Woman Wednesday Issue #37

The Assist Newsletter
September 13, 2022
Woman Wednesday

Name that Woman Trailblazer: American photographer, musician, vegetarian cookbook author and advocate, animal-rights activist, who was born on 24th September 1941. “The real you” of music icons like the Rolling Stones, Jimi Hendrix, the Beatles, and Sir Paul McCartney are among the stars that her own eyes and those of her camera had captured throughout the years. She was the muse behind “Maybe I’m Amazed”, and “My Love” just to mention a few songs by her ultra famous husband.

👉 Click here to reveal this woman.


Meet Jessica Chessare 👋


Jessica Chessare


I’m Jess, an avid mental health advocate, aspiring world traveler, dancing queen, crime junkie, lifelong learner, and resource for my humans.

I currently live in the beautiful city of Chicago (yes, the actual downtown part) and work at a logistics-technology start-up (Loadsmart) as a People Operations Generalist.

🔗 Want to connect with Jessica? Say “hi” on LinkedIn and Instagram.


Need Some Motivation?


Bonusly motivation gif

Motivation is a crucial component for employee engagement and overall success in any organization.

So while it’s normal for everyone’s motivation level to dip from time to time, it’s a real problem when you and your team are consistently uninspired and disengaged.

That’s why we’re sharing 20 of our favorite ways to increase and sustain motivation in any workplace with this free download:

  • ✨The single thing that will boost motivation for 70% of employees
  • 🙌 Low- and no-cost ideas to effectively motivate your team
  • 🧠 Exactly why these methods are so powerful

Get motivated


Jessica’s Secrets


Q: How did you get into your current role/industry?
I will be honest, I struggled when I first started college. The idea of selecting what I was going to do for the rest of my life at 18 really stressed me out, and I ended up changing my major 3 times before deciding to leave my dream college to move back home and attend community college until I felt confident in what I would be majoring in.

Once I completed my general eds, I began attending North Central College in Naperville, IL. It was here that I stumbled upon personality psychology and fell in love with it. Thanks to a wonderful professor, Dr. Karl Kelley, I was introduced to the beauty of statistics and I/O psychology.

I’ve always struggled to make decisions, but statistics taught me that there is a way to utilize data to make better decisions. Coupling this idea with I/O Psychology, or the science of human behavior in the workplace, I realized my dream job was to help people LOVE their workplace.

Fast Forward to today and I am very proud of my career thus far and the experience I have gained from the companies I have worked for.

I was reached out to by a recruiter on LinkedIn to interview for a role with Loadsmart where I met our Director of People, Catalina, and Sr. HRBP Laura. Laura and Catalina struck me as the types of women I aspired to be, and I knew from then on that I wanted to work with them and build out an awesome People and Experiences Team at Loadsmart!

Q: What’s something you do to help boost your productivity?
A: I use color-coordinated calendar blocks and Sunsuma!

Every week, I set up my calendar and coordinate my tasks using the Sunsama tool. I ensure to block off time for projects I am working on, administrative work, email/slack, breaks, and “open calendar time”. My calendar is my life, if it isn’t on my calendar…it does not exist. I even schedule time to workout, eat, call my friends and family.

It sounds so silly but it really works!

Sunsuma is super user-friendly, I actually found it through The Assist newsletter! They have a 14-day free trial so you can try it before you buy.

I have tried just about every other task manager tool out there and this is the only one that has worked well for me. I could go on and on about Sunsuma so instead, I suggest giving it a try for yourself!

Q: How do you find work-life balance?
A: I take work-life balance very seriously.

I have burned myself out of a role that I loved before and since then I have taken steps to ensure I don’t do that again. I am lucky to work for a company that has a flexible PTO benefit, meaning there isn’t a set number of days I can take off in a year. I also utilize teamwork and delegating!

Sunsama does this really cool thing where it actually shows you a breakdown of where you spent your time each week. If I notice I didn’t have much personal time, or breaks, I will change up my calendar the next day to include the necessary breaks to stay productive throughout the day.

Something else I do is journal and go to therapy. I use my journal to do a self check-in to see how I am feeling. I will go back and reflect on these journal entries and take notice of my mindset. If I notice my mindset seems to be more negative, I make more time to do the things that I enjoy. I also think therapy is something everyone can benefit from, even when you are in a healthy state mentally.

Q: What’s the best piece of professional advice you’ve received so far?
A: There are three!
1. Don’t get caught up in a job title, especially when you are newer to the workforce. Job titles and duties differ from company to company. The ability to gain relevant experience and mobility are more important than a fancy title.

2. Protect your time and your calendar. In the age of open calendars, don’t be afraid to decline a meeting or ask for a different time if it doesn’t fit your schedule.

3. Never forget your WHY! Being a career oriented woman, it can feel uncomfortable doing something for yourself. Never forget that everything you are doing is for your WHY. I do what I do everyday so that I can have the freedom to do what I want in my “free time” (like take a 10 day Euro-trip 😊). 

Q: What’s your favorite software or app that helps with your workflow?
A: Sunsama!!! 

Q: What’s a book or podcast you’d recommend to a colleague?
A: A book I recommend is Atomic Habits by James Clear – a total game changer.

A non-self-help book I love and read over and over again is The Alchemist by Paulo Coelho.

For podcasts – I listen to all sorts of them, but obsess over True Crime. Morbid and Crime Junkie are my two favorites. 

Q: What do you like to do in your free time outside of work?
A: I don’t like to use the term “in my free time” because I enjoy living an active/busy lifestyle.

Free time for me is the end or the beginning of the day before my schedule starts. When I have scheduled “free time” it is usually full of different activities such as attending concerts, exercising, spending time with my family and adorable 5-year-old niece, traveling, hiking, or just beep-bopping around the city with my friends and significant other.

I love trying new things and exploring! Living in Chicago means there are endless opportunities to do just that. I am lucky to work for an employer that promotes work-life balance so I am given the time I need to be productive and enjoy the life I am building.

📓 If you don’t journal already, check out why you should make time for it.

Read about how to protect your time and calendar.


Old habits die hard — so try this 🤗


Sunsama banner

What helps with productivity (especially on a #nobones day)?

Having a foundation of good, small habits that add up to propel you forward — even when you have zero motivation.

Sunsama combines a digital planner with daily prompts that help you build good habits over time.

Try it for free today

P.S. Their Focus Mode is a game changer 👌.


Don’t be afraid to change!


When I first started my career, I was a perfectionist and felt like I was always trying to prove myself.

In doing so, I tended to bite off way more than I could chew and would put myself on an island trying to keep my “do/say” ratio above 90%.

I also was afraid to ask for help or admit that I didn’t know how to do something. I ended up burning myself out really quickly with this mentality, and my “do/say” ratio would fall.

Since then, I have learned that my biggest asset is my team and my ability to learn.

I changed my perfectionist mentality and over-communicated with my team. I always ask for help when I need it. I also am not afraid to tell anyone “I don’t know” or delegate a portion of a task to someone who already knows how to do it when on a tight deadline.


Our awesome partners help keep our content free 🥰


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📝 Need to put together an employee wellness survey? Check out these examples and templates.
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Know any go-getters? Send them our way.


Do you have a mentor, colleague, family member or friend who inspires you on a regular basis?

Give them some much deserved kudos and shout them out to our growing TA community.

Nominate someone here

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