6 Tips for being a CEO without ruining your kids' lives. I hope.

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I get questions all the time about how I manage having kids and a startup at the same time. After trying to answer the question a few times, I realized that there’s the pretty-much-BS answer about how it’s all about being clear on your values. Or there's the complicated, too-long-for-interviews answer.

To really get tips for being a CEO with young kids, you’d have to hang out with me for a day. Like, last Tuesday. Which was just another day of being a parent and running a startup. Except this day starts at midnight. When I decide that I am not going to go to sleep because I have to get up at 3:30 a.m. to drive to Milwaukee to catch a plane to Atlanta at 7 a.m. And here's the first tip:

1. Get sleep. The kind that is not warm and sweet.
I decide I'll stay up late and work but what I find is that I'm mostly eating. First coffee. Then coffee doused in sugar. Then peanut butter and jelly sandwiches, which I covet each morning I make them for school lunches. But normally I restrain myself.

I see now I'm too stressed for normal restraint, so I go to bed.

My three-year-old is in my bed. If I get in, he will snuggle and whisper “I love you” in his sleep. But when I get up to go to the airport, he'll have a fit, because what kid wouldn't hate to wake to his mom leaving his house in the middle of the night?

To shield my son from childhood trauma I take him out of my bed and put him in bed with my ex husband, who is sleeping in the bedroom down the hall so that I can leave on business trips.

2. Be great at business travel. But get out of it whenever you can.
I set the Blackberry for 3:30 a.m. And when it wakes me I feel like I slept for ten seconds. But this crappy itinerary was my idea. Because I was so excited to go in and out in one day and not have to stay in a hotel.

At my gate I write a blog post, and I feel really good that I can do it at 5a.m. in an airport on no sleep. I send it to my editor and tell him I'm a star for sending it a day early — usually I send it an hour before I want to post it.

Then the flight is delayed. Then it's broken and delayed. Then it's probably not happening. Then I see that I will not get to my meeting if I wait for the next flight. But another airline has four, gloriously direct flights that get there in time. I am happy.

Until I hear that the cheapest ticket is $1200. So I call Atlanta to say that my flight was cancelled and I can't get another.

3. Go to the office when you could go home. Go home later with impunity.
I want to go home and sleep. But I go to the office because we are getting ready to pitch to VCs. We have a lot of great ideas for what we are building for the community. And we are obsessed with the news that Gen Y is not using social media at as high a rate as Gen X is.

I spew the statistics about how bloggers are higher earning and higher educated than most people, and the average Twitter user is nearly 40 years old. We see our spot in the world, and we draw on flip charts and make PowerPoint slides, and then the nanny calls.

And I remember that since I'm not in Atlanta, I can take my son to his T-ball game. So I leave. Here's something Gen Y really hates: when Gen Xers bolt out the door early to deal with their kids.

4. Prioritize. And keeping the kids from screaming comes first.
I pick up my sons and they want shorts for T-ball. I'm happy about this because I can run in the house for their shorts and check my twitter feed, which is hard to read on my Blackberry.

In the house I grab a diet Coke and the fridge light doesn't work. I am so focused on shorts that it takes me two more light switches to realize my electricity has been turned off.

Then I remember that paying the bill was on my to do list. Somewhere. Under blogging and investors and T-ball. Yes, I know this is totally irresponsible. But the bill got too big at the end of last year, when my company was not paying salaries and I was not paying most bills.

Also, last week I took half the money for the electric bill and bought my six-year-old a new violin. I told myself that was OK because the violin teacher said his fingers were missing the notes because the violin was too small, and solving that problem seemed more important than paying the electric bill on time.

So I go to T-ball. Because it's way easier to deal with no electricity when kids are consumed with swinging bats at each other.

5. Get as much help as you can afford. But there will never be enough.
I call the house manager, who has written “pay electric bill” on a post-it maybe ten days in a row, and I tell her the lights are off. She gives me a plan for getting electricity back the next day. Her plan entails paying the bill in person, and stopping at the grocery store for treats, and going to McDonald's Playland, so the kids are quiet while I'm on the phone with the electric company.

The six-year-old asks what we're doing. I say, “The Internet is turned off. I have to turn it on again.”

I know this is very serious to him. Because he is consumed with watching YouTube to find out how to win levels in Super Paper Mario on the Wii.

