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

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  1. Joanne
    Joanne says:

    Congrats! Seriously. I’m getting married to a guy I’ve never shared a timezone with. The only way to know if it’ll work is to DO IT.

  2. Amanda
    Amanda says:

    I grew up in a small town in New England. Graduating class of 90, largest to ever go through my school.

    I went to the top engineering school in the country. I had friends in my class who went to Ivies and “Little Ivies”.

    College admission offices get that you can’t take all APs your senior year because they aren’t offered at your school. The question in their minds are instead, what did you do to replace that opportunity.

    And what is great in a small school is you can really make yourself stand out in any way you’d like and everyone is willing to help. So, there is no orchestra? If your son really wants to play, he can work with the music teacher to start a chamber music group. No private soccer coaching? Work with the soccer coach to go to AAU camps or similar. The opportunities are there, you just find them a bit differently than you do in the city.

  3. Tristan Lee
    Tristan Lee says:

    Hello Penelope. I agree that one of the ways to deal with doubt is to just go for it and have faith in what you’re doing.

    If you sit back and always wonder “what-if”, then you’ll always have this regret that fills you up from inside.

    I’m glad you made a decision, instead of being doubtful. Whatever happens, it’ll just make you stronger.

    Thanks for sharing this story and I hope things work out with the farmer and your family.

  4. Anna
    Anna says:

    It may not seem related, but I have to wonder:
    Does the farmer call you Penelope, or Adrienne?
    What do your kids think your first name is? When they grow up, will they introduce you as Penelope or Adrienne?

    • Penelope Trunk
      Penelope Trunk says:

      So many people ask me this! The farmer calls me Penelope. Sometimes he calls me P. The kids introduce me as Penelope. They know that I have another name, but they know almost no one ever uses it.


  5. Rosie
    Rosie says:

    Hi Penelope,

    I’ve been reading your blog for a long time now and just wanted to come across and wish you all the best with this new change in your life. Even though I only know “the farmer” from your articles, this sounds like a lovely way to raise a contented family. I hope you’ll all be very happy together, learn a lot from this new experience, and discover lots of wonderful benefits from living away from the city!

    Congratulations to you all!

  6. Michaela
    Michaela says:

    I love, love, love this story. Small towns can be limiting socially and academically but ultimately if someone wants to be a high achiever the town is usually very supportive of their efforts. I grew up on a farm in SW Minnesota and went on to do a bunch of cool things yet now my 5-year plan is to own a small farm of my own. Good luck and congratulations!

    • Rita
      Rita says:

      I grew up on a farm in SW Minnesota too, and I echo your analysis of small towns. Went far away to college, now looking at top law schools… my brother is thinking about taking over the farm and eventually I will probably help him.

  7. medXcentral (Jim)
    medXcentral (Jim) says:

    OK Penelope… I’m compelled. I respect your intellect and your Brazen honesty. I find it refreshing. But it also opens a can of worms… in so much as, if I pose the question in my head, from one raging intellect to another, I must also take responsibility for the doubt it may perpetuate regarding the “commitment” contemplated in this post. I don’t wish to be perceived as “that guy.” But, again, your honesty strikes a chord with me and I feel compelled…and would like to believe that it will be received in the helpful, open, honest spirit as it is intended. So… *gulp*… here’ya go;

    Why would you marry someone with truly demonstrated “commitment issues?”

    I understand “faith.” I’m an inherent risk taker and believer. I support independence and freedom at every corner. I don’t even know you and I’d back your decision because of your honesty and bravery…and my belief in a persons right to try whatever they believe will work. (God knows that’s how I live my life…undefined by others.) But this decision is H-U-G-E.

    Please be certain to examine it carefully. Don’t forget the reality of the damage caused by a failed marriage.

    My wish? My wish would be that it works out perfectly for you and your children. All the best to you and yours. Sincerely.

  8. barchbo
    barchbo says:

    It’s not always bad to worry – it means you care!

    I wish you the very, very best. I love reading your blog and think you are absolutely delightful. Of course, I deal with Asperger cases almost every day – but you’re my favorite. I hope you can see how inspiring and encouraging your willingness to share your story and your struggles are. It makes a difference to a lot of people.

