The big secret to a more simple life

I’ve been an amazingly consistent blogger lately. My secret is that I’ve been calling Carmen a lot and dictating my posts to her.

In the middle of my blogging flurry, I read this book to my son, Flat Broke by Gary Paulsen. Its about this kid who can see businesses everywhere in all kinds of talents that other people have, and he ends up making money from all his friends.

Throughout the book I was thinking, “Oh my God, I have to do this with Carmen. I have to start selling her services because everyone can be a great blogger if they could dictate posts while they’re driving. Now all the people who are driving to and from work can now be big bloggers and love their commute too! Stay‑at‑home moms can do a blog post every time they drive to ballet lessons!”

So I pitched the idea to Carmen, except I didn’t tell Carmen about how the boy in the book pissed everyone off because he was making money from all the things they do, and he ended up with no friends and no money. Instead, I just told her that I thought I could sell her services as a court reporter.

My plan was just to publish her phone number on my site and everyone can pay me money to call Carmen. And I pay Carmen. And I know that Carmen totally does not charge enough on her own, because I want to jump for joy and high-five myself every time I dictate a blog post to her. So I know that you would want to do that too, and I know that I could easily charge double her rate.

So at first Carmen got really excited, but then she got to thinking how this idea would complicate her life, which of course it would, because I would ask all the time, “Carmen, did you get that call?” and “Carmen, that guy is calling,” and “Carmen, you’ve got two people waiting for you.” It would be crazy. So Carmen said no because she wants a life that’s more simple.

Which made me think I’m like Carmen: I want a simple life too. I realize no one would believe that, not even Carmen.

But you know what? It’s true that I want a simple life. And wanting that life is how I ended up doing both homeschooling and my new company, which I’m still too scared to announce to you because you’re all going to be really critical, and I can’t deal with criticism right now—I’m just trying to make my company look like a company that you’re not going to criticize. You probably didn’t even know that I care about your criticism.

So, you can’t see my company now, but I’m still talking about it.

And the reason that I homeschool and have a company is because it simplifies my life. Here’s how: if you send your kids to school, you have to do everything according to the school schedule. You’ve got to be there to pick up your kid, and you have to get them to school on time. I never did that but at least I hired someone to do that.

Plus you have to do homework—which we never did. And that was the problem because then the kids realized that we were sending them to a place we didn’t respect. But really, my kids were doing coloring projects in second grade. Coloring. In second grade. There’s no way I’m going to manage my kid doing coloring projects at that age. And then there was family reading night. School interrupts my family’s reading time to drag us to family reading night at school. Insane.

All the things that you have to do for school are insane. They totally interrupt your flow, interrupt your ability to manage your family, and interrupt your ability to manage your career.  So once I took my kids out of school, we could all just do what I want, which means we go to Las Vegas for my speaking engagements, or we take a trip to New York with no set ending, because my son can read in the member’s lounge at the National History Museum while I do a coaching call.

So this is why taking my kids out of school allowed me to have a more simple life, because then it’s just me making the schedule and doing what’s best for us.

The other reason that having a company makes a more simple life for me is because I’m most comfortable leading an army, and I’m least comfortable when I have no army to lead. So if I don’t have a company, it’s me doing everything. This means that I have to manage my own calendar, which is largely impossible for me, because I’m dyslexic. And it means that I need to manage the back end of my web site which makes me want to kill myself.

So what I really need to do is have a group of people where we’re all doing my vision together.  That’s really fun for me. The problem was I didn’t have a vision or a group of people. All I had was me at home managing every single little detail of my life. So I worked really hard to develop an idea that was bigger than my blog so that I could get funding and have everybody marching to my grand idea. It’s actually a way to simplify my life because it’s so easy for me to manage a team of people, and so easy for me to think of my big idea and go pitch it to people.

