So you are a current AirPods Pro user, and you are trying to figure out if the new Second Generation AirPods Pro are worth the upgrade. In this video I will walk you through where they’ve improved, where they’re the same and ultimately if I think they are worth the $250 upgrade over the AirPods you already have in your pocket.

Initial Impressions

  • Quality of life Changes
    • Charging via Apple Watch charger is a nifty gimmick
    • Charge chime
    • Legitimate Find My support
    • Battery life was already very good, it was nearly never an issue, but it is even better.
  • Better sound quality
    • Old AirPods Pro were acceptable sound quality. I knew they didn’t sound as good as my Hifiman Sundara’s but they were so damn convenient and could be open or closed back depending on my use case.
    • The sounds quality of the new AirPods Pro are actually good. I enjoy listening to music on them.
  • Much better Transparency + Noise Cancelling
    • Most importantly I work best with a sense of calm. Noise Cancellation is perfect for generating that Focus. It is even useful when in a room that is relatively quiet.
    • It leads to me getting pulled into fewer distractions.
    • It creates a more intimate interaction with whatever I’m doing
    • One of my greatest tips for achieving flow state and doing deep work
    • Majority of the time I can’t tell whether I have my headphones in or not when in transparency mode. It is that good now.
    • The pressure people often associate with Noise Cancelling is also gone. It still gives you that isolation but without
    • I’m that weirdo that they built Adaptive Transparency for. I used to weird the AirPods Pro (Gen 1) to concerts just in their “Off” mode.
      • I recently went to a Landmvrks & Miss May I show with these and wore them the entire time. They stayed in my ears the whole time despite utter chaos and sounded great without the fatigue after the show. They probably aren’t technically legitimate ear protection, but if you are one of those people who wants to hear the show and not have tinnitus, it is somewhat of a happy medium.
  • The connect speed has improved a bit, but don’t expect a wholly different AirPods experience. and this is a good segue into my

Cons / Wishlist * It still suffers from the same issue where you are listening to something on your computer and get a phone call and try to answer it on the phone and the AirPods don’t want to switch to the phone. * Another use-case I have is I will be listening to something on my Mac, pause it, grab my phone and try to make a call either by Siri or by tapping on my phone and it will try to use the handset audio instead of the AirPods. * The last one of their use cases is when you receive a call and for whatever reason your AirPods don’t pick it up, but then you answer and try to switch the call to AirPods and it’s an option, but takes forever to connect or it just never connects and you just sit there why the caller tries to tell you something that you’re never going to hear. * Supposedly the new MacOS that comes out later this fall gives you full calling and handoff support, hopefully that will solve this rough spot. * I don’t understand the spatial audio trend. It doesn’t change or improve the headphones in any significant way, but maybe it will morph into something useful in the future. Perhaps this is all a test bed / precursor for the audio in Apple’s upcoming VR/AR headsets, but as of yet it just feels like a gimmick


  • The AirPods Pro Gen 2’s are a sizeable upgrade from 2019’s initial AirPods Pro. If you are a daily driver of the AirPods Pro or a working professional who uses AirPods to focus, these are an easy upgrade in my book. For me personally, I use the original AirPods each day and these are an easy recommendation. If you aren’t using your current AirPods Pro daily or the $250 price tag seems a little steep, then your current AirPods will continue to suffice.

AirPods Pro (2nd Generation) — AirPods Pro (1st Generation) — Deep Work (Cal Newport) —