How to deal with doubt: Take a leap

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The farmer broke up with me five times the first five months we were together, last year. So I learned that he had huge commitment issues.

I tried to do the advisable thing to do when you're with someone who has commitment issues. I tried to fall in love with someone else. But I didn't. I only missed the farmer more.

So I told myself that it's okay to be with someone who has commitment issues, as long as I am having fun.

But my kids grew to love the farm, and the farmer, almost as quickly as I did. This makes sense. My oldest son was with me on my first visit to the farm, and if you have ever been on a working farm you know that to kids, it's like Disney World.

So my kids were constantly asking to go to the farm, and constantly trying to figure out, what is the farmer? A friend? An uncle? And why did I kiss him if he's not in my family?

This is not a good path for kids if the relationship isn't going toward marriage. So I waited until a day when the farmer and I were holding hands, walking between rows of corn higher than our heads. And I told him that I can't keep bringing the kids to the farm because we're not getting married and I'm scared the kids will get hurt.

The farmer didn't say anything for five minutes. And then he said, “Okay. Let's get married.”

It's taken me months to tell people. It's taken me months because I sort of don't believe it.

I didn't want to write that I'm worried. You will tell me, in the comments section, “Don't get married if you are worried!” But I'm not sure I'd ever NOT worry.

How can I not worry about marrying a farmer? I will be moving, with my kids, to his farm. The farm is in the absolute middle of nowhere, outside the town of Darlington, WI. And now, I guess this will be my debut in Darlington, because I'm pretty sure there will be no blog outranking me for that search term.

But if I didn't marry the farmer, I would be worried, forever, that I should have married him.

So it's not a hard decision to marry him. I have been married before, and I don't think I'm going to change much, so I know what I need, and I know what I have to offer, and we are a good fit.

And, I have Asperger Syndrome, which could be summarized as raging intellect and acute sensitivity to outside input. So the farm is a perfect spot for my mind to explore while outside-my-mind is calm.

But I worry about the farm for my kids. One of my kids also has Asperger Syndrome, and he is completely addicted to the farm and the animals, and the farmer's calm, slow, sunny demeanor. My other son does not have Asperger's and probably does not need of the serenity of life on the farm.

Not that serenity is bad. And the family life that grows from farming is intimate and grounded and full of routine. All good things for kids.

But I grew up in a world where everything was open to me. Check out my high school: New Trier. It's always ranked in the top twenty-five high schools in the country. I remember the principal telling us that the top 500 kids in our graduating class would go to colleges where most would be the valedictorians of their class.

At the time I didn't understand how this could be. But now I understand that in order to compete at the top of the academic field, you need to be the number-one student in your small town.

Maybe not number one academically. But number one in soccer if you want to play soccer in college. And number-one in cello if you want to play in an orchestra in college.

Wait. No. It's worse than that. Because in Darlington, there is no orchestra in high school. So where will my son play his cello in high school if he wants to play in college? And how will my boys learn to play soccer at a high enough level to play in college if all the kids on the coasts are getting private coaching? Where is the private coaching in Darlington?

It's scary how limiting the choices are when you live in a place like Darlington. But competition is scary to me as well.

The reason I couldn't keep playing professional beach volleyball is that I didn't care enough about winning. To get to the very top of anything, you have to think you're going to die if you don't win.

That's not me.

I belong on a farm, where life is slow, and rhythmic, and people are not breathing down my throat about getting the best of everything.

The farmer and I discuss this a lot. He went to graduate school for biology and hated it and went back to the farm. He thinks he could have done anything, so why won't my kids be able to choose anything?

I am not sure. I am not sure if it's my proximity to overachievers that gave me opportunities, or it's my innate optimism and intelligence.

Then he tells me that what I really would have wanted from my childhood is to feel love and security, and why don't we just focus on giving the kids that?

He's right. But it's hard for me to act on that. So I think this marriage and move are leaps of faith for me, hoping that love and security will trump opportunity and achievement. I hope I'm making a good decision for my sons.

The Story of the Farmer – From the First Day We Met:

June 2008 New Way to Measure Blog ROI

June 2008 How I started taming my workaholic tendencies

Oct. 2008 Self-sabotage is never limited to just one part of your life

Nov. 2008 Think of networking as a lifestyle, not an event

July 2009 The sign of a great career is having great opportunities, and saying no

Sept. 2009 How to deal with an insane commute

Oct. 2009 How to deal with doubt: Take a leap

250 replies
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  1. jb
    jb says:

    after reading this, I read your first post where you introduced him. Knowing the outcome makes the first one much more moving.

    Congratulations, best wishes and all that.

