- The Jill James
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- The drunken elephant in the room
The drunken elephant in the room
2026 planning? Come on, lady.
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Two-steppin’ on the table, she don’t need a dance floor
Don’t hate me. I know America is drunk and needs to go home. But it’s late August, and this is when we start 2026 planning. I’ve already done a couple of client offsites and built my own initial forecast.
In 2025, what even is planning? When it feels like economic policy is being set by a drunken elephant on a rampage, even I see the appeal of waiting for a tiny ounce of sober certainty. For small but growing businesses, it can feel like that drunken elephant is running at you as you dodge a pelting hailstorm of opportunities and challenges.
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.
Governments, companies, and households all spend the most in calendar Q4. While the American government may not be sobering up yet, 60% of consumers say they’re cutting back on discretionary spending. Corporate buyers are either already in planning overdrive or will be doing another year of quick turnaround budgeting requests. When your customer asks you to be a part of their spending plan, are you ready to answer? If you're not ready to join the conversation in the next few weeks, you're making next year harder on yourself.
I can't promise a smooth 2026. But I can give you the best shot possible at being in the conversation.
Over the next few weeks, I’ll be writing more about strategic planning -- macroeconomic conditions, operating costs and benefits renewals, and growth outlooks. But this week, I’m going to encourage you to start the process by controlling what you can control.
All strategic planning starts by looking within. How have you changed? What do you want and need? What’s different about the leader you are now, or that you want to be? How do you want to show up in the world?
If you skip this step, even the best tactical plan and growth forecast will be wrong for you.
I’ve updated my blog post, Five Questions to Guide Your 2026 Strategic Planning. Even if you’re not ready to face a spreadsheet, let alone sit at a desk, you can ask yourself these questions. My hope for you is that, by starting here, you’ll have a strong framework for evaluating the more tactical information I give you over the next few weeks.
If you’d like to talk about your forecast, goals, planning, or affinity for Shaboozey, grab 20 minutes with me next week.
Get your pipeline right
Come through, readers! It was a week of “yes and” in the support inbox. First up, establishing and fixing your pipeline.
If my recent LinkedIn poll about your pipeline health made you squeamish, here’s a potential solution. From September 16-19, the team at Smart Gets Paid is bringing back their CRM Setup Bootcamp. Over 4 days, you'll build a fully functional CRM pipeline tailored to your business, get organized, and create systems that help you close clients faster.
In a nutshell, that thing you know you've needed to do forever? The Smart Gets Paid team is going to do it with you in a matter of hours. This program is designed for women consultants who have been in business for a couple of years and are earning at least $120k in annual revenue. (But if you’re well on your way and want to stay out of Hot Mess territory, also you.)
Your 4-day implementation plan:
Day 1: Pipeline setup - see your revenue potential instantly
Day 2: Contact management - stop leads from going quiet
Day 3: Strategic tagging - turn your network into opportunities
Day 4: Business planning - make your CRM work for your goals
From a friend of the newsletter who attended last year: “I didn’t think I had time to do this, but as usual, your nudge was the right one. This was great!”
Your investment: $297 if you register by August 22. After that, $497. Get on it and save that $200!
The CRM Setup Bootcamp, September 16th-19th, 2025 smartgetspaid.com/crm
Up your joy factor
Another reply from last week’s newsletter about making space for joy was from longtime friend of the newsletter, Alison French, who reminded me that she and a partner offer free public workshops on reclaiming your joy at work. The team also offers in-person corporate and virtual versions for team leaders to redefine their journeys to unleash their joy. Learn more by contacting Alison directly.
Media Kit
My monitor, myself: I was today years old when I learned portable second monitors were a thing. As a regular user of TV-sized data reports, my productivity craters when I’m confined to alt-tabbing on my laptop. I will be getting one asap to add to my backpack office. Wired offers this best of back to school tech summary, many of which are fantastic for working on the move.
Speaking of drunk: Cult whisky brand Uncle Nearest was hit with a lawsuit this week by their lender, claiming the owners defaulted on bank loans and lines of credit. The owners are claiming their CFO went rogue and defrauded the company. You know I love a juicy story of failed corporate financial controls. Keep the checkbook, kids.
Some other beginning’s end: I get calls regularly about whether a last-minute sale might be possible, instead of just shutting down a company. Are you curious about what might have value in a wind-down, and how you make the sale? This week’s episode of Odd Lots has delightfully weird examples of things that have resale value and some alternatives to declaring corporate bankruptcy. I LOL’d several times at the gross biotech stuff, which included (spoiler alert)...a freezer full of human heads and some choice collected secretions.
Pub quiz: Happy 75th birthday to my dad, Scoop. If you find yourself in the Green Bay / Sheboygan, Wisconsin area on Tuesday nights, pop by the OT Sports Bar in Valders for his pub trivia contest. He puts together an original ten-round challenge every week. August 26 is Back to School themed. Treat yourself to a pint of Spotted Cow and a basket of cheese curds, and tell him I sent ya.
Thank you for reading! I love your feedback -- please hit reply or email me at [email protected] with thoughts and suggestions. See you next week.