Make better decisions for yourself by watching decisions celebrities make

, ,

This week’s poll is about celebrities because I love peeking into their lives in order to see the world in new ways. I love learning so much that I think that's even why I spent so much time with the farmer even though it was bad for a long time before I stopped dating him. I was learning so much about farming and how people make life decisions in the context of that profession. So the learning part is sort of addictive to me. And in that respect, my attraction to the farmer is similar to my attraction to Madonna, Britney, Ashton, and Brad.

If you don’t read about celebrities, you’re missing a big learning moment. Of course, you’re missing a learning moment by not dating a farmer, too. But some things are more time-consuming than others. And I have to say that flipping through People has relatively high payoff. Here are some reasons I do it:

1. Use celebrity messes to gauge how you’re doing in your own failures.
One of my (many) past therapists told me that you can’t really tell how well you’re doing until something bad happens. Most of us manage ourselves fine when everything is going well. We discover our level of resilience only when things go poorly (download movies).

But how do you learn about this when most people hide themselves when things are bad? Most people hide and most people don’t talk about what’s truly sucking in their life, so we don’t really see how their resilience is tested until their problems are so over the top that they’re uncontrollably leaking into all aspects of life.

The best place to see people coping with the dark, dirty side of sunshine and roses is People magazine (or your favorite stand-in, like the Enquirer or, on an especially smutty week, New York magazine). This is where people can’t hide their problems because they have made their lives public property to further their careers. We benefit because we see what people do to stay resilient.

Sure, you cannot compare yourself to a celebrity when they are dressing for the Oscars and you’re going to a party, too. But you can compare when they are getting dumped by their lying boyfriend and you are in love with a liar as well.

2. Dress yourself like a celebrity by picking one to mimic.
When I wrote about Sarah Palin spending lots of money on clothes and Michelle Obama knowing how to work J Crew, there was a lot of hoop-la in the comments section about how you need to learn how to dress right for your body.

If you live in NYC or LA, it’s not that hard—most women there are good at dressing themselves. Looking good is super important because there's no shortage of competition. Not so true in the Midwest. (I would know—I’m there right now. ) Just as you get more happy being around happy people, you dress better being around good dressers.

People magazine is a way to compensate for a lack of role models in your town. Look for someone who has the same body type as you and start watching what they wear. It’ll save you a lot of time and a lot of mistakes.

3. Know the rules to follow by noting the rules celebrities ignore.
The smaller our world, the more constrained we are by social norms. Sometimes that’s good because being part of a community is important. But often it’s mentally constraining. I like reading the perspectives of celebrities because they are exposed to a wide variety of things that I am not. So they have fresh perspectives on topics I am not as smart about.

Celebrities use a more diverse arsenal of tools than most of us do to manage our own brands, like marrying someone a lot older to look like a more serious actor. And celebrities feel less of a need to adhere to rules that do not help them to be their true selves, like, don’t have six kids in four years or you’ll go crazy. I like watching people make their own rules for themselves—not necessarily the choices I would make. But I like seeing what happens.

52 replies
  1. gregcnorca.aim
    gregcnorca.aim says:

    I don’t think watching the colorful lives of Celebs, (i.e. Brittany Spears or Lindsey Lohan) will teach people much about anything other than that humans are entirely fallible.

    A group of hollywood Celebs, like pro athletes, and people in all walks of life, from Wall Street to skid row, are predisposed to bad choices because of how they are raised by their parents, barring mental disorders. I think the one piece of advice I would have is this: teach your children to not care anymore about celebrities and athletes any more than they do their own neighbors.

    The world would likely be a much better place. And all the attention at the grocery store magazine rack might shift to something slightly more profound or even constructive!

  2. Joselle Palacios
    Joselle Palacios says:

    I chose Britney. I grew up on Madonna but Britney (and Gwen) is putting out the songs Madonna should. Amazingly catchy, epic pop music. “Womanizer” took time to grow on me (I actually loved nervous breakdown-era “Gimme More” so much more) but it’s a great song. While watching Britney Spears break down, I had a strong sense she would be okay. And I totally related to her marrying a hot, scummy, baby daddy, backup dancer. I think she’s doing great. Madonna’s new album bores me, although I think she’s handling her divorce beautifully, so I respect her. And, she’s Madonna. I will always love her.