  9. Dave Wheeler
    Dave Wheeler says:

    Congratulations! It sounds like a new adventure is beginning … with the prerequisite challenges, obstacles and learning opportunities. I’m sure I speak for all your readers when I say that we look forward to learning about your experiences, both good and bad, as you step into a new stage in your life. (And I’m sure you already know how to “watch your step” at the farm.)
    Best of luck for a long and enjoyable marriage !

  10. Jennifer K
    Jennifer K says:

    Congratulations Penelope!! I’m very happy for you. I’d never tell you not to get married because you are worried. Like you said, Marriage is a leap of faith. It’s always a little scary jumping into the unknown. It’s a lot of hard work but if your instincts are telling you it’s right, you will be fine.

  11. Morgan
    Morgan says:


    I think you’re right about the giving-your-kids-what-you-didn’t-have part. They will thank you later. And, other people on farms are driven too. Check out The Pioneer Woman. So many comments.

  12. Barbara Ling, Virtual Coach
    Barbara Ling, Virtual Coach says:


    I think the paths we find ourselves taking have been shown to us by our guardian angels; the lessons we choose to learn are precious gifts we could not obtain anywhere else UNLESS we took that leap of faith.

    Best wishes for you and your family!!

  13. JB
    JB says:

    The farmer is right. Kids–and people of all ages–need to feel love and need to feel secure. If you give them that, then they can achieve anything.

    And what of these achievements? Really, who cares if your kid is a valedictorian? Who cares if they go out to make a bazillion dollars when they’re older? I’m not saying that we shouldn’t challenge our kids (and ourselves) to be the best people they can be and to live up to their potential, but maybe we ought to stop with the “you have to be #1 or you suck” kind of thinking. A lot of #2s, 3s, and 47s are doing fine in this world.

    We as parents (and people in general) ought to be emphasizing compassion in addition to competitiveness. Our job is to raise productive, well-adjusted adults–not world class cellists and soccer stars. I think I’d rather raise a kid who always appreciates music or sports rather than one who gets burned out on them before s/he hits high school.

    So, sorry for the rant. I really meant to say good luck. Take the leap. But in the meantime, cut yourself–and your kids–some slack.

  14. Heidi at BankerGirl
    Heidi at BankerGirl says:

    Congratulations, P! I grew up on a farm near a small town (population 800) in Iowa and even though we didn’t have an orchestra or swim team, I don’t feel that limited my choices at all.

    I do, however, think that peer pressure and peer activity are big leading indicators of success later in life. In my high school it was almost looked-down-upon to be smart, so I dropped out of TAG and AP courses because I didn’t want to stand out. When I was in junior high and high school, I failed to recognize how important WHERE you go to college really is in setting the path for your life. I had good grades, applied to state schools, and got in and did fine, but if I had to do it again I would try to graduate valedictorian and get into an Ivy League school just to take advantage of the relationships that are formed in that type of environment. I was nearly 30 years old before I understood that being surrounded by individuals who are driven and intellectually curious helps drive me. Now I seek those people out. I wish I had done it sooner in life.

    BUT since you have the pedigree and the background (something my parents, fantastic people with no post-secondary education lacked) to identify these opportunities for your kids and make sure that they’re making the right choices.

    I guess that’s just a long way of saying, your kids will be fine. Go ahead and take the leap. You could do a lot worse for your kids than raising them on a farm in the Midwest.

    Again, congrats!

  15. Jen
    Jen says:

    oh, congratulations – I’m so happy for you that I’m almost tearing up (ok, that may be because I haven’t had much sleep and it’s pretty early here). Best of luck!

  16. Ann
    Ann says:

    Congratulations, Penelope!

    Fifteen years ago, I married a small town guy and moved to that small town with a seven-year-old. It took a long time for me to be comfortable here — mainly because I’m a little bit of a snob. My son, on the other hand,took to small town life like a duck to water.

    I’m lucky my husband and son are sweet, compassionate people. They have been very patient as I worked through my snobbery.

    I’ve come to realize that marching band and football are as good as cello and soccer.

    Also (and I always knew this on some level) kids own themselves from the minute they are born. You can put a cello in front of a kid, but if he wants to play tuba, he’ll find a way to ditch the cello and play tuba.

