By: Andy Lesser, Owner of Caring Helpdesk, LLC
August 13, 2025
Running a business is a constant balancing act. You’ve got to manage people, processes, and expectations - yours included - without losing sight of why you started in the first place. The trick isn’t in doing everything for everyone; it’s in knowing what works, setting clear boundaries, and sticking to them. Success often comes down to consistency, fairness, and making choices that strengthen your team and keep your operations smooth.
The customer is not always right.
In order to run a successful business, you need to stay in charge of your process. Treating your customers with respect does not mean you need to bend your rules, compromise your values, or put your employees in bad situations in order to appease a customer. It is always okay to say "no" if you feel that it will benefit your customers, your company, and yourself overall.
Set rules.
It is absolutely necessary to establish guidelines not only for how your business operates, but for how your customers should navigate within that process. It is also necessary to establish firm understandings for what type of behavior is expected from your clients and staff, and what will not be tolerated.
Pay fairly.
Pay fairly based on what you charge your customers. Give bonuses. Thank your staff regularly. This is one of the most overlooked aspects to a successful and long-lasting business.
Do not expect to make more money every year.
Really. I know we live in a capitalist economy where the line is supposed to just continually go up, but it doesn’t need to, and it probably won’t. You can be very successful without making more money every year. Sometimes you might even make less, and that’s okay. As long as you’re doing well, your employees are doing well, and you’re continuing to provide great service and improve, you have nothing to worry about, no matter what anyone says.
Do NOT obsess over adding more customers.
Again, this is all about not obsessing over constantly growing your business, ESPECIALLY if you don’t have the staff OR if you simply don’t want to grow much bigger. Take a step back and evaluate before committing to more growth. You do NOT have to grow. It’s okay to stay the size you are.
Look for ways to provide more of what you do well.
Do NOT expand your business into too many areas or endlessly roll out new service offerings, subscriptions, or promotions. This is exhausting and annoying for customers, and actually can get confusing for your staff as well.
Commit to consistency.
The customer should know what to expect and get it each time, on time.
Always quality-check.
Make sure to have quality-check procedures in place for every single job. Do not skip this because whenever you do, it’s always the time you make a huge mistake.
Give credits.
Give new customers a first-time discount. Give credits when you make mistakes.
Do NOT overcharge.
Do not overcharge for services, add automatic margins over cost, or add hidden charges or fees to your bills. Do NOT bill for the time it would take for a human to do the tasks you're letting AI do in 15 seconds. Pass savings along to your customers! Personally check your invoices before they go out to ensure they look correct.
Hire right the first time.
Be almost too detailed in your job descriptions about exactly what your business does and does not do and what you are looking for. Do not oversell what your business does and do not overpromise. List your pay rate. You want the people you hire to know exactly what you do and to have exactly the right skills for the job. Make sure to assess their competence for the tasks during your interviewing process with real-world examples.
There’s no replacement for experience.
You just have to go through it. The failures, the 18 hour days, the customer threatening to call the Better Business Bureau because you didn’t answer their call at 2:00 am, or asking you to work for free on your wedding day. Until you have run your own business for a while, you don’t really know what it’s like or what it takes to make it successful. You can’t read your way to a good business.
Business ownership is not passive.
Despite what you might have seen on TikTok, owning a business is not going to be a passive investment. Even if you get it to a point where eventually you’re only working a few hours a day, successful businesses require an extreme amount of focus, engagement, and commitment on a daily basis, even when you’re on vacation. If you’d like to get moderate returns on an investment and you have some cash lying around, it would be better for you to just invest in the stock market and take that vacation uninterrupted.
Being aggressive and sociable will only get you so far.
You can try to emulate people you see on YouTube who claim to have multi-million dollar businesses, and that might work, but at the end of the day, most people value people who are authentic and empathetic. They want you to listen to their concerns and needs and they want the assurance that you will have the solutions that they need to solve their problems. The loudest voice in the room can be the most comforting, but it rarely is.
You don’t have to over-promote but you do have to promote.
Sure, you can spend tons of money to monopolize every billboard in town, and that might work for some companies, but it doesn’t work for most small businesses, and it typically is a giant waste of ad spend. The same goes for attending endless conferences, networking events, and Zoom meetings. When it comes to advertising your business, there is a sweet spot, and it is different for everyone. Don’t fall into the trap of spending way too much money and time on advertising, and don’t get complacent and forget to promote your business at all.
Learn who your advocates are, learn who your detractors are.
Every business and every person is going to have its advocates and its detractors. The earlier you can start identifying them, the better off you will be. Stick with your advocates. Make sure you value them as resources, partners, and allies for your business and make sure you thank them regularly.
Don’t use social media for personal posting.
Period.
Don’t talk about work 24/7 at home.
This one took me a long time to learn and I still struggle with it because when you work from home, your work can so easily blend in with your life. But try really hard to make sure your work isn’t your life. Try really hard.
Get all your financial, legal, and HR ducks in a row.