So, really, simplifying your life is arranging everything so that you’re doing only what you’re great at. Everybody can make money and have a life that feels simple to them if they focus on doing what they’re great at. We get into trouble when we get distracted by opportunities for us to do things we’re not great at. And we benefit from surrounding ourselves with people like Carmen who are great at turning down opportunities outside of their sweet spot.

56 replies
  1. Sheena
    Sheena says:

    It’s so interesting to me that you’re scared to announce your business because you fear we’ll criticize you. I think most readers here are always excited to see what you’ll do next and watch the journey i.e. homeschooling. I also fear announcing my business to friends/family because I don’t think they’ll get it. So, I’m wondering — and maybe your answer to this can help you feel more comfortable sharing with us — what advice would you give me to get over my fear of announcing my startup?

    • Maria
      Maria says:

      Thats’s actually a great question Sheena. I would love to hear Penelope answer that because I find myself holding back my ideas from a fear of criticism too.

      • Penelope Trunk
        Penelope Trunk says:

        Okay. That’s a good question. I have a lot on my plate right now, and the company is actually making money, but we’re making money in a business-to-business way. Which means the site looks awful.

        But the site is really for you guys – you’ll like the site, I think. And it’ll be a great place for me to grow my relationship with my blog community. Which, I think we all know is something I care a ton about.

        So, I am not announcing the company because we are focusing on the business-to-business part and not the site and I want to tell you guys to go check out my company when we make a consumer site.


        • Annie Kip
          Annie Kip says:

          I have read that being happy and excited is actually a more vulnerable place for most people (especially in our 9/11 world where we now know that bad things can happen out of the blue) – even more than being alone, broke, or unemployed. It is just when we realize that we might have some good stuff going on (like healthy, happy kids or an awesome new company!) that we feel we have the most to lose, so we either distance ourselves or protect ourselves in various ways to keep from feeling the vulnerable feeling. I know I do this and I think it is an okay coping mechanism, as long as we realize that we are doing it and make the choice consciously. We all have to wait for the time that feels right and safe to expose what makes us so happy. I am really glad to see how excited you are about your new project and I am looking forward to hearing about it when you are ready!

    • CMBG
      CMBG says:

      Read the book “Quiet,” by Susan Cain. There are good reasons for keeping a new project under wraps until it is prudent to announce it. Most people don’t wait long enough; they announce way too early. Listen to your instincts, not other people.

  2. Kirsten
    Kirsten says:

    Loved this post. It’s amazing how you often write about a topic right when I need it. Penelope-as-oracle for the win!

  3. Maria
    Maria says:

    I love how you live outside the box and do what works for you. I bet your kids are really benefiting from your innovative approach to business, rules, education. Kudos!

  4. Dee
    Dee says:

    How long do you think it will take, reading your blog, for my wife to convert to the homeschooling idea?

    Is simplicity best? or Simply the easiest?

    • mh
      mh says:


      Tell us more about your wife.

      In our family, homeschool was a husband idea, and then we found out two or three other sets of friends were homeschooling, and then everything sort of coalesced.

      At first, homeschool was a simplicity thing, then it was a high- achievement thing, and now it’s a freedom thing for our family. The reasons we started homeschooling are still there, but the reason we’re still homeschooling is all the freedom.

    • annie
      annie says:

      For me homeschooling has been about trust. Trust that your kids want to learn things. Trust that you can teach them about things that are important to being a civic minded human (kindness, cooperation, personal goals) better than anyone else can. Trust that the big picture doesn’t involve test scores (when was the last time you talked about your SAT scores at a cocktail party?). Trust that taking a different path will yield exceptional and interesting results.

  5. Marty Madera
    Marty Madera says:

    You provide great insight from what may seem a little crazy ideas at first, but I always read all the way to the end because I know you will express what many know to be true, but find hard to say themselves. I recommend your blog to many people. If they they think you are a little crazy at times, I am sure they think I am too. Keep up the great work!

  6. John
    John says:

    Holy cow, your blogging is not just more consistent lately; it keeps getting better and better and better.

