Kindness vs Assertiveness

I was the second last to leave work today. I was supposed to leave earlier but couldn't. The only other person was the company CEO (here from Asia). Everyone says he's horrible to deal with because he just "doesn't understand".

I remembered how the marketing manager complained last time that she had to wait till 7:30, just to drive him to the station. And how she has to pick him up in the morning.

So today, before I left, I wondered, "Do I have to drive him to the station since there's no one else here?" Then I thought that if I offer once, it'd be expected of me. I reasoned that if I was in another country and wanted a lift to the station (which was a reasonable 20 minute walk), I would ask. I wouldn't wait for an offer. Or I might just decide to take the walk and not rely on other people. (I mean, I used to walk 25 minutes to one job every day and that didn't kill me.)

I said good bye to him (as innocently as possible, like I was completely unaware that I should offer him a lift) and left. His face didn't show happiness.

Since that moment, all the way up till now, I have guilt prickling at my conscience. What if this act of kindness would've put me in a better light with him? What if this extra effort would've been noticed and rewarded? What if he needs to fire someone and he'd choose me because I didn't offer him a lift? What if, what if. It's driving me crazy.

A similar thing happened last Friday at work. During a meeting, I had a question at the back of my mind that was on the verge of slipping into darkness. Then there was a pause in the conversation and I was about to ask that question before I've forgotten it completely, but Eve beat me to it and asked something else.

Instead of waiting for her question to be answered, I asked my one. So one of the managers answered my question, completely forgetting about Eve's. I didn't mean to interrupt her, but it just rolled off my tongue. I was going to fix this by bringing attention to Eve's question but then the managers wouldn't stop talking. They talked for so long, Eve's question became irrelevant.

When we got back to our desks, I kept thinking that I should apologise to her for cutting in. But imagining her laughing and saying, "I didn't even realise!" and thinking I was too sensitive stopped me. I left without mentioning anything. It still bugs me a little because Eve has been so wonderful to me and I don't want her to think any less of me.

These two incidents made me think - is it better to be extra kind, risking having people take advantage of you or being more assertive and accidentally making others uncomfortable?

(Of course the right answer would be to have a balance, but in practice, it's not that simple; one is always more on one side than the other.)