He explains to his younger brother, “This is serious. If we don't fix the Internet, Mommy won't be able to work. And neither will her helpers. And people will not see penelopetrunk.com.”

6. Don't be sneaky. Kids always catch it.
Once I pay the bill, the sun is almost setting, and I need a plan for being in the house in the dark. The house manager makes a plan: Go to a hotel.

But I don't want to because the kids will know something is wrong. I worry they will be messed up from living in an unstable household. They will grow up wanting to work at the same job at the same company for 60 years because my unstable startup life made them crazy.

So I get them very tired at Playland. They run and scream and I almost pass out on the table because now I am going on three hours of sleep in 24 hours.

Then I take them home to perfectly choreographed sequence of pajamas-book-bed just before the sun sets. They fall asleep and don't even notice there's no light.

Then I realize that I didn't get flashlights. So I get the Dora the Explorer flash light out of my six-year-old's room and wave it around a little to test it. He asks what I'm doing.

I ignore him.

He goes to the bathroom to pee. He says, “Hey. The lights don't work.”

“Yeah. I know. Just pee and go to bed.”

“Hey. My bedroom lights don't work.”

I ignore him. I tuck him in and kiss him and I tell him that it might be very dark if he wakes up in the middle of the night, but he can call me.

“Did you not pay the bill for the lights?”

WHAT??? How does he know this? Bills? He knows about bills?

I say, “Yeah. I forgot to pay the bill. But we paid it now. And the lights will be on tomorrow.”

“In time to play the Wii before school?”

“Well. Um. No.”

“You forget so many things. You never forget your work things and you always forget the house things. No mommy forgets more than you do.”

Then he says, “Mommy, I'm scared. I don't know how dark it's going to get. And the house will feel haunted. And what if I can't see you?”

I get the kids out of bed. I decide we'll go to a hotel.

I grab the essentials before the sun goes down in our house: Stuffed animals, my laptop, my purse, and gel from my dermatologist to squash breakouts. Because people like to read falling apart in stories and words. But people start to worry if they see the falling apart in your face.

142 replies
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  1. Marivic Valencia
    Marivic Valencia says:

    I’m completely smitten with the honesty of this post. I’m starting a(nother) business now, and the lesser-of-two-evils decisions are going to be the end of me. 2 in college, 2 heading to college in the fall, and a 3 y/o and I buy a laptop? Shit like that.

    I know the lights are back on for you already. Have a great day Penelope.


  2. Jo
    Jo says:

    Do you worry that maybe the boys are getting their way a bit too much? After a fun day with T-ball, McDonalds, play place, maybe you shouldn’t have gotten them up out of bed and gone to a hotel because your six year old voiced a fear. Is it not more productive to calm him and explain what he can do if he is a afraid? Just thinking in terms of what my parents would have done/said. I’m only 26 with no kids, so it’s just an opinion.

    • Lisa
      Lisa says:

      Yeah I thought that way before I had kids too…when you are trying to work, be a good mom and manage a household you’ll do whatever it takes to make your kids happy and feel good. McDonalds and a hotel never killed anyone…

  3. Alan Wilensky
    Alan Wilensky says:

    Frazzled Careering Careening Careerist.

    The kids will have fond memories of a dynamic, crusading mom that made life interesting and fun while she fought for her piece of the American Dream.

    Then they will get jobs at GE and stay there for 40 years, working their way up from mail room to electromotive light rail draftsmen, to product managers of the MSTGD (Marine Steam Turbine and Gear Division), to minor VP’s of GE Schenectady’s TWR & RE (Toxic waste recycling and Renewable Energy).

    You will be 77, and holding your grandchildren in your lap, when your staid, grown boys hold martinis and don silk smoking jackets, recounting over Thanksgiving dinner to the company assembled (in an assumed, fake wasp accent, betraying their proud, Jewish Heritage, I hope not):

    “Mummy used to dash about in a tizzy, forgetting to pay the electric, while us boys cowered in the dark. She would miss her flights and rush us to a local motel so we could play video games. It was so early oughts!”

    Better a mother like you then the prototypical suburban stereotype made famous in the Rolling Stone’s , “Mothers little helper”.

    What a drag it is getting old.

