Kevin O’Leary: Why Early Retirement Doesn’t Work

Updated : Sep 11, 2019 in Articles

Kevin O’Leary: Why Early Retirement Doesn’t Work

This whole idea of financial independence retire early doesn’t work. Let me tell you why. It happened to me. On the sale of my
first company, I achieved great liquidity and I
thought to myself, “Hey. I’m 36. I can retire now.” I retired for three years. I was bored out of my mind. Working is not
just about money. People don’t understand this very
often until they stop working. Work defines who you are. It provides a place where
you’re social with people. It gives you interaction with people
all day long in an interesting way. It even helps you live longer
and is very, very good for brain health. Staying stimulated is how people
live into their 90s. I’m not kidding. So when am I retiring? Never. Never. I don’t know where I’m going
after I’m dead, but I’ll be working when I get there too.


  • It's a a great advice by Kevin O Leary working on something that stimulate you constantly never bring you down. You always find the purpose whenever you are down and enable you to rejuvenate time after whenever situation arises and demand in different period of your life time. 🌠✨

  • This is the stupidest idea I’ve ever heard. Only people with the most interesting job in the world or the most boring outside life in the world could possibly think this is good advice.

  • this is so true, anyone who disagrees does not have the experience. i am 34 self-made trader and i only have to work part-time and it gets boring, you can't just spend money all the time going out to do stuff.

  • I’ll just say this
    People should strive to retire from the rat race early, not the workforce
    You should still work to keep adding value to society and to yourself as well
    Work part time for a year, go on a month vacation and repeat.
    You’ll enjoy your free time more this way. START A BUSINESS!!!

  • Misses the point (as many financial experts do) yet again. FIRE does not mean ending work, it means ending required work.

  • The funny thing is motivated driven people who usually have the ability to retire early don’t want to While lazy bums Who would love to retire early and do nothing don’t have that option it’s a catch 22 lol

  • I've yet to disagree with anything this man says. He's right. Retire to what? Canada should elect him PM. He serves up truth succinctly and cold-just the way I like it…

  • The Goal of FIRE is not to stop working and laying around all day watching TV. The goal is the flexibility to work on what you want, when you want, with whom you want. I strive for it, because I'd like to have my necessities covered so I can take time off 1-2 months out of the year, and enjoy the holidays with my family. There is no way I will stop working, I love to work, but I don't want to feel panicked if I take more vacation than my paid vacation days.

    Of course FIRE means different things for everyone, but Mr. Wonderful totally missed the point.

  • Ahhhh a middle aged white male not understanding FIRE. Go figure. Had he not been given passes and chances under the table all his life he’d be singing a different song. But of course, all of that is undocumented so he can play the “self-made” card all day.
    FIRE is about making work OPTIONAL so that you don’t have some incompetent middle manager holding your job over your head the rest of your life. I achieved it 4 years ago and have no need or desire to return to the workplace.

  • I thought he was gonna say inflation. That being said, I figured if you have the money to retire, doesn't that mean you can do things? Like fun things? Cruise line? Travel? Things like that.

  • It's no surprise to me that he doesn't seem see the subtle difference between "having to work" and "working by chance", because it really doesn't make much of a difference to hard-working people, since they'd take on a job whether they're interested in it or not, as long as it gets them in the workplace.

  • This video actually proves the point of FIRE. Mr. O'Leary proved it himself on a much larger (unicorn) type of scale, lol. Save and invest (he invested in his own business), build equity, stay focused so when you want to move on to something else you are covered.

    I would say $3.7 billion from Hasbro was a nice buffer for him (much respect), to do what ever he wants, when he wants, with who he wants too…lol. Love Shark Tank!

    Also, working until you die is super awesome, if that is what you see making you happy. How nice is it to have that option though 🙂 , what if you change your mind later? O'Leary is good. If he decides he doesn't want to do Shark Tank anymore tomorrow, he doesn't have to. That's the point.

    Thanks for proving FIRE!

  • Wrong Kevin. It's not having to work a 9-5 at a job you hate with people you hate working with until you die. Instead, financial independence means you can pursue other passions such as opening a bake shop, wood crafting business, or home remodeling business without having the stress and worry of making ends meet.

