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Lessons from Rosie O’Donnell’s Ten Year Big Break


O’Donnell’s Ten Year Big Break

Last month, Rosie O’Donnell appeared on Here’s The Thing, Alec Baldwin’s NPR interview show.

The episode, if heard casually, gives the impression that her break was rapid and inevitable. As a high school senior, we learn, she wrote comedy skits for a school variety show. A local comedy club owner liked the skits and invited O’Donnell to perform a set. She killed.

At this point, it was clear that she would become a comedian. Her break came later when Lorne Michaels and Brandon Tartikoff (former NBC chief) happened to hear her perform at a club where they had come to audition Dana Carvey.

Tartikoff came up to O’Donnell after the show and said simply: “Hi. I want you to call this number at NBC tomorrow. We have a job for you.”

Television, then movies, then her talk show — it all fell into place after that key moment.

This is a classic big break. But if you listen closer to the episode it becomes clear that it was not out of the blue. While telling this story, O’Donnell, as an aside, clarified the timeline of that fateful night by noting: “[Remember that at this point] I had had a decade under my belt of doing standup, right?”

O’Donnell’s big break, in other words, was ten years in the making…

Competing Big Break Theories

If you study people with remarkable careers they often tell stories similar to O’Donnell: they begin with a long period of anonymous striving followed by a break then rapid ascent (see also, Martin and Schwarzenegger).

There are two interpretations of this trend…

  • The first interpretation says that lucky breaks, by definition, are low probability events. Therefore, you have to open yourself up to opportunity again and again and again before you can expect one of these low probability events to finally occur. It took O’Donnell a decade to break out, according to this theory, because the probability that Lorne Michaels and Brandon Tartikoff show up at your show is really low.
  • The second interpretation draws from career capital theory. It tells us that lucky breaks are essentially impossible until after you have developed a rare and valuable skill. At this point, breaks actually become quite probable, so long as you are doing the right things to demonstrate your skill. This theory tells us that it took O’Donnell a decade to break out because this is how long it takes to develop comedy chops. The fact that Michaels and Tartikoff wandered into her show is inconsequential. Once she was excellent, some event like that was bound to happen sooner or later.

The problem with the first interpretations is that it leads people to bounce from thing to thing, always hoping that something unexpectedly hits big, never taking the time to produce real value.

The second interpretation tells us to instead focus on whether or not we have crossed the break threshold — the point at which you are so good you can’t be ignored and a big break has become possible. It’s really hard to cross this threshold in most fields, and if you’re not explicitly pursuing this goal you’ll likely end up in a purgatory of professional but unremarkable skill, playing half-empty clubs, hoping that the right executive happens to walk through the door.


An Administrative Aside: From what I understand, Google Reader no longer exists. This probably explains why my RSS subscriber count recently dropped by 20,000! If you’re an RSS subscriber, I’ve heard good things about Feedly. (My same RSS feed will work, you just need a new reader.) Also, I’m in the middle of a site redesign that will finish up in August/September. As part of this redesign, I’m launching an e-mail list that will allow you to receive my posts, plus some extra content, right in your inbox. Stay tuned for more details…

21 thoughts on “Lessons from Rosie O’Donnell’s Ten Year Big Break”

  1. An alternative to Feedly, if you don’t like its interface, is InoReader. Reliable, feature-rich, and works a lot like Google Reader.

  2. Both of these theories need tempering. The career capital theory doesn’t hold so firmly in real life, especially in softer areas that are meant for mass consumption (like comedy, or any entertainment). For example, Jo Rowling recently came out with a new crime novel under a pseudonym. This novel was not met with the burst of buyers that Harry Potter got. I assume that her talent did not plummet, but that the novel simply did not get lucky.

    What do you think, Cal?

  3. The second interpretation draws from career capital theory. It tells us that lucky breaks are essentially impossible until after you have developed a rare and valuable skill. At this point, breaks actually become quite probable, so long as you are doing the right things to demonstrate your skill.

    So then it seems that an essential step is learning what the right things are to demonstrate that skill. This is where a really good mentor would come in handy or perhaps even just following the example of someone who’s gone before you in the same field, regardless of whether you actually know him or her in real life. I’d be interested to learn more about how one figures out the best way to demonstrate their rare and valuable skill.

    I only just discovered your blog via Ramit’s site and I love it!

  4. Right! People get discouraged when they don’t get their immediate “big break.” It’s common knowledge now that success takes time but we underestimate just how much, don’t we?

  5. Cal, you had me until you mentioned Rosie O’Donell and Alec Baldwin. Talk about people who I wish to learn nothing from.

  6. Cal, Let’s look again at sheer luck. Here is a passage from Anne Applebaum’s thoughtful review of Sheryl Sandberg’s inspirational book for women Lean In. Anne Applebaum knows about earning her own success, having won the Pulitzer Prize for her book Gulagg in 2004, and she is a former member of the editorial board and current columnist at the Washington Post. Applebaum writes:

    At Harvard, . . . Sandberg happened to take a class with Summers, who happened to hire her as a research assistant before he happened to become treasury secretary. Upon arriving in the government, he made her his chief of staff.

