I’ve been writing for this blog for about two years now. It’s been interesting to learn how readers view the boss. Many people who comment are the boss, some want to be the boss, and others just have an opinion about the boss.

I started my business when I was 22, and I was as naïve as anyone. I now have about 100 employees, and my guess is that over the years I have had 300 or 400 call me boss (and a few other things). As of today, my average employee has been with me for nine years, which makes each and every one of them far above average. I can tell you one thing with great certainty — what it’s like to be a boss is not something you can fully appreciate until you have been one. The trials and tribulations, the joy and grief come in all different shapes and sizes. As do the dilemmas.

Paul Downs, my You’re the Boss colleague, has written about the boss’s struggle to weigh profits against kindness. That really stuck with me — because I would like to think of myself as kind, but I also know that, as the boss, you sometimes have to do things that others will perceive as unkind. The problem is, there is often a surprisingly fine line between being kind and being kind of stupid or irresponsible or naïve.

Unfortunately, that fine line isn’t always black and white, but it’s what separates the bosses from the civilians and it’s something I have struggled with many times. Over the years, I have had to reconcile what it means to be a kind boss and a good boss. Being a kind boss doesn’t necessarily make you a good boss. I am going to give you some real life examples of issues I’ve wrestled with, and you can all play St. Peter and review my list.

Here are some things I’ve done that I think of as kind:

1. Lent money to employees who found themselves in a bind. I’ve probably done this 200 times, and I almost always get paid back. I’m happy to have been able to help. Contrary to the cynics out there, most people do not abuse the privilege.
2. Guaranteed several car loans. Please note that I guaranteed the loan; I did not co-sign. There is a big difference. I am responsible if the employees don’t pay, but I am not on the title, which would be very bad if they got into an accident — a lawyer’s dream. But my guaranteeing the loan can be the difference between their paying 6 percent interest or 20 percent or even more. I have done this for people who have been with me for more than 10 years, and again, I have been happy to help. When I changed banks, it was one of my considerations – not all banks will do it.
3. Bailed a couple of people out of jail. Did you know you can be arrested for sleeping in your parked car after you have been drinking if the car keys are in the car? This happened to a model employee who’d never been in trouble before (or after). Cook County jail is not a lot of fun.
4. Went to a local high school to talk to teachers about my 17-year-old employee who had an absent father and was being thrown out of school for missing class. Unfortunately, he continued to miss class and ultimately did get thrown out. This was 25 years ago, and there’s no happy ending. Sometimes you can change the course of a person’s life. Sometimes you try and fail.
5. Helped nine people buy houses. (Unfortunately, some of them probably wish they hadn’t bought the houses given the current real estate market.)
6. Gave people time to get their lives back together after they experienced one of life’s inevitable difficulties. How much time? That would take a whole post.
7. And of course I’ve given the usual array of baby gifts, awards, thanks, hospital visits, words of encouragement, support, parties and friendly smiles. Am I the kindest boss? Absolutely not. I don’t yell – but I also don’t ask people about their kids, their weekends or their vacations. It’s not in my personality.

Here are some things I’ve done that in hindsight I think were kind of stupid:

1. Let employees borrow the truck to move. I’d say there is about a 25 percent chance of their hitting something – mostly because they are not used to driving a truck. One tried to drive a 12-foot truck under an 11-foot viaduct. It cost $3,500 to repair. It came back almost like new – and it resulted in a new rule: Don’t ask so I don’t have to tell you no. Truck rentals are cheap enough.
2. Allowed a straight commission sales person who hadn’t been selling enough to go on salary because the person’s spouse had been laid off. Not kind of stupid. Stupid. I eventually had to fire the person because the sales just weren’t there. I was thanked with a fraudulent E.E.O.C. claim. It didn’t go anywhere but it wasted time, money and brain cells.
3. Hired someone’s son, someone’s daughter, someone’s friend, etc., etc. — even though they all had terrible job histories — because I felt the need to help out and give someone a chance. What’s my batting average? A perfect .000. Sometimes, it’s just so hard to say no. Maybe I’ll do it again.
4. Kept trying and trying and trying to get certain people to get their job performances up to a good level. We keep making excuses like, “They’re really trying,” “We could do worse,” “They’re so nice” and “They really need the money.” But the problem is, customers and co-workers deserve to work with people who are competent.

And in many cases, you really aren’t doing the poor performers a favor. Retaining someone who is failing — even with lots of training and support — does NOT make you kind. It probably makes you a bad boss if your definition of a bad boss is someone who doesn’t do what’s necessary for the health of the company. I’m kind of O.K. with that.

Jay Goltz owns five small businesses in Chicago.

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