
Updated for 2025: Practical AI & Business Moves
Entrepreneur lessons – At times, we need to give a little more thought to our actions as business owners, especially when it involves clients. Here are a few of the hardest lessons I’ve learned over the years. I hope they can save you a lot of time and misery.
### Be Careful Who You Surround Yourself With
I had a situation a few years back where I took a “friend” to an event because she was out of work and I knew there would be people there who could help her get back into her field. The VP of the company wanted me to ride with him to the event, and I sat in the lobby with her while he got dressed. When the VP came downstairs and was ready to go, she complained that her feet were hurting, and we were walking too fast. That was the first warning sign. We get to the event after the VP and I slow down for her, and she speaks to everybody, having a drink which leads to another and another. She gets drunk and I can hear her slurring her words and speaking loudly while I’m talking to colleagues on the balcony. That was the second warning. I pull her to the side and tell her, “You are drunk and you are talking too loud; bring it down a few notches.” She agrees, and 10 minutes later, she is even louder. That was the third warning. I am humiliated and embarrassed, and my client is being cordial but I can tell he is not impressed.
I opt to leave the event early just to get her out of there. As we leave, she goes for the final coup-de-gras and asks several people for their cards. I was mortified as they all lied and said they didn’t bring any cards. That was the fourth warning. We leave, and she takes off her shoes and is complaining about her feet again as we end up in a coffee shop, and she is now fully drunk. I couldn’t believe I invited her, knowing she had a drinking problem, but I was trying to help her get a job. The next day at another event, I had one glass of wine to try to relax after the mishap the night before, and I got tipsy myself. I usually don’t drink. Now I have made my own impression. While the client still does business with me, they have not invited me to any of their events since, and it’s been three years. I mentioned to her that she made a fool of herself, and I was trying to help her, but she told me I was overthinking it and that I should not care what the client thinks. She said she wasn’t that drunk.
Lesson Learned: I have a bad habit of always looking out for others, even to my own detriment. I should have escorted her back to her car and sent her back home when she complained about her feet and wanted the client to wait while she tried to maneuver in high heels that she couldn’t wear. All of this could have been avoided if I had stopped everything right there or not invited her at all, knowing her history. I have to take full responsibility for this grave error for trying to help a “friend” out. I put the word friend in quotes because we have to know who our true friends are. There are some people who act like they are your friend just to reap some of the benefits of your hard work, to pick your brain, and drain you. My uncle told me when I was a boy that you must always make sure you deal with people in just about every circumstance who have as much to lose as you do. That’s how you establish trust.
### Consistently Develop a Relationship with Clients
In my field, people call clients only when they want something. In the interest of their time, I have done the same. I was once told by a client that I only call when I want something. I was dumbfounded by that because I thought, what else would I call for? Then I realized that in the true art of selling, you should reach out to your clients every now and then to have a regular conversation. There is always room at the end to do a quick pitch, but you never want your clients to avoid your calls. I make sure I know my clients and I know things about them that we can talk about besides sales. In the long run, they greatly appreciate that. They know that you are there for business, but going the extra mile will put you miles ahead of your competitors.
### Take a Vacation
I rarely do this, but it is so important. The more you work, the harder it is to leave your business in the hands of others. You fear that they will destroy your business, but that’s rarely the case. Your business can survive for a few days without you, and the benefit is that when you get back, you are ready to take on your job with a new perspective, fresh eyes, and new energy. You can even take a mini-vacation in a nicer part of your city for a few days or somewhere close. With AI and automation tools, you can also ensure that your business runs smoothly while you’re away by setting up automated workflows and monitoring systems.
### Treat Yourself
Take yourself to lunch, a movie, or the museum once a week. If you are over 50, AARP has amazing coupon deals where you can try different restaurants and various entertainment functions. Whatever it is you like to do, pick a day to do it and do it alone or with another positive entrepreneur. In today’s creator economy, taking time for yourself can also inspire new ideas and creativity that can be leveraged in your business.
### Watch Your Accounting and Taxes
This is very important. Make sure your finances are on point. With AI-powered accounting tools, you can automate many financial tasks, ensuring accuracy and efficiency. This allows you to focus more on strategy and