If you were enjoying the last of summer and missed last week’s email on September dates to know, read or listen online. Several tax deadlines are coming up mid-month.

September is the time for deep thinking. In my business, we’ve entered peak 2025 planning season. 

In recent conversations, I’ve noticed some themes. After a few years of just trying to stay in business, we’re ready to make bets again. And that means taking an intentional look at where you stand today and where you want to go. What’s changed, and what do you want to do about it? 

Today, I want to share with you the change-driven questions that we’re evaluating.

I put this list in order from broadest to narrowest, but if it feels better, you can start at the bottom with the questions about you and work up to the big picture.

How has the world changed? How is it changing?

Your view on the world is a central part of your business design. What problems do you want to solve? What impacts do you want to have? What opportunities do you see? Are they fads or trends? Are you feeling generally optimistic, pessimistic, or neutral?

How have business conditions changed?

A year ago, many of us were firmly in Camp US Recession. How are you feeling now? 

The macro business environment affects all of us: taxes, political conditions, interest rates, competitive consolidation, access to capital, supply chains, and automation. What’s your outlook on the overall business environment in the next 12-18 months? 

If you haven’t played with any systems in the past two years, guess what? Software can do a lot more stuff, and it’s easier to use the tools you already have to standardize and automate. How does this impact you? 

Work structures have also changed. More people are taking on side hustles or contracting. Many of us want to work shorter weeks or more flexible hours. Remote work is now stable and established. Is it time to redesign how your company works?

How has my industry changed?

Did your peers go all-in on borrowing using cheap money, and are now facing serious cutbacks and reduced teams? Have they left a gap where you can compete for customers? 

Is your industry growing, mature, or consolidating? Maybe you were the new, hot thing and now everyone is copying you. Or perhaps your industry made 600 shows two years ago and now will make only 418. Understand where your industry is in its lifecycle.

Look at innovation and who has access to talent. Consider retirements, sales, expansion and consolidation. What’s the state of supply chains and availability of raw materials or inputs? Where are your competitors investing in technology, and is that useful? Would it make sense to buy someone else’s company, or sell yours?

How has my customer changed?

I hope this is the most enjoyable part of this process for you. This question is best answered by talking to your customers directly, which often opens the door to more personal connection. What are their personal goals? What do they wish they could do? Are they expecting more or less demand? What kinds of budget changes are they dealing with? Ask about leadership changes and outlook, and how you can help. 

If this feels awkward, watch Alex Carter’s TED talk with her tip on the two words you can say to get people talking.  

How has my business changed?

Unless you started in the last year, you’ve been through some things. Consider:

• How your goals and decisions from last year have played out 

• Team structure and support needs

• Cost changes and suppliers

• Gross margins for your flagship products

• Whether and how you want to grow

You know what’s working for you and what isn’t. What do you want to change? This is the space to think about everything you’ve learned and experienced, and use your data and financial reports to check your actual performance.

Ultimately, you have to feel great about showing up to your business every day. It’s still a job, but it’s one you can shape and bend your job to your vision of the world as it should be. Some things to think about: 

• Self-care needs

• Family needs

• Financial needs

• Physical / mental / medical health needs

If you don’t like where you are, change it. For some clues on where to start, revisit my Love / Hate exercise to organize ideas for restructuring your personal work to bring you more joy in the next 12-18 months. 

If you’d like support in thinking through these questions, or you’re feeling stuck, I’m happy to talk with you and help you organize your ideas. Schedule 20 minutes here. We’ll also dig into these in September’s AMA (details below).

Later this week, I’ll send out more specific information for those of you who might want to work with me and my team on your business design and strategic plan. If you want to get a jump on that, reply to this email with 2025 PLANNING in the subject line.

September AMA: All the Money Stuff

Our next AMA is Thursday, September 12 at 10 AM Pacific. Use this link to add the details to your calendar. You are welcome to invite friends -- they can register here.

Have a question for the AMA? Submit it here.

Media Kit 

USA Today: Workers are feeling Labor Day, and it may affect your upcoming travel plans. Thousands of unionized hotel workers across Hilton, Hyatt, and Marriott chains are currently on strike. Several airlines are also operating under threat of flight attendant walkouts. United Airlines flight attendants have voted to strike, which could begin as soon as three weeks from now. While American Airlines and Southwest Airlines have recently reached deals with their crews, Alaska Airlines also remains under walkout threat. Flights attendants are protesting large raises for executives while they are asked to work for free during preflight and boarding.

Blogspot: If you’d like to go down the academic rabbit hole on corporate lifecycles and valuations, check out NYU Stern professor Aswathan Damoradan’s blog. It’s his specialty and he’s a frequent podcast guest on the subject. Roll around in all the glorious data, charts, and graphs.

DAC Advisory: My tax accountant, DAC Advisory Services, published this excellent summary of self-employment taxes -- who has to pay them and where they might be lurking in your personal transactions. Keep an eye on your backyard farming and liturgical side hustles. 

Quartz: Is rosé passé? Sales of wine fell significantly this summer. Is this a sign of cost inflation, a general move toward health, or just the logical conclusion of six years spent slurping tannic pink stuff?