    I think it’s funny that the author of that book had his entrepreneur protagonist wind up broke and friendless. In real life, he winds up with all the friends, all the money, and dating the hottest girl in the class.

  7. Tricia
    Tricia says:

    I keep wondering if Siri (or like service) can transcribe long passages for me. I suppose the biggest issue is not just talking in a stream of consciousness. You have to have a slightly organized article in your head … so maybe that’s actually what takes more work than the typing part. :-)

    • Penelope Trunk
      Penelope Trunk says:

      That’s true about being organized beforehand. I have really rough outlines that I use when I dictate to Carmen, and I have to do it during daylight.

      I tried using Siri and realized that you have to actually train Siri to understand you — a lot like Dragon Dictation, which i also tried. I have no patience to train a computer to understand my voice. Just the idea of it makes me feel like someone on the Jetson’s dumped the job of walking the dog on me.


  8. Mark W.
    Mark W. says:

    The mentions of education, new company, and criticism of a new venture remind me of a recent article that I read here – .

    Specifically, the first three paragraphs –

    “In the 18th century, the French philosophers invented l’esprit critique. Centuries later, it seems we French people value criticism over a lot of things – such as enthusiasm, for instance. As a French entrepreneur living in San Francisco, I’m always sad and frustrated when I read posts like Kira Newman’s on why Facebook would have never started in Paris: not because of her (I’m not one to shoot the messenger), but because it’s filled with criticisms originating from my fellow Frenchmen.

    When I relocated to San Francisco, we happened to rent our Paris apartment to an American family and I remember perfectly what their little girl told me when I asked about her experience after a year in a French school. She felt it was not so great because it was always about what was wrong, never about what was right. Similarly, it seems that whenever we have to address the French or Parisian tech startup scene, everyone thinks they’re being asked to criticize the system and highlight what doesn’t work. That’s of course not the way people here talk about Silicon Valley – even though it’s far from flawless – but neither is it the way New York or even Las Vegas, London, or Chilean entrepreneurs talk about their own tech hubs (yet all of them have “problems,” at least compared to Silicon Valley).

    We have to stop criticizing and change our song to talk about perspectives, solutions, and encouraging stories. Let me try.”

    The author is addressing European Startups but maybe it’s not limited to just Europe. In any case, I look forward to your announcement of more startup details when you’re ready.

  9. Felicia
    Felicia says:

    Love to hear that Carmen is in her “right job” and that it works for her in terms of freedom (and hopefully in terms of money too).

    That is my dream, even though I’m still in a transition about what that is (right job), including the money piece. The simplicity is key for me, too. Every year I get closer. When I read about people like Carmen and people like you, doing your right jobs, it gives me hope. Great post, thank you.

  10. Kristin
    Kristin says:

    girlfriend, you forgot to actually link to Yefet’s post in the 3rd to last paragraph.

    hire me to be your last pair of eyes here before going live ;)

  11. Ellen
    Ellen says:

    I don’t understand how you travel all over the place with the crazy schedule and the kids. Doesn’t one of your kids have aspergers? doesn’t the crazy schedule get to him? we are getting our son tested for aspergers (i have no clue why it didn’t occur to me, but he’s pretty textbook) and the one thing i cannot do is keep a crazy schedule. he goes insane without a routine. he is only five, though. does it get better as they get older?

  12. Old friend from far away
    Old friend from far away says:

    Hi Penelope. I always enjoy your writing. Sort of wish you still wrote “fiction” although I can see you love what you are doing now an lots of time I see the same kind of fiction-like story telling on your blog. I was kind of inspired by thinking of Carmen and the idea that a friend could possibly get other friends work. I would be the Carmen in this scenario. Because of health issues I have been out in the work world for a long time and in general am not good at and don’t really have ideas about what a I could do for money. I have practice writing but mostly creatively and doing artwork and also am a good encouraging but incisive critiquer of other peoples artwork and writing. I am also good at brainstorming on projects I believe in and have helped friends in various creative fields including visual art, film, fiction and nonfiction, poetry and animation over the years. Because of the health issues I’ve done what I could but also needed to rest a lot. From being alone for years I need solitude but also feel a bit isolated and would like to have contact with others. I am at the tail end of your dreaded baby boom. Don’t know if this is appropriate but if any of your readers have ideas for someone in my situation or are in a similar situation I would so appreciate hearing about it. Thanks for the provocative and often moving and/or humorous reads.