  • This is a great point, but just because you got bored, doesn't mean that it doesn't work for everybody. Take a look at

  • Kevin, what you may not realize, is that automation may make a ton of jobs obsolete. Say you finish school at 22 and get a job in an industry, work in it until your 40s, and then the industry dies, you are out of work due to being replaced by robots. You are not old enough to collect CPP/OAS in Canada or Social Security in the US for another 15-20 years. What gives? How are you surviving with $0 income for decades?

  • I'm just getting spun up on what F.I.R.E. represents and by the way I love Shark Tank and Mr. Wonderful. He spoke to the Retire Early aspect of F.I.R.E., which I believe he is correct. The description of this video, as written, provides a slant that would allow one to believe that Mr. Wonderful is saying that F.I.R.E does not work. Bad Media!!!

  • Fire is about having the freedom to pursue your interests. If that's working till you're dead, you have that freedom but it's not a requirement. FIRE went completely over his head.

  • Work inherently has stress. People who handle them well do not believe in FIRE because they have coped well. However, people who cant handle work stress well aspire to FIRE. In their minds, they can work do what they like, be stress free and earn money. It's unfortunately a mirage.

  • I retired at 54….wasn't rich but had enough to live on with a small farm…put on 30 lbs in 3 months…so I went back to work…he's right!!!

  • This coming from a businessman… don’t quit your job folks!

    Not everyone gets bored so easily, maybe you are just a boring person then.

  • people always need a purpose , that's it . somebody find it in business , jobs or any other passion and somebody find it in religion or philosophy .

  • this movement went right over his head.. it's about retiring early so you can do the things you Really want to work on. not because you Have to work

  • FIRE just allows you to do exactly what you want to do. If Kevin wants to work for his life, its his prerogative. Not everyone wants what he does.

  • Once you obtain a certain level of wealth, u want to help others and change the world. Its not about money at that point.

  • But video games are work, they are desirable work. There are different kinds of people some who enjoy work and the social status that comes with it and some like being beach bums. You can still retire and just work on personal projects such as books, indie games and videos, or selling handmade things online and just become a handy man and gardener at your house and help out your community and town at events and planning.

  • nobody said it's about stop doing things …. it's about having the freedom to start doing the ones you really want and are interested in.

  • The point was to retire from boring monotonous work and pursue something you love. If your job happens to be your passion, then jackpot.

  • I'm pretty sure most jobs offer vacations days, but there is a limit to how many days you get to relax though.

  • Financial independence is more about independence from corporate America. You can become a park ranger, or a birthday clown once you are financially free. I ma personally planning to go back to school for a PhD in history once I am Financially independent.

  • Yep, he misses the point. If you can live off the 4% (or 5%, etc) rule and make $20-30k doing whatever you want, that is freedom. The public should think of it as the FI (Financially Independent) movement, instead of FIRE. Eliminate the "Retirement Early". Instead focus on having enough… so you can work and do whatever you want. And the money you make, may be less, but you're waking up everyday the way you want to knowing you have enough investments to withdraw from.

  • That's a problem if you don't know where you're going after you die. That's probably the reason why you say at the beginning that work defines who you are. If you believe in God you know what defines you and you also know where you are going when you die. The greatest things i love doing pay very little or anything at all, but are still very meaningful to myself and others and can fall under FIRE

  • 'Work definies who you are'
    Interesting that the fillowing Images weren't of people picking up garbage or scrubbing toilettes.. 😉

  • Hey. I am quite content to play computer games and watch movies all day long. If you NEED to work to enjoy life, maybe it's because you haven't found any pursuits outside of work that bring you joy?

  • These big shots are against FIRE because they lose power and wealth. FIRE people usually lean on the minimalist side and will not waste money on junk most corporations push on us. On the power side many people will be quitting corporate jobs and therefore will not have control over a growing segment of the population.

    It is this losing control aspect that really scares the elites. As long as the masses keep their noses to the grindstone and do as they are told everything will be fine. Secret societies are formed just for the purpose of controlling people let’s not forget that

  • Kevin
    I can’t agree with you more
    I am around your age and still working in the emergency room as an ER doctor. I recognize works value on my mental health, social interactions as well as physical health
    After my 12 hour shifts I go work out in a gym-and consider myself blessed to be able to continue this lifestyle. I am with you
    after I’m gone maybe we can meet up and start a business up there

    Phillip Silverstein

  • Wonder how many factory jobs he worked. And as previously stated…you can still work, but do it somewhere you want to be.

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