Good plans feel unsteady

Cullen left. It’s unclear if he has dumped Melissa. I think he has. (If you missed earlier installments on this story, here’s where I find Cullen in Melissa’s bed.)

This photo is from when Cullen was excited to be in lots of photos on my blog.

Good plans feel unsteady

It was the day that a TV writer emailed me about adapting my blog for the big screen. Or semi-big screen. Or whatever we are calling TV now, but I have to say, as an aside, that TV is the new hipster medium because episodes allow for more character development than a single movie. I heard this from the Farmer, and he’s not a guy who could make this stuff up. And we are watching Breaking Bad and I want to be absurd and funny like those writers.

This is what happened with Cullen. He agreed to redesign my blog in exchange for free room and board. And then he realized he didn’t have time to do that, because he has a full time job.

Meanwhile, we were having big Facebook drama on the farm because Melissa does not feel like she has a boyfriend unless the guy puts in on his Facebook status. So Cullen did that.

And then, the day after the status changed I told them that I think they need to live together as boyfriend and girlfriend somewhere else because it’s not working for us here on the farm.

So Cullen went back to Austin. He told Melissa that she can come back with him, but he doesn’t want to live with her.

Melissa said, “How come you want to live with me on the farm but you don’t want to live with me in Austin?”

Cullen said, “I don’t know. That’s a good question.”

Melissa decided to stay on the farm. Cullen decided to go. But they decided that neither of them will change their Facebook status. Cullen said, “I’ll be back.” And maybe to show that, or maybe because they were so cheap, he left his green rubber boots behind.

We said goodbye to Cullen at 6am when he left to catch an 8:30 am plane. Melissa drove him to the airport.

But not really. Because five minutes after Cullen says to me, “Okay. See you soon. I’ll be back,” he said to Melissa in the car, “I actually don’t have a plane ticket. I have a train ticket. I just didn’t want to tell Penelope.”

I’m not sure why. I do not have anything against trains.

Three days pass. Cullen writes an email to Melissa explaining why he had to leave. We read it at lunch even though I told Melissa she is not allowed to bring her iPhone to lunch.

The Farmer reads the email and says, “Guys should never send stuff to girls in writing. They just show it to all their friends.”

Melissa tells me she is going to die if I don’t write on my blog that Cullen and Melissa are not together. “I need closure,” she says.

I tell her I have to write about careers.

Melissa says, “Why? You never write about careers. Anyway, look at James Altucher. He’s a finance blogger who doesn’t force himself to focus on finance. And we love reading his blog.”

“When I am independently wealthy like James Altucher then I’ll write about your love life.”

The Farmer says, “Penelope’s career advice chapters are like the whaling chapters in Moby Dick. You like the storyline about psychotic behavior, but you need the whaling chapters to keep things based in reality.”

I wish there were something on Facebook for me to quantify how much I am in love with the Farmer. I give him a ten for his combination of intellect and strength to hold my goat down so I can milk her. I think maybe I can make a plan for my blog that is a little scary because I feel secure with the Farmer. You need to feel secure in one place to create instability in another.

Melissa gives me more blogging instructions: “I want to make sure you write that I’m sad.”

The Farmer shakes his head. “No. You can’t do that.”

“Why?” I ask.

“Do you two know anything about playing hard to get?”

I laugh. The Farmer broke up with me about 50 times. Twenty-five of those times were because he thought he should be the one doing the chasing. “Guys do the chasing,” he would tell me. And then I’d kiss him.

“No,” I say. “Melissa and I have no idea how to play hard to get.”

The Farmer says, “You cannot email Cullen to tell him you miss him. That gives him an opening. He left, and he has to make his own opening to come back. People care more about their plans if they make the plan themselves.”

This seems true. It seems true for all plans. For all departures. For all entrances. And you can tell if it’s your own plan by how lost you feel. People who do their own plans feel lost most of the time. People who do other peoples’ plans feel on track most of the time.

Melissa says, “Fine. Is that going to be your post? Fine. But I want to take a picture for the blog post about being sad.”


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  1. Ann
    Ann says:

    Can we read more about the goats? They’re more attractive, more intelligent, and more interesting than those two inconsequential airheads you’re boring us with.

