Why the Hardest Time of Kevin O'Leary's Life was Going on Vacation

After selling his first business, Kevin O'Leary made one decision he's always regretted.

Get social with Inc. on:

[thanks]

"Worked so hard forgot how to vacation."
-Kevin O'Leary

[robertgray]

He is so right when he says "for an entrepreneur, when you cannot compete its like jail."

[kalMHe]

Did I just see the ISLAND OF MALTA in the back ground ?! Wow...this Made me miss Malta again !!

[Ryan-jxvh]

When you have access to unlimited leisure time it becomes mundane. You need the contrast.

[puppy-and-me]

I understand what he means. Its like when bodybuilders need to take time off from their training. When what you do makes you feel so good, you can't fathom taking yourself away from it.

[MichaelDeLaRosa]

Totally feel him, as an athlete when you take an unexpected vacation. You lose the days to better yourself

[sterlthepearl]

"If you never worked again you would be completely unfulfilled". Tony Robbins

[toprightchannel]

Uplifting character. If your mind is used to working at a certain pace a vacation is unpleasant, there's not enough stimulus to keep your spirit going.

[manictiger]

I totally get it.
Asking me to not be there for the opening bell of the stock market is like asking me to hammer a nail into my hand.

[eamonnobearra]

Totally relate, currently stuck in Cleveland for the past three weeks. I appreciate being with my family but all I can think about is the progress I am losing out Back home to Galway, Ireland on Friday >:)

[PrestigeNumismatics]

Picture at 0:35 is Kyrenia harbour in Northern Cyprus. I used to live there.

[metalfingers]

Mattel's acquisition of The Learning Company has been referred to as "one of the worst acquisitions of all time". Kevin wanted to re-acquire TLC from Mattel. Please Mattel lost as much as 3.6 Billion dollars as soon as it acquired TLC for 4.2 Billion dollars. Making a deal with Kevin is like making a deal with the Devil.

[advocatusdiaboli]

I had this feeling when I quit my job to study. It was the most horribly thing.

[RogerDiotte]

First mistake...Beach...I've never been to one for a vacation, but then again I live beside Lake Superior. However my rule is to see as much as I can where I live which is Canada...I go West to BC and it's never the same each time I go...Amazing and you don't SIT.

[nebojsa]

Maybe I'm not from this planet. When I work I feel like I'm in jail. When I go on vacation, I'm a new man. I start living life. I see work life as fake life and not working, going to nature, visit other countries I see as real life.

[henrygarner]

Interesting thoughts. I like his viewpoint.

[Erinswain]

36 months is a long time to have to not do what you love. He loves business and being productive. That’s what he’s saying. I get it.

[Omar_Facio]

this is my "fear" although its a stupid way to use the word fear. If I become motivated to become a hard working entrepreneur and make it big (which, of course, is in no way easy) so I could have a life of rich luxury and travel, in order to get there I'd have to make some pretty big mentality changes and by the time I get there, I'd have changed so much I wouldn't even want my original wants anymore and instead my brain would be stuck on work mode 24/7 and would feel anxiety over being on vacation because of all the time being "wasted." Cause time is money!

[kingraiderr]

Why is he using a laptop from the silent era ?

[RobGravelle]

Every time I go on vacation I'm climbing the walls for the first 3 days.