  2. Kathy
    Kathy says:

    Congratulations!! I have been following your posts, and I’m so happy you found a great guy that will be not only perfect for you, but for your sons as well! Living on the farm will be great for them! Opportunities will still come along. My cousin went to Cornell (did not attend the Agriculture program) after growing up on a farm.

  3. Deb
    Deb says:

    I didn’t go to New Trier, but my high school was also big, and excellent, and gave me a lot of opportunities, but…
    One of my friends drove/was driven three hours every weekend to play league soccer, which was the only way for her to be on a team that would get her the Division I college soccer scholarship she eventually did get. She played for the high school too, and she was a star, but that was secondary. Madison is close enough for you to do a similar thing for your kids.
    And as others have pointed out, there are some excellent opportunities for online classes, including AP classes that you wouldn’t even have to pay for, if Wisconsin has an online academy, as many states do.
    I think your kids will be just fine, mostly because you and the farmer recognize the importance of supporting them, and giving them a loving environment. Those are the two things that are most important. Your own background makes it clear that some kids can succeed, even if they come from horrible home circumstances, but the odds go way up for kids whose parents are unconditionally loving, and are supportive of their dreams.

  4. haemin
    haemin says:

    Congratulations, Penelope! I think anything worth pursuing requires some leap of faith. I’m so excited that you are going for this; and I’m confident that your kids will do great. I know you don’t post a lot (or any?) photos on this blog, but when the wedding happens, I’d love to see a photo or two of the big day! Congratulations again. Wishing you both the very best.

  5. Bob Bennett
    Bob Bennett says:

    Congratulations! I agree with most here, just love the kids and they will turn out fine. It really doesn’t matter where you are from, just where you are going. If your sons have half of your perseverance, they will do whatever they want in life and be happy. Enjoy your life together!

    PS. I enjoy your open and honest writing.

  6. Kim
    Kim says:

    First and foremost, congratulations! I must say, however, that your insinuation regarding the lack of opportunity in smaller towns reeks of the snobbery that residents of said smaller towns face on a constant basis. I did not attend a private school (some would say I graduated from one of the worst public school systems in the country); I did not attend an Ivy League college (some would say I graduated from a mediocre, at best, state school); I did attend a “top 25 regional” graduate school (and, realizing that it wasn’t Ivy League, I must say the opportunities were not terribly different from those I encountered at the undergraduate state school but it cost me a hell of a lot more money) and I did not land a job at a big investment firm. I couldn’t have done any of those things as I had my first child when I was 19; there was no money for a diploma from Harvard and there weren’t enough hours in my day for a job at an investment bank. However, through all of my mediocrity, I have gained a sense of self worth and confidence that will take me wherever I choose to go.
    With that said, I admit that I have not chosen to go anywhere. This is not because I don’t have a desire to try new things or prove to the world that those of us born in mediocre areas can, in fact, beat the hell out of those who weren’t; it is because I am the single mother of two children who have grown up here and who need the support of their extended family. I have sacrificed a big career (thus far – I fully intend to capitalize on my experience and knowledge when my kids are in college) and much bigger money, but the result is well worth the sacrifice. My kids are growing up in a loving, familiar environment and although they might not have access to the best coaches, trainers and musicians; they have me. I can do anything I want to do and, based on my experience, I can do it better than 90% of the population. My self confidence translates into their self confidence; I am absolutely convinced that my children can do whatever they want to do and I remind them of that everyday. Differences in environment do not translate to differences in desire, ability or intelligence; at the end of the day, aren’t those a few of the most important characteristics of highly successful individuals regardless of their origin?

  7. Brad
    Brad says:

    On an obscurely related topic, composer Vic Mizzy just died.

    “Gree-een Acres is the place to be …”

  8. Alan Wilensky
    Alan Wilensky says:


    Mazel Tov; I will skip the intermarriage manifesto because you are a sophisticated woman.

    So, you are betting the farm with the Farmer, or on the Farmer?

    Betting the Farm….

    One word before signatures: Background-Check.

  9. Maria
    Maria says:

    I think you have a very romanticized view of life on a farm. Do you and your sons ever actually work side-by-side with The Farmer? And will that be the expectation once you’re living on the farm?

  10. Rebecca
    Rebecca says:

    A loving marriage is an indescribable blessing. Best wishes to you, and congratulations to the farmer!

    If it makes you feel better, I credit my high-achieving ways partly to having grown up on a farm, in middle-of-nowhere Georgia, until age 13. We were so far out, we couldn’t even get cable! Although it was lonely sometimes (I was an only child), it encouraged me to read ALL THE TIME and to develop a broad imagination. It’s also lovely to spend so much time close to the natural environment and to have the freedom to enjoy outdoor pets like dogs and horses that are harder to keep in the city or the ‘burbs.

  11. Carly
    Carly says:

    Congratulations Penelope!