    • ResuMAYDAY
      ResuMAYDAY says:

      Agreed!! It’s a few days into their new relationship, and Melissa can’t be bothered to look happy, or…pulse-ish. Maybe they both knew that Cullen was about to dump her. That would explain her expression, and CERTAINLY explains his! Sorry…not a Melissa fan. Either she’s not as brilliant as you think she is, or you’ve just been keeping her brilliance to yourself. I’m a fan of the farmer.
      I love the goat pictures – they are definitely worthy of more space in your blog.

  2. Roberta Warshaw
    Roberta Warshaw says:

    Love the goat in the boots! Great shot.

    Sorry for Melissa but she should get over it rather quickly since they weren’t together long enough to really get into it…..

    • Jacob Roeland
      Jacob Roeland says:

      That doesn’t mean that what they had wasn’t real or that she didn’t really care about him or that she won’t miss them. You can’t just say “Oh she should get over him quickly; they weren’t together long enough for anything” because you don’t know them, don’t know how they actually felt.

  3. Sally
    Sally says:

    Yes! People care more about their plans if they make themselves. and yes again! People who do their own plans feel lost most of the time. I think that’s the whole appeal of your blog–from someone who feels lost most of the time. And furthermore yes! you need to feel secure in one place to create instability in another. The story about the star crossed lovers is just an entry point. Thanks for a terrific post.

  4. Ella
    Ella says:

    Those goats are so cute and your pics are really improving…

    I agree with the other reader, I also want to read more about the goats and the farm. Your posts make me miss being on one.

    Personally, I think the farmer has a lot of good advice.

  5. sadya
    sadya says:

    The end is so damn hilarious. I really wanna know whose idea was it to take the pics of the goat with the boots. And you are so right about people who do their own plans feel lost most of the time. Really good post.

  6. former shepherd
    former shepherd says:

    I remember a crude joke about barn boots and sheep (or in Cullen’s a case a goat). Seems like it was something about beasteality…

  7. cheryl
    cheryl says:

    First, Melissa is darling! And Cullen’s green boots? Also darling. And the goat playing with Cullen’s green boots? Even more darling! Lots of cuteness in this post.

    And the Farmer is so right… we do care more, when we make our own plans.

    I have a feeling we haven’t seen the last of Cullen. There are always twists and turns in life. If he wants to come back, he’ll find a way.

  8. chris Keller
    chris Keller says:

    I see many lessons in this post. Lessons that apply across the lines–could be career lessons, could be relationship lessons, could be start-up lessons, could be plain ole wisdom, hard-won:

    You can only take so much of total immersion. Then you have to take a step back and ask yourself if you are heading towards fanaticism. Falling in love is a kind of fanaticism . . . IMO.

    Blending families is fraught.

    If you are making your own plans v going with someone else’s plans, you will find out how generous you are/feel. You will find out if you can compromise and how much you are willing to compromise. You may find out that you know little about how to be generous . . . that you were never “taught” this skill/quality. You may want to teach yourself how to be generous and how to compromise.

    Playing hard to get is just a way of testing a relationship, testing the other in a relationship. It amounts to stressing the other/relationship in order to see how strong it is. It is like pushing–like the army where you do a gazillion push-ups when the sergeant says so. No good reason except to assess your “loyalty”. If you like this style, you should be in the army . . . IMO.

    No face time. Indirect forms of communication. No sex = More tests; = More push-me-pull-me.

    It isn’t working out for you at the farm. On the farm, there is the original family, only recently stabilized. There is added livestock, a new business or two, gardens, fields to tend, and the original animal husbandry. Coming up is the summer, where 2 boys need a lot of input, supervision, teaching, coaching in order to take their next steps. The kids, though they weren’t mentioned in this post, should take top priority. Give them your best energies! IMO.

    The stability is precious. Cultivate it.

  9. Brad
    Brad says:

    The farmer is right. In this post the eclectic world-traveling careerist Melissa comes off like a needy schoolgirl. Of course Cullen has probably already read this, so the hard-to-get angle is blown.

    • Penelope Trunk
      Penelope Trunk says:

      I am pretty certain that every woman who is a world-traveler careerist has, at times, been a needy schoolgirl as well. Women are complicated. Everyone is complicated.

      This reminds me of when I read that it’s common knowledge among call girls that the more power the guy has in business the more likely he is going to want to be dominated in some weird, nonstandard way in bed. Reading this info made me realize that men who have huge careers and put their I’m-a-leader selves up front all day long are just like everyone else in that they are multifaceted, with different needs in different circumstances. Actually, the image of the CEO as a masochist really liberated me to think outside of hierarchies at work.