  4. J
    J says:

    Two things:
    1. I liked the honesty of this post, and learnig how much kids pick up on, but it made me sad. I know it would hurt my feelings to be called a forgetful mommy, so I hope you are doing okay with it and taking it in stride.

    2. I know you don’t care about typos and you don’t think others should either, but they are distracting. Why doesn’t youe editor fix thse things? (See how distracting those typos were? :-))

    • Penelope Trunk
      Penelope Trunk says:

      Oh, I do care about the typos. I am impossible to edit — I obsessively change random words up til the last second before I publish. And I always seem to add typos.

      There are a few proofreaders who subscribe to the blog, and I get regular emails from them.

      Hopefully I’ve fixed all the typos in this post.

      And, thanks for caring :)


      • Sital
        Sital says:

        i’m soo glad its not just me that does this!

        my articles get proofed, but then i change things at the last minute – and invariably leave a new typo which. i used to kick myself when i saw the errors on publishing. but now realise it’s not the end of the world ;)

      • Amy
        Amy says:

        You’re lucky to have an editor! Anyway, I didn’t see any typos when reading just now, and I am a pretty picky reader too, so you are probably safe.

        I really like the honesty of this post and while I’m only 21, I wish more mommy bloggers would write about their ATTEMPTS to maintain that work / life balance. Not just a “5 Ways To Keep Your Work / Life Balance In Check.” I will probably be dealing with this stuff down the road and it’s nice to hear someone’s true voice and personality shine through in their blog. Well done!

  5. Cheryl Allin
    Cheryl Allin says:

    Wow, you’re brave! This hits awfully close to home for me, LOL. There have been times when lights were shut off for us, too. Kids are amazingly smart, but don’t beat yourself up too much. You know you have to choose your battles and not sweat the small stuff – balancing your passions with your responsibilities means there will be times you might get it wrong or wrongish, but you also don’t want to be a Mommy-zombie and give them too much power. You’re doing great, don’t kill yourself with guilt. They’ll grow up with fantastic stories and unique little personalities and that is how is should be.

  6. Carol Saha
    Carol Saha says:

    You have no idea how much I envy you. I have a best friend who is driven, motivated like you. I had to admit to myself that I will never be like you. I don’t like being tired and having that achey feeling from not enough sleep. Sleep, not work, is a priority for me. But when I read your blog posts it makes me aware of how much life I’m not living.

    • LP
      LP says:

      Carol – There are alot of different ways to ‘live life to the fullest’. Luxuriating in the many physical and psychological pleasures of life, like sleep, is a perfectly fine way of ‘getting the most out of life’. I also admire people who are very, very goal-driven, but they give up (or never experience) things that we laid-back folks take for granted, I think.

  7. Marivic Valencia
    Marivic Valencia says:

    I’m completely smitten with the honesty of this post. I’m starting a(nother) business now, and the lesser-of-two-evils decisions are going to be the end of me. 2 in college, 2 heading to college in the fall, and a 3 y/o and I buy a laptop? Sh*t like that.

    I know the lights are back on for you already. Have a great day Penelope.


  8. genXmom
    genXmom says:

    Glowsticks – those chemical ones that you bend and shake that glow for 8 hours. I keep a few on hand for when the nightlight bulb burns out or the electricity goes out in a thunderstorm.

  9. genXmom
    genXmom says:

    Keep some glowsticks in the house – the kind you bend and shake that glow for 8 hours. They are my backup temporary nightlight plan for when the bulb burns out or a thunderstorm knocks out the electricity. Plus they are really fun.

    • Jyoti
      Jyoti says:

      Hi GenXmom! I just read this blog post from 2009, and saw your tip about keeping the bend-to-light glow lights for backup. What a great idea! I just added them to my to do list! Thanks for the great tip!
      Also, to Penelope, thank you for writing this – I keep looking for the courage to strike out on my own, hopefully reading more of these will help me decide one way or another if I am willing and able to put in what it really takes.
      Thank you!

  10. Me Thinks
    Me Thinks says:

    Love this post!

    I’m no CEO or managing my own company but working a very demanding job full time from home (gah I miss an office!) and being single parent with about 75% custody to two small kids, I can totally relate.

