What is The Toughest Business Decision You’ve Ever Made?

Decision, decision, decision.

As you have already known, as the company owner and CEO, the make or break of your company is determined by your decisions. You see, business decisions are like dominoes. What you’ve decided today will impact tomorrow, next week, next month and even years to come – the domino effect.

Business decisions

The problem is, not all of your decisions are the right ones. Chances are, you will make bad decisions, and that’s okay.

But what if you don’t like the impact of the decisions you’ve made? Well, you can’t just turn back time and alter your bad decisions. But, for sure, you can respond to it.

Here’s a question for you: What’s the biggest decision you’ve made – that brings you success but you somewhat regret it?

For me, I somewhat regret my decision not to enter online business arena quicker. I spend nearly five years struggling with my business service shops, only to saw it plunge into the oblivion.

The failure itself is an enormous learning experience for me. But I kind of regret it as I lose valuable time that could carry my online business a bit higher. But then, without the learning experience, I’m not sure I have the experience and hustle that I have right now. So, it’s a mixed blessing.

Here’s an example from a public figure I follow, Gary Vaynerchuk, the social media guru, the CEO of Wine Library and Vaynermedia, and a prolific investor on Uber, Twitter, Birch Box and dozens of other startups. For him, there’s one big decision he has made: Going all out in his personal branding.

Putting himself to the public creates enormous consequences, for better or worse. He was bashed a lot on the mainstream media, but raved by may (the Vayniacs and Vaynernations – informal communities of Gary Vaynerchuk’s followers.)

Gary Vaynerchuk is an accomplished businessman with great track records. Being a self-promoter can backfire as his efforts might overshadow his accomplishment. On the flip side, his personal branding efforts have helped him in securing big name clients for his Vaynermedia and other business ventures.

Again, it’s kind of a mixed blessing, but I know one thing for sure, Gary knows that he’s made the decision, and he needs to go all out with his decision.


Decisions have to be made. It’s better to take the shot and miss than not taking the shot at all.

You need to make one, good or bad, and live with the consequences while trying to do things better by making yet another decision. Rinse and repeat, and that’s how entrepreneurs and business people (should) roll 🙂

Now over to you…

What is the toughest business decision you’ve ever made? Is it a good or bad one? Do you regret it and wish that you’d take a better decision? Please share with us!