050: How to Do a Do-Over: Interview with Jon Acuff

Doing something well requires time and focus. There are always other tasks competing for our attention. It’s the job of an artist to focus on the right things and ignore the distractions.

050: How to Do a Do-Over: Interview with Jon Acuff

This week on The Portfolio Life I talk with my friend Jon Acuff about his new book Do Over. Jon and I talk about starting over and how that doesn’t mean you’re necessarily starting from scratch.

Listen in as we talk about being brave, starting new things, and what it really takes to do a do-over.

Listen to the podcast

To listen to the show, click the player below. (If you’re reading this via email, click here).

You can also listen at iTunes or on Stitcher.

What a “do-over” looks like

Jon Acuff is a New York Times bestselling author and someone I’ve followed for years. He’s also a good friend.

Jon’s story is that he got his dream job, wrote a book about it, and then walked away from it. Through the challenging and confusing experience of beginning again (which he shares in his latest book), he learned what bravery is all about.

During our conversation, we talked about comparison and the fear of missing out. In being a writer, there’s always the temptation to watch what others are doing and think you ought to be doing that, too. But just because something is working well for someone else doesn’t mean it’s right for you.

We often overfill our calendars and say yes to any opportunity that comes our way. But pretty soon, we’re no longer doing our best work. The way we get back to putting first things first, according to Jon, is to be honest.

Sometimes, it’s easier to tell people what they want to hear than to tell them the truth. Jon is an honest writer who cares about people. Relationships aren’t always easy, he admits; they’re often awkward and messy. But connecting with others is worth the struggle — there’s value in community.

Jon’s writing is full of humor and truth that’s presented in a way that’s easy to digest. “I share intuitive ideas in counterintuitive ways,” he told me. And I couldn’t agree more. That’s never been more evident than in his latest book, Do Over, released earlier this week. If you’re feeling stuck, this book will give you what you need to begin again.

Show highlights

In this episode, Jon and I discuss:

  • Why Jon walked away from his dream job
  • The struggle between telling the truth and saying things that will be shared
  • The benefits of community
  • The single most important thing authors need to remember
  • Jon’s biggest fears he’s currently facing
  • And so much more!


Have you ever been stuck and in need of a do-over? Share in the comments.

24 thoughts on “050: How to Do a Do-Over: Interview with Jon Acuff

    1. That’s a great question, Ralph. I loved the way Jon addressed this realistically. You can’t do everything, but you can focus on a few things that matter. And we all have to work out that process with our own fear and trembling, it seems.

  1. Jeff – this is the first time I took the opportunity to listen to your podcast. Outstanding! It really helped to center me on the singular focus of writing. Very beneficial.
    I will be living in an RV four days per week for the next few months (until our home sells and we relocate due to a new job) and my game plan is to simply make use of the isolated time Jon spoke about to get in the game and pursue what matters most to me. Thanks for the kick in the pants. BTW, looking forward to your book arriving in the mail, perhaps today!

  2. Really loved this one Jeff and Jon. Richard Foster wrote one of my favorite books – A Celebration of Discipline – along time ago – I believe Richard was in his 30’s. As relevant as that book still is today – I bet it would be written differently if he wrote it today.

  3. And, if I may provide one more bit that really struck home with me. Jon clearly has an awesome wife. Someone has to be there to keep your ego in check. We could all list numerous examples of authors, bloggers, podcasters, etc. who have probably veered into the ego worship category – maybe even unknowingly. Good stuff.

  4. This was pretty cool stuff. I enjoy hearing Jon and Jeff talk about writing.

    One point that struck me was saying that being alone is selfishness. I don’t believe it is. We all need our own little space to retreat to to gather our thoughts and ourselves. It helps us be better when we around people, as it gives us a bit of a break. And writers may be a group of people that needs to be alone more than others : ) That doesn’t mean it’s being selfish, it means it’s the way we get stuff done.

    1. Interesting. Great point, Elise. I think you’re right. That said, sometimes being alone, for me, can lead to selfish thinking. I can too easily get used to solitude. Community for me can sometimes be a discipline.

      1. That totally makes sense, a light bulb went off when you said that. I am a mix of personalities, where I really enjoy gatherings and concerts with large groups of people, but I also need my space. I’ve been through times where I’d go to work and when I’d get home, hide away, and on the weekends, wouldn’t even go to church because I didn’t want to be around anybody. Right now, I work at home mostly, and have found that I could be happy maintaining that and just being at home around no one, but I really need that community and feel a ton better when I seek it out. Some days, it’s just harder than other days to get out there and seek that and be there for other people.

  5. It was so refreshing to hear an interviewee/celebrity author speak so much truth about the way things really are rather than glamorizing it or making it sexy. I believe that Jon not only cares about the craft of writing, he cares about how the writers manage their lives. Thank you for caring enough to tell us the truth.

  6. Yes, it is refreshing to hear two friends have an honest talk about writing. Jeff, I hope you invite Jon back for another podcast. This was very eye opening and just what I needed to hear today. I am in the midst of a “do over.” I am retiring from a job I’ve had for 21 years. So this podcast was very much needed. Thanks so much.

  7. Love the line “I don’t have to finish the whole relationship in this thing I’m writing”. I think that is such an important idea to embrace as a writer. We always have more words but for some reason I have to remind myself over and over that I don’t have to “finish” it all on this page. Great interview!

  8. Jon’s kind spirit is as inspiring as what he’s saying. My best bit: 3rd grade self wondering if he’d written brave. In this age of internet success, staying true to the calling in our bellies is no small deal.

    Thanks for this.

  9. Jeff, I always love reading or listening to your work. You always do a great job. Thanks for always bringing great art to the world! I’m a year into a do-over! I have definitely learned that it wasn’t a full set back, because what you learn along the way never leaves you. It just sets you up better for the next chapter!

  10. Jeff! Oh, dear Jeff. Thank you so much for interviewing Jon Acuff. I’ve admired him for a long time and, a couple of weeks ago, I’ve discovered your own books and interviews.

    This podcast, in particular, was a gift! I am going trough a Do-Over myself: just graduated from college and am currently designing my own path as a writer.

    The high point of this podcast, for me, was when Jon said that is nice to know that are people out there doing the same things that we are. Something like: “I am here too and this is how I am dealing with this stuff”.

    That’s the hole point of expressing yourself through writing, I believe.

    THANK you so much for this talk.

  11. Jon said something that really hit me hard; “Its about the book.” I needed to hear that. Thanks, Jeff.

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