I have a new column debuting on Yahoo! Finance today. I’m very excited.

Yahoo contacted me in November, right after I moved to Madison. And right after I signed the contract, they were all about the head shot.

This makes sense. Yahoo wants everyone to look good. Totally reasonable. If nothing else, there’s the fact that good looking people are more successful at work than ugly people. (Thanks, Jordyn)

So anyway, I sent Yahoo the photo you see here, on the sidebar. And they were not impressed. In case you don’t know the seriousness that is Yahoo! Finance, you can look at the headshots of the other columnists and see that my photo would have looked really unprofessional.

Probably because it is: My aunt took it of me and my cousin, at a party, eight years ago. So it’s not just kind of old, I also had to chop the photo up to get rid of the party and my cousin.

But I really love the photo. Please notice my eyebrows. They’re perfect. This photo is from the time in my life when the only responsibilities I had in the world were to run my company, please my venture capital firm, and look hot enough to find someone to marry. My eyebrows were always meticulous.

Yahoo insisted on a new photo. I immediately went into panic mode, worrying that I wouldn’t get one I liked.

I do know a thing or two about head shots. I had one taken in New York City when I was writing a column for Business 2.0 magazine. Here’s what happened: I gave birth on a Friday and they demanded that I take a photo on the following Wednesday. I said, No. Forget it. I am too fat. I said, Run an illustration of me until I lose the weight. They still said no.

So I capitulated. The night before the photo session I was up nonstop with the baby, but at 8 a.m., I went, baby in tow, because I had just read about how reliable people are reliable all the time and I wanted to be one of those people.

I went without showering, I brought one, black, dirty shirt, and I had not slept well for weeks. I walked into the room and there were seven people there to take care of all the stuff I needed: hair, makeup, they brought clothes for me, they had a caterer; it was amazing. There was a person in charge of making wind blow my hair. And the photos were incredible. No one would ever know how crappy I looked.

So when Yahoo said I needed another photo, I knew I wanted another miracle-working photographer, but I knew there would be no one in Madison who specializes in wind for hair.

I became a lunatic. Thank god I had signed the contract already because I was literally calling my contact at Yahoo three or four times a day stressing about how to do a photograph in Madison. Or Chicago.

Tech columnist Eric Benderoff writes in the Chicago Tribune about how online photos are the new self-portrait and a form of digital self-expression, and how people judge you as soon as they see the photo.

All stuff that made me a wreck about scheduling the photo for my head shot. But at the end of that article there’s a quote from a photographer who says, “If you portray yourself with honesty, people will respond to that.”

That sounds true to me. And you know what? I had the pictures taken in Madison. There was no wind and no catering, and I brought my own clothes. But I really like the result: Check out the new, Madison me.

54 replies
  1. Eric
    Eric says:

    Dear Penelope,

    I think your picture on this blog is great, real and human. No offense, but if I did not know better, I would not recognise you (not that its an ugly picture, but just different). I guess for a more professional look, we cannot just take pictures in our Hawaii shirts and bermudas…. I took my first picture in a suit a few years back and thought to myself…. Who is that guy?

    Anyway talking about looking at ourselves, does anyone hate listening to a recording of their own voice… I am like, who the **** is that guy, he should not be allowed near a microphone!

    Yahoo… its the weekend here on the Island state!

  2. Per-Morten
    Per-Morten says:

    Hi Penelope

    You look nice on both pictures. I have been reading your blog for some weeks now and I enjoy it very much. It's a great inspiration to me. Especially since I have started to blog my self (in Norwegian so far). I am looking forward to follow your articles on Yahoo to. Good look.

  3. Diana
    Diana says:

    My jaw literally dropped when I saw the Yahoo! photo! You look great! I had to click back and forth between your blog and your Yahoo page trying to convince myself that it was the same person. The smile convinced me. :) The hair and make-up are great; they really bring your features out. And I actually like your eyebrows MORE in the new photo. :) Congratulations on the new column!!

  4. Rick
    Rick says:


    You clearly got good advice from the Yahoo! Finance folks. And, your decision to just go with a local photographer turned out to be exactly right, too: your new head shot is the quintessential seriously smart, amazingly gorgeous columnist!

    Keep the old shot on your blog, though…my sense of it is, that’s portraying the personal Penelope, while the Yahoo! head shot is more of your work-you. If you can’t be the real, vulnerable you here, where else??

    Love your blog, and looking forward to your column at Yahoo!

  5. Benjamin Strong
    Benjamin Strong says:

    I came into the office this morning, fired up the coffee pot, warmed up the computer, sadly- bought a sausage mcmuffin with egg (so much for New Years resolutions) and started to read your blog. I also turned on the classic music station here in New York.

