Jessica Lahey on Parenting, Desirable Difficulties, The Gift of Failure, Self-Efficacy, and The Addiction Inoculation (#553)

Artist's rendering of Jessica Lahey
Illustration via 99designs

Did you make someone feel seen or heard today?

— Jessica Lahey

Jessica Lahey (@jesslahey) is the author of the New York Times bestselling book The Gift of Failure: How the Best Parents Learn to Let Go So Their Children Can Succeed and The Addiction Inoculation: Raising Healthy Kids in a Culture of Dependence. Over twenty years, Jessica has taught every grade from sixth to twelfth in both public and private schools and spent five years teaching in a drug and alcohol rehab for adolescents in Vermont. She currently serves as a recovery coach at Sana at Stowe, a medical detox and recovery center in Stowe, Vermont, where 100 percent of her salary goes to a scholarship fund for young adults.

Jessica writes about education, parenting, and child welfare for The Washington Post, The New York Times, and The Atlantic, is a book critic for Air Mail, and wrote the educational curriculum for Amazon Kids’ award-winning The Stinky and Dirty Show. She co-hosts the #AmWriting podcast with bestselling authors KJ Dell’Antonia and Sarina Bowen from her house in Vermont, where she lives with her husband, two sons, and a lot of dogs.

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Listen to the episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Stitcher, Castbox, Google Podcasts, Amazon Musicor on your favorite podcast platform.

Brought to you by Wealthfront automated investing and Athletic Greens all-in-one nutritional supplement.

The transcript of this episode can be found here. Transcripts of all episodes can be found here.

#553: Jessica Lahey on Parenting, Desirable Difficulties, The Gift of Failure, Self-Efficacy, and The Addiction Inoculation

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What was your favorite quote or lesson from this episode? Please let me know in the comments.


Want to hear another episode with a writer Jessica and I both admire? Listen to my conversation with award-winning author Mary Karr, in which we discuss curiosity and presence as a solution to fear, the role spirituality plays in maintaining her sobriety as a former atheist, coping with and expressing the aftermath of trauma, what she wished she’d known about therapy when she was younger, and much more.

#479: Mary Karr — The Master of Memoir on Creative Process and Finding Gifts in the Suffering
  • Connect with Jessica Lahey:

Website | Twitter | Facebook | Instagram


  • Why is Jessica fond of Nobel Peace Prize winner Albert Schweitzer’s intention to make his life his argument? [05:21]
  • As someone who’s educated children from grades sixth to 12th, what does Jessica consider the most difficult cohort of students, and what would she change about the structure of when and how this group is commonly instructed? [07:50]
  • What do I like about this particular grade — to the point I once considered specializing in teaching it? [13:29]
  • What was “taking a nap” code for in Jessica’s extended family? [14:54]
  • Why is June 7th, 2013 an important date for Jessica? [17:10]
  • Why it’s important to understand the roots of an addiction if we want to gain control over it. [20:20]
  • Jessica acknowledges the practical application of psychedelics — provided the recipient has a fully-formed adult brain. [23:15]
  • Did Jessica’s commitment to writing a book influence how seriously she took the conversation with her father that changed her life? What most helped her adapt to the changes she knew she had to make in the aftermath? What has she found unhelpful? [24:37]
  • What was the catalyst for The Atlantic article that evolved into The Gift of Failure? What are the book’s main theses? [30:39]
  • Confidence vs. competence when trying to foster a child’s self-esteem. [36:43]
  • How did writing The Gift of Failure affect Jessica’s parenting style? [42:07]
  • Why instilling hope in a child is so crucial to their lifelong well-being. [46:05]
  • What books and activities keep Jessica aligned along the path of hope and optimism? [49:34]
  • What did Jessica find surprising in her research about preventing substance use and abuse in kids? [52:49]
  • What does it look like to be a recovery coach at Sana? What is the format? [55:34]
  • Why did Jessica decide to write Addiction Inoculation? [1:00:16]
  • If “Just say no” is an ineffective script, what are some better ways for parents to guide their children toward making better decisions when they’re exposed to drugs and alcohol? [1:01:18]
  • Advice for parents who get the dreaded phone call that their child has been caught up in non-ideal behavior. [1:06:19]
  • A favorite failure. [1:10:29]
  • Examples of what made Jessica’s “not-to-do” checklist when she was writing her second book, and how she audits her own work for clarity. [1:15:21]
  • Writers whose work Jessica finds deserving of extra attention. [1:21:20]
  • Best investments of time, money, or energy. [1:29:13]
  • What would Jessica’s billboard say (provided she were allowed to post one in her home state)? [1:33:57]
  • Visible quotations and objects on hand that serve to inspire Jessica on a daily basis. [1:35:27]
  • Parting thoughts on the challenges of releasing a book during a pandemic, having (rather than avoiding) difficult conversations, why Jessica thinks I’d be a fantastic ninth-grade teacher, and Jessica’s dream. [1:41:25]


“I decided I would make my life my argument.”
— Albert Schweitzer

“Rigidity is the bane of my existence.”
— Jessica Lahey

“Recovery looks different for different people.”
— Jessica Lahey

“Did you make someone feel seen or heard today?”
— Jessica Lahey

“There is nothing worse than taking a kid who is just figuring the world out and then telling them, at every turn, that their perceptions are inaccurate.”
— Jessica Lahey

“Resourcefulness only comes from having tried something and screwed it up and tried it again and all that, and having support throughout that process with someone who actually believes in your ability to be resourceful.”
— Jessica Lahey

A lot of what I write about is, ‘We’re not doing this right. Oh, look, I’m not doing this right. How can I do better and learn from it?’ which is super fun and a little humiliating.”
— Jessica Lahey

Listen to the episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Stitcher, Castbox, Google Podcasts, Amazon Musicor on your favorite podcast platform.


