Assurance Guest Blogger: Organize Spontaneity!

Blog ,

By: Tony Chimino

I’ve become a master at organizing my spontaneity – a complete oxymoron, I know. This is who I’ve become. As Assurance has grown, it seems I’ve got less and less time to be spontaneous. In fact, demands on my time are so crazy nowadays, it’s hard sometimes just to find the time to think and reflect. And this isn’t good, as I do a lot of foolish things and genuinely need time for reflection.

That’s why over the past two years, I’ve learned to organize my schedule in a way that forces me to do “spontaneous” things that’re important to me. It goes like this. Every Monday, I get to work at 6 a.m., which is early, even for me. From 6-7 a.m. I look at my calendar for the week and begin to schedule my “spontaneous” things. I keep a list of them at my desk so I know what to do. To give you a taste, here are the things I schedule time for:

1. Leaving birthday and anniversary messages for my employees
2. Walking around the building and talking to employees
3. Writing electronic “high fives” to employees who’ve done a great job
4. Talking to my spouse about how her week is going
5. Sending texts to my kids on random items
6. Leaving messages for clients to thank them for business
7. Calling prospects and setting up lunch and dinner meetings
8. Checking LinkedIn and other social media platforms
9. Thinking about the company and our current strategies

I know this might seem crazy to many of you, but literally this is the only thing that works for me. On my schedule each week, there are many 15 and 30 minute meetings that’re labeled private, allowing me to accomplish some of the above items. It’s relieved a lot of stress for me as I know I have everything organized I want to accomplish. Additionally, I do schedule in my workouts each week. If I don’t schedule these, they for sure won’t be done either.

My approach may not work for everyone, but I encourage you to search for a way to organize the small, essential parts of your week that don’t always make it on the calendar. Thanks, and have a great, organized and spontaneous week!


Assurance is one of the largest and most awarded independent insurance brokerages in the U.S. and a proud partner of Women in Manufacturing. As our monthly guest blogger, content from Assurance's blog that pertains to women in the manufacturing sector will be published regularly.

About the Author: Anthony (Tony) Chimino has been the CEO of Assurance for over ten years. His driving ideology for the company is a complete and dedicated focus on creating value for clients through business, benefits and risk management improvements.