Melissa says to me, “The reason you’re not writing is because you’re hiding. And if you hide something from blog readers you can’t cope. So you don’t write.”

I tell Melissa, “If you’re going to move to New York then David should put some of his huge salary in your bank account.”

Melissa says, “Don’t change the subject when you can’t face reality.”

I say, “You shouldn’t relocate for a boyfriend to a city where he is making a boatload and you’re not.”

“You should pay me more.”

“Yeah. I should make ten million dollars a day and pay you five.”

“You can pay me from your new startup.”

“No. Really. It’s a real company. I can’t put you on the P&L when there are investors. There is no line on the P&L for Penelope’s friend.”

“I can tell you’re going to put this conversation on the blog. If you’re going to complain about David not giving me money, don’t use David’s name.”

“I’m using his name. He’s an ISTJ. He doesn’t care about me using his name. He just cares that he’s right. So I’ll just tell everyone: David is smart. He is right all the time because when he isn’t going to be right, he doesn’t talk.”

“Can you delete that last part, about not talking?”

“No.”

There is a conversation intermission where Melissa sends me links like the one about the Jewish intellectual writing about the sociopolitics inside the state prison where he’s locked up. Then I talk on the phone to people who I am probably late for. But people who know me know that I am late for lots of calls, and maybe they don’t notice anymore.

Then there’s a break for me to eat some candy out of my kids’ Halloween candy which I bought from them, in October, because candy is evil. I stashed it and forgot about it. But I just found it and I’m working on the Twizzlers and then going to Snickers.

Melissa is not eating. She doesn’t eat. She is anorexic in a high functioning way. Like a high-functioning alcoholic. If you saw her, she would eat. Like, if you saw an alcoholic, they’d drink lemonade, straight up.

Melissa calls me later to bug me about David’s name on the blog.

I say, “I have to use David’s name because I’m using Roger’s name.”

“Who’s Roger?”

“The guy advising the startup I’m joining.”

“I thought you can’t write about the startup.”

I get off the phone. I cannot talk about the startup with Melissa because she is really excited to work there and then I get nervous it’s going to be another case of all my friends at one startup and me having a nervous breakdown that we are out of funding and my friends are going to lose their jobs and starve.

The startup is a secret because I’m not really working there yet, and no one is going to want their name on this blog, except for Roger.

In our first conversation he brought up the Menendez trial.

I said, “That’s my favorite trial!”

Did you read about it? It’s from the 90s. Here’s a link. Two boys killed their parents. I impress Roger with my knowledge of the case and say, “I thought the child abuse claim was really persuasive when the boys said they gave their dad cinnamon to eat becuase it changes the taste of semen.”

It turns out that Roger testified at the trial. He says the dad really was the worst person he ever met.

Roger has principles. Good. That’s important if I’m joining the company. Also, Roger is 60something with a young daughter and I expect him to be married to a 20something model, but he’s married to a 49something entrepreneur. He’ll be good for me.

I ask Ed, an investor from Brazen Careerist, if he thinks I should join this new company. Ed says you forget how terrible and hard startups are when you’re in between startups, but then you remember when you’re there. And they really just ruin your life.

I am paraphrasing. Because he’s actually running Brazen Careerist now, and surely he’d want to tell you that the company is doing great and he loves it. But I love him because he’s honest. The guy’s a millionaire a million times over and he’s not sugar coating the startup world.

Roger is not sugar coating either. It’s just that I can’t give you details because Roger is not as used to working with me. Ed can put up with anything. I need that in a co-worker.

It’s why I work with Melissa.

I am scared to do another startup which is why I can’t even tell you. For other people, signing the papers would be the big commitment. For me, it’s naming the company on my blog.

Matthew tried to talk with me three times today and I was too preoccupied with the new company to pay attention to him. I forgot to say goodbye when I left. He called me to tell me that I’ve been oblivious to him. He is a very low maintenance guy. For him to say that is a big deal. And I had flashbacks to when I launched my last company, and I didn’t pay attention to anything but the company and then, before I knew it, I was getting a divorce.

