Can you get a career back after your kids grow up?

I coach lots of parents who look at scaling back work and worry about what they’ll do when their kids grow up. If you are one of those people, you are about to save the $350 coaching fee.

What you want to do for work when your kids are young is not what you want to do for work when your kids are grown. For one thing, you can’t imagine what will be available when your kid is 18. Also, you can’t imagine what you’ll be like when your kids grow up.

Shortly after I raised $500,000 for Quistic, I realized my kids needed a lot more attention than I was giving them. I tried to adjust how I spent my time, but more pressure made me feel more crazy. So, finally, at a board meeting, I explained to investors that running a startup is so intense that it’s actually as inflexible as working 9 to 5 (which is really 8-7)  in an office, and I am missing too much of my kids’ childhoods.

I assumed the investors would replace me as CEO, but they told me to just slow down the growth of the company. “Take a few years break,” they said.

We agreed that when the kids got older I’d start scaling the company again. I was relieved to not have to give up everything permanently. I could go back.

But now the kids are older, and going back to that life feels like taking a step back. Last year I forced myself to try something new and I offered a one-year writing program. I loved it. All year long I talked with people about their writing, and books we love, authors we hate. It was exciting to watch people in the course become great writers over twelve months’ time.

Earlier in my life, I taught one-day writing courses at Brown and Cornell and told everyone my real job is launching startups. I have changed. That’s how I know you will, too. You will do something you did not consider before you had kids. And you will be good at it. It’s just so hard to imagine until you give it a try.

Another industry I said I’d never be a part of is publishing. It didn’t make sense to me when there was so much more money in startups. But I’m offering the one-year writing program again this year, and I’ve added something really special: a book deal. The best writers from this year’s program will be published in an anthology. I’m excited for the book to be special and important to the writers who are published. I want the book to be nice to hold and fun to read; it should be the quirky book people leave out on the table to share with their friends.

I am so happy to have spent the last year cultivating a group of writers — many of whom had never really written before. And I am happy to offer the program for a second year to people who want to be part of my writing program. We will all grow together because I’m still growing into my new choice too. As a startup founder, I used my platform to promote other startup founders and their companies. This year I will use my platform to promote other writers and their stories.

This turn of heart is not anything I expected years ago when I admitted I had to scale down my career. At that time I was disappointed and terrified. But I didn’t need to be so scared. It turns out each of us has a new episode in our career when our kids get older.  We get a new chance to decide what we want. And we get to look
at the world in a fresh way as we enlist people to help us get what we want.

Not all of you have thought about writing before, but many of you have. And I hope you’ll consider joining me for this year’s writing program and all the potential that comes with it. For all of us.

Here’s the information about this year’s writing course. The price is $1550 now, but the price will go up February 1, 2020. Sign up now!

12 replies
  1. Kitty Kilian
    Kitty Kilian says:

    An American friend told me a high school career advisor had asked her daughter: ‘What do you want to do for your FIRST career?’

    Such a great way of phrasing a life full of choice.

    For people considering buying the writing course: if you are serious about writing, go for it! Penelope is such a warm and giving teacher. The weekly classes on literature and all aspects of writing alone are worth it.

  2. Torn
    Torn says:

    I have loved and followed P’s writing for years, but I have to say that as a coach she is mean. When I arranged for my husband to chat to her he ended up more demotivated. Maybe my fault, but telling someone they are a deadbeat is not helpful. forewarned is forearmed

    • Penelope Trunk
      Penelope Trunk says:

      I think this might be true about my coaching. Well, except for being mean – I am not mean because you have to know someone and care about them to devote energy toward being mean. But I am coaching people I don’t know. So I’d have no reason to be mean.

      However, not knowing the person, coupled with me having Aspergers, gives me the ability to be completely honest in a coaching session. I am not a coach that will inspire you with platitudes and praise. There are a million coaches for that, and they are way less expensive than I am.