    The lowest moment in my life was when my daughter said “mommy, you love work more than you love us”. Ugh. Trying to explain to your kids that you are building a comfortable life for them isn’t always easy. Personally I think having the electric turned off might not be a bad experience – they know now why you work: to pay the electric bill!

    • jessica
      jessica says:

      Hilarious. I forwarded this article to my friends. Finding the balance is so tough. I got my graduate degree at Saint Leo while I was working full time and taking care of my family. It was definitely a juggle but I managed. Even though I’m sure my family felt neglected. Not that I graduated though I can make it up to them :)

  11. Helen Romeo
    Helen Romeo says:

    Penelope, I love this post. You are human after all! – as many of those who dissed you as ‘crazy’ in previous comments might now think to themselves. It’s so easy to equate success with some sort of de-personalising of the person concerned. But at the end of the day, as we say here in England, even the Queen has to sit on the loo! So, even CEOs struggle with parenting and the demands of career – despite the myth of the ‘super woman’. I have a friend (a ‘yummy Dad’ as we call it) who is basically ‘Mom’ to his son at our school. His wife, the breadwinner, works 24/6 being Partner at a top law firm. But she admitted to me she can never shake the seeping guilt at being away from her kids when she’s at work and away from her work when she’s with her kids…. what more to say. I think at least you’ve made peace emotionally with your choice: good for you. And Good Luck! You deserve it!

    • Maus
      Maus says:

      Umm, no, I still think P is bipolar and currently sharing her manic phase with us. Does that make her less human? No, of course not; but it does make me (and I suspect others) worry about her and her kids. If having lights was important enought to decampt to a hotel for one night, then why didn’t P make it a priority to pay the power bill on time? I don’t buy the “busy CEO” malarky.

  12. Jake
    Jake says:

    Well, your credit rating just took a nice wallop. Could it be that you, the queen of the online life, don’t even pay your bills online? You could teach your kid to do that, not to mention your ex or domestic staff.

  13. Editormum
    Editormum says:

    And why doesn’t your house manager, to whom you pay a salary, pay the routine household bills FOR you? If I were paying someone to manage my home, that would DEFINITELY be one of their responsibilities. There would be a separate checking account for the Editormum Household, into which I would deposit the household budget once a month. And the house manager would pay household bills from that account.

    Since paying the bills is obviously not what your house manager does, and since you have a nanny for the kids (in addition to an ex who sleeps over when needed), then just what are you paying this person to do?

    • Penelope Trunk
      Penelope Trunk says:

      What the house manager does is covered in other posts — people ask all the time. Search house manager in the sidebar of the blog.

      Re paying bills: You need a steady income in order to have automatic bill payment set up. If you cannot pay everything (like when my company misses a paycheck) then you cannot do it automatically. And then paying bills becomes a series of hard decisions that cannot be delegated.


      • Julie
        Julie says:

        Whether the power bill was paid or not, who pays it, who doesn’t–I don’t care about the little factual crises some people are having here (“why doesn’t your house manager do it?”, etc.)…
        I think regardless of those questions, it makes a great point.
        Frankly, perhaps it’s totally fiction, the bill never reached the cut off point–who cares!
        The story told here is one many can identify with and it really grounds people. I am tired of people who publicly seem to “Get it all right.” I like seeing such human-ness and I like seeing someone who isn’t openly terrified of “the man” (the power company, your credit report, etc.). It’s just life…that’s what this post reminded me. I don’t care if she gets free electricity and she made it all up to make her point. House manager, schmanager, this piece made sense. :)

  14. Mark W.
    Mark W. says:

    I think you worry too much. It’s both good and bad with a lot of dependencies.
    As an example – “I worry they will be messed up from living in an unstable household. They will grow up wanting to work at the same job at the same company for 60 years because my unstable startup life made them crazy.”
    Your kids are going to do what they feel like doing – just like their mother. I can remember asking my father what he thought I should be doing after high school/studying in college. He wouldn’t say and just told me it was up to me. I still think that he did it right by letting me make my own career decisions while still offering guidance by answering specific questions I asked him.
    Twice in my life I have gone without sleep for 70+ hours. It was when I was much younger and driven. I value my sleep more now and it is good for my health. There’s 24 hours in a day and I do my best to spend it as efficiently as possible as I see fit. The older I get the more value I ascribe to my time.
    As a final note I laughed quite a bit while reading this post. A lot of good humor. You really should work on getting more sleep and eating better though. Tough to do with your lifestyle.