So while I was on the phone talking about the new cap chart for the company, I got waxed. “Everything off!” I said, with the mute button on. Maybe making time for waxing keeps marriages to entrepreneurs from falling apart. But the odds are bad. I see myself slipping into startup hell again and it’s like anorexia or alcoholism: I’m just hoping that I can look high-functioning.

Here’s what you need to know about startups: being the tenth person in a startup is fine. If you like working long hours on projects that constantly get cancelled, then startup life is for you. But being responsible for the funding of the company, finding a profitable business mode, getting the company off the ground, these are jobs for crazy people. Because it’s so disruptive to your life that it’s questionable whether it’s worth it. Especially if you have kids.

And now at last, I am coming to my point. And you will see the title of this post is not a mistake.

My editor saw this post and said, “Remember how you told me that your mom gets all her information about your life from your blog? Well, you should send this post to her. Because she’s the only one who will care.”

So I did what every good writer does in the face of rejection: Hate myself and cease all forms of genuine productivity. My first phase of non-productivity is making a list – most important thing on top with a star. Then I get another pen and outline the star. I buy Jelly pens that ooze ink to make runny gooshy outlines of star shapes.

I could do a whole page of  stars – anything to avoid dealing with not having a blog post. It’s not like I don’t have ideas. I have a confidence problem. It’s so much easier to do things on the list that don’t matter. Sometimes I think the point of making a to do list is so I can organize things into categories: things I must do to be happy and things I will do to procrastinate making myself happy.

I do the things on the list that do not have stars:

I call Rob at TypeCoach and scream at him that I hate his new web page. I tell him my readers would all buy an in-depth report of their personality type if they could find it. I say, “How can you be so good at personality type and so terrible at web design?” He solves the problem by giving me a custom URL on his site  so I don’t have to see pages I hate.

I cut a couple of deals for doing PR on my blog and I get a lot of money from them and I immediately go shopping on Anthropologie. Research says that shopping is a good way to make you feel better. But not when what you really want to do is post on your blog. It used to be that research was inadequate because they left out women. Now it’s inadequate because they leave out bloggers.

The last thing I do to procrastinate was sweep. Melissa sent me this link to a $100 French broom. She said it’s like sunglasses: splurge on something you use every day. So I bought it and it didn’t even come with a handle. So I sweep with my $100 broom and I do not feel better about my productivity, although cleaning does make women want to have sex. Unfortunately it’s when the men clean. And that’s doesn’t happen here unless you count the pig shit that gets tracked into the kitchen.

I sit down to write this post: Forty billion words about how to decide if you should do a startup. But you don’t care. Or if you do, here’s a post to help you decide  so I don’t need another.

What you really need to know is that you will ruin your life if you don’t do the most important thing on your list every day. We get self-esteem from getting things done that matter. Not everything on our list matters to us. There is stuff that is there because it should be there, like things that involve making money, and there is stuff there because it fills our soul. You have to do the stuff that makes you feel good about yourself. Do it first. I put it off for a week, and it ruined my week.

Doing that first thing takes extra focus because the thing that matters most is the thing that’s hardest to do – it’s easier to do something when there’s nothing at stake. It’s why one-night stands are always the best sex.

And actually, I think that’s the big risk for me in doing another startup: I’m scared that my attention will be too splintered and I won’t write on the blog enough to feel good about myself. I’m scared I’ll get lost on my to do list, and that’s the worst way to manage a career.

66 replies
  1. John
    John says:

    You will ruin your life if you don’t do the most important thing on your list every day.

    Wow. This is brilliant. I’ve never heard anything quite like this before.

    And I’m realizing that this is how I ruined my life.

    You are amazing, Penelope.

    • Nalin
      Nalin says:

      your life must have been truly pathetic if it was ruined by not doing the most important thing on your list every day. who are you? a 16-year-old school girl?

      • Sarah
        Sarah says:

        You just judged a person’s life based on about three sentences…and you’re calling the other person a 16-year-old schoolgirl?