    Perhaps this will ease your mind regarding farm life for kids. I was born and lived in the city until about age 10 when my family moved up north to a farm. At the age of 20 I moved back to the big city and I honestly feel that I had a better upbringing then most of my city friends. It’s true that they had some opportunities that I did not, like being on the top athletic teams in the country, having newer books and computers in their schools. But the things I learned and the the freedom and opportunities I gained being on a farm are life lessons that I took with me. I learned to drive before anyone else, I can build and fix just about anything and being in a small community gives you a real sense of belonging that you don’t get in a city. The athletic teams at my school were still very competitive but every kid got a chance to be on a team, not just the best kids. We also learned to be very creative with ourselves, because there wasn’t as much to do as in the city. I helped bring animals into the world, nursed them when they were sick and buried them when they died, and most of my city friends have never even had pets.

    I am glad that I had the chance to experience life on a farm and feel that it made me a stronger and hardier person today.

    Good luck!

  12. Marissa
    Marissa says:

    Congratulations! This is pretty amazing. I wish you and your family all the best. Just go for it! The farmer sounds really amazing and dreamy. I like that you balance each other out. Best of luck!

  13. JH
    JH says:


    I wouldn’t worry too much about lack of opportunities for your boys. A lot of the opportunities in life are acquired through the experience one gains in taking the road less traveled.

    I think the typical middle to upper middle class person who lives in a rural area tends to develop stronger life skills than a comparable city person. When your nearest neighbor is 5 miles away, you tend to develop a stronger sense self reliance and imagination. Also, one tends to appreciate their family a bit more.

    All of the farmers I’ve met have been pretty well rounded. They have to know business, they have to know mechanical stuff, and they have to know the science of agriculture.

    Best of Luck.

  14. Elle
    Elle says:


    This is such great news and its so incredibly brave of you to take the leap. I’ve been with my partner (who is not nearly a farmer but rather a computer nerd) for 10 years and i’m not ready to take that leap – you’re a better woman than I.

    Small towns are a great way for kids to have perspective in their lives. Once they get out into the big wide world they truly appreciate the time they had where life was simpler, and often more enjoyable; where people said hello in the street and enjoyed playing outdoors – as opposed to sitting inside in an apartment playing video games against someone on the otherside of the world.

    If you’re going to live on the farm, will you get married on (or around) the farm somewhere?


  15. Jess
    Jess says:

    I, too, got married even though I was worried about it. Like you, I knew I would be worried about it no matter what. So far, it has been the best choice I have ever made. My husband deployed a month after we got married. It was still the best choice I have ever made.

    I am envious of your soon-to-be farm life and look forward to (hopefully) more farm-related posts :).


  16. Jennifer
    Jennifer says:


    I’ve only recently discovered your blog and I’ve read almost all of it. Sometimes the topics scare me, but I read on. You are funny, smart, and will ultimately make the right choice for YOU.

    I married my husband after six months. People thought we were crazy (or I was having a baby, which I wasn’t). We are happy and just celebrated our 13th wedding anniversary (lucky 13).

    So take the leap of faith and figure out what is good for you.

    BTW, life on the farm sounds amazing for you, the farmer, and most importantly, your boys.

    Good luck and congrats!


  17. Dillinger
    Dillinger says:

    “because I'm pretty sure there will be no blog outranking me for that search term”

    Sorry, but Johnny Depp has you beaten there.

  18. megan
    megan says:

    I am impressed by this post. Being able to self-analyze to such a degree is a skill, and takes courage. Adding children to the mix I’m sure only increases the need for both the skill and the courage. The honesty and lack of sarcasm in this post made it heart-felt and I’m sure you and the farmer will be successful in your marriage.

  19. priscilla
    priscilla says:

    i heart the farmer. i think he’s good for you. cause, ya know… i can tell over the internet.

    congratulations. i wish you guys many years of happiness together.

  20. S. Cruz
    S. Cruz says:

    P: your kids will be OK living on a farm. They’ll find what they need. I’m a long time tech guy and now live in a rural/farming border area (still consulting with tech co’s and writing) and came to realize that I prefer the company of farmers to VC’s. They’re more interesting people.

    It sounds like the farmer knows what he’s getting himself into, as do you. All is well. Good luck to both of you. It’s great fun reading what you write.

  21. Tara
    Tara says:

    Congratulations, Penelope. So happy for you. My husband and i had our first date the end of August, got engaged on Oct 9 and married on Dec. 5–and that was 28 years ago. Sometimes, the leap is what it takes! Much happiness.

  22. Sheila Scarborough
    Sheila Scarborough says:

    Well, somehow I could sort of see this coming, really. I’m thrilled for you and the farmer.

