Generalizing about generations is good for you


One of the most popular posts here is What Generation are You? Take the Test. I’m sure one reason it’s popular is that people like tests. We all want self-knowledge, but we want it handed to us on a silver platter, not thrown at us in clumps of dirt by our families, or served up with Kleenex at therapy.

But the other reason I think that post is so popular is because people are generally indignant that they are pinned into a generation merely because of the date they were born.

People don’t like to be told they are similar to everyone else. But that’s ridiculous, really. Because feeling special and different is a luxury only for those who are very mainstream. I can tell you, as a person who does not fit in that well, I work very hard to fit in. You think the eccentrics are trying to be eccentric, but they are not. It’s not fun to be eccentric if you really are. It’s only fun to be eccentric if you aren’t.

So people don’t like to be told that they are typical of their generation. They don’t like to feel typical. They like to point out how they are different. Daniel Gilbert, professor of psychology at Harvard, has done a lot of research about how we are obsessed about our individuality. For example, most people think we are poor jugglers, but, of course, almost all of us are average jugglers.

So it makes sense that people complain about being grouped by generation. One of the biggest complainers is Ben Cascnocha. Of course. He’s not a normal college kid. He started a business when he was 14, and he is in college thinking that maybe he could learn more out of college, and he generally shows up in places that you would not expect a 21-year-old to be. But even Casnocha is typical for his generation. For example, Gen Y is entrepreneurial, very self-confident, technology-focused, and socially responsible.

So here’s an idea, embrace the generational generalizations, and learn something about yourself. We all want self-knowledge, sure. But there is broad self-knowledge, about where you fit in history. Talking about generations is talking about history, as it happens. The speed of information is allowing us to see ourselves in history as we go.

One great application of this is Baby Name Wizard, where you can see how your name fits in history. When was it popular? When did it tank? There is something about putting ourselves into an historical context that is fascinating. If you don’t believe me, I dare you to click on that link and leave without typing in two or three names. It’s impossible.

So take a step back and look at yourself in historical context of your generation. Instead of bitching about how no one can completely fit into a generalization, fit yourself in, for a bit, and find new context. People ask me why I love writing about generations, and I tell them, all the time, that learning about Gen Y, and how to get along with them, has forced me to be more optimistic and has challenged me to be more self-confident. I am a typical Xer. Sure, I’m eccentric, but I have several Gen X harbingers: Latchkey kid, cynical about stability, passion for grassroots, community action.

By examining how I fit into the generations, I can see the larger context of myself and my community. And the larger a context you can see yourself in, the more varied your self-knowledge will be. When it comes to making choices in your life, you will make better choices with better self-knowledge—understanding how you are the same as other people. If you know how you are the same, you can leverage the knowledge and research what has come before you.

You are probably an average juggler. You are probably part of your generation. You probably hate being told you are regular and typical. But let me tell you something. The best way to solve your career problems is to recognize that you are not the first to have them.

44 replies
  1. prklypr
    prklypr says:

    According to the test, I fall somewhere between Gen X and Y, although chronologically I’m Gen Jones! So where does that leave me, exactly? I’ll tell you: confused. This is another post that readers can blow thru and skip to the one important line (and it happens to be the last one) ‘The best way to solve your career problems is to recognize that you are not the first to have them.’
    Useful advice in ANY situation – just fill in the blank: “The best way to solve your _____ problems is to recognize that you are not the first to have them.” Nuff said.

  2. Shefaly
    Shefaly says:


    It is great you cite Ben because I found my own comment on his post which is appropriate enough to cut-and-paste here, intact:

    “Collective consciousness may be over-stated but so is individual intelligence/ rationality/ smarts.

    As that great sage of all things wise, Homer Simpson said: “Never underestimate the power of stupid people in large numbers”.

    That is why collective generalisations are made. As warnings. Not about those who are outliers but about those who populate the big bulge in the middle…”.

  3. Shefaly
    Shefaly says:


    With that Baby Name Wizard, have you tried any Indian or Chinese names with that tool? Even the commonest names from India and China?

    The tool doesn’t recognise those names when millions have those names given to them by their parents.

    The tool demonstrates how generalisations can be culture specific and narrowly focused, and ultimately meaningless if applied broadly. But of course, never underestimate the power of stupid people in large numbers, eh!

