How many times have you told yourself it’s going to work out? From a business transaction to a relationship? You think your optimism and hope will somehow miraculously overcome objective reality. You see memes on social media telling you to keep going. Heck, I tell people if you can get through the other side it will be okay. But the thing I DON’T say is that it will work out.

Getting through a difficult relationship or failed business venture are life obstacles. You will be okay. As long as you are on the planet you will survive life’s many curve balls thrown at you.

But our collective irrational optimism is what more than likely caused the failure. Our own internal inability to give up actually makes it worse.  The societal pressures of failure are so extreme that we are blinded by our own unchecked optimism.

When I was in high school I was the class President and honored to be able to give a speech at commencement and I ended with a quote from Winston Churchill. “Never, Never, never quit”. That was actually paraphrasing him. He actually said “never give in”. I was a seventeen year old naive teenager who had already overcome a lot and was on my way to college. Even though I was told I would be dead or in jail, I made it past what many believed was an inevitable early end. My view of the world and understanding of how the universe worked was still developing.

I still stand by what Winston Churchill said and my paraphrasing. His speech was also a commencement speech and he was really speaking to his country, and the world about fighting Hitler and the Nazi regime. He was trying to literally rally the troops. But, in war and in life many times in order to win. We need to retreat. We need to step back, look at the entire picture and rationally think about our reality.

Things aren’t just going to work out because you saw some motivational speaker on TiKTok tell you so.  Some random quote by an unknown person on Instagram is not what you should cling on to.  These huckster charlatans selling rainbows and unicorns are selling a fallacy.  They sell hope.  They sell fear and they sell unrealistic expectations.  Failure can be a permanent thing or temporary.  It all depends on how you decide to look at it.  I always tell people I’ve never failed at anything.  But I have lost BIG many times because I was not an objective realist.

How do I know this? I’ve lost more than I’ve succeeded. When I objectively look at my losses. I could have avoided all of them. As an entrepreneur we always have to have optimism. But, what becomes dangerous is our unyielding perseverance to never, never, never give up. It’s not honorable to not acknowledge that you are about to hit an iceberg and hit it because you think you are unsinkable. Your life isn’t a movie that will just work out. The reality is, you will have to change course almost daily. You will have to evaluate your business and relationships often in order for them to be successful.

Sometimes you will have to fold even if you have the best hand. Many times in order to succeed we have to sit out a few games or fold even the winning hand because you know that what’s next could destroy you. In fact Churchill went on to say “-never give in UNLESS to convictions of honour and good sense”. This part of his actual speech is what I’m trying to drive home. Churchill also said “I’m addressing myself”, he was not only speaking to the students at the commencement speech and the world but also to himself.  Even one of the greatest leaders in modern history needed to remind himself to always look at each situation with objective realism.

We’ve all heard this one, it’s not the battle it’s the war. Sun Tzu said in The Art of War. “If you know the enemy and know yourself, you need not fear the result of a hundred battles. If you know yourself but not the enemy, for every victory gained you will suffer defeat. If you know neither the enemy nor yourself, you will succumb in every battle.”

There is so much to deconstruct from this quote originally published in the 5th century BC. But if you don’t know yourself. If you can’t self-evaluate you will most likely lose. If you know yourself but can’t be objective with understanding the enemy, your wins could actually be losses. In other words you got lucky. You didn’t really evaluate the entire picture but you still won. That is not sustainable.

If you have followed me and read my columns throughout the years.  I am a very optimistic person.  Optimism I believe is a necessary element of happiness and success.  But like anything in life, too much of it can bring you down.  Have hope but be realistic, be optimistic about the future but constantly evaluate yourself and situations.  Don’t be afraid to retreat if necessary in order to avoid a loss.  And as one of my favorite rappers Ice Cube said.  “Check yo’ self before you wreck yo’ self.”


Michael Alden, a graduate of Suffolk Law School and a three-time Wall Street Journal and USA Today Best Seller, is from Beverly, MA.  He has contributed to Forbes, Huffington Post, CNBC and, Entrepreneur, and was awarded Boston’s 40 Under 40 Award.  To learn more about Michael Alden, visit here. You can also find him on Facebook, Twitter, Instagram and Snapchat @MikeAlden2012