    More and more I see the need to “get out of my head” when I spend too much time online. If you do too, then the remote farm location will (overall) help and not hurt your business, I would think.

    Congratulations and mazel tov!

  23. sifi
    sifi says:

    Warm wishes. What a wonderful feeling, to take the leap of faith with someone you love. It’s all very Jane Austen. The happy ending is a new beginning.

    I would not have missed growing up in the sticks! It was wonderful and boring and beautiful and sad and inspiring. And I had lots of time to THINK about whatever inspired my fancy. Lots of brilliant writers come off those backwater farms. That’s one reason why.

  24. Liz Guthridge
    Liz Guthridge says:

    Congratulations, Penelope to you, the Farmer and your kids!

    You raised thoughtful questions in your blog and have received some great advice. I’ll just add the following:

    –Having been engaged for about 11 years before I agreed to get married on April Fool’s Day (my choice) in 2003, I often wonder why I waited. (I always felt like I was Carrie in Sex & the City. I was fine being a fiance and okay with the idea of being a wife; I just didn’t want to be a bride.) I’m so delighted you’re moving forward, especially since you have children. (My now husband finally convinced me to marry him because he didn’t want our puppy living in an unwed household.)

    –Living in a small midwestern town and a farming community provides its own educational and cultural opportunities, as many of your readers have noted. And when it’s time to apply to colleges, those of us from tiny towns and small schools can stand out more than those from New Trier and other well-respected and big schools.

    — Being out in the sticks these days doesn’t mean you’re out of sight and out of mind. The internet and everything associated with it can keep you connected to the world. The connectivity we have today is so wonderful, compared to just a few years ago.

    Enjoy! And please keep all of us a part of your new life! We want to hear how you’re doing.

  25. spleeness
    spleeness says:

    Oh Penelope!! I want to hug you. This is wonderful! I could tell right from the very beginning that your thing with the farmer was special. I’m so happy for you.

    There’s nothing wrong with being worried. We all worry. We also take chances and root for love. It’s a beautiful thing and makes me so happy to read it. Thank you for sharing the great news!

  26. Gayle
    Gayle says:

    This made me smile to read this, for the forthrightness with which you’re putting out your concerns and the love and faith that you have to move into and through great doubt. One of my teachers once told me that fear and hope always rise together. :) Congratulations!!!

  27. Mark W.
    Mark W. says:

    I wish the best to you, the farmer, and the kids. Farm life is not easy but it is rewarding in many ways. Take care of yourself when you do have to commute. Right now I’m thinking snow tires for your vehicle should be at the top of your list. Also I think you’ll need to get some good Internet connectivity on the farm if you don’t already have it. The list goes on and come to think of it I’ll probably worry more than you. :)

  28. David
    David says:

    Congrats Penelope!

    I wouldn’t worry that you’re worrying. I think everyone worries about marriage – whether they are making the right choice or not. It’s easy to start overanalyzing, to get cold feet, to feel panicky, etc. That’s normal behavior and happens when it comes to making any big decisions in life. But you know yourself best and if this feels right in your heart, I say go for it!

    I knew you two were a perfect match when I read this Tweet…

  29. Jennifer
    Jennifer says:

    Congratulations, Penelope! My husband and I have been dealing with the very same questions in our career/parenting choices and wondering which is better for the kids: a life that is achievement & opportunity oriented, or one that focuses on love, family and intimacy and to hell with the rat race. It’s a constant question of balance, and your concern–the very fact that you care so much–is what will make all the difference for your sons. For them, as for us all, it’s about the process…the journey…the caring. Wishing you and The Farmer a very happy future together! (And I can just hear the Judge or Rabbi or Minister or whatever intoning, “Do you, Penelope, take This Farmer as your lawfully wedded husband…” :-)

  30. Susan
    Susan says:

    Congrats! Hope you blog about the wedding in real time… better yet, do a live feed! Invite us all!

    You can only love and support your kids, trust that you’ll know -how- to achieve that as situations arise.

  31. dr aletta
    dr aletta says:

    When I got married at 30, I absolutely knew I was doing the right thing. I loved the guy, he was ‘a good fit.’ So why was I having panic attacks? I got my ass back in therapy and worked it out. I was scared to death of becoming a grown up, an adult, one of them. Not to say that will happen to you, not at all. What I mean to say is, you can be doing the right thing, for you and the kids, and still be scared, nervous, ambivalent. For many of us getting married isn’t blissful, it’s a dare. A double dog dare, to tolerate the ambivalence, to take that leap of faith, to go boldly into the next great adventure. My adventure is 25 years old now and still going strong.

    P.S. My nephews grew up on a farm in rural Eastern Kansas. One is a tenure track professor of architecture on the faculty of a state University and the other is a financial big wig in Washington DC. Your kids will be fine.

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