  13. Old friend from far away
    Old friend from far away says:

    oops, guess I couldn’t be a proofreader. I meant I have NOT been in the work world for a while and also see other typos or think-os. Anyway thanks all.

  14. tatiana
    tatiana says:

    I really like this: “So, really, simplifying your life is arranging everything so that you’re doing only what you’re great at.”

    Which is true. I think it was you who wrote about how people fixate on their weaknesses and trying to make them strong instead of pursuing their strengths. There’s also these anti- feelings regarding doing something that’s easy and we’re all expected to struggle (especially if we want success). And if you’re not struggling, then that means you’re just lucky and are considered different.

    Which is annoying.

    So most people don’t know what they’re good at, which is why we have so many personality tests. I classify as an ISFP, which is nifty, but don’t know what to do with it. But I also don’t know what I’m good at (other than napping and sharing links). But it’s hard to be objective about my subjective experiences because I’m viewing them through a specific, and relatively tarnished lens.

    So I think my goal is to figure out what I want my life to look like and what skills I already have that I can use to get there.

    • Penelope Trunk
      Penelope Trunk says:

      Tatiana, your comment is a great window into why we each have so much trouble doing what we’re good at. It’s never what we expected.

      I am okay being a parent if I can run the household like a company (when people visit they can’t believe how structured and goal oriented daily life here is given that we unschool). But whenI ran our house like a day care center I ended up in the mental ward – literally.

      So my problem, initially, was that I couldn’t imagine running a family like a company so I felt like a failure.

      You are the opposite – you are in great shape to run a family because your strengths are fun, detail-oriented and caring for people. Everyone’s dream parent. What you need to do is someone create that scenario at work.

      It means that just like I’m an unconventional parents, you will be an unconventional worker, because you don’t really get paid to do fun, detailed work that relates to people – mostly we volunteer for stuff like that. (Which is why I give money instead of volunteering.)

      My point here is that so often it’s completely obvious what we’re great at, but also completely inconvenient, given where we are in life. And the trick is to stick to what you’re good at even if it makes little sense for where you are in life right now.

      Life changes so fast. Anyone in their sweet spot now, won’t be in five years. And vice versa. We have to all be on our toes.


  15. Jana Miller
    Jana Miller says:

    “We get into trouble when we get distracted by opportunities for us to do things we’re not great at. And we benefit from surrounding ourselves with people like Carmen who are great at turning down opportunities outside of their sweet spot.” Love this! I’m sure we all know someone who tries to do everything well…and often it’s us :)

  16. me
    me says:

    I long for a simple life as you’ve described it. I love working on great ideas run by great leaders. I have a feeling I’d be a good player on Team P.

    I plan on working for another 10 years or so & then I’ll quit & be ready to join your army !

  17. Gemma Campbell
    Gemma Campbell says:

    I’m so glad Carmen is helping you to post more consistently. Your blog is the first blog I’ve ever really cared about and it’s the only one I read every single new post on. I even went back and read every single post on homeschooling you have on this site which took me a few months. I love popping onto your site once a week or so and finding several posts to catch up on.
    Thanks for posting.

  18. Xihla
    Xihla says:

    I am truly and totally inspired by you.

    I love how you do what you do, and not following anyone, but focus on what works for you.

    I totally need to arrange my life,so that it is on my own terms, so I can do what I love doing. It’s a bit of a challenge for me, but lately things seem to be falling to place. Though slowly, but they are.

    thanks for sharing!