  4. GenerationXpert
    GenerationXpert says:

    I think that most people do fit in with their generation. That’s why when I meet another Gen Xer, I know I can show my true humor. I find that Xer humor seems to piss off everyone except Xers.

  5. Veronica Sawyer
    Veronica Sawyer says:

    Shefaly – the Baby Name Wizard only tracks the top 1000 names for babies born in the US each year. Not every name that has existed on earth since the beginning of time.

  6. Caitlin
    Caitlin says:

    I’m not American but it’s probable that the Australian cultural trends for baby names may be somewhat similar, with some exceptions (such as Kylie!). My name started to rise in popularity in the 1970s when I was born but peaked massively in the late 1980s and early 1990s, so I guess I have a Gen Y name.

    Here is another tool that people might find interesting: Basically it tells you where in the world particular surnames are most common (based on instances per million of population. Nearly every English, Irish, Greek and Chinese name I could think of was most prevalent in Australia than anywhere else. Try your own name!

  7. irene
    irene says:

    As fascinating as it is to read the psuedo-career musings of a 40+ woman who keeps trying to fit in with those in their 20s, I’m ending my blog subscription. What happened to the *useful* stuff? Either make with the stuff I really need to know, not the touchy-feely “who *am* I?” junk, or let it all fall into the navel-gazing posts you seem to think the rest of the world really wants to know about. As a twenty-something, I find one of the most annoying traits are those who are as self-obsessed as you are; trust me, no one really wants to know the status of your pubic hair.

  8. Jessica Bond
    Jessica Bond says:

    The name wizard is interesting…generational analysis is useful…but most important is knowing the most unique person, yourself and those unique qualities that we all have to fulfill our life’s destiny.

    Jessica Bond

  9. Werner von Wallenrod
    Werner von Wallenrod says:

    I think the real objection many people have to gen X/Y/boomer/etc generation talk (although I agree that the reason you give about people not wanting to be judged as a group is true, too) is that it’s all generalizations based on anecdotal observation. It’s really the exact same thing as astrology, just swap “I’m a typical gen Xer” for “I’m a typical scorpio” or whichever (and in my own anecdotal experience, both concepts seem to appeal to the same types of people).

    You say, “Gen Y is entrepreneurial, very self-confident, technology-focused, and socially responsible.” Of course, anyone can choose to see that in themselves or not, depending on how they choose to identify. Even the least entrepreneurial guy on Earth could think back to that time he made a cup of tea without anyone asking him to, or when he took that job as a paperboy. And the biggest entrepeneur of all time could say “that’s right; I’m so not like that because of that time I listened to that authority figure.”

    It’s fun if you take it like “for entertainment purposes only” advice from LaToya Jackson and her Psychic Friends Network; but I’ve yet to see any real personal knowledge produced by these discussions above the “white people have names like Lenny, and black people have names like Karl” level.

    Of course, you probably already know this as a fellow blogger-whose-pseudonym-has-three-E’s-in-it. After all, we’re the real self-starters of this world.

  10. Leanne
    Leanne says:

    Hello P … I am wondering what makes you believe you are eccentric … I don’t get that notion from your blog, your corporate site or your book …

    What bits have you left hidden from your reading public that lead you down the path of eccentricity …

  11. Ben Casnocha
    Ben Casnocha says:

    Agreed that people overestimate their specialness. But let me again present my perspective.

    It’s fine to make generational generalizations. It’s just harder to make it about Gen Y than prior ones. Why? Because the web has allowed us to develop true individual identities in ways past generations could not.

    For example, starting a company is much easier today than ever before, and that’s allowing more young people to start companies and self-identify as an entrepreneur. The same is true of countless of other interests or hobbies for which the web offers communities of like minds.

    So more and more young people, at a younger and younger age, break through the constraints imposed on them by their physical geography or biological age, and develop an individual interest by accessing information and connections online.

    I’m with you on the value of self-knowledge. But studying generational stereotypes doesn’t strike me as a very good way to get there.

  12. Shefaly
    Shefaly says:

    @ Veronica Sawyer

    I know.

    However the web is not just like John Lennon in imagination but also in reality! People from all over the globe read this blog – not just people born in the US.

  13. Don B.
    Don B. says:

    Your last sentence is the key. Somebody has had your problem before. What did they do? It can help with ideas.