  15. Nisha
    Nisha says:

    This is one of those posts that’s so refreshingly honest I am going to bookmark it and re-read on days when I am sleep-deprived and stressed out.

  16. Jay
    Jay says:

    “To really get tips for being a CEO with young kids, you’d have to hang out with me for a day. Like, last Tuesday. Which was just another day of being a parent and running a startup.”

    Yikes. If this truly was “just another day,” I can’t help but worry about the long-term effects of this much stress on your well-being. I don’t know if you’ve already done this, but I think a post on how you manage this amount of stress would be a very interesting read.

    I have a lot of things going on in my life (including two boys under 6), and I don’t have anywhere near this level of stress. Yet it’s still a struggle. I’d love to hear what you do to cope.

  17. Carla
    Carla says:

    First, I am in shock that you can send peanut butter and jelly sandwiches to your kids’ school. Every school where I live has banned PB for fear of allergic anaphylactic reactions. I wish I could send PB & J to school!

    And I love this day-in-a-life post. I have one to share. A few months back I missed the deadline to sign my son up for baseball by two days but the league refused to guarantee him a spot, even though I begged and pleaded. I lost a night sleep and the respect of my 8 year old on that one. Fortunately, another league with a sign up deadline two days later took him. Then the first league moved their waitlist and offered my son a spot. And he said “It’s okay now mommy. I forgive you for dropping the ball.”

  18. Albert Francis
    Albert Francis says:

    What about, blogging less and spending more time with your kids and making sure the lights will stay on? Just my 2 cents…

  19. kim
    kim says:

    I love it.. your so honest and entertaining and that is so true to life…thank you for reminding me that this is how it is!! lol…and its ok to rob peter sometimes to pay paul and to forget to pay the electicity bill… your a good mom and thank you for sharing it!!

  20. Tiffany
    Tiffany says:

    I really enjoyed this post and it made me laugh to think that you were being scolded about bills from your son. Its amazing how much kids pick up and understand. At least you can rest in knowing that you’re raising a kid who knows the importance of bills and responsibility; even if its b/c the world may essentially end without his morning wii time.

    Take care!

  21. anonymous
    anonymous says:


    I could go four months without paying my electric bill and still keep the lights on.

    Exactly how far behind are you that they actually killed the lights? You alluded that you were at least one month behind when you talked about bill pay.

  22. Annie
    Annie says:

    I love this post, but I am afraid it is because even my very worst, most frazzled days as a working mother of three have not been quite this bad (yet!) But I can totally relate. The one trap I do think we should not fall into is making bad judgment calls and parenting decisions because we are overcome by guilt (and exhaustion). I think you may have done that with the hotel decision, Penelope. You were exhausted and feeling awful about the situation, so when your son expressed his fear, you reacted dramatically by whisking them off to the hotel. Probably a few minutes of talking it through, give him a flashlight to keep with him, etc. would have calmed him down. Too many reactions like that and he will start to think he has you wrapped around his finger, i.e., catch mommy in a guilty/tired state and I can get whatever I want!! I know this from firsthand experience so I’m not judging, just commiserating.

  23. Green Taylor Simms
    Green Taylor Simms says:

    I fail to see the correlation between points 3 and 4, perhaps you can extrapolate on them when point 6 comes and bites you in the ass.

  24. Chris Mahan
    Chris Mahan says:

    Ack! You bad mom! You go to your room NOW!!!

    Eh, no. You stay right where you are and keep steering the ship through the storms. Yes, some waves will come crashing down on deck and sweep crewmembers down. Yes, sometimes the rolling and swerving and maddening metal groaning noises will make you sick to your stomach, put your headache on overdrive and threaten your personal sense of sanity.

    Yeah, it’s tough. Remember though that the best sailors are those who have gone through the worst storms. So batten down the hatches and shout in the intercom Scotty, I need more power!

    With such a brave, humble, and fearless captain, the HMS Penelope is sure to master the storms and reach its destination unscathed, its cargo safe, its crew tougher and more experienced.

