Webinar on Friday, Wedding on Saturday


I’m getting married on Saturday. We will talk about that in a minute. First, I want to address the recent onslaught of complainers who have entered my life.

  1. People who tell me I’ve jumped the shark. Honestly, I had never even heard this idiom until people started writing it in my comments section. But I’ve been writing about my personal life for ten years, and anyway, the people who complain that I don’t write enough career advice are always the people who most love to read my posts about sex.
  2. People who tell me I should record the webinars. Look. I know I should. But I don’t control it. Ryan Paugh does. Fortunately, we have a bitch session network on Brazen Careerist, and Ryan is in charge of it. So you should go there and tell him to record the webinar this Friday.
  3. People at my office who wonder why I’m not there. Have I ever told you guys how much I love waking up every day and having a wide span of time to be by myself? I wish I had paid more attention to recess. I always spent recess alone. Just to get a break from everyone. Nothing has changed since fourth grade except that it’s not the playground, it’s Starbucks.

Now. For the wedding. Here’s what I’m wearing:

I am obsessed with boots, and I buy a new pair of boots at Target every month. I think it’s because if I wear heavy socks with them then they squeeze my feet the way a hug machine might, and it helps me relax. Also, I never knew about how important weights are for self-regulation until I took my son to occupational therapy. Now I’m convinced that the boots are a little heavier than shoes, and that also are somehow is helping me focus. So I’ve pretty much stopped wearing shoes. And I was thinking of going back to shoes for the wedding, but we’re getting married on the farm, and the farmer always tells me to wear boots on the farm.

I don’t have the dress yet, but I’ll find one tomorrow. I think white will match well. I wasn’t going to get white, but my sons are suspicious that it’s not a real wedding if there is not white dress.

The second important thing you need to know is that this week’s webinar is Friday, April 14, at 1pm central. Sign up here. The topic is How to Figure Out Where to Live. I have written about this topic a lot. How where you live affects your happiness. How it affects your career, but I’ve never written about how it affects your boots.

These are the last pair of boots I bought when I lived in New York City. They were from Banana Republic.

People really underestimate how much cheaper it is to live in the boondocks than in a major city. It’s not just that the prices are lower for things you’d normally buy. It’s not just that there are no expensive stores. It’s that you stop valuing expensive stuff because no one else has it.

I never bought clothes at Target before I lived in Madison, but there are simply no high-end stores here, so there is no drive to have high-end clothes (until I fly in to NY or LA.) So I buy a lot less of everything, and I buy much cheaper versions of a lot of things than I would ever dream of buying if I lived in a larger city.

More on that in the webinar, of course. And, by the way, here are the boots I’ll be wearing in the webinar, because in video land, no one knows what you’re wearing below your waist:

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    • Toulie
      Toulie says:

      As I approach my 30th wedding anniversary I am always amazed at the work, the incredible marriage school I’ve been through. Yeah, after college I figured I was done with formal education, but being, staying and trying at least, to excel at marriage is my real legacy. Congratulations

  1. Andy
    Andy says:

    Ms Trunk:

    Thank you for sharing so much about your work and life. I’m trying to find ways to sift out the useful tidbits and apply them to my life.

    Best of luck with the wedding and the marriage!

  2. helen
    helen says:

    I am another person you don’t know wishing you a happy wedding day…the wedding boots are beautiful! love your posts…

  3. Charlene
    Charlene says:

    Very interesting about the boots; my Asperger’s daughter loves boots and I hadn’t even thought about the weight factor. I see more boots in her future. And congratulations on your wedding.

  4. Siddhartha
    Siddhartha says:

    Haha, I love how you verbally slapped those whiners. They deserved it.

    After all, the last time I checked I wasn’t paying to read this blog so what obligation do you have? It’s like someone hanging out in my living room and then complaining about my conversations with my friends.

    I see it as an opportunity to spend time with a witty, intelligent, diverse and remarkable woman. I’m happy to just hear you talk about whatever’s on your mind.

    Sometimes it’s funny, sometimes insightful, sometimes relevant to my life, sometimes not. But always entertaining.

    Go get ’em. And have a blissful wedding, you deserve it.

  5. wendi Knox
    wendi Knox says:

    I’ve never heard that shark expression myself. All I know if that you are brave enough to be yourself and that is inspirational. May you walk in joy no matter what you have on your feet. Oh and one more thing:

  6. LPC
    LPC says:

    Holy Mother of God. Penelope Trunk just showed Liberty of London wellies on her blog. My entire mapping of significance has to be reset:).

  7. Ilana
    Ilana says:

    Happy wedding – enjoy!

    P.S. Wearing boots will make the whole glass-stomping thing a safe affair… Quite practical, actually.

  8. Seb
    Seb says:

    Penelope… Love the floear wedding boots… Love your blog, your spirit, your determination and wisdom… Savory every moment!

  9. Deborah
    Deborah says:

    P – best wishes and a sweet new chapter for your little family. Are you going to web cam the wedding too? Just kidding. xx D

  10. JenG
    JenG says:

    First, I don’t think I’ve told you congrats yet, so let me get that out of the way: CONGRATS!

    Second, this post resonated with me so much. It was a recent relevation to me that my current job, while good in many ways, requires too much extroversion for me. It wears me out so much I have no time for my friends on the weekends. Sometimes, if I’ve been in meetings all day, it even impacts my relationships with my family. How could I not have realized that all these years?!

    Although I could easily pursue a high-profile job, it’s clear I’m best suited for part time work (like consulting) or more solitary activities. I make the transition this summer. It almost feels like I’m marrying the new me…


  11. J Richardson
    J Richardson says:

    I love the “wedding” boots! And best wishes to you and “The Farmer” for a very long and happy life together.