    I don’t give a crap about Ashton. He’s dull. But he once said something about relationships (not the same one in your poll) that was so astute. I was shocked.

    I’m glad you picked Brad over Angelina. He’s infinitely more compelling, although I love her simple clothes. He also was more electrifying in Mr. and Mrs. Smith. He’s a damn fine actor. Angelina hasn’t impressed me since Girl, Interrupted.

    I used to be much more celebrity-obsessed. Now, I just read and glance at tabloids every once in a while (when I read People, I feel less dirty and I feel like it’s the truth). Celebrities raised me when I was a teenager (especially Courtney Love, which explains my early-20’s). Seriously, I learned a lot. People who say, “Who cares what’s going on in celebrities’ lives,” are lying or boring. It’s drama. It’s fun. It’s totally human to be nosy.

    My all-time favorite is Kate Winslet. I’ll buy any magazine she’s on the cover of. And though her body is totally perfect and sexy (see Dec’s Vanity Fair. My my god), yes, she is sortakindabarely “fat” in Hollywood so I love her more. I always check out what America Ferrara is wearing because I’m curvier. Glamour used to be good for body type-appropriate fashion but they suck now.

    Um, PT, I could go on. So, I’ll stop now.

  3. Blanket Statement
    Blanket Statement says:

    You make the comment:

    If you live in NYC or LA, it’s not that hard – most women there are good at dressing themselves. Looking good is super important because there's no shortage of competition. Not so true in the Midwest. (I would know – I’m there right now. )

    I think you may be a little off on this one. The midwest includes Chicago and Minneapolis. People there look pretty good. Ever walk down Nicollett past Target’s corporate headquarters? People there look pretty good.

    You might also want to explore other areas in and around Madison like Shorewood Hills or Middleton.

    • Jessi
      Jessi says:

      While it's true that there are good looking people in the midwest, there are much more in NYC and LA. The industries in these cities are much more focused on looks, and the populations are higher, so by probability alone you're bound to see more.

      It's unlikely you'd run into a group of models out on the town in the midwest, but you will every night in New York. I moved here from Chicago earlier this year, and even though I hate to admit it, I think about my outfits, hair and makeup all the time. It's impossible not to, I'm surrounded by it. I even get my eyebrows done every month, something that never even crossed my mind in Chicago.

    • Penelope Trunk
      Penelope Trunk says:

      Okay. I can’t resist. Now everyone knows what I’m dealing with here in Wisconsin. Seriously. I live in Middleton, WI (referenced in the comment). And seriously, there are people in Wisconsin who think there are cities here that are comparable to NYC and LA. Seriously.


      • More questions....
        More questions.... says:

        The girls outside of Target are beautiful, I was just out there on a business trip.

        What I’d like to know is who in Wisconsin thinks that Milwaukee, Green Bay, Madison, Lacrosse, etc. compares to NYC or LA? I’d really like to meet these people, do they really exist? Have they ever been to either coast? Do they have a high school education? In what context are they comparing Wisconsin cities to NY or LA?

        Those are the real questions…

      • class factotum
        class factotum says:

        Or maybe there are people in Wisconsin who don’t care about how they do it in NY or LA. :)


        Freezing and couldn’t care less about fashion as long as I am warm in Milwaukee

        PS To More questions: I have a master’s degree from a top-20 school, so I am smart enough by your standards to make this observation.

  4. Don B.
    Don B. says:

    I would pick a different group and a magazine to learn from. Better to be a bit deep in the shallow end than to be a bit shallow in the deep end.

  5. Jin Stevens
    Jin Stevens says:

    Hi Penelope!

    First time responding on your blog, though I’ve been lurking for a couple of weeks.

    My wife uses People magazine for exactly what you describe. Seeing celebrities in degrees of distress seems alleviates her own stress. It’s hard to get too upset about your erratic, micromanaging boss when you see people balloon in weight, get thrown into mental institutions or hear about their latest attempt at keeping their sex tapes off the Internet. She finds it great therapy.

    However, identifying with celebrities just doesn’t work for me. I just can’t empathize / imagine how it would be to be surrounded by a gazillion paparazzi or fret about appearing in someone’s worst dressed list, etc. Maybe it just comes down to the fact that as much as I resist it I have a middle class perspective that those sorts of things are just beyond the pale of what I’d consider a living normally.