    When I got to the bottom of your blog and went to click to see your photo the radio started playing Jeremiah Clarke’s Trumput Voluntary! How regal! What a way to view someone’s new Yahoo photo!

    The picture looks great.

    I was going to schedule my “organic” portrait for this month but the weather changed and it started snowing. I guess I will wait until spring for my outdoor “organic” head shot.

    Congratulations on your latest accomplishment.

  6. Andy
    Andy says:

    Thumbs Up: For the Yahoo Column, that kicks ass and it’s a great picture!

    Thumbs Down: For the no comments @ Yahoo. I know it’s a column but it’d still be cool if we could comment. I was going to say that there are a number of services out there that convert voicemail to email which could then be listened to and filed. Something like j2.com or gotvoice.com

    @Benjamin: You can get some whole wheat English muffins, some Canadian bacon, and naturally slender american cheese and make really healthy egg mcmuffins at home. Just beat and egg in a bowl and microwave it for a couple minutes until its solid, while that’s going toast your English muffin and throw your cheese and Canadian bacon on just before its done so it gets warmed through.

    * * * * * *

    Hi, Andy.

    Good point about the no comments on Yahoo. I I’ll put a link to the column on my blog so that people can comment here.

    Also, thank you so much for breaking new ground on the blog: The first to post a recipe.


  7. Ramit
    Ramit says:

    The photo looks great, but even better, your voice carries right over into your columns. Congratulations–this is awesome news and you’re perfect for the job.

  8. Jason Alba
    Jason Alba says:

    I never noticed your eyebrows, but now that you mention it, yes they are quite nice :p

    What an awesome gig you got, congratulations, its amazing company you are writing with! And both pictures, imho, are outstanding. The one on this blog is casual but honest, the one on Yahoo is really, really nice.

  9. Mary
    Mary says:

    Michael and Laura are screaming to make chocolate chip cookies, but to hell with them–

    Congratulations on the Yahoo column–and that photograph!! It’s great. You certainly look better than the other columnists : )

    I’m extremely happy for you.

  10. Tom Morgan
    Tom Morgan says:

    Congratulations on becoming part of the Yahoo Finance team and for sharing with us the importance of good pictures on the web.

    I love both of the pictures because they reveal your happy / fun loving nature at different times in your life. Thanks for sharing the personal side of your life while also educating us on the real world.

  11. Emily
    Emily says:

    Penelope, both your photos look great. The new one is quite professional, but still you.

    Don’t worry about losing your honesty – you definitely have the same honest, intelligent smile. Even leftie news guru Amy Goodman had to get rid of her dredlocks for a more restrained bob when Pacifica’s Democracy Now started broadcasting on TV.

  12. Penelope Trunk
    Penelope Trunk says:

    Hey, everyone. Thank you for all the nice comments. I really appreciate all your support. And it’s nice to know that the photo has widespread approval :)


  13. Richie
    Richie says:

    I’d like to add my congralations, Penelope!

    Your column looks set to be a big success. Good luck!

    By the way, I actually prefer your photo on this site. It’s more natural and attractive. IMHO, of course.

  14. michael gibbons
    michael gibbons says:

    Penelope, first I think you look fine — there is certainly less hoo in their Yah then when Godin was cruising the halls over there! Ya know! Anyway looked at those Finance headshots — look(are)like cardboard cutouts — anyway — Got Photoshop? I suggest take the Suze Orman picture and PS in some brunette hair –submit that — Yahoooooooo!

  15. NatalieM
    NatalieM says:

    Hi Penelope,
    First of all, i wanted to offer my sincere congrats on the Yahoo! column – it’s one of my favorite feature on Yahoo! and i read a couple of column authors consistently (okay – Laura is just great). You do have an amazing writing style.

    On the second note, though, i have to say that i did not like your Madison photo that much (the old one, with perfect eyebrows is very charming). And it’s purely for the reasons the way your Madison photo is made. Your face look flat and one dimensional. E.g. if you look at the pictures of other columnists – their faces have volume, shades and natural colors. Your face looks too light and it does not have much volume at all. If it is at all possible, I’d ask Harold Mass, Ben Stein or Jack Guttentag where their photos were made (heh, it looks like those guys had their photos taken in the same studio!).

  16. Lena West
    Lena West says:

    Congrats on the Yahoo gig!

    I TOTALLY know what you mean about photos. When I started guest blogging for Small Biz Technology, the Editor (a close friend and colleague), Ramon Ray, told me that the photo I was *totally* in love with was grainy and wasn’t going to work. *gasp! clutch the pearls!* He was nice about it, as Ramon ALWAYS is, but I *dreaded* the thought of taking new head shots.

    You should know that the last time I had headshots taken, my eyebrows were so over tweezed that I looked like Cruella DeVille with a tan. Yuk!

