Never Be Afraid to Fail

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success versus failureThat dirty little word that everyone hates is going to come up a lot in this post.  Failure!  That is right, the word that so many are afraid to think about because of what can happen.  How do you handle failure?  Do you dislike the thought of it or do you embrace it?  For those that don’t know me very well, I am the type of person that likes to give it to you straight.  Look at my post last week about how credit cards are not evil.  Some may not like how I deliver my message, but it seems to resonate with others.  I am OK with that. I have always enjoyed people that don’t beat around the bush.  I am a no BS kind of man.  I am about to lay down some more truth today!

Failure Sucks

Don’t get me wrong, there is nothing fun about failing at something.  No matter what you are trying to accomplish, failure doesn’t feel great. I have never met anyone that goes out and strives to fail. That type of mentality wouldn’t get you far.  There are really two types of people when it comes to failure.  Those that embrace it and learn from their failures and those who are so afraid to fail that they never try to succeed.  I am one that embraces failure.  I don’t like failing, but I understand that I will many times in my life.  The key take away is to move on from it.  Failure sucks, but you don’t get to succeed unless you try!

Let Failure Motivate You

I can’t even count all of the ways that I have tried to make money over the years.  I have been a part of a few get rich quick schemes.  Those failed miserably.  I have tried to sell wholesale items on eBay.  I have tried many different businesses as a kid.  My mind is always about being an entrepreneur.  While not full time, I get my kicks out of earning side income.  I thrive on it, but I sure have failed numerous times in the past.

What makes me different than some is I continue to strive to succeed. If one failed venture gets me down, I learn from my mistakes and I try again.  I created and ran 15 other blogs before I did it right with Debt Roundup.  I ran two other consulting companies before I got it right with my current one.  I have failed. I will continue to fail. I will continue to get up, dust myself off, and get back on the damn horse.

I am fully motivated by my previous failures.  I have had quite a few, but I never let them get me down. Yes, I might step back for a bit and let the realization that I failed sink in, but I never just stop striving for more.  When you quit because you can’t handle failure, then you will never be the type of person that succeeds in making more money.  You need to be a go-getter. You need to be a hustler, baby!  Making money is all about willingness to try new things.  People make money by being different.  They make money by providing something other people are willing to pay for.  They also work hard to stand out from the crowd.  That is how you make more money.

Let Failure Guide You

Before I start running through this one, let me stop and give you a definition of insanity by our good friend Einstein.

doing the same thing over and over again and expecting different results.

There are some that continue to fail at the same thing, but try it again hoping for a different result. That is insane.  You need to let your failures guide you.  Let them help you tweak your system.  If you don’t take the time to learn from your previous failures, then you will never find the path toward success.  Success is only achieved by constantly learning how to better yourself and your process.  If you just follow the same path, then you will end up knocking on failure’s door each and every time.  Making extra money is not easy, nor is it quick.  It takes time and energy to achieve. It takes the drive to make whatever venture successful. It also takes guts to get over the failures and keep on going.  If you aren’t learning from failure, then you aren’t doing it right!  Failure should be embraced, but never accepted.


What do you think of failure?  Do you think it is necessary to fail before you can truly understand how to succeed?


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  1. I think that failure is often what defines a person. However, I honestly believe that imaginary failure is far worse than any actual failure we ever encounter. Basically, like you said, fear is far too often a deterrent…but it’s more the fear of the unknown than the actual failure. For me, that unknown fear is what kept me down for so long…and still at times. Always a learning process though.

    I loved this post, so much of my growing up was with a quote based on this theory! Thanks for sharing!
    Jacquelyn recently posted…Black HoleMy Profile

  2. Failure is scary but it happens to the best of us. I have failed many times in my life but found myself on my feet over and over again. I have learned so much from my failures and have been able to change things because of it.

    I still hold myself back somewhat for fear to fail, but I’m learning slowly that if I don’t try I will never find out if I would succeed. Failure is scary but I also don’t want to keep saying to myself “what if”
    Aldo @ MDN recently posted…Asset Allocation – Where Do I Invest My Money?My Profile

  3. Great message! I have been one of those people that have been paralyzed by fear before. I learned that it was getting me no where, fast. You’re going to be living with a lot of regrets and “what ifs?” if you never put yourself out there and try. Most of the time, the worst case scenario is not going to happen, and you’ll feel better for it! Maybe you should add “motivational speaker” to your side hustles, Grayson =).
    E.M. recently posted…Choose Wealth! Be A Millionaire By Midlife: A ReviewMy Profile

  4. Nice one sir! While failure is generally never fun, I find it often provides the best learning opportunities. I like to take those things I’ve learned and use them to push me to succeed next time. It can be easy to just not try things because of fear of failure, but you’ll just spin your wheels and get nowhere as you said.
    John recently posted…What’s Keeping You From Chasing Your Dreams?My Profile

  5. Hi Grayson, great article. I’m a big believer in what you say, although it’s taken me a long time to shake the fear of failure, and to embrace trying new things along with the possibility of failing (perhaps the school grading systems stuck very hard with me!). It’s a challenging thing to train yourself to go ‘towards’ the fear, rather than hide comfortably from it, but it always seems to make life better when you embrace it, regardless of the outcome.

    I’ve definitely learned a tremendous amount from some of my biggest investment mistakes, which has dramatically changed my behaviours and attitudes as an investor. Of course at the time I always wish it hadn’t happened, but I wouldn’t be who and where I am today without these mistakes (or perhaps we’ll just call them ‘experiences’!).
    Jason @ Islands of Investing recently posted…What’s a ‘P/E ratio’? (Part 3) – Potential pitfalls and a real life exampleMy Profile


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