The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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11 Replies to “Jessica Lahey on Parenting, Desirable Difficulties, The Gift of Failure, Self-Efficacy, and The Addiction Inoculation (#553)”

  1. Re your 5 Bullet Friday post – two more interviewers that you might consider evaluating (after seeing the Mike Wallace doc) are Tim Russert and Ted Koppel.

  2. Tim, I really miss hearing your own personal thoughts and ideas and opinions. Of course, we still get a lot of your voice in your interviews and side comments, but it’s been a really long time since you’ve written (or put out through some form of media) anything that comes directly from your own brain. Even your email newsletters are mostly just quotes from other people and sponsored products. Where did *you* go?

  3. Great episode. Valuable to hear about the writerly tools that you can use – a space of pages; the idea that it doesn’t necessarily need to follow the rules – and thanks Tim for actually unpacking it more precisely so it’s more easily understood.

    As a recovering addict – nearly a decade sober – I have to agree that being too rigid isn’t good, but also what someone else on your Podcast mentioned I believe: keep your vices close to you. For a while I still hung around people that were deeply engaged in my former lifestyle as a test: was I tempted? Had I actually become bored with everything that I escaped. I did this for about 5 years on occasion.

    Surprise, surprise: I was never tempted.

    Appreciate the work, Tim & team.

  4. I must admit I had a few cringe moments during this episode. I can’t count how many times I used the “the europeans let their kids drink” montage when my kids were growing up. I love that your podcast takes us down personal an business roads. So much to learn in life. And on unasked for parenting advice since it seems to be a common thread as of late(I have 3 grown kids), all they really want is your unconditional love(like molly), your attention(like at spirit rock) and your ability to say sorry when you fuck things up(this mostly works on teens not so much on 3 years olds) This was an incredibly important episode. Thank you for the light you shine on to so many important topics.

  5. Hi Tim,

    Thanks for this (one of many) great podcast. Like you I’m considering starting a family and would love to share this conversation with my partner, although he’s not the kind to listen to a lengthy podcast, nor to read an extensive post, and prefers content in his native language French.

    Have you ever thought of making a visual synthesis of your podcast ? A mindmap, RSA animate, motion design, or powerpoint ?

    Also if I can help you make your content available to the (my) French people – who generally suck at English – so I can finally share your stuff with my peers, I’d be glad to be of assistance.

    Thanks for doing what you do, you’re great.

    All the best !

  6. Thanks Tim for introducing me to the work of Jessica Lahey. I found this conversation very engaging, fun and informative in a variety of topics.
    As a parent of three young (and very different) children, having myself grown up in a very lax culture with regards to alcohol consumption for youngsters, this presented key starting facts that I will now research further to guide my children and empower them to make healthy choices and build the tools to navigate the societal pressures that will naturally arise.
    I also learned about what an addiction “enabler” person can be in our circles, something very specific and useful.
    Loved the details about writing process and tools.

  7. Interesting, isn’t anxiety just trauma and or even generational trauma?

    To me that seems to be the case. You van talk about genetics but the again, how did it get into to genes?

  8. Tim,

    I am sorry for posting this publicly as it really is intended as a private message to you, but I have no idea how to get it to you otherwise (the old email I had that worked years ago bounced).

    I have heard you on your podcast, including this one, over the past year and perhaps more reference your contemplation and consideration in terms of starting a family. I have also heard your guests repeatedly say how rewarding it was, and, e.g., John Doerr say his biggest regret was not starting sooner, and going bigger.

    I understand you are an avid researcher, and want to learn as much as possible on the subject. As a father myself, I also know (or maybe I should say, believe) there is no “answer” to parenting. There is parenting your children, and in reality, parenting each child as every individual is their own ever-changing snowflake.

    As a serial entrepreneur you know that the only way to really learn entrepreneurship is to do it. The same is true in spades with parenting.

    I don’t know you personally, but I know you have been an immeasurable gift in my own life, and that of so many others I know, respect, and love. You will fuck up as a parent. You will also be the most incredible father to your child/children because of who you are, and also because you will be their father.

    Please don’t fall into analysis paralysis here. You will be an amazing father.

    My apologies for overstepping. I just know the gift you have given me, and can only imagine how much larger and more extended it will be for your own children, so please get started!


    Andrew McConnell

    1. Hello, Middlebury!

      Thanks for extending your invitation to Tim, and we did link to your school in the Selected Links section! (You’ll find it shortly after the listed sponsors on this page.)


      Team Tim Ferriss