I hate having to earn money, but I like knowing what makes me valuable

The only way I find out what people value most about me is by having to sell something. Otherwise I’m just guessing. And I pretty much always guess wrong. Like I thought I was so great at writing about sex, but I only made money writing about careers. Now I understand why careers was more valuable: it’s easier for people to talk about their sex life than their finances, and careers are about money.

It took a while for me to face that I wasn’t one of the best entrepreneurs, but I was one of the best coaches. I could tell because even though I wouldn’t say publicly that I coach people, people kept contacting me to coach them.

Now, I see this happening with parenting.

I never wanted to be known for parenting. I needed to keep supporting my kids financially, and topics in business were way more lucrative than parenting. This was clear when I got fired from my favorite career columnist gig because I wrote too much about being pregnant. Also, I was basically a single parent, and I felt that being a single parent was like having a disease that all the married parents stayed away from.

Now that my kids are in college, I thought I’d be so excited to go back to an adults-only world. But often when I see something new I think: this would be so fun with kids. I have a hunch my orientation has always been kids, which surprises me. But most of the money I’ve earned as an empty nester is from helping families identify hurdles and goals, and setting up systems to get kids what they need.

It’s ironic because I just spent 20 years struggling as a parent. And the whole time I wanted to talk with someone who had lined up services and had a plan — for ADHD, dyslexia, OCD, picky eating, unschooling. I wanted to talk with someone who had taken their kids out of school without having a plan. I wanted a mentor who got their kids from homeschool to college. It was hard to find help for that stuff. So I did tons of things wrong.

I think we are most valuable to people in the areas where we’ve taken the most risks. Because everyone wants help when things feel shaky, and in that moment, someone who has been shaky before seems like they would have great advice.

 

 

17 replies
  1. Christy
    Christy says:

    I remember when you started you homeschooling blog. It was ( I think) before my daughter was born. I read it because it was engaging, just as your unconventional career advice is engaging. I have always valued your posts. I read them all. I see your value as a writer, even when I disagree with your thesis (which isn’t all that often). Is love to be coached by you, but that’s not in the cards right now. I’m mostly just grateful when you share your voice. Thank you.

    Reply
    • Penelope
      Penelope says:

      I appreciate you saying this! I have a difficult time knowing how to umderstand where it fits in my world. What to do with it. I don’t like having it separate. It feels untidy. But your comment helps me make sense of how things fit together. Thank you.

      Penelope

      Reply
  2. JIm Grey
    JIm Grey says:

    You’re remarkable for being able to see past what you want to what you offer that’s actually valuable. This probably kept you well afloat all these years.

    Reply
    • Penelope
      Penelope says:

      I would be happy if, at the end of my life, my kids said, “She kept herself well afloat.” But I think they probably have a different interpretation.

      Penelope

      Reply
  3. Melanie Gao
    Melanie Gao says:

    A coaching session with you is on my bucket list – hopefully we can do that in 2025. I will count on you to give me the truth from your perspective. That’s a hard thing to find sometimes!

    Reply
  4. Kristina Owens
    Kristina Owens says:

    I’ve always felt like you’re speaking directly to me and I look up to you, as a writer, mother, woman and human. I’m raising a son. He will be 4 this month. I planned to homeschool him before he was born. I’m unsure now but this week when he said he wanted to jump the fence at forest school and come home I’m thinking we will.

    Reply
  5. Kristina Owens
    Kristina Owens says:

    I always feel like you’re speaking directly to me and like I’m still a little college girl reading your blog admiring you but now I’m a mom to a nearly 4 year old boy and I haven’t been able to really come close to utilizing your career advice and I think it’s definitely because I need to take way more risks and I take less the older I keep getting. Thank you for being you.

    Reply
    • Penelope
      Penelope says:

      If it’s any consolation, I’m not sure I’ve been able to really use my career advice either. Much easier to tell other people what to do :)

      Penelope

      Reply
  6. harris497
    harris497 says:

    Penny,
    Over the years, I have come to see that your super powers are your perceptiveness, your honesty and your courage in saying what you think even if you know it is going to be unpopular. Couple these characteristics with the fact that when someone is intelligent, they often have many options available for self actualization, and that is a blessing and often a curse. You know what makes you valuable, the problem is you get bored and lose the urge to persist beyond…
    I have no answers for you, but I know that as you say, self knowledge confers personal power/value. I hope my little perspective helps. Your writing has helped me in the past.
    My2centsworth,
    D

    Reply
    • Penelope
      Penelope says:

      That’s good insight. Thank you. I am trying to stay focused on what I’ll be good at. I don’t know if it was a good idea to go to Harvard. I think the pace of academia, and the fear of controversy among people who need tenure makes me a bad fit.

      Penelope

      Reply
  7. Summer Opsal
    Summer Opsal says:

    I had two coaching calls with you about ten years ago, and you pretty much crushed all my plans to go back to school or pursue a career too heavily. Now, I am a mom of three and have started homeschooling my 7-year-old son. I recently brought up my old plans with my husband … laughing about how quickly you poo-pooed them. I loved my coaching calls with you.

    Reply
    • Penelope
      Penelope says:

      This makes me so happy! It makes a huge difference to me to hear stories like yours. And I remember our first call. You were so earnest and trying so hard. I think I remember the phone calls best when the person seems ready to change.

      Penelope

      Reply
  8. Ron
    Ron says:

    Thank you for sharing your journey all these years. As a fellow writer, it’s often lonely and you don’t hear much about one’s work. I admire your work and appreciate your point-of-view. Your writing style is engaging and you are willing to show the not so nice side of some of the topics.

    Reply
  9. Ovett Edwards
    Ovett Edwards says:

    I feel like I used to get notified about new posts… didn’t get anything this time (just happened to swing by.)

    Reply
  10. Jim
    Jim says:

    Just took a picture on my 60th b-day, with my wife and kids. The kids are now both just out of college. A relative saw the photo and said, “you have a lot to be proud of.” I’m not really the “being proud” type. But I looked at the photo and did realize that everything has pretty much worked out Ok despite all the chaos over the years. And getting through the chaos was helped out every now and then by reading one of your posts. So thanks for that. :-)

    Reply

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