Five years ago, I was in the throes of my last startup, Brazen Careerist. During that time we were always running out of money, and I was always traveling to raise money.

At one meeting in the Washington, DC area, there were five guys in a room, and I did my pitch. I told them about the history of the company, why the future looks good, what the plan was – I’m very good at pitching. In fact, some people would say that my problem is that I’m way better at pitching a company than running a company.

At the end of my pitch, one of the partners in the venture capital firm said, “That was great. I really appreciate you coming down here. And let me ask you something: Who is taking care of your kids right now?”

I thought I was going to blush from being so angry, so I strained not to show any emotion. I remembered how my mom, on her first job interview in 1972, had to have a note from my dad that said the kids were being taken care of by a babysitter. I thought to myself, I am so sick of running a startup and I want to tell this guy to fuck off.

I said, “My husband takes care of the kids.”

This was not entirely true. I mean, he did. Sometimes. But I had two full-time nannies. It’s just that men don’t like to hear about nannies. They want to feel like I’m like them – with a stay-at-home spouse. So I imply that.

But shortly after that meeting I gave up the CEO position at my company. Not because I was sick of men asking me who is taking care of my kids. I stepped down because I felt guilty that I wasn’t spending enough time with my kids.

If you have two full-time nannies, you can delegate every single thing, if you want. In hindsight, I’m not sure what I did beyond hugging and kissing them and having some meals together. I missed a lot.

So it’s a relief to be homeschooling. I like having them with me all day. I like knowing they are in the room next to me. And I like that I can work and be available to them. I know what’s going on in their lives because I make the decisions instead of having the nanny do it.

In fact, it’s working so well that I think I can launch another startup, but this time it’ll be from my house, and it looks like I can raise almost all the money on the phone, so I don’t have to travel very much.

But I was on the phone with an investor, and I said, “Hold on. My kids are screaming for me and I have to tell them I’m on a call.”

The guy said, “Oh – do you need to get off the phone?”

“No, it’s fine. This is a good time for me to talk.”

“I always worry when I hear kids in the background. I once produced a movie where a dad is working on the weekend and the little girl comes into his office and says, ‘Daddy, I wish I were one of your clients.'”

He’s criticizing me. It’s his way of asking, “Who’s taking care of your kids?”

I’m home with my kids all day. His kids are in school all day. The guilt trip never starts, because we’re a homeschool family.

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12 replies
  1. Natalie Lang
    Natalie Lang says:

    I’ve missed your posts! It’s so interesting learning about start ups from your candid writing.

  2. CJ
    CJ says:

    That is one of your most perfectly ended pieces!! I was so worried those ending lines were going down the path of feeling guilty and having to defend yourself.

    Even when I screw up something with my children, I own it and then feel such strength from the inner voice that says, “I am here, I am present…they know every single day with love & security, I am here and they get the support AND freedom every kid deserves.”

    I am definitely steeling the (modified) line: “the guilt never starts because we’re an unschool family.”

  3. Mark W.
    Mark W. says:

    You’ve written about sexual harassment but what you’ve described in this post I don’t think falls into that category. I’ll think of it as and call it parenting harassment.

  4. Amy K.
    Amy K. says:

    In the comments section of your excellent and very honest post “5 Things I was Wrong About” (on the career blog), someone asked you what you got wrong about homschooling. You said:

    “…I thought homeschooling would get rid of my guilt. But it doesn’t. I always worry I’m doing enough for my kids. In fact, I have started seeing a psychologist to deal with the incessant guilt. I can’t stand it. I hate the self-doubt and self-hatred that pops up when I think about what I could be doing better for my kids.”

    So what has changed in the last few weeks?

    Oh, and that investor sounds like a clueless dick. Sorry about that.

    • Penelope Trunk
      Penelope Trunk says:

      Amy, good sleuthing! I actually thought of writing this post because of that comment you found. I realized, though, that the level of self-doubt I have has gone down so much. When the guy asked me who is taking care of my kids, I felt bad for weeks. When the guy said that to me this time, I felt like he is clueless. I still felt bad both times, but the decrease in guilt is so huge, that I feel, most of all, grateful that I’m home with my kids.


  5. Sadya
    Sadya says:

    All parents – homeschooling ones or school-sending ones, all of them feel guilty about not being good enough parents. It’s hardwired into them to feel that what they are doing isnt going to be enough for their kids.

    When you don’t have kids, you feel guilty over not being good to your parents/ spouse/ friends/ siblings.

    Noone really lives a guilt-free life. Its one of things that makes us want to improve.

    • Penelope Trunk
      Penelope Trunk says:

      Oh. I’m seeing this now, after I wrote a response to Amy. But Sadya, your response is better than mine. So this is my thumbs up to your comment :)


  6. Heather Sanders
    Heather Sanders says:

    There isn’t a man or woman outside my home that can make me feel guilty about the hours I spend working from home while simultaneously homeschooling my kids.

    My guilt is always my own. I make myself own it.

    I teach my kids that guilt is something to dissect. It is one of two things: 1) our conscious telling us we need to initiate a change, or 2) a lie we allow room for in our mind.

    Neither are acceptable.

    If it is #1, we need to make it right.
    If it is #2, we need to face the fear at the base of the lie. Usually it is because we are making decisions others do not agree with, do not understand, or do not support.

    We allow the guilt because otherwise we have to face the rejection. Rejection is hard to face – even when it is rooted in falsehood.

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