  25. Maggie
    Maggie says:

    The one thing about you that’s still a mystery to me is your finances. I wish you’d go into as much detail about money as you do about sex. I’m not being facetious or trying to be rude–I honestly want to know how you do finances, and, if you’re really ok with working as much as you do yet not having enough money to pay the electric bill.

    Sometimes, you’re a six (or more?) figure entrepreneur who can afford to pay a house manager $50k a year plus a nanny and a maid. Then, sometimes you’re penniless and can’t afford to put your bills on autopay because your balance may be zero on any given day. Which is it? How can you be both of these extremes? Or is that just life as an entrepreneur? Is it the thrill of going from poor to rich to poor again that makes it exciting? Or is the eventual hope that you stay at rich?

    • Terry
      Terry says:

      Penelope can be both of these extremes because she is a self-absorbed, pathological liar. She is CEO of a blog, for Pete’s sake. Not exactly IBM or GE. As for her income, as the saying goes, people who continually flaunt what they make generally don’t make what they flaunt :-(

    • Shefaly
      Shefaly says:


      I don’t know about PT’s finances but when one works a non-traditional gig, income can vary hugely by week or month. The only place where cash-inflow is predictable month after month is a ‘job’. However for all lives, cash-outflow, alas, is predictable more or less. Which means, net of outflow, the graph showing money can look quite scraggly.

      If self-discipline in finances were easier, well, we would not be in the financial mess we are in, would we?

    • Penelope Trunk
      Penelope Trunk says:

      Maggie, the short answer to your question is: yes. It’s the nature of the business.

      Only 7% of startups receive seed funding from venture capital firms. Running one of those companies makes for an extremely volatile life, which is probably why it’s more than 90% men. The divorce rate among this group is nearly 50% above average, and most entrepreneurs I know personally who fall in the 7% of seed funding from venture capital firms blame their divorce on their insanely volatile financial life.

      I wrote more on this –about my own finances — further down in the string…


    • Bart
      Bart says:

      Maggie, Maggie, Maggie. There’s no 6 figure salary. Never has been. Might be someday.

  26. Irina I
    Irina I says:

    Great post! I think as long as you are telling your kids that you love them and feeding them and a few other positive things, they will grow up psychologically stable.

  27. Milena Thomas
    Milena Thomas says:

    I’d love to meet these mythical parents that don’t “mess up” their kids. Every kid gets messed up in their own special way, it’s unavoidable and a basic psychological fact.

    • Penelope Trunk
      Penelope Trunk says:

      I spent all night deciding whether or not to answer this comment. Well, these five comments, which all ask the same thing: Why are you running out of money if you have household help?

      I hope that my answering these comments will make you think twice about the assumptions you make about someone else’s finances.

      I traveled for the company 25 of the last 30 weeks. I have two young kids, and I’m a single mother. There is no way I could do this company if I didn’t have household help. So the company pays for someone to manage personal stuff while I’m gone — a lot like other CEOs have an assistant. Otherwise everything in my personal life would fall apart when I am traveling.

      It’s a precondition I have for doing the company, and it’s something I’ve been able to negotiate. It’s rare to see this in a startup, but only because it’s *extremely* rare that a single mom of a very young kids would even think of being CEO of a venture-backed startup.

      A company like this one has very erratic finances. I have gone without pay many times in the last two years. Additionally, I have a child with Autism. It would take too much space to explain to you why this is one of the most expensive disabilities around, but it is. And, for example, I have spent about $40,000 in legal fees to just to force schools to adhere to IDEA standards.

      The way that I feel okay about having a very risky career that almost no other woman in my shoes would choose, is that I end up making financial choices that other people would never make, but they are right for my family. For example, we have a pretty nice violin for a six-year-old but we have no sofa.

      I think if you dug underneath any family’s finances, you would find odd decisions they have made that are right for them but that you would not agree with. I think this is why people are more willing to talk about sex than money: There is more widespread agreement about how to make good decisions about sex than there is about how to make good decisions about money.


      • KMS
        KMS says:

        “There is more widespread agreement about how to make good decisions about sex than there is about how to make good decisions about money. ”

        That sounds like the topic of a great blog post for you.

      • Jim
        Jim says:

        The upside of this is that the “house manager’s” salary will be added back to the free cash flow to the the firm when you are valued (assuming you make an exit).