    Maybe it’s gender related? Because while I don’t know how many guys would peruse celebrity gossip rags (I do on occasion), most guys I know would pick up a sports daily…perhaps use sports as an equivalent mechanism to gauge success / failure?

  6. Dan
    Dan says:

    Britney is “gifted”? How, exactly? Anyone can gyrate on stage while lip syncing to a computer-enhanced voice.

    Brad Pitt is a loathsome skirt chaser, married to perhaps the biggest nutjob in Hollywood. Madonna is way over the hill for what she does.

    At least Kutcher is sticking with his old (literally) lady. So I guess I pick him, although there’s nothing of value to learn from any of them.

  7. Alice Bachini-Smith
    Alice Bachini-Smith says:

    I’m glad you’re sticking up for celeb-mag reading. There’s plenty of meaning in pop culture you can’t get elsewhere. It’s zeitgeist stuff, because as you say, celebs are exposed to things we’re not (thank goodness). For instance, Angelina Jolie telling the media how she doesn’t read the celeb magazines- don’t listen to gossip about yourself is a good rule.

    I wish she’d wear a non-black dress sometime though.

  8. prklypr
    prklypr says:

    Whoa! During an especially smutty week you turn to…New York Magazine?? C’mon – comparing People (or even worse, the National Enquirer) to New York Magazine is like comparing NY Newsday to the NY Times. Well, OK, maybe not the Times… but really? I’ve been a NY Mag reader for 25 years and I’d never call it a celebrity gossip rag – although the online Daily Intel blog is pretty juicy…People is my fave indulgence for short business trips and pedicures. You can read an issue cover-to-cover in under an hour.

  9. Anca
    Anca says:

    I may not live in NYC, but I live a couple blocks from the Nordstrom HQ — and watching all the 20- or 30-something women that work there walk into work in the morning is like my own little slice of NYC fashion. Makes me want to hit the gym so I can look hot in expensive clothes too (which is exactly what I’m going to do right now).

  10. Peter Fletcher
    Peter Fletcher says:

    And don’t forget the entourage Pen. You gotta have an entourage. All the cool people have an entourage. And some paparazzi. If you don’t have one/them hire go and get some. They’re available for hire. Entourage + paparazzi = big star. Big star = good things, no questions.

  11. Mark W.
    Mark W. says:

    That’s funny. You get People magazine to read about celebrities and peek into their lives and here we are reading your blog and peeking into your life. :)
    BTW, I voted for Britney – not because I’m a fan of hers – but because I also enjoy watching her bootstrapping her career and I want to see her succeed.

  12. Marsha Keeffer
    Marsha Keeffer says:

    Middleton? Maybe Madison instead?

    Here’s what I learned from Britney – drugs mean you’re paying money to get stupid. They can take you from the top of your game to the basement. Think Circus is new? Has anyone seen Christina Aguilera’s video of Hurt? She used the circus theme two years ago. Britney’s work is repetitive and old-looking. And would you really want someone (even your dad) to be your conservator and have the legal right to control all your money, along with what you wear, eat and purchase? Yeah, some of the songs are good. But just good doesn’t really do it, does it? I’ll believe she’s in true comeback mode when the probate judge says she can handle her affairs by herself.

  13. LaDawn
    LaDawn says:

    Penelope – You have well and truly lost your mind. You might want to consider leaving WI. Readers, do not waste your time comparing yourselves to celebrities. Under no circumstances should they be used as a baseline on how to look, act or what to wear. They have plastic surgery. Their clothes/shoes budget is huge or they are given their clothes by designers to encourage people to buy their clothes. Many/most of them wear wigs to avoid having to do their hair. It is an artificial environment wholly unsuitable for real people who have real lives.

  14. Seth
    Seth says:

    You’re stressed about financing so you publish a post in which you recommend that your 26k+ subscribers pattern their life-choices based on what they observe of celebrities?

    1. Pick a guy who doesn’t bow to you and set up a time to just grab coffee and talk. Just talk. For an hour. That’s the only plan.
    2. Buy a couple Full-spectrum lighting units if you haven’t already. The last thing you need in the snowy woods is less sunlight. Supplement it with artificial sunlight. It’ll help.
    3. Write down your top questions about the financing situation and go to bed. All the old VC and bank boys have been in bed for hours.

