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Jill James Wrapped
The “urgent” email you need to make your escape
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It’s Christmas Eve. Somehow.
Time is a social construct.
Anyway, if you didn’t read every issue of this newsletter this year, I don’t blame you. The past 11 months have been something else. And December has a way of compressing time, attention, and energy. End-of-year work still has to get done. Family logistics don’t magically resolve themselves. Travel plans exist until seven inches of rain arrive in a bomb cyclone. And at some point, the calendar stops being aspirational and starts being factual.
So instead of adding something new to your already overflowing plate today, I pulled together a short list of the most popular issues from this year that many of you replied to, forwarded, or came back to later. If one slipped past you, this is an easy way to catch up.
Nothing urgent.
Nothing heavy.
They’re easy reads you can enjoy while you’re waiting for something to finish in the oven…or when you’re gifting yourself a few minutes of escape before someone else in your family asks, “So, how’s business?”
Predictions and endings
From January 8, some predictions for the year ahead: you’re going to worry too much about AI-related noise instead of committing to learning how it works and deciding how you want to engage with it. There will be even more noisy headlines that distract you, sap your energy, and make you afraid. The fundamentals of business will not change -- your pipeline and gross margin will still be your most important metrics. How did I do?
I struggle with using the phrase “purpose-driven” in a world where McKinsey, the world’s foremost leader in downsizing, has a purpose-driven consulting unit. What if your purpose is to bring down democracy? Strip me of my civil rights? It’s still a purpose-driven business.
Uncertainty creates indecision. That means it’s time to put some extra work into lead generation and increasing your sales pipeline. If you’re a decisive person, you might find a deal or opportunity as others are waiting to see what happens. People are looking for things -- a break, an escape, a reliable answer, a mid-priced good of respectable quality -- where there may not have been demand over the past two or three years.
One of the first things I do for my clients is assess their profitability so they can pay themselves. When we raise their profitability, it also increases their tax bills. The common refrain: “I don’t mind paying what I owe, I just don’t want to pay more than I should.” It’s entirely fair to acknowledge that making a big payment to the IRS feels painful, even for the most generous and socially-inclined souls. Which is why I’ve spent much of this December in meetings about income optimization.
Happy Hard Pants Month
Hey, remember when the market tanked due to tariffs? Uncertain environments are full of opportunities for problem-solving. Small businesses lead recoveries because we are nimble. Start with joining some new conversations, even if you can’t see an immediate payoff.
I’m all-in on self-cleaning toilets
Notes from Japan: these are the robots I want. Nobody needs to clean a toilet. The technology is relatively inexpensive and reliable enough to eliminate the job but for periodic checks (as long as you can hit the bowl, gents). One to read if you’re wishing for some Toto porcelain under the tree.
Big breadwinner energy
Notes from the credit card bill I got after Japan. When you’re self-funded, it’s hard to not think zero-sum about that money. You’re paying someone instead of paying yourself. You may think, I didn’t get paid this much when I was at this level. I’m paying this person more than I pay myself, and I’m taking all the risk. A good read if you’re planning to grow your team next year.
The drunken elephant in the room
The truth is, even in the most stable of times, planning is just setting goals and taking some calculated risks to give you the best shot of reaching them. It’s defining a path for yourself and conscientiously evaluating what might stand in your way. It doesn't mean the plan won't change. But it does mean you're going to try intentionally to move in a desired direction.
4 trends and how to use them now
Social media usage is starting to fall, in part because we’ve entered the uncanny valley of AI, where we don’t trust things that seem almost too real, and also because people are realizing that real-life experiences matter. When asked what they would do with $1 million in marketing money now, half of CMOs and founders said real-world gatherings, offices, and experiences.
When it’s time for the next chapter
In the past 18 months, I’m seeing a lot more business owners considering whether it’s time to move on from a business they’ve built. Maybe the business you thought you wanted to run forever is not challenging you, or you want to try something else. Perhaps someone else wants to take over leadership -- an employee or family member. If you have a glimmer of an exit on the horizon, read this one.
Important Dates
I hope you’ve finished your end-of-year checklist and are ready for a long winter’s nap. Two more closing dates to keep in mind:
December 26-29: Last day for most payroll runs with direct deposit
December 31: Last day to open a 401(k) retirement account or make purchases for 2025 qualified expense deductions
May your ham be the only thing spiraling this holiday season.
Media Kit
Yes, “brain rot” is real. Across dozens of studies, heavy use of TikTok-style content scroll is leading to weaker attention spans, lower impulse control, and higher levels of anxiety and mental fatigue. Yes, we all deserve to briefly escape this dark timeline by watching some silly Reels. But when platforms are engineered to make boredom impossible, what happens to focus and self-regulation? I will be conducting an intensive data study on my group of one during this school break.
LinkedIn’s new algorithm now rewards familiarity over novelty. If your LinkedIn feed feels like an endless parade of nauseating “Here’s what watching my son play Little League taught me about shortening the sales cycle” posts, you’re not imagining it. Why? LinkedIn’s AI is very good at serving you more of what already worked, and very bad at recognizing something genuinely new. As a result, a brain-drain by thoughtful people has begun.
The AI arms race is getting expensive, and the math looks awkward. Et tu, AI? Every innovation cycle, we hear why profits don’t matter. And then, they do. Earlier this year, consulting firm Bain estimated that by 2030, AI companies will need about US$2 trillion in annual revenue just to pay for computing power demand -- and they’re likely to come up roughly $800 billion short. Somebody’s hearing the ghost of James Earl Jones say, “If you build the data centers, the profits will come.” (And it’s still not heaven, it’s literally Iowa.) Growth, infrastructure, and profitability still have to line up eventually, no matter how much Sam Altman floods the zone.
Thank you for reading! Please send your feedback and questions by replying to this email or contacting me at [email protected]. Or you can schedule a free 20-minute Strategy Session with me for early January.
