What’s Luck Got to do With It?

In a recent post by my buddy @jamesoliverjr, founder of WeMontage, he asked if successful entrepreneurs are just lucky. He concluded success boils down to luck, and he is not alone.

From a distance, some success stories defy logic, but a consistent pattern emerges upon closer examination. This is true for a number of successful entrepreneurs and peak performers of all types.


photo credit: wilhei55 via photopin cc

Let’s see if we can uncover this mystery by dissecting one of these “lucky” individuals. For this experiment, Bill Gates is the perfect specimen.

So, what is the pattern?


Many talk about following your passion but the ultra successful have something closer to obsession. To understand the difference, study the lyrics of the 1980s hit “Every Breath You Take” by The Police:

Every breath you take

And every move you make

Every bond you break, every step you take

I’ll be watching you


Every single day

And every word you say

Every game you play, every night you stay

I’ll be watching you


Oh can’t you see

You belong to me

How my poor heart aches

With every step you take…


Clearly, this guy needs a restraining order.

A passion is something you love but can do without, while an obsession is something you have to have now and will do almost anything to get. The word obsession carries a negative connotation, but how else would you describe someone like Gates? Judge for yourself.

In interviews, Gates describes his early exposure to programming and how he coded for up to twenty to thirty hours a week in his early teens. While his parents slept, he would sneak out in the middle of the night to code at a nearby university. The fact he did not have permission to use the university computers was not enough to stop him. He needed to code. By the time he was seventeen, Gates logged thousands of hours of programming experience. This during a time when few others had access to computers at all.

Passion? This behavior sounds like something much stronger and puts the next trait on autopilot.

Insane Effort

This is not ordinary effort but painstaking, tedious work that would make most people want to yank their eyeballs out. You would think this obsessed group has a special contract with the universe granting them 30 hours in a day. The difference is they steal time where others kill it. Instead of playing Farmville while standing in line at the DMV, they read, research, plan and write. They start the day hours before everyone else and stay up long after their friends enter dreamland.

Quick Action

An obsession is difficult to hide, because the obsessed become so consumed in the activity. If the need arises for someone with his or her skills, everyone knows whom to call.

This happened with Gates during his senior year of high school when he was asked to work on a project with TRW. He jumped at the opportunity to further pursue his obsession. He spent the spring coding under the tutelage of a much older and seasoned programmer, like the young padawan Sky Walker learning at the feet of Yoda.

Surely, those around him marveled over his stroke of “luck,” but he was not lucky. He was ready!

When opportunities come along, there is no need for the obsessed to get ready or prepare. Preparation happens years in advance.


Though this group is anything but balanced, they recognize the need to have others around them who are. Gates started Microsoft with Paul Allen, who was three years older and more mature. He later hired his friend Steve Ballmer to manage the business side of Microsoft. Would Gates have been as successful without his team of balancers? We can never know for sure, but I doubt it.

What’s Luck Got to do With It?

Even Gates describes himself as lucky because of the access he had to computers, but his small group of piers had the same access. What they lacked was the obsession.

We can all learn a lot by studying the lives of the so-called “lucky” instead of attributing their success to the alignment of the planets. Then, we need to analyze ourselves to see how we measure up.

If your obsession involves standing outside of Macy’s for hours watching the girl at the counter, seek professional help. If it is a skill or talent with the potential to provide value or solve problems, go for it. But find some strong personalities who can pull your head out of the weeds and provide you with a balanced focus.

Godspeed and I look forward to seeing you in The Players Lounge.

What do you think, is success dependent on luck, or the right sequence of actions? Please leave your comments below!

Derrick Jones
Derrick Jones is a former Marine, serial entrepreneur of three tech start-ups and author of "Presidents, Pilots & Entrepreneurs - Lessons from the Trenches for the Everyday Entrepreneur." In his book, he chronicles what he calls the good, the bad and the ugly of entrepreneurship with key lessons for beginning entrepreneurs. He is a regular speaker at schools and trade organization on the subjects of entrepreneurship, leadership and technology. He mentors aspiring entrepreneurs on his own time and through his volunteer work with SCORE. He also shares his experiences on his blog www.PresidentsPilotsEntrepreneurs.com.
Derrick Jones

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  1. Daniel Hebert says:

    Love this post Derrick! I'm with you on this one – I don't really believe in luck when it comes to success. Luck is something that's involved when you gamble – an obsession/skill is not a gamble, it's something you work hard at.

