Simplifying life has nothing to do with all your stuff

I have never filed my taxes on time. Ever. It’s very annoying when people blame every little thing on their parents, so I’m not going to tell you that year after year my mom would let my dad do their taxes, my dad would wait until the last minute, and then he’d ask my mom to sign at 11:45 pm so he could drive to the post office and get it postmarked and she would say she has to read it and he would throw a fit. Then the police would come and stop the fight.

You might ask why did my mom not trust my dad, or why did they did not hire an accountant when they were earning truckloads of money, or why did they not file for an extension?

But we will not explore any of that because I’m too old to be a person who blames everything on my parents. Anyway, I hire an accountant. But I get an extension every year. According to this Salt Lake accountant people who file late don’t have the patience for all the bookkeeping. That’s probably true. I want to do better than my parents, and I have to start somewhere, so this year I decided to file on time.

To do something hard, like taxes, I need an hour to gather my stuff and send it to the accountant. And today is the deadline for getting on the accountant’s calendar. Fortunately I have a bunch of hour-long time slots that would be great for gathering tax info.

I write my to do list because that’s what people who get stuff done do. Then they do the first thing on their list first. I sort of do that. I make A’s, B’s and C’s.

I get up at 5 am because productive people are early risers. Do not tell me there are productive late risers. That’s like when people tell me they know where everything is on their messy desk. The research says  people who have messy desks look overwhelmed and unproductive. And if you look that way then people treat you that way and then you become that.

Everyone on the farm gets up early for chores. So by 5:30 am I already don’t want to do my A’s so I tell Matthew and my son that I have a great video for them to watch. It’s one I just found in my email: First Kiss. A video artist had twenty people who have never met each other kiss.  Ten seconds into the video my son, who has been known to search suspiciously sexual terms in YouTube, can recognize this as more art than porn and he goes back to his Rainbow Loom. Matthew and I watch. It’s touching. And disturbing.

So I watch three times.

Then I organize the boots. There are a lot of boots on a farm. And I organize the spices. The bigger my list the more organized our boots are.

Now, since there is not an hour left to do my taxes, so I send an email to Cassie:

I’m teaching you about about working with people, okay?  You don’t work with Paul and he doesn’t take orders from you. So it’s insubordinate that you emailed him. I don’t care, and I don’t think he does either, but I think you have no idea that this is jarringly awful office politics that you exhibit here. I think it’s why people hate working with you.

And Cassie writes back:

Paul and I have a system, which we created because you are so terrible at office politics. Everytime you send him directions to change something he calls or emails me to find out what you are talking about. You give him such vague instructions that he has no idea what to do.

Stressing over whether I am incompetent at management takes the rest of my hour.

The next hour I have is after I make breakfast and do music practice with the kids. I check my email first, which you should not do. You should do the first thing on your to do list and then use email as a reward system. Melita Smilovic sent me a link to a speech she gave about our coaching session. I told her her resume sucks. And she still liked the coaching session. I am happy.  She tells me to start looking at the video at 8:45 but I watch the whole thing because it’s so much better than doing my taxes.

Now I have used fifteen minutes of my hour. So I can’t do taxes. I do fun things on my list that are not A’s. No one has high priority items on their to do list that are fun because if they are fun you do them before they even get on the list.

I read that people who skip going to the gym and get mad at themselves about it stop going to the gym. But people who tell themselves it’s okay, just start going now—those people are lifelong gym-goers. I have to go into Madison for my son’s violin lesson. But instead of scolding myself for pissing away tons of time, I tell myself it’s okay. I can organize my tax stuff in the car. People who meet their personal goals cut themselves slack.

I start sorting through piles of disorganized papers while Carla drives. Having a driver means you have more time to tell yourself you’re going to do the number-one thing on your to do list.

We stop at a hotel for a bathroom. And there is a wedding vendor convention and I have to go in, of course. And the first booth is Ken whose company is Flip’n Sweet, and he can make a flip book of people doing something in just one minute. The examples are wedding couples kissing. He lets my son do a little dance and then we have a flip book. So fun!

We get in the car and I’m flipping instead of doing taxes, and Carla says, “Remember that article in New York magazine about the prisoners who starved themselves to protest the inhumane nature of solitary confinement? They should use these flip books to create protest materials.”

I wish I thought of that idea. Then I could have crossed out on my to do list: Make time for thinking clever thoughts.

