I love Amy and Glynn, too. For your goal of writing interesting monologs, I would suggest that you start that goal VERY small. Start out just by writing something that you want to say. Doesn’t have to be interesting or perfect. You might start with writing for 10-15 minutes a day, or maybe even 5, if that works better for you to get started. You can write a LOT in 5 minutes if you don’t include editing, which you shouldn’t be doing at this writing stage. It should be an amount that you can develop into a daily practice that won’t seem like a big deal. (Think about when and where you can fit that into your life.) Once you get writing regularly, you can expand the time and expand on what you write about. Leave interesting out of it because, especially at the beginning, it draws out a need for perfection and can lead to frustration at not having something interesting enough to say. Later, you can go back to edit these pieces and decide what’s interesting or not. You may be inspired to take something you wrote in a more interesting direction. By starting small and with low expectations, you’ll wind up with many more interesting dialogues because you’ll do so much more writing.
For your future-self vision, you are envisioning things you will DO, not how you will BE. How do you want to BE so that you will actually DO (and not just dream about) the things you describe?
So many are plagued with mountains of guilt and, as you say, it’s that very guilt that’s holding them back. So, how can you banish that? You’ve already taken the first step, that is to acknowledge it. What are some self-forgiveness/wipe-the-slate-clean processes that have worked for you in the past? WE can develop this into an interesting discussion.