    Did you ready the Outliers by Malcolm Gladwell? He used Bill Gates as an example, but in a different context. He mentioned that Bill Gates (along with other successful programers) were all born within a certain timeframe, which presented them with the right opportunities for becoming successful. The difference between Gates and other non-successful programers was the ability for Gates to recognize the opportunity, and become obsessed with it – which allowed him to get his 10,000 hours of practice (hours necessary to develop an expertise) earlier than most of his colleagues. It wasn't luck that made Gates successful, but an obsession, and an ability to recognize opportunities. :)

    • djoneslucid says:

      Yep, I love that book. I went back to it while working on this post to get specific references. As part of my research and why I took longer to post (sorry DJ), I studied the clinical differences between passion and obsession. Obsession can be pretty dangerous and scary, but in the right context with the right team, it can be phenomenal. Obsessives like Gates eventually mature and move on to other endeavors, but I'll bet he still codes just for fun in the wee hours of the night.

  2. djoneslucid says:

    Oh, in case anyone is wondering, I asked James if it was okay for me to write a response to his post. We both thought it would be a good idea to get cross conversation going.

  3. rayhiltz says:

    Enjoyed this post also. I think a lot about what makes someone a success. Leaving the definition of success aside, I believe that obsession is the driver that permits people to take advantage of the time and space they're born into and blaze the trail of innovation.
    This happens not only to the Jobs and Gates of the world but also people driven to help others with practically zero resources.

    • djoneslucid says:

      So true. Think of other peak performers. Championship boxer Floyd Mayweather is a great example. He grew up in a boxing family and started training at a very young age. What's unique about him is that he trains year around and does not drink or do drugs during his off period. Even though he clubs, he always leaves before everyone else and gets up at 2am to run. The guy is a maniac with his craft!

  4. Obsession…..its not just a cologne that makes you think of the 80's. Love this post, and I totally believe that obsession is the driver that will put you in a position to reach the "lucky" state. I feel as if, without obsession, luck wouldn't stand have a chance to be a topic worth discussing.

    • djoneslucid says:

      Without it there would be almost no luck at all because the opportunities will not come. Gates was asked to work on the TRW project because of his obsession. No one else was qualified to be that "lucky."

  5. Great job Derrick, I completely agree with the sentiment in this post. Personally, I believe luck is the result of consistent hard work. If you keep at it in a manner described in your post, never letting up and staying "with it" luck appears in the form of an opportunity. That opportunity would not be there if one gave up, sure more work hard all their lives and never realize the level of success that say Gates has, but, now we are into gauging ones definition of success. Great thought provoking post, love it…

  6. James Oliver, Jr. says:

    Actually, I believe my conclusion was not that success boiled down to luck in a vacuum; it also assumed things like hard work, dedication, focus, preparation etc., were required. I also loved the comment someone made at my post, which is alluded to here, about the importance of timing. Good timing is critical.

    For example, when I tried to launch my lifestyle magazine for Black golf enthusiasts called, Seven Under, back in 2005, the final iteration of my business plan called for digital distribution of the publication, which drastically reduced printing and mailing costs from a significant percentage of sales to zero! (Here's a link to a post about another key reason the magazine never launched, desperation: http://www.bespokesolutionsllc.com/desperation-ca

    However, a career magazine person who was advising a potential investor shot down my business plan as completely untenable. Meanwhile, a few months ago (7 years later) I read Newsweek was no longer publishing print editions of their publication.

    The point is, while I recognized the obvious inherent economic benefits of dramatically altering the mainstream idea of what a magazine business model was supposed to be back then, my timing was way off (i.e., I was way ahead of my time with that distribution strategy).

    I do find it a little incredulous to use Bill Gates, one the richest men in the world, as an example here though. In my view, to do so implies that if you're passionate, obsessive, OCD, well-timed, focused, etc., you will necessarily enjoy the pinnacle of success. Seems like a stretch to me.

    I admit I'm a little cynical. But that's my two cents.

    • djoneslucid says:

      I dig your wit lol. The question about luck was related to entrepreneurs themselves, not their individual ventures. Gates failed his first time out. His first company was Traf-O-Data, and he took what he learned from that failure and started Microsoft. In your list of attributes, you missed the most important one: seeking balance by assembling a strong team.

      To say Gates is a bad example implies he has some sort of special powers or, well, "luck." And this is why I used him as my example. So many think he was just lucking or in the right place at the right time. But fail to realize he was deep in the grind for years and years pursuing an obsession that turned out to be pretty useful and valuable to world.

      I won't dispute that timing plays a role but Gates also experienced bad timing with Traf-O-Data. Yet, he kept going because the obsession drove him to. He had the good sense to know Traf-O-Data was finished but he knew there was something else. Plus he stuck with what he was best at and was the most obsessed with. It drove him to work at a blistering pace for hours on end.