I cannot organize my taxes because the wedding stop made us late for violin so I have to call the teacher to convince her to wait for us.

On the drive home I don’t even pretend I’m going to do taxes because good time managers are realists. So I read my articles from my folder of articles to read later. One is about the book Happier by Tal Ben-Shar.  The research in his book says we would be happier by doing these things:

  • Create rituals around the things we love to do.
  • Express gratitude for the good things in our lives.
  • Set meaningful goals that reflect our values and interests.
  • Play to our strengths instead of dwelling on weaknesses.
  • Simplify our lives — not just the stuff, but the time.

And then I realize: The way for me to be better than my parents isn’t to do my taxes on time. That would be nice. But really I need to not give myself choices about how I spend my time. The more choices I have throughout the day, the more decisions I make, the more willpower I need, the more I get distracted from paying attention to the building blocks of a fulfilling life: gratitude, meaning, and ritual.

Being productive means simplifying how you use your time. Which in turn, simplifies your life.



60 replies
    • Chris M.
      Chris M. says:

      Rebecca, I’ll never understand people like you or Penelope. I have my own business and consequently have a lot of documents to compile for taxes. But immediately after each expense (or as soon as I get home), I enter it in a Google drive spreadsheet. It only takes a few seconds that way. I also copy and paste rent and other recurring payments to the same spreadsheet, so coming tax season, I just need to send it to the accountant along with a few printouts received by mail.

      I’m not saying that to brag about my level of organization (I’m not very organized, especially at home), but because I know my level of stress would grow up exponentially if I kept postponing dealing with taxes the way Penelope describes. Since I know I’d have to end up doing it anyway, I’d never be able to entirely remove the task from my mind.

      The sooner it’s done, the happier I become, remembering that I’ve already crossed that item off my list, and there will be no guilt whatever I decide to do next (read articles, organize my boots, take a nap). So I highly recommend trying to create a habit out of organizing your tax info throughout the year (perhaps using a fun folder if electronic files don’t appeal to you).

      • Liz
        Liz says:

        Chris, I appreciate and am grateful for your advice in your comments. However, I cannot understand why you would start your comments with such a condescending sentence. Otherwise, ignoring that, it is useful, and positive.

        • Chris M.
          Chris M. says:

          Heh, it goes to show how different communication styles can come across. It was never my intention to be condescending, or make you feel inferior because of the way you deal with taxes, Rebecca, so my apologies for the way I sounded.

          I was just trying to express my true puzzlement because as averse I am to paperwork, I’m even more averse to the increasing stress of postponing dealing with it (because it will be at the back of my mind until I finally take care of it).

          @Tracy: I’m a big fan of Myers Briggs, and made my husband take the test so it would be easier for me to understand his reaction to things (which often don’t match mine at all). But even though we have opposite Myers Briggs profiles, we both want to get rid of taxes as soon as possible, because we’d both suffer terribly having the task at the back of our mind as a pending item. Since bureaucracy won’t go away, even though I understand quite well not wanting to deal with it (renewing a driver license, filing taxes, etc., are a nightmare to me), we just prefer to shorten the pain period by taking care of it as soon as possible!

      • Tracy
        Tracy says:

        Chris, never say never – I recommend Penelope’s Myers Briggs course. It makes your realise why everyone isn’t like you and why that really matters.

        • Margeaux
          Margeaux says:

          But some people just have lousy work habits, which isn’t a personality trait, but an acquired characteristic. It’s possible to improve, if ones wants to do so.

      • Melissa
        Melissa says:

        I use FreeAgent –– –– which I believe it’s the best option out there for doing your books and keeping it in the cloud. Plus, it has interesting reports to run and pretty graphs to look at. Which is maybe why I’m so good at keeping up with it.

        You can get a discount on the monthly subscription if you use my referral code: 42ladscs


  1. Thi
    Thi says:

    Maybe organizing your boots wasn’t the most time efficient thing to do. But it will look like you are productive. Then you can actually be productive.

    The “messy desk” principle can apply to boots too.

  2. Sarah M
    Sarah M says:

    Not giving yourself so many choices about your time makes sense. Anne Lamotte says, “Butt in seat”. My version is “Shut up and do the thing.”

  3. Amber
    Amber says:

    Sure, simplifying is not all about stuff and people tend to forget the time piece but don’t you think it’s much easier to have a messy desk (look disorganized) when you have too much stuff?