  19. Chelsea
    Chelsea says:

    I love this post so much. I just love it.

    After taking your ‘Find Your Dream Job’ course and having our coaching session, I have been telling my friends that the key to being happy at your job has to do with being good at your job. And, it’s the same way with being happy in life and living a simpler life. So I copied this and put it on a sticky note on my computer, so that I can read it and remind myself of it everyday:

    “So, really, simplifying your life is arranging everything so that you’re doing only what you’re great at. Everybody can make money and have a life that feels simple to them if they focus on doing what they’re great at. We get into trouble when we get distracted by opportunities for us to do things we’re not great at. And we benefit from surrounding ourselves with people like Carmen who are great at turning down opportunities outside of their sweet spot.”

    Thanks for another great post, Penelope.

  20. Jo
    Jo says:

    Penelope, I have a blog post request for you – one of the reasons I love to read your blog is that you are an ENTJ, and a female, and you write about that experience so eloquently.
    My 8yo daughter is an ENTJ, and she would so love to have an army to lead. Daily attempts to have the entire family marching to the beat of her own drum mostly end badly for everyone.
    I so want to be a good parent to her, and help her grow into the person she is destined to be. I try to help her understand how the people around her feel when she tries to steamroller them into doing what she wants. I am attempting to give her some social ‘pattern cards’ so that she can look like she cares about social niceties, even though she really doesn’t! But I don’t want to squash her naturally bombastic nature either, because the world will need her one day.
    She doesn’t have Asperger’s, and is a really good actor. She can deliberately act ‘normal’ until she gets tired of it. She discovered the Pippi Longstocking books the other day, and is thrilled to find a book about someone just like her, and indeed, I can imagine her carrying out every one of Pippi’s crazy exploits.
    My question is this – can you imagine what great parenting would look like for an ENTJ girl? I know your childhood wasn’t ideal in any way, but can you tell me how you think your best imagined childhood might have looked like?
    I am an INFP, and apart from our shared love of language and ideas, I have very few insights into the way her inner life works..
    I am so glad you are working your way towards a place where you and your family can all be doing what you want to stay happy and sane.

  21. darja
    darja says:

    i love your blog. when our two babies go to sleep, your posts make me get out of the bed to go online. my husband understands that, actually i think he is kind of grateful that i focus on you and not on him who is as tired as i am.

    i don’t like to comment on your articles, though, because i am not a native speaker and suffer from so severe sleep deprivation due to breastfeeding lately that i hardly can communicate in any language any more.

    but i still have to tell you about hunter-gatherers.
    there is not a single society of hunter-gatherers who works more then 6 hours a day.
    and when they do, then it is because they hunt (in a group of people they feel comfortable with) for several days and then have another several days doing social activities.

    why is this important for us? because we spent over 99% of our evolutionary time living in that continuum, in that setting, working under that set of rules
    (i can hardly imagine that myself…in spite of having a ph.d in the field, the time scale always overwhelms me).

    so yes – we should be doing exactly what you say, simplify in terms of doing what we are good at and feel comfortable with, even if it is leading an army.
    but not more then 6 hours a day.
    (and not more then 4 days a week!)
    that seems to be best suited for combining work, family and personal life. greetings from berlin

  22. maximillian
    maximillian says:

    I needed to read that right now because i suck at doing a whole bunch of little things in my life and work but its good to hear simplify to what you’re great at…

    always need to hear that…now i need to engineer that =)

    great post. keep doing what you’re doing and keep up with your army…

  23. Sadya
    Sadya says:

    I can’t exactly pinpoint when and why I started hating the phone. It probably started with my 1st job when my boss taught how to lie when people called for her.
    The phone basically represents something that requires urgency of thought. My dread of having long conversations has probably contributed more to the lack of a love-life.

    The written word, or rather the typed word gives me more solace than the impromptu spoken word.