      I noticed a few years ago that a lot of people contact me because their career coach or psychologist or mentor told them to have a session with me. I realized that when a counselor-type person does not feel like they are getting through to their client, they send their client to me because I’ll be totally blunt and tell the truth right away.

      It’s not actually all that difficult to know what someone else’s problem is. But it’s really difficult to tell them their problem when the truth will make them very sad. It’s unpleasant to tell people the truth. We think we want to know the truth, but most of the time the truth is shocking. We thought the truth would be easier.

      I’m not different than everyone else in that the truth about me is hard for me to hear, too. But I’m different because I’ll tell you the truth when I am on the phone with you. It’s really difficult for any of us to make good decisions when it’s so hard to get someone to tell us the truth.


  3. Tony
    Tony says:

    Publishing is one of the few industries that I find interesting from a business perspective. How do you decided which books will sell? What goes into getting a book on shelves? How is inventory managed? How do you keep your author pipeline moving etc etc. I tried finding books about it but most books were aimed at people wanting to get published, not what the business side of publishing looks like.

  4. Sarah
    Sarah says:

    Hi Penelope,

    Thank you for sharing your personal testimony. It is never easy managing a startup with kids. Highly recommend Rise ( for more inspiration and stories about other Women leaders in the workplace.

  5. Amy D. Kovach
    Amy D. Kovach says:

    From the vantage point of being 62, I truly believe that younger people (esp women) worry too much about taking time off for parenting (in terms of their career track). I also don’t believe it is necessary to take the entire 18 years completely off either. But a career has a long arc – I will probably work another decade or so. So the years that I stepped away from the workforce (from when my first child was born until my second was in elementary school) – probably about 8-9 years – really don’t matter anymore. I had my children when I was 24/27. I’ve been working for several decades now. I work in sales and was able to flex my schedule to allow me to attend school sports/events and manage sick/snow/holidays without too much difficulty. I think sales is a great field for mothers but I have found that they shy away for fear of the fluctuations in income. Now that I am older, the flexibility in my schedule allows me to spend time with my granddaughter and do other things that are important to me. And to retire incrementally, which I prefer.
    The work world is changing so quickly now – whether you step away or work straight through, your career is probably going to have various chapters to it, and you will need to reinvent yourself along the way anyway.
    I will never ever regret the time I spent with my children. I even home-schooled grades K-1 which was almost unheard of back in those days.
    I wish more couples would use their pre-parenting years to set the table for one parent staying home. Some basic economic planning can make it possible but often people are too committed to living at the top of their income to be willing to make the necessary changes.
    Just my $.02.

  6. Essays Chief
    Essays Chief says:

    The post is interesting. It asks can you get a career back after your kids grow up. The article mentions that what you would like to do for work when your kids are young is not what you would like to do for work when your kids are matured. For one thing, you can’t visualize what will be obtainable when your kid is matured.

  7. Morgan
    Morgan says:

    Hi Penelope,

    I think you are probably right about this. I am homeschooling two boys, age 7 and 3, who are chasing each other around the kitchen as I type. I’ve just finished the last piece of cake to cope with my grief. I’ve wanted to be a writer since I was 9, but I don’t have the emotional bandwidth to do it and parent. And by the time they are old enough for me to look at doing it again, I will probably have discovered my love for plumbing, or something.

    The challenge, maybe, is learning to be the best you can in the present, when your universe says, “No for another 15 years.” I think obsessively about my “career.” I work as a freelance editor right now. But probably I should just come to terms with doing whatever I can to pay bills and leave myself functional for parenting. Life is such a pain in the butt sometimes.

    I bet your class is awesome. Good luck with it, and the parenting end too. I respect that you try so hard to figure out what the best thing to do is. It is such a muddle.


  8. Bett
    Bett says:

    Hi Penelope,
    Thank you for writing this.
    I love your honesty and how you show up in the world.
    When will the live sessions be for the writing course?
    What do you think is the minimum and ideal time commitment per week for it?

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