    I think you’re approaching your transition with absolutely the correct attitude. I wish you and your family all the happiness in the world.

  17. Jackie1776
    Jackie1776 says:

    CONGRATS!!! I am so happy for you that I am tearing up at my desk at work.

    Some unsolicited advice, offered because I think it could help your new marriage succeed: From your previous posts, it’s clear that the two of you have very different styles of handling money. And although your income is higher, it seems as if it’s historically been more volatile than his, and its future is more uncertain (yes, your company is funded and doing great right now, but startups are risky and anything could happen).

    So, I think things will run smoother in your marriage financially if you two can find a way to keep your household’s regular, basic monthly bills/necessities within HIS income. Then use YOUR income for investing, luxuries, spending money, buying stuff (furniture, clothes, etc.), etc. You can still have joint marital finances/accounts, but setting up 2 checking accounts (one for his income and household necessities, one for your income and discretionary spending) makes it very clear what money is for what.

    I think doing this would help your marriage on several levels:

    1) You can both worry less about how the future success or failure of your company will impact your family’s financial survival.

    2) He still gets to do the male provider thing, since “his” money would cover the roof over your heads, the utilities, the groceries, etc.

    3) You will have less reason to fight about you spending money on something that he thinks is frivolous, because you’ll pay for those things out of “your” money that you earned and that you pre-agreed was for “extra” stuff.

    (Of course, since he would be paying for all the necessities, you should use some of “your” money to buy things for him and his farm, too.)

    Whether you take my advice or not, I hope that you two invest some time up front thinking and talking about how you’re going to merge/manage your finances. You’re very different in this area and that could cause problems in your marriage later if you don’t begin with a good financial plan that you both can live with.

  18. Lucie
    Lucie says:

    Um, I think this is a leap of insanity not faith. Try living with the farmer on the farm for 6-8 months and then see how you feel.

    Two different backgrounds, two different worlds. I predict intense culture shock in your future. Of course, all this can be overcome if you have similar goals and values but from what you have written, that doesn’t strike me as exactly your case.

    At the heart of it, the farmer seems sounds like a do-it-yourselfer and you, girlfriend, are not. How does the farmer feel about the house assistant and nanny? You also strike me as a little needy. The farmer sounds more solitary and self reliant.

    So, I advice drinking the milk for a few months before buying the cow. Oh, and get a prenup!

    • JR
      JR says:

      Dang right. Visiting a farm and living on a farm are vastly different things. (You forgot to mention her cleaning service. PT will be the first farm wife I know with domestic staff.)

      • Erin
        Erin says:

        I’ve known farming families with domestic staff. It’s actually not uncommon.

        It’s definitely a different life and farms, by their nature, tend to be far from urban centres, but they’re not void of luxury. In fact, I grew up around farming families who felt a cleaning service was essential.

        Farming is a business, like any other, and sometimes you need support staff.

  19. Alexis Grant
    Alexis Grant says:

    Thanks for sharing this. Congratulations! You’re right to take that leap. Too many people don’t — and they live life not knowing that it could be better. You’ll never have those regrets.

  20. Carla Shore
    Carla Shore says:

    Mazel tov.

    Not that it’s any of my business, but now I wonder what happens with your arrangement with the boys’ father. Is he moving to the farm too? ;-) I’ve always admired your ability to maintain such a congenial relationship with your ex.

  21. Beth
    Beth says:

    If this helps, I grew up in Wisconsin on a farm, near a town much smaller than Darlington. I now work with international companies helping them set up their sales and marketing plans to enter the US market, and have lived in 3 different countries.

    It’s not where you grow up or how big your graduating class is (class of 45 people) or how high the school is rated. It’s what they decide they want to do, and what they are willing to do to get there…

    • Jessica
      Jessica says:

      I agree. Similar story – small farm girl from a 300 person town in SD and have now lived all over the US, working for Fortune 100 companies even after attending a “state school”. Instill in your kids a sense of adventure, wonder, and curiousity – they will seek out success on their own.

  22. Veronica Sawyer
    Veronica Sawyer says:

    Mazel tov!

    It sounds like you’re approaching marriage and this life-change in a very pragmatic way. I think that’s the way it should be. It is working for me!