        If it doesn’t resonate with you, fine. No reason to tear other people down. We have different weaknesses and often can’t comprehend those of other people (much less have empathy for them, apparently). For me, I totally get Penelope’s message — when I don’t do what’s at the top of my list, it wears on my self-esteem and sense of self-worth. And at the same time, I have a very hard time doing those same things — even small tasks can be a big mental obstacle for me. It may not make sense to you — it doesn’t make sense to my husband, who is very good plowing through a to-do list — but that’s my struggle. Maybe John’s is something similar. Or not. But either way, it doesn’t make him pathetic.

  2. Suzanne
    Suzanne says:

    Hi Penelope,

    Because you seem to know everyone: do you have a terrific freelance fiction editor you can recommend? I’ve self-published four books, and would like to hire an editor for my current novel ( approx 100k).

    I’m ready to take my writing to the next level and see the role of an editor like that of a athletic coach, or cello teacher. Many years ago, I was a competitive swimmer. By moving to a better coach, I moved from performing at the local level, to the national level.

    I am a 51 year-old woman, who has finally decided that working for myself, doing something I love, is the best career strategy for an ‘older’ woman. Best of all, I’m happier than I’ve ever been in my life.

    P.S. love your blog. Good luck with your new start-up

    Thank you!
    Suzanne

  3. Tiana Kai
    Tiana Kai says:

    For me it is some cardio and pilates and now that I don’t make time in the morning I see it slipping further away. It’s the best thing I can do for myself yet have given up on it for some time. Excuse #1 the classes are aweful… I’m in Florence, Italy and the classes really are horrible. Of course, I can take a course and teach pilates myself or do it at home which would be even more convenient… Hmmm I really need to get on it!

  4. Armchair Freud
    Armchair Freud says:

    >It’s why one-night stands are always the best sex.

    Oh honey. I hate to armchair Freud. But if that’s how you feel, I think you just aren’t doing it right.

    I’ll trade you some sex advice for some career advice.

  5. Jessica
    Jessica says:

    Why are you putting yourself through this startup hell again? It seems almost self-destructive. Take the weekend off from your to-do list (even the starred items) and spend some time with your husband: It’s Father’s Day. :)

  6. L Tabak
    L Tabak says:

    Wow, the Menendez trial. I’m trying to remember a Roger (a Princeton pal?)…I have most of the Court TV broadcasts in a box of about 40 VCR tapes. In the weeks after the boys’ arrest, long before the trial, I wrote a 10,000 word story for the Princeton, NJ local alternative newspaper. I broke a lot of new ground with that story since I knew so many of the people close to the Menendezes. Tracked down the mom’s college roomate from the year when Kitty and Jose met; first interview with the young man who had lived with the family in Beverly Hills a month before the killings (we were tennis buddies), spoke with the family where the younger Menendez brother was staying in Israel when his arrest warrant was issued (he was reading Ayn Rand). Strange, disturbing memories. And yes, Papa Menendez was scary.

    • Gwen Fyfe
      Gwen Fyfe says:

      Princeton has an alternative newspaper? How did I not know about this when I lived there?

  7. Melissa
    Melissa says:

    Now I feel like a fool for turning down a sponsored link for online gambling on my blog.

    This was back in the early days when my daily readership was in the double-digits. And for a long time it was the most money I’d been offered for any sponsored item.

    I like the way you handled it. But I couldn’t believe that your Anthropologie link wasn’t an affiliate! I hope you’re making some sort of commission from them.

    • John
      John says:

      Actually, Melissa, you were right; Penelope is wrong. Or at least she’s making a naive mistake.

      Google is quite aggressive about down ranking sites – even this one – that link to poker or porn sites.

      It’s why poker sites are so aggressive about throwing around cash just to get a link. They’re looking for people that don’t understand that Google will make them pay for it.

  8. Kristin Keckeisen
    Kristin Keckeisen says:

    Thank you! I needed that – I just did it and I feel SO MUCH BETTER! One of the things I love about you is that you always make me feel like I’m right, that even if I’m not always doing what I know I should be doing, at least I know what it is. And today you convinced me to do it…

  9. Gary
    Gary says:

    Mother of God, woman, I feel like I’ve just ridden 30 miles in a Mexico City taxicab! Chardonnay! Serenity Now!

