Generosity Challenge: Bless the Boss

Simple Ways to Bless Your Boss (Because Generosity is Not Just for Those in “Need”)

Appreciating those we often take for granted

Bosses often have to be the bad guys. They deliver the soul-crushing news of a layoff, they take the hits when their team messes up.

With Michael Scott being the people-pleaser he is, I’m surprised he lasted so long as regional manager. Then again, he did spend a lot of the show blaming corporate and attempting to avoid responsibility.

(If you haven’t noticed, I like to include references from The Office in my Medium posts. To clarify, I love Michael and I am not hating on him. I am simply using him to illustrate a point.)

With that being said, here is the next prompt from the 40-day generosity challenge I have embarked on:

Today, we’re turning our generosity loose on bosses, managers, pastors and head teachers. Our culture doesn’t always bless upwards. But generosity goes all ways. We often only think to focus our generosity on those in dire straits, but when we bless upwards, we discover something that changes us, too.

Here is the first post detailing the beginning of my generosity journey:

Children (or their parents) are an example to us

I think elementary school teachers are the shining example of “bosses” who receive the sort of generosity that we can start to think of giving to others.

As a kid, I remember that around Christmas time and the end of the school year, I would go around giving gifts to each of my teachers. My mom is a school assistant librarian, and even though she’s not a teacher, she still receives an abundance of Starbucks gift cards and other goodies throughout the year from kind students and their parents.

So why do teachers receive so many gifts? I have a theory that it’s because parents recognize what teachers do for their children, which often involves a great deal of sacrifice––of patience, energy, and probably also sanity.

Parents know better than anyone what a thankless task it can be to take care of these children.

However, as these children get older, and go through high school and university, their teachers receive fewer and fewer gifts. Yet I would argue that those in charge of these students, who soon enter the workforce, still have a largely thankless task.

Okay, let’s pause here.

This piece is not about why bosses deserve gifts from us. It’s not a strict “give, give, give.” It’s not meant to preach that receiving gifts is somehow imperative.

I simply want to invite each of us to find a greater appreciation for those who have leadership roles in our lives. Whether or not it leads to an act of generosity, that appreciation and valuing of a fellow human being is the important first step (40acts).

We often take our bosses for granted

This is often the case for anyone in a position of leadership. When doing their jobs right (which I won’t claim to always be the case), bosses are the ones who look out for the wellbeing of their team. They make hard decisions. And as I mentioned before, they often have to do things that make them look like the bad guy.

It can be easy for those under them to take their decisions personally, or to want nothing to do with them outside of a professional context.

Often, this causes us not to see the hard work and thought that go into what they do.

It’s like when we were little kindergarteners and didn’t realize that our teachers had lives outside of school. But the fact is that our bosses, and others in charge of us, are also real people, with real lives and real feelings.

So now that I’ve rambled about why we should show generosity towards our bosses, here are some action steps.

Examples from my life

• I’ve been teaching ESL with a co-leader since January. A few classes ago he “assigned” our students to find their favourite donut flavour at Tim Horton’s. I decided to send him a gift card to Tim Horton’s, along with a note of appreciation about how I’ve enjoyed teaching with him and learning from him!
• I brought a couple packets of milk tea powder to church with me. I was planning to use one for myself, and the second one was to give to whoever I was prompted to give it to. When the boss of the team I volunteer on came in with a box of chocolates for all of us (that’s generosity right there!) I decided to offer her one of the packets, because 1) who can resist milk tea, and 2) milk tea is a blessing to anyone’s day. And then I gave the second one to my friend, who was also my boss during an internship I did last year. (I’ve got plenty more at home to enjoy myself.)

It can be that simple.

Also, I feel like I should mention: I don’t tell these people that I’m doing these acts “for a challenge.” Because that’s not the way I see it.

The challenge itself is not the end goal; it is the conduit of a journey that is about each individual stop, and about growing my own heart for others as I take the journey.

Each time I open a new prompt, I get excited. Because here’s a new opportunity to get creative with generosity, and hopefully brighten someone else’s day just a little bit!

Generosity is something that starts in the heart. As today’s prompt says:

Gratitude is about much more than money. [It is about] our attitudes, desires, and behaviours (40acts).

Action steps for different areas of your life

From today’s prompt

• Thank the boss. Take a moment to start the work day letting them know they’re appreciated by those around them (specifically you).
• Leave them a nice note — and talk to one of their friends and see what kind of gift card you could slip in there too.
• Take them out for a meal, bake them a cake, or give them a voucher for a meal.

My ideas (for a covid context!)

• If you’re living with your parents: Next time you’re out buying yourself a coffee or a little snack, think of your parents who might enjoy a little something to break up the monotony of home life
• For pretty much anyone: Online gift cards are a thing! Most of the big chain stores have them, and you could also get one for a food delivery service. You can even send them with a digital note attached––great choice during a pandemic!
• For a boss: Write them a LinkedIn recommendation. I’m personally not on LinkedIn (yet) but it seems like a big deal in the professional world, and besides boosting their mood, this could also boost others’ opinion of them and… future prospects? (idea from Careerstone Group)
• For a professor: Write them a good review! I’m not sure if profs actually read these (these posts tend to either speak very well of some profs, and very negatively of others). But think about it: these “rate my prof” sites are public, and anyone can go in there and look at students’ opinions of any particular prof. It can only mean good things for the prof if there are a few uplifting reviews in there.
• For a prof, boss, or any other leader: If you see them in person, take time to thank them for what they do, and give them a specific piece of encouragement about something you personally appreciate about them. If everything is virtual, shoot them an email or text. EVEN BETTER, which especially applies to the student context: after lectures or other online classes, profs often stay on the call for a few extra minutes if students have questions. Stick around and tell them your encouragement “in person,” because that will mean a lot to them! And it could even lead into a longer conversation where you get to hear more about their life, and get to know them as a person (because remember, they have a real life and real feelings!)

Okay, that’s it for this post on blessing upwards: bosses, parents, teachers, and beyond! Not that the poor are worth any less (“downwards”), but we have a tendency to attribute directions and hierarchies to people.

This is just to say that all people can be recipients of our generosity! Not dependent on THEIR worth, but based on OUR OWN heart posture.

If you’re interested in joining the 40-day generosity challenge, it’s never too late! You can find the prompts here.

Note: the prompts at this link may be in a different order or have different content from what I’ve been posting, but any opportunity for generosity can be a good one.

Here is my post on creating a generosity fund: