delayed gratification, is to fall in love with the processes of delayed gratification (the boredom, frustrations, etc...) so you can come out successful, and also maintain your achievement streak.

5) Creativity Block

It is inevitable to run out of ideas, even though you have the highest IQ or spatial intelligence. However, there are practical ways to stimulate your creative process when encountering a creative rut, I talked more about that in this post.

Creativity is one great benefit of working with a team and also having a solid research system aside from your normal work process. Even as a writer I depend on blogs, books, content, and studies to curate my topics.

Creativity is about recycling what has been done or said before in a unique way. Most people (including me) adopt the mainstream thought that- being creative is “thinking outside the box”. But from my experience as a creative writer, I have found that statement to be incomplete.

The complete statement should be: thinking outside the box, with the knowledge you’ve taken from others in the past or in the present. According to David Bowie;

“The only art I’ll ever study is stuff that I can steal from.”

If you enjoyed reading this article you can mail your comments, thoughts, questions and concerns to-

This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.

© 2021 Preye Raymond

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