  23. Addy
    Addy says:

    hey I couldn’t help at comment on your post. you probably wont read this because its buried under the other comments. I recently moved to Virginia to be with someone. it wasn’t quite a farm but it was a big difference from New York and Massachusetts where i grew up. I didn’t have kids so it was easier to pick up and go to be with this person. Along the way there has been some doubt, sometimes some regret. but the benefits for me outweighed the negatives. as for “limiting” your children. Honestly we live in a day and age where, as long as you have internet connectivity, you aren’t limited to anything. That doesn’t help with playing the cello but maybe there are other instruments that he might enjoy that wouldn’t require an orchestra. In the end you have to do whats best for you and your children. Honestly if things are working out now the way they are whos to say that it shouldn’t stay that way. Marriage is not the be all end all of relationships. As long as your kids see you’re happy they will be happy. Maybe marriage is something you want to consider once your kids grow up. I’m not trying to dissuade you from marrying the guy.. but rather to open up your options to more than just 1) marry him 2) break up with him. There are plenty of other options in between. good luck, and congrats either way (either on the marriage, or on having someone you care enough about to even consider marrying even if the times not right yet)

  24. Heather
    Heather says:

    Congrats Penelope! I completely understand this worry of yours:

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

    I had that as well so I married the salesman and we are 21 years married.

  25. Thursday Bram
    Thursday Bram says:

    I think there are actually some major long-term benefits for kids growing up in the country that make up for the some of the opportunities that are harder to get to. Most of the people I know that grew up on farms or otherwise outside of big cities are a little more independent, a little better at problem solving and a little better at planning. When you know that you can’t just run to the store, you have to be able to adapt and plan ahead more than your city-dwelling counterparts.

    And, by the way, Mazel Tov!

  26. M
    M says:

    Congratulations! I grew up on a farm not very far from Darlington and did the “#1” thing at a small school. I don’t feel it limited my choices at all. In fact, pulling the “I grew up on a farm” card in essays appeals strongly to the our inherited yeoman farmer myth and can net all kinds of acceptance letters and scholarships for your kids. And, after a decade of wandering, I’m planning on a farm and family of my own in the next few years. Dig your roots in deep, undulate with the seasons, work hard, get reliable high speed wi-fi, and enjoy!

  27. J (the regular poster one)
    J (the regular poster one) says:

    Congratulations; I wish you the best!

    I understand your concerns. I grew up on the east coast and attended private schools and went to an ivy league university, and i wonder sometimes how my life would be different if i weren’t always around ‘overachievers’. There is something to be said for environments that foster lots of opportunities. But given how you grew up, and given that this is on your mind, i’m confident you will find ways to make sure your boys have everything they need.

  28. Eva Lyford
    Eva Lyford says:

    Congratulations, sincerely! I wish you both a long and happy life together full of serenity and love.

    There’s plenty of successful people who come from small towns. They may not be as flashy or as public about their success as are some others; and their definition of success may be unique to themselves. But I would suspect that as a % of population most successful US people come from urban areas because most US people come from urban areas.

  29. Lindsey T.
    Lindsey T. says:

    Penelope! Congrats! This is so great. When I started reading this post, I had no idea what was to come. Best wishes to you both. Do you plan to get married at the farm? :)

  30. Kelsey Halling
    Kelsey Halling says:


    Although I was raised on the East Coast, my parents are midwestern, and I spent many summers in Minnesota and Wisconsin, and think the midwest is a great place to raise kids.

    I’ve been reading for a while, and even though we’re total strangers, I am very happy for both you and the farmer. Best of luck.

  31. Joanne Tombrakos
    Joanne Tombrakos says:

    Love that you are taking the leap! That is what life is all about, taking leaps and having faith in your instincts.
    This could be the start of a whole new blog…life on the farm!

  32. Yanik
    Yanik says:

    Congratulations Penelope! Enjoy your new life on the Farm. The farmer is very wise to focus on love and security for your sons. Truly, this is what children need to thrive. Don’t worry about your kids too much, everything is still open to them thanks to the Internet.

  33. sophie
    sophie says:

    Congratulations P!
    I feel very happy for you reading this and touched by your realization of what’s important for your kids.