  10. Diana Fisher
    Diana Fisher says:

    This post is perfect because it reveals the personalities of three different characters so effectively. You know just what to share with us to give us a glimpse into who they are. I know why you love Melissa. She reminds me of one of my 5 daughters. And I know why you are so much in love with your Farmer because I have one just like him. Sometimes they say things and you just want to write down the wisdom, the witticisms, the Farmer-isms, so you can keep them to share again later. And sometimes you’re lucky enough to have a notebook handy. And a camera. Looking forward to hearing more about the TV developments. I hope they can bring your true voice to a script so we don’t lose any of you.

  11. Diana
    Diana says:

    Tell me again why is Melissa there?? Sorry, that’s a train wreck waiting to happen.
    As for the farmer– he is a great partner for you, I am so glad you are together!

  12. Harriet May
    Harriet May says:

    I think I have felt lost since college because I am no longer following someone else’s plan. I think this is common. But I have no idea how to get most of the things I want… I’m in awe of all the people who seem like they know what they’re doing from the start. But I think they must be either faking or fabricating the story after the fact, right?

    I love the sad goat picture. I think that’s how I feel most of the time, but not because Cullen left.

    • Margaret Goerig
      Margaret Goerig says:

      “I’m in awe of all the people who seem like they know what they’re doing from the start. But I think they must be either faking or fabricating the story after the fact, right?”

      Just because someone seems like they know what they are doing, it doesn’t mean they do, or that they’re not scared of being out on a limb, or that they don’t think of quitting and going back to something conventional every single day. History is full of people who have done something extraordinary enough to get put in the books and it’s not that they are made of anything different from the rest of us; they’re just willing to write the script, as opposed to following one that’s written for them.

  13. Robin
    Robin says:

    Penelope, you are a genius and a prophet. In our neck of the woods everyone has a friend like Melissa come thru their home from time to time. Some of us house actors in the summer for profit and drama.
    Anyway, this post is also great parenting advice – the plans they make themselves and feeling lost part.
    And I love your husband because he is so grounded and literate and wise all at the same time. You two are a good pair.

  14. Lisa
    Lisa says:

    Moby Dick’s whaling chapter? I love the Farmer too now. What a smart man. Too bad you two aren’t having babies. That’d be one hell of a genetic combo. Oh well, just enjoy the genes in their currently expressed mode.

    • Jenn
      Jenn says:

      Agreed, well not about the babies. That’s neither here nor there, in my opinion. But I am grateful to hear someone address the reason for the whaling chapters in Moby Dick. They were a great mystery to me and I was never sure why they had not been burned in a fire long before now. I may have to give them a second look now that I am not just trying to get through the novel.

  15. Susan
    Susan says:

    I loved this. I think you are just so deft at cutting things down to basics with this great, stripped-down style. And like others said, the Farmer has great advice and the goat pics are sweet. But it’s the combined elements that just worked for me. Thanks!

  16. Noel
    Noel says:

    Penelope, I just wanted to say thanks for writing this post. It was exactly what I needed to hear this morning.

  17. Monica
    Monica says:

    I’m trying to say something without being mean spirited…which is a bit how I feel, but not what I want to express…

    But what the hay. That chick will move on. She’s skinny and not black. Those are the primary qualifications for femalish desirability in the US of A. She can have any one of a multitude of dudes.

    The goats are way more interesting.

    • Tanya
      Tanya says:

      I agree that Melissa will land on her feet. I would also love to hear your thoughts on how blackness affects desirability.

      • Monica
        Monica says:

        Race obviously doesn’t affect desirability

        …but culturally it’s a different matter. Go to any large dating site and check out the number of guys who specify they will date any sort of female except a black one is only exceeded by the number who will date any sort of female except a fat one.

        Melissa has nearly unlimited dated potential. She can probably find a guy who will put up any degree of silliness because of her cultural desirability.

        She’ll be fine.

      • Penelope Trunk
        Penelope Trunk says:

        I have to agree with Monica. There is great, great dating data on the OKCupid blog. And they slice the dating data a million ways and it always comes out that black women have a hard time on dating sites.

