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Pushing yourself just enough
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Some days, I sit down to do my work and I just don't want to start. There is plenty of work on the list, but none of it is interesting or even remotely challenging to me. I can blow through a list of bill payments, phone calls, and meeting schedules like it's nobody's business. But, it's boring as crap and - sadly - even when I do go through a big list like that, I rarely feel any sense of accomplishment.
A couple of weeks ago, I mentioned that I wanted to explore finding and using the right level of challenge. It's a topic I've been thinking about a lot lately, especially as I've been experimenting with Robot Kara. (See the What's Coming Up section below, because I'm finally ready to introduce her!). As I'm typing this, I'm using a set of research notes that Robot Kara now programmatically makes for me based on a set of instructions she built for herself using my prompt. She waded through all of my book notes and found quotes and resources related to the topic so that I can pull from them as I want to. Additionally, right now she's churning through a massive project of building a database I've been thinking about building since I started Monarch Strategies four years ago. While it's going to cost me a bit in extra usage credits for Claude Cowork, it's worth every penny as this is worth thousands of dollars in potential future revenue. And, it's a project that would have been menial, slow, and tedious for me to build - meaning that the time spent wouldn't have netted any potential value. Now, for less than $200, I'm getting the tool I want in less than a day and I can move forward with it to the next part of my vision. That next part is what's actually interesting to me - and what will potentially bring in revenue for my small business. Unfortunately, this big obstacle has been in my way for years. Now, AI can clear it in less than a day.
This is what AI can do for us. It can do the menial, so we can focus on the interpersonal human work that is so, so much more important.
When you talk about challenge and how finding the right level of challenge can motivate you, Mihaly Csikszentmihalyi's idea of flow comes up a lot. When the challenge level is right in your sweet spot - just at the edge of what you know you can do - you feel like time stands still and you could get anything done. One day last week, I looked up from my work and three hours had passed and it felt like 20 minutes or less. It was magical because I was doing the work that I loved to do and I was doing it well and it felt amazing. Because I've been thinking about challenge a lot lately — and how to get your work to the right level to sustain motivation — I've been drawing on BJ Fogg's research. Fogg suggests using both floor lowering and ceiling raising as techniques for using challenge as a motivational tool. To lower the floor, you break a big task into smaller chunks. I would add to this in the day of AI, you ask the AI to help you with steps that felt impossible before - either because they were too boring or just too hard. To raise the ceiling, you add constraints like time or a specific creative constraint or you go after a harder variant.
Where do you need to lower the floor or raise the ceiling to get you back into a project? Could AI help in some way with that? Let's chat. Hit reply on this email or click the link below to chat in Circle.
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Some Other Things You Might Find Interesting
What I Published This Week
- Nothing specific (although see the video below for the sermon I preached this past Sunday). I've got a couple of things coming this week AND check out the Robot Intro session below! I'd love to see you there.
What's Coming Up?
I’m so excited to introduce you to Robot Kara! She’s actually the one who publishes these newsletters now. Come to this free session to learn how I’m using Claude Cowork, Obsidian, and Wispr Flow to automate the busy work so I that I can focus on creation.
May 08, 2026 14:00
(Eastern Time (US & Canada))
For the last couple of months, I have been building and fine tuning a Robot version of myself. Now I am ready for you to meet her.
Join me for this interactive session where you will get to see how I am using Claude, Wispr Flow, and Obsidian to automate many of my routine workflows and get back to the work that I love - writing and creating.
I also added several new sessions of our regular community events this week. For the latest details check out the Events area in Circle as well as the Obsidian Office Hours section. Here are links to the next sessions of our regular events:
May 08, 2026 09:00
(Eastern Time (US & Canada))
Need to "get organized"? Avoiding making calls to doctors, lawyers, insurance, or others? Need to get prepared for taxes? Come join us for a Facts of Life Book Power Hour. Log on at the start time, declare your intention, and then I'll put on some music (breakout rooms will be available for those who prefer to work in silence) and we'll all work for about 50 minutes. At the end of the hour, celebrate your progress with others.
May 11, 2026 10:00
(Eastern Time (US & Canada))
Join us for the bi-weekly Obsidian Office Hours Session.
Office Hours are a time to ask questions about Obsidian. If you have a question, reply to the event with your questions - or attend live and you can get your question answered in the session.
When appropriate, office hours sessions will be recorded and the recording posted here.
May 11, 2026 09:00
(Eastern Time (US & Canada))
Do you want to get a better handle on your finances? If so, join me for a free one hour workshop to talk all things money. This is a great time to hold your own financial date with yourself (which I talk about in the Facts of Life Book Course). Get financial questions answered, see software tools like YNAB in action, or just chat about money. This is a judgment free zone so come with your questions.
Sermon - Easter Acts: A Checklist for Church Life
I had the opportunity to preach at my home church again this past Sunday. This is the second time that I've continued the sermon series of our senior pastor so I've delivered a sermon that had it's basic design parameters (scripture & title) assigned as constraints. I could easily ask to simply preach on something different, but as with our newsletter topic this week, these constraints provided a "raise the ceiling" limitation that gave me a challenge to work within.
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