Best Laid Plans

BLP #119: Live from Our Planning Retreat: Interview with Joshua Unger

November 7, 2022

Well, this was a lot of fun! Josh is a seasoned podcast guest now, having starred on BOBW in 2019!

selfie from some planning retreat of the past

He does not plan exactly the way I do. BUT I feel I have had some influence, and I’m pretty sure he would agree!

We discuss different planning styles, planning as a Questioner, and his somewhat minimalist toolkit. We did not discuss digital planning much — but I can assure you he does not abide by Inbox Zero. And I love him anyway.

Josh’s Planner Stack:

Josh’s quote: “This makes me look more organized than I am.”
Filofax notebook, closed

Products mentioned in Ursula’s Planner Peace segment:

Commit30 standard size, ShePlans undated weekly and a Scribbles That Matters Dotcross Planner

BLPA note: I mentioned BLPA towards the end of the ep, not realizing it would be full by the air date. Waitlist can be found via this link or up at the BLPA tab – I will be giving those on the waitlist first access for round 2 (signups in Feb; round 2 starts in April!).

Episode Sponsors:

Financial Gym: Individualized personal training – for your financial fitness. For more information, go to for more info and use code plans to get 20% off your first year of membership! 


  • Reply Alexis November 7, 2022 at 8:13 am

    I loved this podcast! I was always wondering what other people who are not upholders plan! 🙂 I always wish I could just make goals and uphold.

  • Reply Jessica November 7, 2022 at 12:40 pm

    Loved this episode! It’s so fun to hear you and Josh together, and I love your planning retreats – I love working on goal and habit planning with my partner too!
    I’m a questioner, and 100% agree with take what works, leave what doesn’t. Some of my advice for questioners planning:
    -Figure out goals that you fully buy into – take the time to think it through / do research / understand and address your skepticism. Identify your values and define goals that stem from them.
    -Prevent your goals from requiring decisions. Questioners are known for analysis paralysis. To avoid this, whenever you can, make the decision once then have the rest be auto-pilot. For example, once auto-donations are set up, you don’t have to think about it frequently. Once you’ve switched what your daily breakfast is, same thing.
    -Questioners are really good at finding loopholes – find systems to avoid loopholes, or get good at recognizing them and reminding yourself that they are loopholes! I find that naming the loophole when I’m using it helps me to refrain from using it.
    -For me, I like to have a less structured list of to-dos (perhaps with general priorities or categories, but no hard schedules), then pick from the list when I’m looking to do something. This makes sure everything gets done but lets me feel like I’m not sticking to some outdated priority order or schedule.
    -PUT YOUR LISTS IN A PLACE THAT YOU WILL LOOK AT THEM. I heard this issue come up with the interview with Josh too – for me, something about having a planner feels too arbitrary and I don’t end up looking at it. Instead, I use a “TO DO” event each Monday on my outlook calendar for work lists, and a white board in my living room for home lists.

    • Reply Allee November 7, 2022 at 2:01 pm

      As a fellow questioner, these tips ring true and are helpful! Thanks!

    • Reply Sarah Hart-Unger November 7, 2022 at 2:10 pm

      Love these!! And I bet Josh will too. Thank you!!!

  • Reply Katie November 7, 2022 at 1:13 pm

    Congratulations on your sell-out of BLPA! I’m a small business owner and I’d be very interested to learn how you are setting up the business end of your new endeavor. Will you keep these finances separate – separate bank account, budget, taxes, etc. Tips, best practices, planning for the business as it grows, etc. Maybe a future podcast episode? Thanks!

    • Reply Sarah Hart-Unger November 7, 2022 at 2:10 pm

      I have more to learn than to teach at this point!!!! Scheduling a meeting with our accountant is on this week’s list!

  • Reply Lisa of Lisa's Yarns November 7, 2022 at 1:23 pm

    This was a fun listen! I’m also an upholder married to a questioner. That’s the set-up in Gretchen’s marriage, too. Do we just attract questioners or what? But my husband is NOT a planner! He exclusively uses electronic and then we have a wall calendar in our kitchen where I put non-work stuff + work travel. He has come to see the benefits of planning, though, as it’s the only way we see friends as the days of spontaneous planning are kind of over for the most part? He might even set up a recurring guys night which I never thought he’d do but he’s seeing it’s the only way to consistently get some time away with his friends. But he doesn’t love talking about long-range planning – like where will we retire! I mean it is far away and it could change depending on where our kids end up but I love talking about the kind of areas we’d be drawn to whereas he’s rather not talk about something so hypothetical since so much could change.

  • Reply Amanda November 7, 2022 at 1:45 pm

    Filofax!! I’m not the only one kicking it old school. 😉

  • Reply Betsy Knoche November 7, 2022 at 3:44 pm

    Hi, Sarah. Somehow I missed signing up for the Academy. I am subscribed to the newsletter and read the blog consistently. Was it an email I missed? I signed up for the wait list

    • Reply Sarah Hart-Unger November 7, 2022 at 3:55 pm

      It was a link in the November newsletter as I had promised subscribers they would get first access. I’m sure there will be space in round 2- I just feel like I need to limit the first round to ensure it goes really smoothly and to make sure I can support everyone!

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