      • cheryl
        cheryl says:

        “I think this is why people are more willing to talk about sex than money: There is more widespread agreement about how to make good decisions about sex than there is about how to make good decisions about money.”

        I absolutely agree. In fact, I wrote a short theatre piece about this last year, and our theatre company is using it as the jumping-off point for our new full-length show about abundance.

        We asked a lot of community members to participate in the research for and creating of this show. One thing we learned: All of the folks who participated feel that the minute you start talking about money in a specific, personal way, someone will make judgments about you (positive or negative). And those judgments will affect your relationship with that person–even if it’s in a small, subtle, or subconscious way. These folks were equally as concerned about getting judged for being good with money as getting judged for being bad with money. In this group, both ends and everything in the middle carries baggage.

      • Sara
        Sara says:

        I am SO SO SO glad that you posted this. OF COURSE your start-up should pay the cost of your house manager, since your start-up’s value and viability are so closely tied to your availability.

        These are the kind of choices and opportunities that don’t occur to people, because they’re not something that’s seen/talked about. We’re familiar with the idea of a company paying for a car or a cell phone or a laptop — but this is enhancing your ability to add value WAY more than any of those three things could.

      • le
        le says:

        why I love you the most – a well written, well thought thru and insightful response – thanks matey le

  28. Lee
    Lee says:

    I think that inorder to retain any integrity and validity you do need to explain your financial situation because there are quite a few contradictions regarding your life style.

    If you can afford household staff then you should be able to afford to pay your utilities. If you had money to spend on a hotel room you certainly had money to pay bills.

    You’re credibility is on shakey ground and I think your flying by the seat of your pants. Not someone I’d take advice from seriously.

  29. Nicholas Crawford
    Nicholas Crawford says:

    The most insightful part:
    “Here's something Gen Y really hates: when Gen Xers bolt out the door early to deal with their kids.”

    I see that on a daily basis, and as my kid’s due date looms (10 days!), I remind myself that I don’t want to be like that to my co-workers either.

    • KateNonymous
      KateNonymous says:

      Gen X hated it when Baby Boomers did it (yes, plenty of them did), and Gen Whatever will hate it when Gen Y does it. It’s not generational, it’s lifestage.

  30. Isha Akula
    Isha Akula says:

    Ms. Trunk, (or who ever is being paid to read these comments and follow through)

    The go to a random post button thingie doesnt work! I now have to manually search your blog to procrastinate.

    • Penelope Trunk
      Penelope Trunk says:

      Thanks. I read all the comments myself, btw. The comments are my favorite part of the blog. And I use the random post button as a procrastinator as well, so it will get fixed fast :)


      • Gerty
        Gerty says:

        Also, this is completely unrelated but when are you going to change your poll, the one that has been up there about people going to therapy?

  31. Monique
    Monique says:

    Penelope, as a mom who juggles about three very different consulting gigs while also parenting two young children, I really enjoyed this post. Not sure if this is helpful, but in terms of balance, I seek for balance to my weeks, not my days. There are days that are consumed by work, and others when family is the focus. But, at the end of the week, I strive for a feeling of balance. I don’t always succeed, but that’s the goal, anyway.

    Thanks for the honesty!

  32. Mike McDermott
    Mike McDermott says:

    What a great article. It was a very honest look at a stressed out GenX parent (like myself). We all try so hard, so impossibly hard to be everything to everybody.
    Thank you for sharing your experience!

  33. fanf
    fanf says:

    Okay… this was a busy day !
    Your position as a CEO and a mother is pretty courageous for sure. If your kids can see it, you won’t ruin their live. Because examples of parents fighting for they passion/duty (or whatever important for them) and loving their family are great picture for kids. This is what I think.
    Good luck for the next day :)

  34. Jan Hogle
    Jan Hogle says:

    HA! I still remember when our electricity was cut off 40 years ago when my parents couldn’t pay the bill! Whatever. We all just do the best we can — we’re all “good-enough parents.”

  35. Jan Hogle
    Jan Hogle says:

    When I was a teenager in the late 60s, I used to come home from school wishing my mom worked outside the home, like other mothers I knew of, so that I could have some peace and quiet after a long day in classes, instead of being bombarded with questions and instructions. When I went off to college I had 3 goals: 1) never be poor again; 2) find a long-term companion; 3) be “professional” at something. Achieved. And worth noting what’s not listed.