    My kids were also raised in a small Wisconsin town, with graduating high school classes of less than 100. Today they are grown and very successful. Some still live in Wisconsin, others have moved out East. Like everyone above said, kids choose their own way no matter what direction we parents push them. Who’s to say your sons will want to play cello or soccer in 1-2 years anyway, wherever they live? By then it may be guitar and football. Or 4-H.

    If you and the farmer always provide a loving home for your boys, one where they feel accepted and secure, they can manage fitting into a new school and meeting new people. Growing up on a farm as a bonded family will give your boys values for life that far exceed orchestra and soccer. Strength, security, self-knowledge and love.

    May God guide and bless you in this new chapter of your life. He can make it work.

  34. sabrina
    sabrina says:

    Mazel tov!

    And, I sympathize on the worrying front. Worrying is just a zero sum problem. Being stuck with the “coulda woulda shoulda” worry sucks a great deal, and sometimes I wish I could trade it in for the “tried, and boy howdy, did that work out badly” kind instead. So I say go for it, and to hell with “if you’re worried, don’t do it!”

    p.s. if the farmer doesn’t already, get him to put in a couple rows of supersweet corn just for you guys to eat at home. Used to date a guy whose family did that on their farm, always had the white-and-yellow kind of supersweet corn. A little salt on it, ZOMG, best food on the entire *planet*. You’re a midwesterner now, which means you should totally MARRY HIM FOR THE SWEET CORN.

    • Penelope Trunk
      Penelope Trunk says:

      The farmer will read through the comments tonight. And he will get to this one, and he will be so happy.

      He does plant a few rows of sweet corn. And it was so fun to pick and eat and give away to friends.


      • Erin
        Erin says:

        On the food tip…being a local, I was thinking, “Congratulations! Now I really have to try this guy’s meat!”

  35. trese
    trese says:

    No matter the size of the high school, you can still provide opportunities to your children. And, they can still achieve great things. My high school graduating class had 30 people. I grew up in a farming community of 700 residents. I am currently working on a PhD and doing great! An added bonus, my best friend from school is still my best friend. The community is so small that they become your family too.

  36. From a small town
    From a small town says:

    I grew up in a town of 900 people, 2 hours from the closest “city” and 6 hours from the closest city anyone has every heard of. I have a PhD from Stanford University — anything is possible.

  37. Gretel
    Gretel says:

    I’m wondering what this means for the kids’ time w/ their dad. It sounds like he was a pretty integral part of the schedule / daily life — staying at the house and such. And I think I remember reading that the farm is a bit of a drive. What are your thoughts or plans around that change / relationship?

    • Caitlin
      Caitlin says:

      I’m sure that Penelope, her ex, and the farmer will find a way to making sure that the children’s father remains an integral part of their lives. It’s not like she’s moving interstate or overseas.

      She said it was a long commute to Madison but her ex-husband would not be ‘commuting’ if he drove out to see his kids. Nor would she, if she drove them to see her.

    • Jackie1776
      Jackie1776 says:

      My parents lived 2 hours apart after they divorced, and they would each drive halfway and meet at a gas station in the middle to trade kids. My brother and I now both feel compelled to always stop at that gas station when we pass it and buy snacks and crap. :)

    • Ranjit
      Ranjit says:

      Probably a week, and then another blogpost on how to learn to listen to your “2nd voice” and change your mind.

      • Melania Rosseau
        Melania Rosseau says:

        Nah, Ranjit: It lasted a full six weeks.
        The soap opera is getting better by the minute. Good writing; check out the post from Dec 5 or 6. It has tears and everything

  38. Eduardo Di Lascio
    Eduardo Di Lascio says:

    Dear Penelope

    First of all, I like you a lot. And then goes the flak:

    You should come to visit São Paulo someday. It would give you a completely new perspective about Darlignton.

    Every time you talk about Asperger`s, it sounds like you are a little too happy about this diagnose, since it so conveniently justifies a big part of your behaviour.

    I don`t think that you “worry” too much. You are a counter-phobic person.

    Congratulations for the marriage. Wish you two all the best.

    • Caitlin
      Caitlin says:

      Do you mean that America is the land of opportunity wherever you are in it, compared with many countries in the world? Or something else about Sao Paulo? I’m curious!

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