    Good luck!


  15. Ariella
    Ariella says:

    OK, just have to comment on this. Penelope, I, too, am from NYC and moved to Madison, WI. You’re right: some people here dress straight out of the LL Bean catalogue or worse — just like some people on the streets of NJ and NYC. However, some people here dress fashionably and care what they look like and check out the fashion mags just like you do.

    I am probably in the middle. I am an attorney and at work I dress stylishly in suits or trousers and sweaters. I wear nice boots. I dress for my body type. And most people think I am “stylish”, whatever that means (or so they tell me). On weekends, though, I dress in whatever the hell I feel like. And it’s not because I’m unstylish or from the Midwest — I’m not! I’m not a midwestern girl and I’m not unstylish.

    It’s too bad that you can’t see past your NYC elitism. It took me a while, too. We moved here around the same time and although Madison is definitely NOT NYC, it’s also NOT International Falls, MN, or some similar small town.

    Now, as for the actual content of your post? I don’t know if it’s true and you can’t really know what’s actually happening in celebrities’ lives. For example, my husband and I are having martial trouble right now and are talking divorce, though I think we can sort things out. You rarely hear about celeb couples who are trying to work things out; you hear about them after they’ve split or worked it out.

  16. Susan Greene
    Susan Greene says:

    I often find that watching celebrities is the best way to learn what NOT to do. Perhaps they dress better than me, but when it comes to running their life, most are monumental screw-ups. I prefer to select role models who are a bit more wholesome.

  17. Hayli
    Hayli says:

    LOL, Milena. In a weird way, celebrities make me feel very blessed. Most of them seem so dysfunctional, superficial, lonely and unhappy. I don’t envy them, but am fascinated by them. It’s like watching big, beautiful fish in an aquarium – it’s hard to turn away. At least in my fishbowl, there aren’t any paparazzi sharks.

  18. deepali
    deepali says:

    I am completely baffled by this. Does a reasonably intelligent person actually need to watch Britney melt down in order to know what to do (and not to do)? Do you really need People magazine to tell you that drugs and a loser husband are not necessarily good ideas? Goodness, now I know what is wrong with this world – everyone is a moron who has to have normal behavior handed to them in the most dumbed down fashion possible.

    But. I suspect this post is more just a way to justify the secret guilty pleasure of reading trashy magazines. Why not just admit it, and not try to dress it up as something “useful”? There isn’t anything wrong with not doing something productive 24/7. I watch crappy TV sometimes, but I’m not acting like it’s some great sociological experiment.

  19. Susan Greene
    Susan Greene says:

    Maybe next you can do a post on why it’s good to watch the Jerry Springer show. A healthy dose of nuts and sluts is just the thing to make you feel better. Title that post, “If you thought your life sucked…”

  20. Shefaly
    Shefaly says:

    Miss P:

    You are slowly becoming the Queen of t-i-c! :-)

    I think there are glossies and there are glossies when it comes to Celeb magazines. Not all sources are created equal. Reading Rolling Stone or Vanity Fair is not on par with reading Hello! or OK! magazine. The raw material being the same, a better interviewer extracts more interesting, probably more abstracted info out of the same celebrity.

    Not all celebrities are worth ‘watching’ either. I, for instance, think – notwithstanding the prejudicial wording of your description of him – Ashton Kutcher gets the real ‘picks and shovels’ of Hollywood better than many who have clocked years there. Likewise JT and Jay-Z and Timbalake better than Coldplay. Some are just smarter businesspeople. Kutcher and Willis also demonstrate poignantly how modern families might look like and how to conduct those affairs (no pun intended) with as little dysfunction as possible.

    Discretion also needs to be exercised in what we can learn. Madonna, for instance, is a good case study in brand reinvention but not in brand extension (remember the horrible films she has acted in?). Diversification (related or unrelated) and sticking-to-the-knitting lessons can also be learnt by observing some, remembering that not everyone can be Stephen Fry.

    My comments are meant in all seriousness by the way. :-)

  21. Michla
    Michla says:

    Hmmm..what an interesting take on celebs lives. Got me to see things from another perspective and for that I am thankful.