  10. Lauren
    Lauren says:

    Well, Penelope, I’ve missed you. I look at my RSS every day and you are the blog I look to see new material from first. Even my least favorite of your posts makes my day to read. So, for God’s sake, do the first thing on your to do list first. :)

  11. Marie (INFP)
    Marie (INFP) says:

    Penelope, you never cease to amaze me. I so needed to read this today, at this moment. I spent the whole day not doing my to do list even though I’d scheduled everything so I could be alone in the office to get these things done.

    You got a wax job and swept the floors, I went to see my therapist and ordered a big lunch from my favorite salad place online instead of calling it in (which took longer).

    Now its 4:55pm and I’m going home having done nothing and feel horrible about self. Or it could be stomachache from the big lunch. Not sure. Anyway, feeling pass and is replaced with INFP creed- it all gets done eventually and you still get a glass of wine at home.

    You’ll tell us everything eventually and think of all the angst you’ll have to draw from with the new start-up!

    Will she be able to maintain second marriage and startup? Will the farmer’s head explode? Will Penelope’s? What about the children? Will Melissa scheme her way into the company? Will Penelope finally take her own advice and prove once and for all she really is a career expert?

    Stay tuned folks!

    • Penelope Trunk
      Penelope Trunk says:

      It’s funny about you saying “will Penelope finally take her own career advice”. I wonder that, too. One of the biggest benefits to me doing so much coaching of other people is that it gets easier and easier to say to myself, “What would I do if I were on the phone with me? What would I tell myself?”

      Penelope

  12. Emily Kramer
    Emily Kramer says:

    I wrote a list the other day and then started at the bottom! I thought that was a good strategy. Like when you write an essay and the most important point sometimes comes in the last paragraph, and then you have to put that up at the. I AM TERRIBLE AT PRIORITIZING. I am great at getting unimportant things. I want to resolve to only do one thing every day and make sure it’s the important thing. I love lists. God help me. AND you too now that your’e doing a startup! I’m excited to hear more.

      • Emily Kramer
        Emily Kramer says:

        Thanks Will! I can’t figure out from the website if there’e a tool or it’s just an e-book you’re supposed to buy to learn the technique. I would also love to know what other readers use to get organized. I’ve used Getting Things Done loosely, and also Morning Pages.

  13. chris
    chris says:

    If it makes you feel any better, I very much want to have sex with my woman when I see her cleaning. It’s not often by any means but there’s a few awesome stories and pics. Good luck with your super-secret startup!

  14. Kelly Exeter
    Kelly Exeter says:

    If this startup stops you writing on your blog I will authorise a search and destroy mission on it all the way from Australia. Don’t let it happen!

  15. Lilly
    Lilly says:

    I agree that that Melissa relocating under the current circumstances is a cause for concern. I hope that Melissa keeps her eyes and options open.

    • Lisa
      Lisa says:

      Why is Melissa moving away with a man who makes a lot of money that she is NOT married to????

      Does he not want to marry to her? Does she not want to marry him?

      What am I missing?

      • Penelope Trunk
        Penelope Trunk says:

        Well, I have actually said the same thing. And Melissa tells me to shut up. So I guess we will have to just wait and watch things unfold. If she were a reality show, I think Melissa turning 29 and moving to NYC with a guy who said he’s not ready to marry her is the season cliff hanger.

        Penelope

      • Pirate Jo
        Pirate Jo says:

        Maybe because she thinks it’ll be a great time? Who cares if they get married or not? And asking the guy for money seems very, very weird, because she’s making her own decision. Entangling their finances sounds like a bad idea.

  16. Chel
    Chel says:

    Good post. Great comments. Halfway through, and then again at the end, I was thinking: So how come you’re not just getting on with #1? The comments made me change my mind. The way you meander through the fields to reach the destination instead of going straight to the point is my failing/usp too. Keep wandering out loud for all of us. ;)
    Oh and take the advice about having the weekend off for husband and family. You need them.