  14. tinyhands
    tinyhands says:

    I think that the problem with generalizations about generations is the implication that one is better than another. Every time (including today) I read you write about X vs. Y, the implication is that one should endeavour to abandon the generalized traits of X in favor of those of Y in order to succeed.

  15. Rachel
    Rachel says:

    Penelope, you always manage to post things that are directly applicable to me at that very moment. I was just reading some blogs the other day, and half the comments were from Gen Yers who were complaining that Gen Y bloggers put all of us into the same group and categorize us the same way. Ok, I get that. But Ben (above) says that studying generational stereotypes is not a good way to attain self-knowledge, and I say, there’s a reason for the stereotypes.

    It’s totally correct to say that Gen Y doesn’t like to be categorized – we want to be individualized. But look at the tags that are placed on us: entrepreneurial, self confident, socially responsible, etc. Those things are all positive, right? Why not be proud of our generation and what we’re doing for ourselves in the workplace – we’re actually changing the workplace!

    And the best way to recognize what characteristics you’re missing and what niches you are not fitting into (but which you’d like to) is to look at where you are in relation to everyone else.

  16. Mark W.
    Mark W. says:

    I have to agree with you that generalizing about generations is a good way to start to gain self knowledge. The same can be said for generalizing about race, religion, economic status, etc. I can find many similarities with people in these various categories as applicable. However it is important to remember that they are generalizations and the weight applied to these generalizations in these various categories will vary by individual. The real work and attainment of self knowledge is knowing the similarities and differences of these various category generalizations as they apply to you.
    Your focus on the generations is mainly on its’ differences in the context of history and the environment people lived. My perspective was mainly one of the commonalities that each generation experiences. I can identify with many gen y experiences as I have lived through them myself. Then I read your blog and other media proclaiming the differences of generations and how meaningful it is and I can understand what you’re saying. In my opinion I think generational differences between people are as significant as race, religion, economic status, etc. because of the time in history they lived in and not mainly or just because of their age differences and thus differences in the amount of their life experiences. I can think of many examples but one that stands out and is demonstrated here is the way people communicate today individually and in communities. I grew up with no Internet so there was no email, blogs, IM, etc. but instead voice mail and typed or handwritten memos. Also research was done primarily or exclusively in the library with books, magazines, newspapers, etc. and search was done by combing through these various hard copy sources. Of course the first search today is done on an engine on the Internet. These experiences are common/similar to my generation (gen jones) so these generational differences are significant when compared to gen Y. Thank you for this post.

  17. Neil C
    Neil C says:

    I agree that self-analysis is important but as you have seen from my previous comments I have a real problem with you advocating us to be more like Gen-Y.

    Outside of being more technological there are a lot of areas I don’t like about them such as a sense of entitlement, not being able to listen and lack of being objective. I believe they have more to learn from Gen Xers & boomers then we have to learn from them. I do not feel this because we are better than them-it is the simple idea that those that have more experience can help guide those that don’t.

    This whole self-esteem movement is crap. I know that Gen Yers feel better about themselves because they didn’t keep score in their soccer games but I can’t tell my boss not to keep score when it comes to our budget so the adjustment to the real world for Gen Yers is harsh. They have a disconnect with reality. The best way to gain self esteem is to accomplish something, not to go to therapy.

  18. Maus
    Maus says:

    Amen. PT’s dictum that Gen Y = “self-confident” should be edited to “self-delusional.” I am happy to share the generalization that my generation scorns the whinining sense of entitlement of these untried, everybody-wins-a-trophy neophytes.

  19. Rachel
    Rachel says:


    Not everyone wins a trophy – we know that. But we believe that we (individually) can win one. We think we have a pretty damn good shot. Don’t you? We should have some entitlement – everyone should, don’t you think? If you are confident in your abilities.

  20. JenX67
    JenX67 says:

    First of all, I hardly ever read other folks’ comments. I just don’t have time. But, today, I did, and boy, howdy. That Caitlin is a real piece of work. Man,oh man. Do you often get nasty grams like that? I don’t know why I am continually surprised. She’s probably jealous that you have a cool name – both of them (Penelope and Adrienned) and she’s stuck being a Caitlin for the rest of her life along with all the other GEN YCaitlins, Brittneys and Ashleys. Hahahahahahaha. Keep writing exactly what you’re writing. This girl won’t know until she’s 40-something how glad you are to not be in your 20s anymore.