    I personally live in LA so I see tons of gorgeous, well-dressed, surgically enhanced, Vuitton/Coach carrying, size 2 women day in and day out. I mean everyone is SKINNY here – I sometimes wonder if anyone eats anything????

    Really, it’s a bit overwhelming in some respects because the normal woman can feel shabby for being less than perfect and a tad bit insecure and drained by the superficial focus on youth, sexiness and fake boobs, fake smiles and fake personality (amongst many other shallow things).

    I guess in all things there is a positive side and so I get that she is just flipping the script here and taking our celebrity obsession and letting it have some value and enlightenment. Whew ~thank goodness I can now find a way to enjoy it without being bored and annoyed by it!!!!

  22. Mark F.
    Mark F. says:

    “Your going to make mistakes in life. It’s what you do after the mistakes that counts.” – Brandi Chastain – US Woman’s Nation soccer team defender – the one who scored the winning goal against China on National television in fromt of 90,000 fans at the LA coliseum only a few yrs ago.
    Brandi missed a penalty kick against the chinese national team a year earlier…she gets a second chance and will be immortalized for scoring and tossing her jersey…No one will remember her “mistake” a year earlier…If you screw up or make a mistake most people don’t remember them unless your a celeb and even then most will forget it over time if you redeem yourself…Tom Cruise making a fool of himself on Oprah, or Britney shaving her head…No one cares they still go to Tom’s Movies and listen to Britney… I don’t think Celebs teach us much of anything except what we already know…they have the same life challenges we all do…and they get through them most of the time…Living is a learning experience!!!

  23. Lane
    Lane says:

    Ok, I work in downtown Milwaukee. I will not say it is ANYTHING like LA or NYC. However, it is relatively fashion-forward in the business districts of Madison and Milwaukee. There are several major differences:

    –In LA or NYC, fashion-consciousness is EVERYWHERE. Midwestern cities? Not as much – you have to work at a forward-thinking firm (not a conservative financial institution where you still have to wear panty-hose and shoes with closed toes), or in the business district (or in MKE’s case, live in the Third Ward or Downtown).

    –Midwest cities display a different set of fashion interests. The fashions tend to revolve around more comfortable experiences. No, not DKNY, but perhaps Northern Face and REI, more comfortable, high-end active fashion. It might sound like a snipe at the Midwest, but it is true.

    Some of it directly has to do with the fact that Midwesterners don’t seem to really care as much for things deemed “frivolous”, such as an evening gown or eyelash extensions (although both options are growing slowly out here). Strangely, the newest Harley Davidson doesn’t count in this category – Wisconsin people work and PLAY hard, and demand the name brands for these pursuits.

    On that note, I’m totally behind a Nordstroms coming in. Those of us who enjoy fashion spend a lot of time on the internet, in Chicago, or patronizing the few boutiques that have cropped up.

  24. Holly Collins
    Holly Collins says:

    I agree with you that it is important to meet new people (or read about people) to learn more–even outside of your comfort zone and expand your horizon. Btw, I would have dated the farmer too, just because, well, how interesting…(I think I even fantasized about that once, too.) I started a concierge business two years ago just for the challenge of learning and doing new things–jumping in and out of peoples lives and their professions, very exciting. And I, at times read about (gulp) the celebs. I do not learn from people like B.Spears or L. Lohan other than appreciate not being rich because one seems to lose themselves when they become rich and they don't seem to want to learn or get an education because…they don’t have to.

  25. Clara
    Clara says:

    I really feel you on this one. I found I was dressing worse because no one around me dressed well. I went looking for inspiration and decided I liked the way Jessica Alba dressed–classy and stylish. So far so good.

  26. Jason Monastra
    Jason Monastra says:

    I did not really take from this the celeb piece, but your comment discussing learning from mistakes, when things go poorly, etc. I think that allows the development of character as you discussed. Thanks for the post.

  27. jenx67
    jenx67 says:

    The line, “One of my (many) past therapists told me that you can’t really tell how well you’re doing until something bad happens,” reminded me of something my sister just told me upon a rough landing at the Nashville Airport. “I thought the plane was going to crash on landing,” she said. “I sat in my seat, softly crying to myself, knowing there was nothing I could do about it.”