      So the real lesson is to find what you do better than anyone else, become the best at it, assemble a team of strong individuals, toss it if it isn't working, then rinse and repeat.

  7. djthistle says:

    "Clearly, this guy needs a restraining order." – I chuckled and then said to myself: This is going to be a good post. :)

    I like how you put it as Insane Effort. It's not just working hard. It's taking it to a new level. It's above and beyond.

    Good stuff Derrick.

  8. djoneslucid says:

    The original subheading was "Work" and realized it was not a strong enough word. Then, I thought to use "Work Ethnic," but that implies a noble choice. But it is not so much a choice as it is a "need." This was fun to write.

  9. Jeff Howell says:

    Does anyone else have the image of Magenta sliding down the stair railing yelling "I'm lucky, you're lucky, we're ALL LUCKY!" stuck in their head now?

    Yeah, I'd rather be ready than lucky. There is something to be said for being in the right place at the right time, but if you're not ready to take advantage, then what's the point?

    • James Oliver, Jr. says:

      Well said, Jeff.

    • Derrick Jones says:

      So true. That combination can make all the difference

    • Demian says:

      So let's flip that on it''s head: what's the point in being ready if you are never lucky? Being ready doesn't make you lucky. That's out of our control. Insane effort doesn't guarantee success. I know average and failures who work hard. I no people who haven't worked a day in their life who are extremely lucky. The point should never be about whether we are successful…it should be about loving what we doing…and doing it whether we get "lucky" or not.

      • djoneslucid says:

        Great point. I would, if you are able to do what you, then you are already lucky, or just smart and courageous.

  10. Demian says:

    First off, how do you define success? I said it in another comment, but I'll say it again: I know people who are lucky and never been obsessed with anything, are lazy. I know people who are obsessed workaholics and are average–even failures.

    Being prepared is meaningless if you never get a lucky break.

    Luck plays a huge part in our success. You pointed out that Gates was chosen to work for TRW. That's a lucky break for him–and not his peers whom you pointed out had equal access to software. I'd love to be able to say that most people make logical decisions (the hiring recruiter objectively evaluated all of the talent before him), but that's just not true–so much of those decisions are gut–or we have a connection with an influencer we got because we happened to show up at one bar instead of another (because it was closed). That's luck.

    I will say this, consistency will make you more successful because you don't give up…how many of us have gotten those lucky breaks but were unprepared for it, only to have a similar situation reappear ten years later when we were ready for it. << But you can't make those opportunities happen.

    We are thinking way to highly of ourselves if we think we are the causes of our success, and not recognizing the luck involved. I'll get off my soapbox now. :)

    • djoneslucid says:

      Good points Demian and I think you hit on some important distinctions. Being obsessed with something you would do for free is not the same as being a workaholic. Many people are workaholics who do not like what they do. This differs greatly from being obsessed or passionate about something you love.

      Gates did not go through an interview process with TRW. Gates used to go to a place called C-Cubed and coded after school for hours. When that company went bankrupt, a company called ISI granted him free computer access in exchange for helping them with a piece of their software. I didn't put this in the article but Gates said, "It was my obsession."

      One of the founders of ISI got a call from TRW looking for talent. Gates was the first and only recommendation. This was not luck. This guy put in the work when few others did because he found a "useful" obsession. Something others could benefit from.

      As for the definition of success, this is in the context of James Oliver's original question. Success in the monetary sense. Not that this is the only form but it's just the context of this discussion.

    • James Oliver, Jr. says:

      BOOM! That's exactly the point I was trying to make in my earlier post here, Demian, when I was on my "soapbox." http://www.steamfeed.com/are-successful-entrepren

      Would love to get your take on it.

  11. What a fantastic article, Derrick! I often find myself discussing the secret of success with people who think I am where I am because I spent my time smelling the flowers and watching YouTube videos.

    While luck may play a role in helping us take our stuff to the next level, the most important element is indeed obsession.

    Without obsession, hard work, and consistency, you will land nowhere. And of course, a hand-picked team of great people who want your success and theirs as much as you do!

    • djoneslucid says:

      So true Cendrine. From a clinical perspective, obsession is a bad thing and points to inadequacy in other areas of one's life according to psychologists. So, I expected a lot of push back on this piece because of the stigma. But the more I dug, the more obvious the pattern. It kept popping up! Some people, Bill Gates included, admit to having an obsession more than a passion.

      So, I conclude obsession can be a really good thing if directed at something useful and if there are others involved to provide balance.

  12. awovi says:

    Hi Derrick, your friend James introduced me to your blog because I also wrote a blog post with the same title. I believe There are some things we have no control over but for those we can control, our attitude will determine whether we are lucky or not.

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