    • MJ
      MJ says:

      ME TOO! I had the same list, and the same goals, and the same omissions (for very, very similiar reasons – add to the misery of having to deal with someone bored and whiny who 1) felt that she had to stay home, because women who worked outside of the home were bad mothers and 2) hated being home and felt “worthless” because she didn’t earn a wage – never, never, never again). And I’ve achieved all three – and added no extra, unwanted factors.

      Glad to hear there are at least 2 of us. And I bet we’ve heard the same crap about our choices from “well meaning” others too. Because you know it is abnormal to not have 2.5 children and flounce around the house in your apron, happily, every day….

  36. Nancy Carle
    Nancy Carle says:

    I enjoy your blog and your sense of humor. Anyone who doesn’t get you or your life isn’t a working mother or doesn’t know one. Sometimes it feels like I am not doing either job well and it is those times when I have to put my head down and know I am doing the best I can. Having children and a support system that get it is the key. It’s a balancing act the day you’ve written about is a sample of what it’s like to be a working mom.

    And by the way I love the sex posts. Women put themselves last and it is good to see that you can put yourself first sometimes.

  37. DaQueenBee4
    DaQueenBee4 says:

    Penelope, you are truly my hero. While watching TV last week the cable was turned off (mid-“iCarly,” of all the times…). My daughter turned to me and said, “Did you forget something, or are we just broke again.”
    I lied and told her I forgot.
    Must be nice to not be feeling the effects of the economy, like some of your other readers. Good for them. I wouldn’t trade my life, despite my chronic stress and current poverty. Both will end one day, which is why I keep waking up each morning.

  38. Michael Nolan
    Michael Nolan says:


    I love the list – very cool stuff. Reminded me of one of my heartbreaking moments.

    When I sold my first business (a group of radio stations) I had to tell my then 10 year old son. He started to cry – his dream was to be like daddy and work at the stations someday.

    An entrepreneur’s business is so closely tied to our personal lives that we forget the impact it has on our kids.

    Great post.


  39. WW
    WW says:

    I just went to a seminar on generations in the workplace (something you know lots about, Penelope). And one presenter talked about the foundational experiences of different generations.

    This generation that are now children are growing up somewhat integrated into their parents careers — I think this will be their foundational experience. By contrast generation x were the “latch key kids” whose parents both worked, and/or who were children of divorce. The millenials have been mentored and structured and given everything they could by their baby boomer parents. Etc.

    So I wouldn’t stress about what this is doing to your kids — it’s making them a part of their generation, whatever we will come to call it.

  40. Jennifer Lynn
    Jennifer Lynn says:


    I really loved this post. And, by the way, I’m sure your kids will be fine. My mom worked growing up, and between that and piano lessons, cheerleading practice, play rehearsals and the rest, she forgot to pay the electric bill once, and our lights were shut off for a night. It was kind of annoying to sit in the car to charge my cell phone, but other than that, it was fine. We read by scented-candle light, b/c that’s all we had at the moment. My sister and I weren’t as young as your kids, but rest assured, nobody was scarred. Except maybe my poor mom–she felt horrible, no matter how much we told her we were fine.

    At the end of the day, I am so glad I had a mom who worked. She was/is magnificent and I wouldn’t have had it any other way.

  41. Angela Connor
    Angela Connor says:

    Keep being the “real” blogger that you are. It sets you apart. You make our lives make sense.
    Great post. Brave of you to share, but that’s just what you do.

  42. Gerrianne
    Gerrianne says:

    Wow, I get your life. It can be so crazy trying to manage it all. I am a life coach and mother of 3 grown children. When they were younger and I was taking them to soccer games, dance lessons, music lessons, eating in the car, trying to remember which field which kid was playing at and work demanding me to be all things to all people, I struggled to find peace within myself about how I was doing my whole life i.e. work, kids, family, friends etc.

    Fast forward to today. I am passionate about people being more connected to themselves and their day to day moments. I have started a blog to help people connect more with the moments of their day and live their life authentically. I think that if I would have known then (when my kids were young) what I know now about living in the moment, being real and listening to my inner wisdom, my life would have been much less chaotic and more fulfilling. I would welcome any thoughts you have about the “in the moment” posts I have created. Take care and good luck with it all.

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