    Eventually, I got him to agree to not use any photos until I have more taken. But, somehow “get new head shots” seems to mysteriously fall off my Palm Pilot calendar. :)


  17. PunditMom
    PunditMom says:

    Congratulations! That is such great news about the new column!

    I thought you looked great on the Yahoo picture before you told the story! That’s amazing how good a professional photographer can make a dirty shirt look! You look fabulous! (And, of course, I DID take a look at the eyebrows on the pic here!)

  18. Recruiting Animal
    Recruiting Animal says:

    Notice how the posting about your appearance garnered the most comments I’ve ever seen on your blog. That’s typical, by the way.

    And of course, I have an opinion. The one on this site is better. Fresh faced with less makeup. (Did I put my foot in it?)

  19. Susan
    Susan says:

    Penelope, I think the new photo is fabulous! You look very pulled together and professional, but your blog photo also has a certain friendly appeal, too. I know just what you mean about fear of photos, because I just had my headshots redone (I’d been using the same photo for the last six years – yikes!). Congrats on your new column!

    * * * * * *

    Hello everyone – take a look at Susan’s blog, The Urban Muse. She has an illustration of herself up top instead of a photo. I like that. Solves so many difficult photo issues, although it creates the problem of where to find a cheap-but-good illustrator.


  20. Dean L Heaton
    Dean L Heaton says:

    Congratulations on the job. As for the photo, going with a professional is always the way to go. I don’t think you’d be asking you Aunt for expert financial advice to put into your column, so we shouldn’t expect our friends and family to do the job of industry experts. Yes we love them and think they’re all very clever, but professionals are there for a reason and using them makes us look more professional and also helps keep the economy turning the way it should. PS, you look stunning.

  21. melanie gao
    melanie gao says:

    I’ve often wondered about the background of your blog picture! I remember you said that was your brother’s first comment about your blog, that you needed a new headshot. The brows are perfect, girl.

    I love the Urban Muse’s picture. I’m sure I can find an artist in China who will do an illustration of you for next to nothing. Let me know if you want me to check it out.

    Congrats on the Yahoo gig! :)

  22. bettina
    bettina says:

    Congratulations on the column! To add my two cents, I prefer the blog photo! When I saw it, it made me think of a wise older sister kind of figure. The yahoo photo looks very good and very professional but less personable, kind of like every other career talk person out there…

  23. Don Dwoske
    Don Dwoske says:

    Just found you on the web.. I think I started on Lifehacker and got here somehow. I live in Boston, so your work with the Globe made me poke around a bit. I’ve read about six of your articles and a handful of your blog posts, I love what you are saying.

    Part of the reason I stayed on your site in the first place is because you look really great in your blog photo. You look like a kind, friendly and genuine person who might have something interesting to say.

    The new Yahoo picture is not nearly as “real” as the photo here. It’s hard to get a professional picture that doesn’t look *too* professional.

    If I were shown the two pictures and asked to choose which person I would want to talk with, I’d choose the blog picture person without hesitating.

  24. A Yahoo Finance Reader
    A Yahoo Finance Reader says:

    Yeah, I just read your Yahoo bit about the “eye cream” deduction you wanted for your photo. Nice. You’d have been better off investing in a paper bag.

  25. Kent
    Kent says:

    Penelope, surely it is your work and not your image that should be more important to Yahoo. If people judge you by your online image and not by your journalistic prowess, are they really worth worrying about it. my guess is not now that the wonderful world of finance is slowly getting better though but I liked the original photograph and there is nothing wrong with windy hair!

  26. Irfan
    Irfan says:

    Yeah, I just read your Yahoo bit about the “eye cream” deduction you wanted for your photo. Nice. You’d have been better off investing in a paper bag.
    journalistic prowess, are they really worth worrying about it. my guess is not now that the wonderful world of finance is slowly getting better

  27. Liverpool Wedding Photographer
    Liverpool Wedding Photographer says:

    “If you portray yourself with honesty, people will respond to that.”

    If you portray yourself with honesty then “honest” people will respond to that, especially in business and the people that you develop long term relationships with are those that are honest!

  28. Wedding Photography Surrey
    Wedding Photography Surrey says:

    Your comment, “My eyebrows were perfect!” made me smile. I totally agree with the photographer. On occasion I have been known to extract myself from a family photo and adjust colour in aperture and then place on a background in photoshop. Not the best but gets the result that needed.

  29. Mike
    Mike says:

    internet is really god place for advertising of photos. About 90% of European people can see your website! it’ s really good!

  30. Susan
    Susan says:

    “If nothing else, there’s the fact that good looking people are more successful at work than ugly people. ”

    Shame on you for that comment. Can’t say I’m interested in anything you have to say after reading that.

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