This is one of the most stressful parts of owning a small business and also one of the areas where you can end up having a ton of liability. Get this squared away immediately and regularly make sure everything is running smoothly. I cannot stress this enough. Try to make sure you have a decent amount of money in reserves to protect your business in case you have a large unexpected business expense.
Try to add 1 new skill you can bring to your business each year.
It’s amazing how this can start to add up over time, enhance the services you offer., and add to your expertise.
Do NOT talk about your clients or their businesses in public.
Confidentiality is absolutely key not only to operating a professional business but to establishing and maintaining the respect and trust of your clients and employees.
Keep your operating costs low.
If you can, try not to have a physical office space or too many “things” for your business. Try to keep your software, etc. to a minimum, only keeping whatever enhances what you do and saves you time.
Do NOT get stuck in the analytics trap.
Use analytics and reporting only when it truly benefits you (i.e., when you’re actually going to use the results right away for a real reason). Every once in a while, analytics and reporting can be a great value-add to present to a client for a progress report and can be useful in that regard to keep an eye on how your business is going more generally, but typically analytics are a waste of time and money, especially when you won’t do anything with the results.
Do not try to please everyone.
You are going to have strengths and weaknesses, both as a person and as a business owner. While you absolutely should work on your weaknesses, stay away from the trap of trying to make yourself and your business “work” for everyone, because it’s not going to. Be true to yourself and run your business the way you want to run it, and you will attract the clients who fit for you. Be upfront with prospective clients about how your business operates. You can even tell them it might not work for everyone. There’s nothing wrong with setting realistic expectations.
Do not be afraid to drop clients.
If a client is not the right fit for you or is a challenge for you or your staff for some reason, don’t be afraid to drop them. You may even want to have a pre-drafted form letter to send to make the process less emotionally fraught. Again, this is all about making sure you shape the business that is right for you and your team and build an infrastructure around you that fits you. Not everyone is going to be the right client for you, and continuing to put up with folks who are not the right fit will be a drain on you and your business.
A business built with intention has staying power. When you keep your standards high, treat your staff well, and resist the pull to chase every new idea or client, you create a foundation that lasts. Growth is great when it makes sense, but so is holding steady when that’s the smarter move. At the end of the day, it’s about building something you can be proud of - one decision, one process, and one solid year at a time. And you and you alone are the person who gets to define what 'success' means - what it looks and feels like.
To discuss your business goals, get feedback on your strategy, or vent about the struggles of small business ownership, book a session with Andy today!
Compiled by: Andy Lesser, Owner of Caring Helpdesk, LLC
August 14th, 2025
Government & Nonprofit Support (Hands-On Help Available)
Some of the most powerful business support programs are government-funded or nonprofit-run — and many of them are free.
SBA – U.S. Small Business Administration
Ideal for all small business owners, the SBA offers funding programs, legal compliance resources, free guides, disaster relief options, and local assistance.
SCORE
If mentorship is what you’re after, SCORE connects you with experienced business mentors for free. You’ll also find webinars, templates, and other educational tools.
Small Business Development Centers (SBDC)
Located across the country, SBDCs offer in-person consulting, training, and help navigating funding opportunities.
Women’s Business Centers (WBC)
Specifically designed for women entrepreneurs, WBCs provide training, funding guidance, and networking events.
Minority Business Development Agency (MBDA)
Tailored for minority-owned businesses, MBDA centers offer development programs, networking opportunities, and funding resources.
Training & Skills Development
Whether you’re brushing up on marketing or diving into business strategy, these platforms can help you level up your skills.
HubSpot Academy
Perfect for anyone looking to boost marketing and sales skills with free, high-quality courses and certificates.
Google for Small Business
Great for digital marketing beginners, this hub includes tools for ads, analytics, and improving your online presence.
LinkedIn Learning
Offers a vast library of courses on general business skills, leadership, and technology — often free with a library card.
Coursera
Affordable, university-backed courses that provide a more formal approach to business training.
Funding & Financial Tools
Finding capital doesn’t have to be overwhelming — these platforms make it easier to access and manage your funding options.
Nav
Helps you understand and build your business credit while matching you with loan opportunities.
Fundera
A one-stop shop for comparing loans and finding the best fit for your business needs.
Kabbage / AmEx Business
Offers flexible credit lines, quick approvals, and cash flow management tools.
Grants.gov
A centralized portal for finding and applying for government grants.
Community & Networking
The right connections can open doors — here are a few platforms to help you find your people.
Hello Alice
A hub for curated grant opportunities, business guidance, and peer networking.
NFIB
Advocates for small business owners while providing legal resources and policy updates.
Facebook Business Resource Hub
Offers tools, guides, and case studies to help you get more from your Facebook and Instagram marketing efforts.
Bottom line: These resources cover every stage of the small business journey — from learning and planning to funding and connecting. Bookmark them, explore what’s available in your area, and make the most of the free and low-cost support at your fingertips.