  21. JenX67
    JenX67 says:

    sorry – i just realized it was “Irene” who said that. My apologies for the sarcastic remark about Caitlin’s name. Nobody in Gen Y is named Irene. Irene is crazy, irrelevant Baby Boomer.

  22. Josh Russo
    Josh Russo says:

    This is pretty good. I’ve felt for years that I was between generations – born in 1973 probably puts me at the tail end of Gen X, but I scored well into Gen Y on the “test”. The baby name wizard, however, put the peak for my name in the 80’s, meaning my parents were very slightly ahead of the curve. Which is, not surprisingly, how I like to describe my “eccentricity”.

    So why do I care? I guess I want to fit in, and this provides some explanation for feeling like I don’t.

    On a related note, I think your parents’ generation plays a role. For example, my wife is the youngest and I’m the oldest, and her parents are 10 years older than mine. My wife is only 3.5 years older than me, but it’s shocked me over the years how different our views on technology and culture are (the Simpsons, online photos of our kids, text messaging, Facebook). It took me years to recognize that we were experiencing what I’ll call an intra-marital generation gap.

  23. Josh Russo
    Josh Russo says:

    Sorry – re-read my post and wanted to clarify that my wife is the oldest in our respective families. Sorry if that was confusing.

  24. Josh Russo
    Josh Russo says:

    Note to self: Get more sleep and proof-read instead of writing clarifications that are more confusing than the original.

    My wife is the youngest and I’m the oldest in our respective families.

  25. Juki Schor
    Juki Schor says:

    Okay, can anybody explain to me what Gen X and Gen Y is? I live in the woods and have a hard time to locate these guys. It would also be interesting to know when a generation starts and when it ends. I mean, do we put people together into one generation who fit generalized character traits or is this related to certain years when they are born? May be it is the same phenomenon that was happening with TV. First TV was imitating life and now life is imitating TV. When it comes to generational generalization, may be first they were conducting studies to find out generalized consumer behaviour in order to optimize their products and advertising, and now people are becoming generalized according to the studies. As you mentioned names, do names have an impact on a generation’s characteristics, meaning, if we have a generation of Roberts and Debbies we can predict that they will have certain living preferences? So, if we need certain qualities in a generation we just make certain names popular?
    Otherwise, eccentric means “out of centre”. I have been there for some time, it didn’t feel funny, I agree with Penelope here, especially not when you have kids. I am glad I have found base camp lately and happily hide in the crowd. Experience also shows that if too many people loose their centre, i.e. eccentric becomes the norm, we often end up with some kind of economic or social crisis…

  26. JenX67
    JenX67 says:

    The birth years commonly accepted for defining Generation X is 1961 to 1981. (X Saves the World, etc.)Some extend it to 1982, but nobody goes earlier than 1961. GenXRising – a blogger, states that identification with Generation X is about a cultural experience, however, and not really held to tight statistics. Birth rates began a sharp decline in 1961 — thus the notion that people born after that decline were not part of the “Baby Boom.”

  27. Juki Schor
    Juki Schor says:

    Thank you JenX67 (Meaning you are Gen X born 67?). So Gen Y is starting after 1981 and Baby Boom ending 1960.
    X Saves the World, etc. meaning what? It feels
    Gen X wasn’t really successful with it…

  28. Arlene
    Arlene says:

    I am a Boomer who has had a Gen X life. Now that times are tough, I’m especially glad of that.

    These will not be good days for America’s more fortunate sons and daughters–traditional Boomers and their Y’er offspring.

    They don’t know how to struggle like “we” do.

  29. Lopez
    Lopez says:

    Ben, also like many from his Generation (Y), is still young enough to believe that most, if not all, that he does is, oh, so unique. That’s not even a generation thing, it is an age thing. I thought that same way too at that age.

    And I also had my own business, of sorts, when I was 14. I mowed lawns, cleaned gutters and window wells, and did other odd jobs. Not very impressive to be sure, especially to the likes of Ben, but a business nonetheless.

  30. Jennifer Ellis
    Jennifer Ellis says:

    This post is actually really timely for me. I was thinking that I wasn’t enough like my generation, not because I’m an individual, but because I’m not tech-y enough or ambitious enough, etc, and I want to be!