  12. rah
    rah says:

    Congrats on your upcoming nuptials! May you and the farmer and your children have many years of bliss and joy together… Someone once told me that the most important day of your marriage isn’t your wedding. It is the day that you think of walking out and you stay. May those days be few and far between.

  13. Alice Bachini-Smith
    Alice Bachini-Smith says:

    I just gave my daughter those boots for her birthday, they’re the best L of L thing Target is doing :) Have you tried flannel sheets? Fabric that feels good is important for Aspergers people too, bedding as well as clothes.

  14. Mary Budge
    Mary Budge says:

    Love the boots Penelope!!! I sure hope you will post some pictures from your wedding. Looking forward to the webinar on Friday. I know where I want to live – Hawaii – I just don’t know how I can live and work there!

  15. Maggie McGary
    Maggie McGary says:

    You have totally not jumped the shark–I am just working on a blog post about how obsessed with you I am. You rock and your blog is my favorite by far–and I read a lot of blogs.

    Wish I had time to send you my 2nd wedding dress–got it on ebay for $9.99 and wore it at the Wynn and it looked awesome.

    Best wishes for a wonderful wedding day and a happy ever after.

  16. Janet
    Janet says:

    Penelope, you sound happy! That makes me happy for you. And I totally relate to your desire to wake up every day and spend a nice long chunk of time at Starbucks…that just became a career goal of mine.

  17. Pam
    Pam says:

    Love the boots – I have some pink with white polka dots too. They’re under my desk at work. Great for HK tropical downpours :) I won’t wish you good luck for your wedding – have fun instead x

  18. Helen
    Helen says:

    Yep…. photos work very well in your blog. Please keep it up!
    Best wishes for the ‘Happy Ever After’ part (not to mention finding the right dress with no time to spare).

  19. Dave Egyes
    Dave Egyes says:

    Congratulations on your wedding! May it be for you a great source of happiness for yourself and your family.

  20. Jens Fiederer
    Jens Fiederer says:

    Just goes to show that even whining has its value – at least when it teaches you idioms!

    This wedding fashion bit is really changing the look of your blog….Manolo the shoe blogger is probably getting nervous about his turf.

  21. Pam
    Pam says:

    p.s. jumping the shark comes from the Brady Bunch – ratings got so low that producers made one of the Brady kids (Mike?) jump over a shark while on waterskis in an effort to boost ratings.

    • Lauren
      Lauren says:

      Not Brady Bunch. Happy Days. Fonzie jumped the shark on waterskis when they were visiting Hollywood.

      Now back to your regularly scheduled comments.

  22. Vicky
    Vicky says:

    For the white dress, just get something you are comfortable and beautiful in and the wedding will be a blast.

  23. Wal Heinrich
    Wal Heinrich says:

    Congratulations! I guess you already know the weather forecast. Fine and a few clouds, it says. Hopefully no rain so you won’t need the rubber boots.

  24. Chuck
    Chuck says:

    Congratulations on your wedding. I wish you and the farmer all the best.

    May this next chapter in your life awe you with wonderment and leave you breathless with joy.

    PS – thanks for being thick-skinned enough not to listen to your detractors.

  25. Bob
    Bob says:

    I like the boots, I sure hope the farmer does.
    You absolutely march to a different drummer. I bet the wedding will be really special.
    Congratulations and best wishes!

  26. Deborah Stephens
    Deborah Stephens says:


    I have figured out why I like your blog so much after stumbling upon it many weeks ago. You live the best advice I was ever given by a very wise and successful guy from Silicon Valley. He told me when I was 22 that “making a living” would be easy but “making a life” is where way too many people stumble.” I think that is what you are doing in your blogs: showing people in a very brave way how to make a life that matters.

  27. Jan Hogle
    Jan Hogle says:

    Congratulations, PT!! I just saw those adorable flowery boots at the Fitchburg Target on Sunday — they caught my eye. I was buying Sock Monkey ballet slippers, which were only available at that particular Target.

    Isn’t Macy’s a “high-end” store? It’s at Hilldale. You must have been there. Moi, I shop at Kohl’s & Target. Who cares. Well, also at J.Jill at Greenway Station on the west side. Have you been there yet? That’s a bit high-end for me but the clothes fit. Also, I’ve lost 23 lbs so must buy new stuff. Hey, have a wonderful day on your wedding day! Will be thinking of you!

  28. Allison
    Allison says:

    I think men in particular have a hard time understanding that women have to incorporate work and life together in order to cope. There is not work/life balance – it’s more of a huge hodgepog of experiences that make up a woman’s life. I have noticed this with my husband. He goes to work – he comes home – the two don’t intermingle. My work follows me home and my home follows me to work (school meetings during the day and classroom functions need to be worked around everything else.) This is how women are happiest and men just don’t get it.

  29. Anita
    Anita says:

    You go girl! Yours is one of the very few blogs I read anymore. Maybe because I’m at such a similar place in my life. Wishing you years of joy and happiness.

  30. J
    J says:

    Congratulations! Let me give “the farmer” the same advice my grandmother gave to my husband before our wedding:

    “Just be nice to her and everything will work out fine.”

    I love that advice.

  31. Sara
    Sara says:


    I think it’s interesting that people are saying that you’ve “jumped the shark,” since that phrase refers to a stale storyline in a fictional series. You’re writing about your ACTUAL LIFE.

    I just shake my head at all of the folks who seem to think that the people who “live inside the magic box” are solely there for entertainment purposes.

  32. Renee
    Renee says:

    I think the “shark” people are control freaks who think life should go a certain way (including yours) and I hope they deal with their issues outside of this forum, they will be much happier for it.

    Cute boots! I got a mult-colored polka-dot pair at Target for $9 and I swear I saw the same pair in Oprah magazine for $60… suckers!

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