Does anyone send monthly progress updates to friends?

I've heard from a lot of entrepreneurs that investor updates keep them accountable. Recently, I just started sharing a "personalized" version of these updates with my close friends -- I'm now building #monthli to productize this. I've only just started, but I've found that it's been helping keep me accountable + feel closer to my friends.

I'm curious if others have any experiences in the positive or negative. On the negative front, it can feel a bit "braggy", feel like it's a chore, etc

I do it occasionally through some Telegram groups I'm in with friends. For example, I share my gym progress with @levelsio @jelmerdeboer @flowen.

Business-related updates I share within some groups as well, including WIP. I actually built a feature called Product Updates for this specific purpose. It's still lacking in functionality, and therefor not widely used but I do 100% agree with the potential of sharing periodic updates.

As for it feeling "braggy", I really think it depends on who you share it with. If they share the same goals and it's a two-way street then it should be okay. For example, sharing my "new benchpress record" is fine in my gym group since other people are sharing as well. However, to share that in WIP, where people don't tend to share that kind of thing, might come across as braggy (although perhaps not with my records 😅). The other way around is true as well. Sharing my revenue numbers in WIP is acceptable, but sharing with non-maker friends is not-done.

I started sharing updates with a few friends last month. On Sunday evening I'm sharing my progress and plans for next two weeks. Mostly to hold my accountable on a long-term view instead of daily progress. Also to keep in touch with them in a non-smalltalk way.

Until now I only got positive responses. Only negative part for me is to actually sit down, think and then write an eMail that makes sense 😄😅

One and a half year ago I was working on a product called Mbassador (a LinkedIn for best friends only). I made a list with my close (business) friends and emailed them once a month with an update. After 8 updates I figured out I was writing for them, but instead I wanted to write for myself... and give them access to my journal. That's when I povited and changed Mbassador into; a journal for founders & makers.

After I figured this out I didn't send out any updates anymore. So, my monthly update was a positive experience after all. But not in the sense that I would recommend it to others, not for close friends or anyway. If you're building a startup and want to inform a business network and early-stage investors, sending out monthly updates are quite common.