  17. Britt Reints
    Britt Reints says:

    :-) You are a champion procrastinator, Penelope.

    But you’re right that doing the most important things on your list is a good way to feel good.

    And often the things that feel the best, eventually, are the things that don’t feel good at first.

  18. Emily ENTP
    Emily ENTP says:

    Penelope,

    I woke up this morning completely bummed that I hadn’t talked to you or anyone in the group since our seminar, so I checked Google reader and was so excited that you had made a post. That was a sweet thing to say and so now I’m going to say a not sweet thing: That was the longest post I have read from you in awhile and I think you were using it as a procrastination tool.

    Do you like roller coasters? You don’t have to for this to work: but I think that ENTJs like being on the roller coaster in action, which means they don’t enjoy the slow drudge up to the top of the roller coaster before it falls (that’s my favorite part, but that’s because ENTPs get off on peak anticipation and are bored by the time the roller coaster is over). Once the start-up is going, you can see it fail and see it thrive, and that’s what you’re really good at doing. You can talk about it and work on it, and I think then you will feel better.

    You’re a great writer and do an amazing job at start-ups and I’m super excited for the actual “baby announcement” of when you post about it in your blog.

    Talk soon,
    Emily

  19. katie
    katie says:

    II had no idea you were procrastinating… I thought it was part of your seminar promotion strategy!! to have the “new grads” post at the top of the page as long as possible while advertising the “how to make the most of your 20s” seminar! But the good thing about your procrastination is that it’s something we all struggle with, so you ended up with a relevant and relatable post. now i’m going to get off the computer and go clean my apt because that was the first thing on my to do list…

  20. Jani
    Jani says:

    If I would have known that this post was going to be about doing the most valuable thing on your to-do list first, I would have taken my procrastination somewhere else! As it stands, I now have no choice but to acknowledge how I have ruined my own week by not writing. This is why I appreciate your blunt honesty – it pushes me to more honestly assess myself. :)

  21. Carmen
    Carmen says:

    I’m too happy and content reading this….and that’s my problem!!!! I feel joy watching others succeed.

    How do I fix that? My happiness for others is impeding my progress. help…

    • Penelope Trunk
      Penelope Trunk says:

      Most people who are happy for other peoples’ success make great co-workers. And since I know you, Carmen, I know that this is true for you. Helping people to be their best selves is such a great trait. And being content is a great trait, too. It’s just that it’s not available to everyone. I think it’s probably how we’re born.

      Penelope

        • Carmen
          Carmen says:

          Good point, Skweekah.
          While trying to find something new to excel at for myself, I’m genuinely happy for other people. I view my own limitations as a threat, not the success of other people.

          • Gary
            Gary says:

            It’s been proven over and over that the happiest, most successful leaders, entertainers and whatnot are those who aren’t afraid to hire people smarter than they are. So why are so many others so paranoid, only tolerating spineless sycophants? They could emulate the giants, but pride prevents their ever breaking through.

  22. Marina
    Marina says:

    As I was reading this my first thought was that you wanted a divorce, but didn’t want to face it, so you were doing the start-up to force the issue. Are you really excited about this start-up, or is it just a way to force yourself to make changes in your personal life?

  23. Mark W.
    Mark W. says:

    The creation of a to-do list can be a very self-serving pursuit. It will depend upon your mindset when you do it. The to-do list is created by you and mostly thought of doing so for the purpose of achieving tasks and goals for yourself.
    However, the items on your to-do list affect other people directly or indirectly. These other people who may be affected, with whom you’re in some sort of relationship or not, may find themselves being on the list in some way without being consulted ahead of time if at all. These scenarios may create conflicts.
    So maybe when a to-do list is created, the creator should be thinking of something similar to the proverbial calendar posted somewhere in the kitchen where everyone posts their activities. It may help to label tasks as solo or joint efforts. And to be clear, even the solo efforts are not really solo when you’re in a relationship or have kids because that’s time away from them.