    Also, I would say the urge to blame stuff on your parents drops dramatically when you have a child.

  4. Tara Sayers Dillard
    Tara Sayers Dillard says:

    Past the age of 25, my cut off, can’t blame the parents…..

    Affects who I let into my life too.

    Of course who wants those people? Parent blamers.

    Have let parent whiners whine only to get the last sentence, ‘So you still blame your parents at your age?’ Hopefully will be stuck in fewer fewer to zero places with those people.

    Lastly, very glad my parents weren’t great at parenting. Got me where I am, and love where I am. Perverse thanks. And we of this parentage can usually spot each other. Life is good, with much laughter, activities, grace, joy….

    Stuck on bad parenting lets them win. Stupid, yes?

    Garden & Be Well, XO Tara

  5. emily
    emily says:

    Another tip is to block out three hours for something that you think will take you an hour. Obviously this means that a lot of other stuff won’t get done that day. But it leaves time for procrastinating, leaving website comments and / or the fact that you’ve probably underestimated the amount of time it takes to do the thing.

    • Penelope Trunk
      Penelope Trunk says:

      Emily, this is a great idea for me. Because I think I’m generally too optimistic with time. Also, the idea of having three hours blocked out and then only using one of them seems yummy – like I suddenly have a bunch of free time which is a great reward for getting my important stuff done.


  6. Maria Killam
    Maria Killam says:

    Of course you give vague instructions, that’s your personality type. I’m exactly the same. I assume everyone around me can multitask like I do and I also expect everyone to drop everything and listen when I’m talking but I’m the worst listener ever, haha. Great post Penelope :)

  7. Lara
    Lara says:

    I am feel blessed that my husband keeps immaculate books and we had our taxes done in record time. I heard from a tax lawyer that you should always take the extension, by the time you send in your taxes all the spots for audits are filled up. Who knows if that is true but worth mentioning.

    Love this!
    Being productive means simplifying how you use your time. Which in turn, simplifies your life.

    I am working on it! Thanks Penelope.

  8. Maxine
    Maxine says:

    You need to delegate the bookkeeping as well as the accounting, and use tools to make it easier for all of you. In this day and age there’s no need to actually be sorting paper at tax time, the important pieces will be in the cloud already shared with your accountant. All your finances will be available in a cloud based accounting application (best is which both your accountant and bookkeeper will have access to.

    • Penelope Trunk
      Penelope Trunk says:

      Thanks, Maxine. You inspire me to get better. Although I can’t help feeling that this is like when I taught a friend to make brisket. To me it’s so easy because I’ve done it many times before and I’m good at it. To someone who doesn’t cook any sort of cooking seems complicated – like another language. I think that might be what taxes are to me.


      • Anna
        Anna says:

        Penelope I took your advice (finally) and hired an assistant I can barely afford. *Best. Move. Ever.* She does all of the things I am bad at, including organizing my tax stuff for a bookkeeper, and she does it way better than I do. YAY!! I am free to build my business.

      • Paxton
        Paxton says:

        This reminds me of something my college physics professor used to say…something along the lines of ‘things are easy once you learn how to do them’

  9. Helene K
    Helene K says:

    I don’t understand what is meant by “simplifying your time”.

    That just sound like bogus to me – something a “life coach” will say that sounds sooo intelligent, but really the person have no idea what it mean.

    A person that actually know what it means would go into details on how to achieve it.

    • Penelope Trunk
      Penelope Trunk says:

      To be fair, the bullet you’re referring to is an excerpt from a book. So he definitely goes into more depth.

      But really, as soon as I read that list I knew exactly what simplifying time meant: we complicate our schedules and our options and our goals for time until it’s too convoluted for us to manage with any modicum of success. Routines, stable goals, lack of choices – these are all things that make time more simple.


    • Angie
      Angie says:

      I have a good example from my own life. I moved a week ago, and within a few days I created a long list of things I needed to buy/find/do in order organize my new house. So I went shopping and was all over the place, trying to find all these things. Then I realized that I was using my time inefficiently by spreading it out like that, so I chose one thing to find: window dressings. Now I didn’t need to go to 10 different stores/websites to find what I needed.

  10. Melita
    Melita says:

    I always wondered why you watched the talk so quickly! I’ll make that the headline of my resume – ‘I’m more interesting than Penelope Trunk’s taxes’.