    The internet is my crutch. And I like it.

  24. Judy Sarden
    Judy Sarden says:

    This is a great post. So relevant to where I am at this stage in my life – homeschooling and buidling a company. Its also comforting to know how much help you get with your worklife. Makes me feel like less of a failure because I can’t get everything done by myself. Having your posts dictated is brilliant! I can only imagine how much more productive I would be if I could actually get stuff done while transporting the kids and waiting for lessons/practices to conclude.

  25. Daniel Fitzpatrick
    Daniel Fitzpatrick says:

    Great post. Learning to say no to activities that don’t add value is usually easier said than done, but definitely worth learning.

  26. Becky Castle Miller
    Becky Castle Miller says:

    I’m pretty sure I’ve said this before, but one of my favorite reasons to read your blog is that it helps me understand my ENTJ husband. This is so him: “The other reason that having a company makes a more simple life for me is because I’m most comfortable leading an army, and I’m least comfortable when I have no army to lead. … So what I really need to do is have a group of people where we’re all doing my vision together. That’s really fun for me.”

  27. SheilaG
    SheilaG says:

    Am I the only person here who thinks it would be incredibly exploitative of Penelope to sell Carmen’s services and pocket half the earnings?

  28. Jack
    Jack says:

    Always looking to simplify my life. It’s so much nicer when you can free the time to do the things you want to do, rather than what others are trying to force upon you.

    Speaking of freeing up time, thanks for the tip on dictating your articles. Much of what I write is too structured for me to dictate smoothly, but I can imagine several types of articles that would actually be better if I dictated them rather than outlining them.

  29. karelys
    karelys says:

    I loved the part on how Carmen simplifies by knowing what is good for her and turning down good opportunities just because they don’t align with the current vision.

    It helped me turn down a good opportunity I had for this good one I am on right now.

    • Carmen
      Carmen says:

      Karelys, I actually found your comment comforting. I’d like to think saying no to what doesn’t feel right is leaving space open in your life for what will feel right down the road. We’re always afraid the opportunities will stop coming if we start saying no, but perhaps it’s the other way around. We discover more about ourselves with a solid “no” than we do with a half-hearted “yes”. And then maybe opportunities start to shape themselves for what we’re best at because we know better what to look for.

  30. Janet Benson
    Janet Benson says:

    I’m really intrigued by the idea of homeschooling, but am a little weary of it. I’m afraid my kids will be missing out on things other kids will be exposed to and experience. That, and also, that I may not be able to handle it and my children will suffer for my inexperience. How did you handle it in the beginning and did you also worry about things like that?

  31. cheddarMN
    cheddarMN says:

    About the “horror” of kids coloring in 2nd grade, I’m not sure why that is so bad. My kids love a new box of crayons even in 4th or 5th grade. Their art now tends to combine crayons with sharpies and colored pencils, but sheesh, there must be better criticisms of second grade than the fact that the kids use crayons.

  32. Jennifer
    Jennifer says:

    I’m Gary Paulsen’s agent and I read your blog to him. Now he wants Kevin to start a blog in the next book and he asked me to thank you for the nice mention and tell you he’s glad your whole world didn’t go to crap like Kev’s did after your big idea.

  33. Jenn
    Jenn says:

    I’m the last person to criticize anyone’s ideas so fire away :)

    I used to think that simplifying my life was another way of saying I was becoming lazy, but as I got older, I realize that its the way to go b/c you can’t be an amazing you unless you keep it simple…another great posts, thanks……

  34. Zach
    Zach says:

    What an interesting take on simplicity. I struggle with figuring out how to simplify, but I never thought of it that way. Your simplifying sounds like my complicating. Just goes to show how personal these decisions can be.

  35. Bimala Raut
    Bimala Raut says:

    Really nice post. You have provided secret to a simple life which inspired me to write. Actually, I become fan of your writing style, Love the way you present every sequence. Thanks for sharing such articles…

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