  24. Skweekah
    Skweekah says:

    It seems to be that this post is about focus and procrastination in general. And, it feels worse when you keep piling on stuff onto your to-do list and it just gets longer and you end up doing nothing on it what so ever. And it eats at you daily and it’s like this cloud that hangs over your psyche. It’s just there. And, then you end up comparing yourself to someone else who seems to be able to focus and commit and complete tasks with ease. And, you then have this lightbult moment where you say to yourself “Just Do It!” and you kinda feel good for a while, that is, until you get stuck in that damn rut again…

    Anyway, I’d better get started on my to do list cause it’s hanging over my head like a dark cloud!!!

  25. Cassie
    Cassie says:

    I’m with you on this, Penelope. When I’m going through a crappy period of life, I often stop writing. Similar to you, I’m almost incapable of not being completely authentic on my blog, and so when I try to write during these times, the tone and topic is dark. This annoys me, causing me to abandon the post and then avoid writing for a while–the one thing I NEED to do, and the one thing that almost always lifts my spirits. When I finally force myself to get back to it, I almost instantly feel better–it’s productive AND therapeutic. It’s funny how I can both love and hate writing so much.

  26. Tracy
    Tracy says:

    Thanks for sharing, interesting turn of events. Your career often seems to have an influence on mine, like a jetstream affects the weather. Looking forward to the reveal.

    So what happens with the cello lessons then ?

  27. Sam Davidson
    Sam Davidson says:

    Fantastic post and accurately captures the start up world. Very good words, too, about finding and doing the things that enrich your soul. I need as many reminders about that as I can get.

    Very well done, P.

  28. Mary
    Mary says:

    My favorite quote of this post:

    “So I did what every good writer does in the face of rejection: Hate myself and cease all forms of genuine productivity.”

    So relieved to see that I am not the only one!

  29. Epictetus
    Epictetus says:

    Penelope — I DEPEND on reading your blog. Your writing transforms my procrastination into productivity. Keep writing, please!

  30. Abi Golland
    Abi Golland says:

    Hi Penelope,

    I am 3 years into my first start up, and now that I just beginning to emerge from ‘start up hell’ have just started writing too (now that my to do list does not resemble a 12 month operational plan in a 4 week timescale – thought I better fill it with something else). Came across your blog and wanted to let you know that you have inspired me. I read your piece about getting started writing, and so this week have done (!). And have also been working on focussing/not procrastinating – so this post is particularly relevant.

    I sat down to write yesterday, and found that every part of me, body and mind tried to sabotage my writing. I thought of everything else that I needed to do, then I felt physically tired/sick/shaky. BUT, I remembered your post about just writing, so I did, thank you. (I did a hokey thing – I wrote all my distractions on a piece of paper and binned it – it really helped)

    Also, your description of start ups, being married to an entrepreneur (run start up business with husband), managing 3 kids – so great to read what you are you up to and SO inspiring. Thanks.

    Abi

  31. topdiablo3
    topdiablo3 says:

    Thank you! I needed that – I just did it and I feel SO MUCH BETTER! One of the things I love about you is that you always make me feel like I’m right, that even if I’m not always doing what I know I should be doing, at least I know what it is. And today you convinced me to do it…

  32. Blair
    Blair says:

    This post is indeed helpful. When you start up, it is necessary to create a list with the most important things to do at the top of the list and then the less important things down the list. And as you move from top to down, you definitely see half of your work DONE! You can also get immense help at 100daychallenge.org, just check it.

  33. Alan
    Alan says:

    Works for me. I get out of bed and sing chromatic scales of long tones. Eight years later I can get on a stage and not get booed off.

    Some days I do peripheral stuff because I can’t face a day of routine.

    About one day a week I am exhausted, though. I mean blotto unconscious exhausted. I mean sit in a chair all day long exhausted. I mean can’t move exhausted.

    And I don’t really work that hard.

  34. cindy
    cindy says:

    Hi Penelope,
    Saw you mentioned MBTI type twice already on your site. I’ve been interested in type theory for the past few years now and finally took a training program to get certified. Could you please suggest some of the ways I can turn this into a freelance gig on the side?
    Thanks.
    Cindy

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