  11. Tracy
    Tracy says:

    I love how this post has so many details of your day – really appeals to the analytical side of me that always wants to know how other people fill their days.

    Since having kids we have so much more routine than before and it does indeed simplify life (although conversely makes things more difficult when out of routine).

    Hope you can get some improvement on the taxes and take a long term view on it – bit better every year.

    If I were you I’d think I’d try to use my blog more regularly to get inspiration for mundane task – kinda like a reverse-mailbag section, but this time readers write in to inspire you to solve your problems.

    I’m now appreciating the irony of giving productivity tips as I’m reading your blog procrastinating on doing a client report that is sitting at the top of my todo list, yawn…

  12. karelys
    karelys says:

    I think making time to think clever thoughts is incredibly important. At first it’s hard because you’re not used to it so inspiration may not struck. But it will become better.

    That’s all I came here to say.

    I have insomnia but not enough energy during insomnia to get up and do something. At the most I flair my arms in the air and breathe and that may gain me a couple more hours of sleep. So I am always dragging. But when I didn’t have insomnia I loved getting up early to drink lots of coffee and stare out the window, into space, at the wall, etc. and think thoughts. It made my whole day better.

  13. Jennifer
    Jennifer says:

    I’m getting the vague instructions part. Loved the article, but seriously, how does one simplify how you use your time? I run a business and educate 3 children from our home. Not to mention all the other lovely life stuff I do. Please tell me how to simplify this!

  14. Sadya
    Sadya says:

    Don’t put doing taxes or anything that has some trauma attached task on a To Do List. Put it on a To Be List.

    When you recall how your parents did their taxes, and you think you don’t want to end up like them. Which means you don’t want to be the parent who does something critical / family related so poorly, and you don’t want to be the spouse who just makes taxes such a painful thing.

    You already know you aren’t good with managing finances, so the procrastination is due to anxiety. It’s ok.
    When your kids will do their taxes with ease and get the help, they might just do so because they might have a memory of you doing it with level headedness.

  15. cindy
    cindy says:

    I totally understand, Penelope. My accountant used to file my extension every year automatically for me because I was never, ever on time.

    Now, the only thing that has gotten me on track with taxes, is that my son is in college and he needs my tax information to file for FAFSA every year by March 1. It is the ONLY thing that has ever worked to get me on track.

  16. Savvy Working Gal
    Savvy Working Gal says:

    I loved Melita Smilovic’s speech about what she learned from her coaching session with you. I still think a video site of your coaching sessions would have made a great business.

  17. Lyn
    Lyn says:

    As a CPA, I will tell you that we love people that file extensions. It alleviates a bit of the pressure from busy season. You may also, inadvertently, get a better result if you extend. Having more time takes some pressure off, and the preparation and review processes may be more thorough. Of course, there are still calculations related to extension/estimate payments, but the work is typically substantially less for that.

    In my opinion, filing your taxes by April 15th isn’t doing it better. It’s one of many correct ways to do it. I think doing it better would entail removing the frantic and/or petrified response from the entire process.

  18. Leslie
    Leslie says:

    My Dad was a CPA so I think I learned about taxes through osmosis. Now, I use software from H and R Block. It prints out the whole thing and plugs in a lot of the data for you. I love how organized it makes me feel. Doing the book keeping is actually harder than the taxes and then of course there are the quarterlies.

  19. Alex
    Alex says:

    “Express gratitude for the good things in our lives.” I feel this is one of the most vital things that people always forget. Thanks for the post!

  20. Marie-INFP
    Marie-INFP says:

    Perhaps you should make an appointment with your accountant and take that full day off from everything.

    Get out the house as early as possible, at 5:00am or so, staying in that sleepy headed, automatic pilot zone, with no time to think as you get ready, until you’re halfway gone in the car.

    If you that won’t work, here’s an extra incentive, have the accountant charge you some astronomical amount, something you could afford to pay but wouldn’t want to, for missing the appointment.

    An ex-executive I EA’d for in Chicago did this with his weekly therapy appointments. For missing a session, it was $1,000 and for the sessions he kept, it was the normal $250.

    He’s bipolar and a classic ENTJ, if ever there was one, so already you can tell where this story’s headed.

    A betting pool goes up in the office after he tells everyone his deal with the therapist. Yet another incentive, since this executive has an ego as big as all outdoors.