  28. rennie
    rennie says:

    I agree with the comment that Midwest cities go by a different set of fashion interests. They’re often geared more toward active-sports-outdoor wear. And why not, that’s the life many Midwesterners live.

    Who is to determine high fashion for any specific locale? Why would a Midwesterner need a size 2 body, fake eyelashes, and whatever is the latest NY/LA fad. Just for the sake of being like LA or NY? But this is Wisconsin. They would FREEZE!

    Personally, I’m thankful I live in the Midwest and don’t have to succumb to such trivialities and superficialness. I think everyone should move to Middleton, WI and learn what really matters in life.

  29. LC
    LC says:

    What interests me about celebrities is seeing how they manage their careers, expanding beyond acting and rebounding from bad choices. Angelina Jolie, who used to play with knives and brag about having sex in limos (never mind the vial of Billy Bob’s blood around her neck) is now the ultimate earth mother/philanthropist. Tom Cruise is reviving his image. Meryl Streep is more commercially successful at 59 than she’s ever been. And I could cite about a dozen more examples.

    As for clothes, you should dress for the environment you’re in. (I love Sarah Palin’s style, by the way, probably because it’s corporate with a slightly sexy edge). I work in technology companies and an Armani suit would be overkill. But nice separates and heels aren’t out of place.

  30. Kat
    Kat says:


    What you’ve just written in your post and comments is one of the most insanely idiotic things I have ever read. At no point in your rambling incoherent blog were you close to anything that could be considered a rational thought.

  31. John
    John says:

    > Make better decisions for yourself by watching decisions celebrities
    > make

    Well, it’s obviously worked for you. That’s why you’re qualified to give other people advice!

  32. jenx67
    jenx67 says:

    You don’t actually mean any of this right? I mean, you’re brilliant. You’re jerking our chains, right? You can’t possibly think that decisions on who one marries should be influenced by branding? You can’t really believe that people on the coasts are just better looking than they are in Wisconsin or where I live, Oklahoma? I mean, there are just more people in New York City. 8 million in that city alone. Only 3 million in all of Oklahoma.

    Penelope – you’re so smart and witty. What is the real reason you’re writing this silly stuff? Are your trying to identify your most loyal followers to see who will tell you what they really think? Better the truth from an enemy than kind lies from a friend? I can’t believe you read People magazine. You remind me of a girl in college who wrote right smack dab in the middle of her term paper “Professor XXXX is a B*t*h!” She wanted to see if she was actually reading it. Of course, it didn’t hurt that her father was on the Board of Trustees.

    I can hardly wait for your post about how rock stars give you the best parenting advice. You’re kind of sneaky.

  33. Leeroy Glinchy
    Leeroy Glinchy says:

    I think that things differ for me. I never lived in LA nor NYC, but I have visited both especially NYC many times.

    I noticed that people dressed a lot better than what I was used to, but the professionals in Philly also dressed better than me, a technician. But I never wanted to dress so well.

    It interfered with my cycling. I thought that it would feel really stuffy in those clothes. In short, I saw the whole looks thing to be a burden.

    Also, I feel that after five minutes of talking to someone, I can tell how intelligent they are. Clothes don’t tell you how intelligent people are, how hard working they are nor even how much they are worth. Wealthy people sometimes dress down. Poor people often get into debt to hide their poverty.

    Anyone can dress in nice clothes, but nobody can grow a new brain (yet).

    I have gone 180 on clothes for many reasons, but I still don’t see the point in competing on playing dress up unless you are a model in which case, all the work is done for you by professionals who put on your make-up and pick out your clothes.

    Sometimes, I wonder why I have no friends… :)

    • sabina
      sabina says:

      I think, I might change your mind. Clothes make me feel powerful, giving me the feeling that I can do it all. Why not to be the best you can be? People are visual and being able to dress neat and pretty makes the life more amazing.  Again, I am a Photographer. We are all different. 

    • sabina
      sabina says:

      I think, I might change your mind. Clothes make me feel powerful, giving me the feeling that I can do it all. Why not to be the best you can be? People are visual and being able to dress neat and pretty makes the life more amazing.  Again, I am a Photographer. We are all different. 

Comments are closed.