Sparing feelings?

I found myself in a situation today and I keep thinking over it, trying to figure out if I could have done or said anything differently, and if I did, what would the outcome have been? To be able to paint the picture I have to start by explaining briefly what I do:

I am currently a Recruitment Consultant and a key worker for my company which is an alternative to education for 16-19 yr olds. In normal circumstances, my role is mostly maintaining relationships and sourcing new referrals to be able to get new pupils enrolled on our study programme. After they have their interview, I also hold their 2 week induction (and many other bits in between, but those are irrelevant for the story).

However, as we do not find ourselves in normal circumstances due to obvious reasons, my role is a bit different now as I find that on top of my normal duties, I have added responsibilities. These have mostly come from the fact that most of our staff has either been furloughed or let go, thus leaving me, my manager and the tutor to oversee the smooth running of service. Needless to say there is a lot of pressure when you are overseeing cca 60 teenagers in between 3 people, but it is also incredibly rewarding when the students do their work and achieve their goals. Not to take anything away from their graft, but you also cannot help but feel a bit like you deserve at least a small tap on the back. Plus, I can never say I am bored when I am working, which for me is a dream as I cannot deal with not having things to do. Lastly, my team mates are awesome, so overall we are smashing it despite the workload which is great.

One of my duties is to personally drop off work (once/week) to those pupils who do not have access to the online teaching platform for some reason or the other. This is all safely done, as I put their work via their letter box, and they leave their completed work on the doorstep for me to pick up.

Today, however, unlike any other day, I have been communicating with either the parents, or learners face to face when going to drop off their work because they were either out already, or they 'forgot' to leave the work on the doorstep. At one particular household the mother was already out, and when she saw me coming, she immediately rushed inside to bring her child's work.

-Honestly, I most times feel like the debt collector when I do the pick-ups and drop offs. Or like in one of those western movies where the whole town runs indoors when they see the bad cowboy coming down the road with that typical Western movie soundtrack playing in the background ( https://www.youtube.com/watch?v=AFa1-kciCb4 ). -

She then comes out and because I do not want to be awkward and seem like the most impersonal person ever, I ask 'How have you been?'. She says that OK, but that she is eager for things to go back to normal as she is now very bored (she is furloughed). Because I normally want people to feel understood, I then proceed to say 'Yeah, I understand what you mean...', then she looks at me and says 'Oh really?' and as if something got a hold of me, the only thing I could bring myself to say was 'Yeah, well I find I get bored, because...I don't work...It's changed. I'm always at home.......working...' the mother: 'You have less to do.'. As if I did not dig myself a big enough hole already, and I actually thought she was throwing me a life rope I said 'Yeah.........' slowly realising I have downplayed the hard work we have been doing these last few weeks...

Anyways, she seemed more reassured, maybe she thought, well at least she is not the only one not doing much, and I guess I feel OK because at the end of the day I did no rub it in her face that I am working and she is not (not that that's how I feel, but that was my main concern when I started blabbing nothing because she caught me off guard, I did not want to hurt her feelings). However, I cannot help but feeling a bit annoyed at myself that I downplayed all the hard work, and overtime we have done these last six weeks to ensure our students have access to the outstanding education they signed up for. I feel like I have let myself down a bit. Obviously seeing the results coming from the learners is the reward and what matters at the end of the day.

Does this happen to anybody else though? And if so, how do you handle it? I do not find it happens often to me, but when it does I do spend a lot of time thinking if I have actually done the right thing by sparing feelings, or if I should have just said it like it was...? I guess there is a time and a place for everything.