    In the nearly two months this went on, he makes exactly 1 session. He once bet double or nothing. A pot which cost him $9,000 plus the miss session. I suggest reverse psychology, to bet he doesn’t go, that was the 1 session he went. His business partner finally puts his foot down. They fought constantly, which eventually led them to therapy. But I had to find another therapist, the executive’s took his wife on a three-week European vacation and so he wasn’t available.

    You can do it, P!

  21. Lisa - Good.Co
    Lisa - Good.Co says:

    I have a friend who gets excited to do her taxes. No joke! She lives in Canada (and tells me she feels sorry for American taxpayers trying to decipher IRS forms), has no kids, is just beginning a freelancing career, and has never had a balance owing. No wonder she looks forward to tax time – it’s like another Christmas that happens in March! Who isn’t excited to get paid? She’s also an INTP, so she really likes forms and being organized.
    As far as simplifying time, I find I’m most productive when I’m removed from personal ‘living’ spaces. To do my work, I lock myself in my office, or head to the coffee shop or library. I have fewer commitments than others, but I find this limits my options to ‘get work stuff done’, and suits me fine.
    Great post! Lisa Chatroop, Good.Co

  22. Lindsey C
    Lindsey C says:

    This makes me feel better: I also watched First Kiss more than once and I mailed my taxes to my accountant today–on his due date. I like that you point out meaning and gratitude.

    Another thing is to schedule time to think and read after two must-do items are done. That is keeping me on track–sometimes.

  23. Erin
    Erin says:

    This is a very interesting observation. For me, I feel the most accomplished and fufilled regarding my use of time when my day has 1 task, but remains unstructured besides that task. I’m an artist & homeschooler, so our lifestyle allows for this flexibility; and my personality as an INFP is geared towards embracing this ambiguity. When I let my feelings & intuitions guide me throughout the day, I learn to trust them more, and so I reaffirm that who I am is a strong and capable person, even if others may see me as unpredictable or chaotic. ^_^ For me, simplifying my life & my time management is summed up in one tennant: follow where today leads you.

  24. Mark W.
    Mark W. says:

    I also procrastinate filing my taxes. I get them done on time with a lot of colorful commentary. Somehow words I have for the IRS that they will never hear make me feel better. One last minute filing while in L.A. found me in a line of cars about 11:30 P.M. with postal workers collecting returns on Century Blvd. near LAX. I may have nearly made the local news because they always used to show the last minute filers on TV.
    And this subject of taxes reminds me that we have a voluntary system according to Sen. Harry Reid – . Argh!

  25. Gentjan AL
    Gentjan AL says:

    come on you cant force the organisation, you have to have a strong reason for it.

    When I dont have to work all the day there is no reason for me to be organized because I know I can complete all my funny to do list.

  26. Yuliya
    Yuliya says:

    I enjoyed Penelope’s writing until I read Tim Ferriss and realized he’s trumped Penelope and then some. That’s why she hates him so much. Her complaints about him sound like a n asinine and childish temper tantrum – largely unfounded and based on personal anecdotes. In the post where she wrote about why she hates him, she sounds like a thrashing, abusive, angry shark held down in a hospital gurney – angry because she didn’t get to his ideas first. His ideas are her ideas on crack and then some. He’s more polished and pulls it all together more nicely. Even Penelope’s friend Melissa likes and quotes his book. You are old news – Tim was and still is the new black. And he seems fairly personable and isn’t an abusive old nasty who passes himself off as good in his writings but is a kook behind closed doors.

  27. Tony H
    Tony H says:

    I like to do little tasks around the house to distract me from stuff such as taxes and I usually end up getting an extension so I know the feeling!

    • Michael
      Michael says:

      Filing an extension is not a good strategy. This can raise red flags for the IRS, and I have been told it can increase the probability of an audit. Try living out of the country and doing taxes in 2 countries!

  28. maximyou
    maximyou says:

    My breakthrough-technology for simplification – follow your bliss. When you dare (to follow your dreams), simplification ensues because you realize there’s only so many dreams that are important enough to deserve your time, and by extension your existence.

    • Tony
      Tony says:

      This is a nice thought, but for me following my dreams means even less time for things like Taxes. I love what I do because of “game” aspect of it. For me, taxes is a now win game, therefore I don’t like to play.

Comments are closed.