        Also, women in their 20s do very very well on dating sites and then things go downhill for women, in terms of the attention their online profile garners.

        I am actually obsessed with the OK Cupid blog. Such interesting stuff there. For example, women who are quirky in their photos get more attention than women who are conventionally beautiful. OK Cupid blog guy surmises that this is because people want to feel a unique connection to the person.


      • Mark W.
        Mark W. says:

        Penelope, have you considered changing the photo of yourself on this blog to one that reflects your new lifestyle on the farm?

      • Tanya
        Tanya says:

        Monica – Disheartening news for my phenotype.

        Penelope – Thanks for the tip about OK Cupid’s blog. Fascinating data.

    • Celine
      Celine says:

      WTF kind of comment is that? What does being black have to do with Melissa’s desirability? She looks and comes off as a needy, whiny girl with no plans for herself and that alone turns a lot of men off. Maybe her being white is a disadvantage for a man who wants more than a clinging vine.

    • Margaret Goerig
      Margaret Goerig says:

      And I’m reminded of that crap psychologist who might get fired (or already did) for publishing an article that said that black women are the least desirable population and that they think they are much more attractive than they really are. It’s toxic thinking and even if some meat heads are propagating this belief on some dating sites, I’m not sure it should be overlooked that they are on dating sites.

  18. DC
    DC says:

    I guess I should just visit the folks in Shullsburg for the first time in several years, take a trip to Darlington and hope to run into Melissa? I mean, cooking is fun. She should cook. She can even use her iPhone, because my iPad is handy for finding recipes. She seems smart, but that guy was all wrong.

  19. Irving Podolsky
    Irving Podolsky says:

    Gonna miss the Cullen/Melissa storyline. Glad you and the Farmer are copacetic again. A goat in boots is cute, but isn’t this little guy stage one of your new start up – goat on a plate? Have you named your dinner yet?

  20. Chris McLaughlin
    Chris McLaughlin says:

    Those two are children. We should go back to the times when children don’t have sex except sneakily, when making it public was done to disgrace you. It was more fun that way. Plus it seemed IMPORTANT. Now, like relationships, it’s just. . . something you do casually, without much thought or development. Like brushing your teeth only without the longterm commitment.

    • DC
      DC says:

      We should also go back to the time when children like that could buy homes and didn’t take out mortgage loans of debt to get a college degree. But you know since those days aren’t coming back…

  21. Elizabeth
    Elizabeth says:

    I think maybe it’s not so clear to the readers here why Melissa plays such a huge role in your life and this blog. I’m sure she’s lovely but it’s all kind of un-interesting (no offence Melissa). I suspect being trapped on a farm makes you think this is all very dramatic and exciting but your perspective is off.

    The Farmer is right; if you want to make a man want you, you have to make him miss you. This is not fair but what is?

  22. CS
    CS says:

    How old are Cullen and Melissa? I want to know. I think they are my age. Both very cute. Hope they end up together.

  23. Bridget
    Bridget says:

    I once met a guy in Telluride Co. spent the day with him and one month later flew to Utah to spend the weekend with him. On Sunday morning he told me he lied. Prepared for the worst like the reason he still has pictures of his wife and family around the house was that he was still married, I hesitantly said Ok. He said, “I am really 38 not 36.” At that moment my fright or flight instinct kicked in. I think it is kind of like the he has a ticket for the train instead of the plane. Why lie about something that insignificant? I don’t think that Cullen was straight with you-Straight being the important word in this sentence. or shall we say he was straight with you but I don’t think that is who Cullen is in Austin. Just a thought…

  24. Brooke Farmer
    Brooke Farmer says:

    First, I love James Altucher’s blog. And I agree with Melissa on that front.

    Second, “You need to feel secure in one place to create instability in another” is so true and yet completely lacking in my world right now. What I wouldn’t give for just one area of my life to seem stable.

  25. Katy
    Katy says:

    I’ve moved since ordering the book. I move frequently right now as I’m couch surfing and unemployed so please don’t take this as some sort of dig that the book is taking too long. How do I change my shipping address?

    • Penelope Trunk
      Penelope Trunk says:

      I should do some sort of study about how the group of people who ordered the book change addresses at what is surely an inordinately high rate. I wonder if this is true of the readers of this blog in general?