    Yesterday, however I was really frustrated because I had to call someone and she didn’t have a signature line with contact information at the bottom of their e-mail. I mentioned it to an older co-worker and she said, “I think signature lines are annyoing. What’d you do with her business card?” As if I knew! I think business cards are annyoing, if all you really have to do is search the person’s name in your e-mail. Maybe I am a bit more Gen Y than I thought.

  31. Shefaly
    Shefaly says:

    @ Rachel:

    You say: “But we believe that we (individually) can win one. We think we have a pretty damn good shot.”

    I suppose believing one has a pretty damn good shot comes from believing in the concept of potential. In that respect I think you will like PT’s post titled “Living up to your potential is BS”. :-)

    When you have untangled the logical quagmire between this post and that one, please do leave a comment here for me (perhaps also Maus). Thanks.

  32. chris keller
    chris keller says:

    I hear Penelope talking about the value “seeing the big picture”. Isn’t that what the labels are all about? Boomers, Gen X, Gen Y are labels, which try to make/capture generalizations about epochs in history? You can probably tell by my use of the terminology, “the big picture,” what generation I come from . . .

    I have a sense, though, of yo-yo-ing back and forth between the generalizations and the individuality: I am a grain of sand on a vast beach, and yo-yo-bingo! I am alone, an individual, sometimes lonely and isolated.

    But rising from the sometimes lonely individuality comes a spark of creativity, sometimes. Personally, I don’t experience the spark of creative problem-solving when I am feeling a part of a generation–only when I am feeling individual and alone.

    So, swinging back and forth from the general to the particular is my experience. Each has its rewards.


  33. Ron Turley
    Ron Turley says:

    I saw your name and blog mentioned in an article about salary transparency, went to the blog, read two entries and linked to two others, and came up with several comments I wish to make. Pretty good inspiration rate.

    Salary Transparency: Not too sure of your thoughts on this as I did not get to a blog entry on the subject.

    I think it is fair to say that the prime reasons for the astronomical, completely unjustified increase in CEO salary is that publicly traded companies have had to publish salaries of the their top people for, what, 30 or so years. I have read that compensation consultants hired by boards looking to replace their CEO research the salaries paid in that industry. They come back with examples from similarly sized companies and suggest that, to get a good person, they will want to offer salary and benefits in the top 25% of this range. It does not take a mathematical genius to see that the net result will be spiralling compensation.

    I work[ed] in a small financial planning shop. There are the two principals, me and two assistants. It is true, that by not quantifying quality (which I have inferred is required in a system of transparent compensation), the bosses were held hostage by one of the assistants who continually asked for a raise. They acquiesced until they were required to let her go because they could no longer afford her.

    I think transparency can (and will) result in equal pay over similar job responsibilities which will inhibit hard work and initiative. In many small offices, advancement is difficult if not impossible – €“ there is no greater position to aspire to. If the pay scale is the same over similar positions, there is nothing to gain by working harder or smarter. You can give greater award to those who are deemed to be more productive. But, this can be a very hard thing to explain to someone in a similar position who has an unrealistic view of their worth. So, the harried executive who does not want to deal with whining employees will, when salaries are known, tend to pay everyone the same – €“ i.e. you have a union type shop; there is no incentive to work harder.

    Generations: I was born in 1949 and the Generation Placement Test put me in Generation Jones. Very interesting as I always thought of myself as a late B[l]oomer. I never really felt that I belonged with the Boomers, did not have the ambition that many developed after living in that hippy commune. I did not relate to The Big Chill, but loved the Return of the Secaucus Seven.

    I had never heard of Generation Jones until today, but did run into some from that group. In 1975, I was teaching a practicum to a grade nine class. When I mentioned my age, one of them lit up, saying that 1949 was the very best year to have been born. He then rhymed off my age at the time of some of the great cultural/historical events of the modern era – €“ advent of rock and roll, assassination of JFK, the Beatles, Haight Asbury, Woodstock. I thought: how sad that he believes he has missed all of these, that, it appeared, the best times were over and he had nothing to look forward to.

    Publishing a Book: I am not exactly sure why I would like to publish a book. Perhaps it would be to show how wrong my first year English prof was to fail me. Perhaps it would validate me in someway – of course I thought that I would be elated and proud the first time I was paid for my writing and it turned out to be anticlimactic – I have no great ideas and cannot write fiction. I have been, over many years, creating micro stories from my life. Most of them are between 800 and 1,000 words; the longest, about 4,000.

