Before I get into this week’s topic, I wanted to celebrate a client, Alex Carter. Alex is a global leader in negotiation training Next week, she’s making her negotiation training available through MasterClass.

I’ve attended Alex’s training in person, and I’ve also seen her in action for the past five years. I had an excellent negotiations professor in business school, and what I learned from Alex -- an attorney by training -- is on a whole other level. I have used her techniques in all facets of life, from coaching my kiddo’s soccer team to settling the financial portion of my high-conflict divorce. She changed how I prepare to get the outcomes I want. 

If you’d like to step up your game, you can pre-enroll in the MasterClass Certificates course this week at a 20% discount. Congratulations, Alex!

I know, I know, you’re just getting the kids back to school. Can I give you a second? 

I get it. I also get the same flood of calls each November from founders: 

“I meant to start annual planning earlier. Can we get it done in the next two weeks?”

They had good intentions. They put it on their goals for the year. They said they’d enjoy summer and then get things on track. But there we are, on the Wednesday before Thanksgiving, trying to make it happen. We can triage, but the reality is, starting in November means we finish in January or February. 

And that’s okay. Better to do something when you can than nothing. But something curious happens next: the following year, the planning happens a lot earlier.

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Instead of November, we start planning in September, August, sometimes even June. Because once you go through a strategic planning cycle, you realize that Q4 is not the time to decide what to do, but to execute your plan. 

Because you see that your customers have already made their big decisions by January. If you have corporate customers, they’re asked to build their annual budgets in the fall. If they intend to keep working with you, they’ll ask you to support their planning process long before January. 

What happens next? You make something up. I’ve seen plenty of founders respond with some version of, “How about we raise prices 5%?” The ol’ SALY, same as last year. That should be enough, right?

And to your credit, you may have a good mental estimate of your costs to know that’s a good enough answer. But in many cases, you’ve just left a good chunk of profit on the table. You made the decision to keep the customer, but you don’t know if it was the right thing for you. 

With even a little bit of time put toward planning, you can avoid guessing. 

Whether you have two hours, half a day, or a full day, I’m going to walk you through what to review, what questions to ask, and what you should leave the session knowing.

Regardless of how much time you have, pull together the basics first.

No shocker here, you’ll need some financial reports. From your accounting system, I recommend:

Why not just the P&L? Because it doesn’t reflect your actual cash. Your P&L is your record for operating expenses and tax deductions. But your cash balances, distributions, and debt payments don’t show up there. 

🔎 Read more: How to value your business before you sell

The second thing is a summary forecast of what other revenue you have coming in for the year. If you have contracts and invoices, you can pull this from your accounting system. If you don’t, write out a quick summary of money you’re owed and what you expect to sell for the rest of the year. 

You need to know where you stand before you start making bets about the future.

Let’s be honest. If you only have two hours, you’re not making an annual plan. You’re building good habits. And that’s okay. 

With your two hours, get grounded on where you stand financially.  

Then ask yourself:

If you aren’t doing monthly or quarterly reviews, you’re probably not going to answer every question that comes up within the time you allowed. Use this time to identify the questions that matter and stake time to work on the answers. Put the follow-up work in your calendar, broken up into 30-90 minute chunks. 

🔎 Read more: How to run a quarterly business review (QBR) that works

That could be researching a trend in your industry or asking Claude to help you understand a competitor. It could also be scheduling time with customers or another founder who’s been where you are and might have some sage advice.

A half day gives you enough time to move from gathering information and organizing yourself to making some decisions. I’d still spend the first hour in the financials -- you want to know how the year is shaping up before you start thinking about next year.

Then ask yourself: How is this business going for me?

If the answer is, “Pretty well,” maybe next year is about doing more of what’s already working. If the answer is, “This isn’t really working the way I hoped,” now we have something to solve.

🔎 Read more: How to find business opportunities in uncertain times

From there, I like to organize my thinking around three buckets:

With half a day, you actually get to start answering some of those questions.

Thinking about a new service? Spend an hour researching it. Wondering if your market is changing? Go look. Curious whether a different pricing model could work? Run some numbers. You have enough time to follow your curiosity while it’s fresh.

Setting aside a day for planning should get you through a good amount of the evaluation, with some critical thinking time. 

I’d break it into three focused work sessions:

🔎 Read more: Here’s what I do for my self-funded founder clients

You probably won’t have every detail settled by the end of the day, but you should know the direction you want to head, have the broad strokes of next year’s goals, and a clear list of the things you still need to figure out and talk to customers about.

You might outline an awesome plan, but it needs to be tested. Don’t skip this step. 

Find time to talk to your customers:

You don’t need to make big decisions in a vacuum. This is why I don’t do “done-in-a-day” planning anymore. As soon as we take those ideas into the world with customers, we inevitably find some adjustments, and sometimes, some new opportunities. 

🔎 Read more: Do you have a messaging problem or a business problem?

That’s why I encourage clients to check in with their own customers, human to human. Ask how things are going, what they’re planning for next year, and what they need from you. And if you’re thinking about taking the business in a new direction, float the idea and see what comes back.

Ready to get started? Great, here’s what you do:

If you’re struggling to get started with annual planning, or your annual planning is creating more questions than answers, book a free 20-minute strategy session. (And if you’re wondering what happens in a 20-minute strategy session with me, this article tells you everything you need to know.)

ICYMI, here are resources you should know about:

When should you pivot your business, and when should you wait? Depending on your specific situation, yes, taking timely, decisive action might be the right call. But when you’re uncomfortable, your first idea is often the one that makes the icky feeling stop the fastest. Being reactive, unfortunately, often leaves the real problem unsolved.

When is growth “enough” growth? If you’re not sure, start by getting clear on what your goals actually are. Because if you don’t know what you want for you, you’re setting yourself up to absorb someone else’s scoreboard for success.

The $1 million, 1-person business. While the “solopreneur unicorn” remains a dream, the number of 1-person businesses reaching $1 million in revenue is growing fast thanks to AI-based processes and vibe coding. A new report from Stripe pulls together business formation data and their own customer results. They’ve even written a how-to revenue playbook for founders who want to rapidly scale on their own. The quiet part from the end: sustaining a business at $1 million-plus in sales over time usually requires building a team, even if they’re not W-2 employees.

Influencer rate-bait. Followers and impressions are no longer enough -- brands want to see engagement when awarding high-value placement deals. Fewer people are able to unlock that sustained interest. Or, as this article says, “You can’t just be showing matcha-Pilates-Alo.” What’s working now? Rage baiting and engaging the hate-watchers. If you’re pursuing brand endorsement deals, you’re feeling this right now. And if you enjoy a good scroll, this trend might be why your favorite creators are trying to make you mad. (Alternate Apple News link to the story above.)