      Anyway, Katy, you can email me directly with the new address. And may your next couch be your best :)


  26. Tzipporah
    Tzipporah says:

    Your most insightful post in a while. Although I think in this case, the insight is coming from the Farmer. :)

    LOVE LOVE LOVE the pictures.

    PS – tell Melissa to stand up straight.

  27. poppygirl
    poppygirl says:

    I can see the TV show now. Seinfeld on the farm. Scary.

    great goat pix.

    The Farmer is rising steadily in my estimation. Funny, smart, and makes literary allusions. Yum.

  28. Mark W.
    Mark W. says:

    “It was the day that a TV writer emailed me about adapting my blog for the big screen.”

    I’ll be interested to read more about this experiment when you’re ready to write about it.

  29. Twister
    Twister says:

    Those photos of the goats are actually really sad. Well, the first one is sad, like the little goat is waiting for the shoes to be filled again; the second photo is like the angry post-breakup “screw you, boots”.

  30. zan
    zan says:

    the body language between cullen and melissa tells the actual tale.

    the farmer is, if i’m not over-extrapolating, the quintessential man.

    and i will be quoting you on my facebook page in a couple of minutes. you expressed a truth (for me) that i’m freshly on the road to facing and forgiving.

  31. Sutah
    Sutah says:

    So what is Melissa going to learn from this experience with Cullen? How do relationship failures compare to business failures? This post on your blog made me think of this blog: The closure of Alisa’s business was the end to the best Whoopie Pies in Southern California. What did Melissa lose when Cullen left? Did she really become that invested in him in that short period of time? What did he bring to her life, besides being his girlfriend on FB, that made him a wonderful man for her to be in a relationship with? It doesn’t sound like he was a man that she could count on. She deserves better than that.

    A relationship to person can be all absorbing, but so can a business. Penelope, you are fortunate to have a good man with common sense to share your life with so that you can take chances.

  32. parker
    parker says:

    the farmer is my favorite character. i come to read penelope’s writing but the farmer is “it”.

  33. Chris Yeh
    Chris Yeh says:

    “The Farmer says, "Penelope's career advice chapters are like the whaling chapters in Moby Dick. You like the storyline about psychotic behavior, but you need the whaling chapters to keep things based in reality."”

    Best. Line. Ever. He truly is a genius.

  34. downfromtheledge
    downfromtheledge says:

    “Never make someone your priority while allowing yourself to be their option.”

    I think there’s a lot to be said for not making it too easy for the guy, and that comes down to who’s doing the chasing. I suck at playing hard to get, because I’d rather just be genuine. Why does it always have to be a game?

    It’s too easy for the guy to end up taking you for granted if it was no challenge to get you (or keep you).

    “If somebody wants to walk out of your life, LET THEM GO.” And then be the first to change your FB status;)

  35. lb
    lb says:

    “Actually, the image of the CEO as a masochist really liberated me to think outside of hierarchies at work.”


    I cant wait to go to the next meeting with my bosses — the next time their big egos get on my damn nerves, i’ll be sure to imagine them wanting to be dominated and all ….

    I feel liberated ALREADY.

  36. Dannielle Blumenthal
    Dannielle Blumenthal says:

    Hi Penelope,

    I just like reading your blog.

    It reminds me of the quote from Forrest Gump:

    “Life is like a box of chocolates…you never know what you’re going to get.”

    Your character in these blogs also reminds me a little of the main character in that TV show, “Weeds.”

    I like that I never know what you’ll say next.

    The photo of the goat in the boots is funny.

    Melissa and Cullen are not very interesting.

    Do you think maybe you lean on her too much?


    The movie of your life, or the TV show or whatever, is going to be good.

    Maybe you could do webisodes in a similar vein as “Between Two Ferns.” Short and funny and honest and awkward. I would watch that.

    Anyway, I am rooting for you. Reading your posts helped me to be more honest in mine. One thing you say that I always keep in mind is something to the effect of – “Being scared to publish the post means you’re doing something right.”

    Good luck,

    Dannielle Blumenthal

  37. Laura Brown
    Laura Brown says:

    Gosh, this is very, very, Penelope-at-her-best. Multi-leveled, multi-layered, simultaneously mundane and poignant. Of course you love the farmer . . . It’s so amazing when someone gets you. And the Moby Dick comparison is so insightful and apt. Having your writing compared to Melville’s is a pretty sweet compliment.

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