    Coincidences like this have a part in the life of any successful person. Bill Gates, for example, has acknowledged how much he benefited from several unlikely pieces of good fortune: unusually early access to computers, teenage proximity to computer labs, the chance to learn programming before anyone else did. “I was very lucky,” he told Malcolm Gladwell at the beginning of an interview about the sources of his success. Gates easily acknowledges the role of chance and fortune—but then he isn’t seeking to package his life story as a source of motivation for others.

    Applebaum’s point is that no recipe for success-for-women could have put Sandberg into Summers’s class and then turned Summers into Secretary of the Treasury.

    What say you, Cal?

    Here’s the URL for the review. It makes many other excellent points.

  7. One note for the email list, Cal. Please, please allow the option to only receive the extra content. I prefer to continue reading your site through RSS, but would still like to sign up for the email list.

  8. I think the successful people we’re talking about have an intuitive feel for the opportunities they should pursue next. That intuition can be “hacked” via courses like the one you and Scott Young are working on (I was happy to be part of the pilot). Of course, intuition isn’t fully hacked by metrics and the metrics we bring in should be backed-up by the instincts we’re trying to build, including confidence. It’s a feedback loop.

    Ultimately, methods like the Career Mastery method build better grounding for those seeking rare and valuable skills. Without good grounding, O’Donnell may have thrown in the towel at five years, Gates may have tossed programming aside as a useless skill, and Sandberg may have slacked off as Summers’ research assistant. I think they knew intuitively that they were building rare and valuable skills.

    I switched to Feedly a few months ago. The only drawback so far is it seems to be wildly inaccurate as to the number of readers on a given site. It’s gotten better since the transition, but it’s still not right. Google appeared to be quite accurate, so I hope they fix that, or at least that Feedburner accurately gets statistics from Feedly.

  9. Mary Campbell Gallagher, J.D., Ph.D.

    I’d like to hear Cal’s answer to your question.

    My answer, although far from comprehensive would be:

    Why did Summers make Sandberg his research assistant? That was clearly the big break through. So in order to answer the question you need to know how Sandberg got that position.

    Was it that she was the best in the class and that attracted the attention of Summers, and then they got talking?

    OR was it the other way round?

    Could Sandberg tell that Summers had potential, and then she had the social intelligence/skills + confidence to approach Summers and get talking to him, building a bond that would mean she could then be carried into positions of power by Summers?

    Clearly she is good at what she does, but she probably has some luck and great soft skills thrown into the mix too.

    Luck is where preparation meets opportunity. She’d obviously prepared by getting good enough at whatever her unique and valuable skills are, but also recognised the opportunities when they arrived.


  10. AC, I would still like to hear what Cal says about luck. Sandberg did not make Summers’s luck. Yes, you’re right about Sandberg’s standout social skills, which Anne Applebaum also acknowledges. And, to be sure, Sandberg was a brilliant undergraduate student of economics, a summa.But if Summers had stayed at Harvard, instead of (luckily) becoming Secretary of the Treasury, Sandberg might have gotten a good graduate fellowship, followed by a good faculty appointment, or perhaps she might even have been made a Junior Fellow. It was not just her own luck, however, it was Summers’s luck, that allowed her to be launched in the direction of her current remarkable position.

  11. I would be interested to read an attempt at trying to apply some more network theory approaches to what you’ve outlined here – I would argue that you need to build enough career capital AND build a large enough and high enough quality career network to get that break. Although maybe that concept is already incorporated in your definition of career capital

  12. Upon further reflection, economists don’t have the same career paths as, say, medievalists. Perhaps economists are so closely tied to the business community that a brilliant Harvard economist like Sandberg would have wound up well-placed in business even without Summers’s having received a Cabinet appointment.

  13. I think that Dr. Campbell Gallagher is largely correct in her point that Sandberg (and many other superstars) did have a stroke of luck, insofar as they were able to demonstrate their skills at such a high level. Cal (Dr. Newport, if we want to be consistent) touches on the importance of applying extraordinary skills in the *right* place in this post.

    In many industries, finding the right place to apply your skills is an exploration. While there are rules of thumb to improve your odds of getting the chance to prove yourself on a big stage, we’re still dealing with unknowns and therefore some degree of luck.

    Notably, standup comedy might offer a clear enough hierarchy of venues, along with a single and relatively unambiguous metric of success, to allow many of the best to consistently rise to the top. But this study demonstrates at least one system without such a clear correlation.

  14. I don’t think the two theories posited are mutually exclusive. I think there are probably a lot of people that are skilled enough to have a “big break.” However, these opportunities are frequently low probability events, and thus, to improve their odds of having a breakthrough, they have to keep putting themselves out there.

    “Sly” Stallone, Jay-Z, Howard Schultz, JK Rowling are all examples of people that were rejected repeatedly before their “big breaks” despite having significant skill/talent.

  15. No he means that if J.K Rowling was not that cool of a writer then it was highly likely that even if she kept sending out her books to publishers it would fail and she won`t get any break.And since her books were too good to ignore at last one of the publishers agreed.The rest is history.


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