3 hills I will absolutely die on

Small business owner edition

Author

Courtney Howard
March 25, 2026

In the March 2026 edition:

  • I usually choose my battles, but these are the small business hills I’ll die on ⛰

  • A series from one of my fave podcasts on “The Business of Black Women”

  • Art delivery! Contemporary art of all kinds, right in your inbox 🖌

Opportunities to be good neighbors this month: Help Missy at Crown Hill Farm raise money to replace her barn roof and keep her animals safe, and support immigrant and refugee neighbors with legal aid, employment assistance, and more by giving to Journey’s End.

SOMETHING USEFUL

3 hills I will absolutely die on

For the most part, I think people should do what works for them even if it’s not something I’d choose for myself. As I tell my 7-year-old son all the time, “Different people do things differently.”

But sometimes, particularly in the business world, I see something egregious being normalized and I think, not on my watch.

I saw this “hills I’ll die on” trend going around on social media a while ago, so I came up with some of my own—The Hills I’ll Die On: Small Business Edition.

These are my counter-arguments to common business scenarios and norms that I think are BS and need to be changed. Here are a few that are top of mind based on recent client conversations:

Your accountant works for you, and they should act like it

This goes for all professional service providers: accountants, lawyers, consultants (myself included!) If you hire someone to provide their expertise in support of your business, they should respect you as a business owner and valued client.

Too often, I’m seeing the opposite (especially now, at tax time). Between my own experiences and stories I hear from my clients, I’ve identified three types of problematic professional service providers:

  1. The arguer: If you dare to ask a question or try to clarify something, they become defensive, and possibly aggressive, so you let it go for the sake of de-escalation. You learn not to ask questions at all.

  2. The ghost: They’re never there when you call, there’s no response to your emails, and you’re left wondering if the work is going to get done at all.

  3. The baffler: They have expertise about a complex topic. But can they explain it to you in a way a regular person could understand? Nope.

    1. This one comes in two types: Condescending (acts like you’re stupid for not understanding) and benign (genuinely tries, but is incapable of simplifying complexity).

These behaviors are red flags. Accountants and other service providers should expect clients to ask questions, check in for updates, and confirm important details. Our businesses are our livelihood and we need to manage important projects even after we’ve delegated them.

Hiring a professional service provider should feel like a relief, but too often it’s just another thing to stress over. If this sounds familiar, it’s time to find someone new to work with.

Growth isn’t always good (and it might make you miserable)

Under capitalism, we’re told that growth is always the goal. It’s assumed that all business owners need to grow, whether that means adding more employees, opening new locations, moving to a larger space, or some other version of “more, bigger, faster.”

I’m not anti-growth. But growth isn’t right for everyone, and it shouldn’t be held up as an unquestionable sign of success.

Growth is really expensive. Yes, hiring people or adding more stores can lead to more revenue…eventually. But in the short term, you’ll incur huge costs long before you see any ROI (if you ever do). Got a loan to finance growth? Now you’re taking on risk, making yourself vulnerable to chaotic economic conditions and unforgiving lenders.

Beyond the financial downsides, growth can change your job in a way that you may not love.

Growing your team means more time managing and less time doing the work that led you to start your business in the first place. Adding locations or even buying a commercial building turns you into a property manager or landlord.

Before you invest or take on debt to fuel growth, clearly define your reasons and goals for pursuing it. Are there other ways to reach those goals? Are you ready to embrace the risks and trade-offs? Growth can become a serious problem if you’re not careful.

You can’t out-work a business operations problem

Even the most anti-hustle folks among us (me 🙋) can admit that sometimes, doing a lot of hard work is the only way to solve a problem. Running a business is difficult and there’s no shortage of things that need to get done, even when everything’s going smoothly.

However, there are problems that can’t be fixed by working harder. Your business may have fundamental operational issues that can’t be addressed by “rising and grinding.”

So if you’re facing a challenge (low sales, fewer customers, declining profits, administrative dysfunction, etc.) don’t immediately assume that the solution is working more, more, more.

  • Hustling harder won’t fix uncontrolled spending and a lack of financial management.

  • Longer hours don’t help if your customer experience is unpleasant and people decide to go somewhere else.

  • Sacrificing your nights and weekends won’t grow your revenue if your prospective customers can’t find you, or don’t trust you.

  • Pouring hours into creating a long-term strategy won’t get you anywhere if you don’t have effective systems and processes to act on that strategy.

So before you spend more time working in your business, consider improving the operational foundation of your business. A solid foundation makes a strong, sustainable business and protects you from burnout.

If any of these resonated with you, or if you want to share the hills you’ll die on, reply to this email. I read and appreciate them all! 💌

SOMETHING NEAT

This month on Vibe Check, one of my must-listen podcasts, hosts Saeed Jones (poet, Harvard lecturer) and Zach Stafford (journalist, author) are doing a fantastic series called “The Business of Black Women”. They’re interviewing Black woman business owners and professionals about their lives, work, and the state of Black business ownership across industries. Check it out:

They’ve been releasing these on Thursdays all month, so there may be a new one tomorrow! 👀

A LITTLE TREAT

Looking at art is calming and inspirational for my analytical brain, but I don’t often find the time to visit galleries or museums.

One simple way to get new art into my life is subscribing to “Art Delivery”, a newsletter from artist Danielle Krysa (AKA The Jealous Curator) where she highlights contemporary artists and shares creative prompts, projects, and advice. Even with just a free subscription, you get five incredible art pieces in your inbox every Saturday! It’s way better than the other stuff on your phone.

Krysa also has a great children’s book that my son loves: How to Spot An Artist: This Might Get Messy, and a book celebrating women artists that I love: A Big Important Art Book: Now With Women!

WORK WITH ME

This newsletter is for everyone, but a one-on-one consulting engagement is tailored to you and your business. Here’s how I can support you:

  • Strategic Action Planning—For solo business owners with a lot to do, and never enough time. We’ll refine, prioritize, and organize your goals, and I’ll create a road map for you to get them done. (My most popular service, now booking late April into May.)

  • Resilience Jumpstart—Turn analysis paralysis into decisive action with affordable 1:1 support to get you moving in the right direction fast.

  • Operations Analysis—Is your business built on a strong foundation? An operations deep dive will tell you exactly what to do to make your business work better from the inside out.

  • General Consulting—Get expert support with business challenges like workload sustainability, financial fundamentals, pricing, client communication, and more.

Thanks for reading—see you next month. If you have a business owner friend who would find this newsletter useful, please share it with them!