    I tried a blog, uploaded one of my better stories, went through the process of registering at Google and waited. No visitors, but me. There was nothing when I Googled words from the blog. The crawler had not registered the site. So much for that. Perhaps it had to do with my low score on the Generation Placement Test,

    Job Hopping: I cannot find it now, but somewhere you had a piece about not being concerned about slow starting offspring. You mention twentysomethings who job hop and often end up back at home. You reassure parents that this is normal and nothing to worry about.

    You accurately describe my 20s – .OK and part of my 30s (hence, perhaps, my lack of affinity to the Boomers). At age 46, I had just left the longest job I had ever had. I had been there four years. Longest before that was 3 yrs 8 months full time followed by 4 months of part time. Before that, it was 20 months and before that, I did not remain at a job for more than a year and several were for only a few months (this during my wandering phase when I would take high paying labour jobs in work camps to make money to travel or to return to school).

    At, oh say, 53, I was describing myself as boringly content. Family life was great and my work life was both professionally and financially rewarding. A year or so later, I realised that I was just plain bored and for several years now, I have been in a Peggy Lee funk ("Is that all there is?"). At times, I long to start over at 25 with the wisdom that I have now and see what life would have been like if I had chosen a career and stuck to it. Don't get me wrong, I have had some great experiences and more careers than some people have had cars, but I just wonder what it would have been like to develop a true expertise, a recognised talent.

    You: When I was reading your bio, I was reminded of colleague/friend who thinks a lot like me, but is very different. She attacks life, sets goals and goes after them. She works hard, but has accomplished many things. I am the complete opposite. I have, more or less, let the river of life take me where it is going. This sounds very passive and I am in many respects, but I feel the river is taking me where I am supposed to go. Attacking life never seems to have worked for me. I love Springsteen's line "like a river that don't know where it is flowing, I took a wrong turn and just kept on going" Well, I am not sure that I took a wrong turn, but I have been going with the flow pretty well all of my life.

    I have not read enough to determine if you are in the group of pop gurus that I have had to suffer at various conferences, the ones who are going to tell me how to lead my life, how to reach true happiness. So far, I like what you say about a number of things. Like your bio and, well, from your photo, I would judge that you are a babe – of course ugly people do not have speaking careers and popular blogs. I may get your book and hope not to be disappointed. I suspect that you do not have much to say to me about life, career and such (I am more or less semi-retired and spending most of my time on volunteer boards), but I think I may like reading your stuff.

  34. PatrickWB
    PatrickWB says:

    I agree with the idea that you should put yourself and your experiences into a greater context. Whether that’s a generational context or some other method of comparison….it’s a good idea.

    I disagree that generalization is a positive, though. You can have universal experiences but unique responses. Putting things into context can help adjust expectations, of course….

    It just seems lazy to paint everyone with the same wide brush. I’ve talked to many annoying Gen Y’ers with an overgrown sense of entitlement and an inability to put down their Crackberry (or Crackbook), but I’ve also met and talked to young, focused, humble people who put my talents and ideas to shame.

    Saying all Gen Y’ers are reward-addicted simpletons is like saying all boomers are tech-resistent albatrosses. Easy to generalize if you’ve had a bad experience with one, but not applicable to everyone in that demographic.

  35. Dale
    Dale says:

    Most people in the US revel in their individuality, both as a community, and as independent entities. This I’ve come to accept. But in the world at large, most of the people that I’ve met see themselves as independent, unique, individuals, but find solace in being a part of a greater community – something Americans tend not to admit. Here, we all love being part of a fashion herd, or a religious herd, but don’t ever tell us that we are not individuals, because that incurs the ire of whoever you are corresponding with.
    This is a shame because as far as I see it, our appreciation of the herd then becomes manifest in zenophobia, ultra nationalism, etc.

    Just a thought.

  36. Wally Bock
    Wally Bock says:

    In my experience the Generational comparisons are more helpful to track or analyze social trends than they are as guides to individual behavior. And Dale makes a valid point that cultures around the world value different things. That’s important because the Generational Cycle work by Straus and Howe was only done on the cycle of US generations.

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