Day in the Life: Jessie Deschane

Day in the Life: Virtual Assistant Jessie Deschane | Ever wonder what a typical day is like for a side hustler Virtual Assistant? Now’s your chance! In today’s Day in the Life series, Jessie Deschane shares the ins and outs of being a part-time Virtual Assistant, while also working a full-time job, from start to finish. Enjoy!

Hiya & happy Wednesday! Today’s Day in the Life guest is my very own Virtual Assistant, Jessie Deschane!

Fun story of how we started working together: She signed up for my email list and replied back to one of my emails with a super heartfelt email sharing how much she loved my content and a few questions she had about starting a business.

I replied back and offered to hop on the phone with her to give her a few tips (a perk of being on my email list, I offer free coaching calls, woo!)

We chatted and it was a super great call. Flash forward to a few months later when my business started blowing up and I was like “JESSIE HAAAALP ME” and the rest is history!

Proof that replying back to people’s email newsletters can grow your client list 😉

We even got to meet up in real life a few months ago when I was in Chicago. So fun!

Day in the Life: Virtual Assistant Jessie Deschane

So happy to share her day in the life. Hope you enjoy!

Want to be featured in the series? You can check out the guidelines and how to submit here. I’d love to feature you!

Day in the Life: Jessie Deschane of

Hey, hey! So happy to be sharing my Day in the Life post with you. I’m a Wisconsin-native that fell in love with a boy on Instagram and moved to Chicago in January of this year. I work full-time as a (dog mom) community manager for a Chicago startup, run my own lifestyle blog AND just started my virtual assistant/business manager business a few months back. And fun fact – Brittney is a client of mine!

For this post, I chose a random day where I didn’t get to spend as much time working on my business as I would’ve liked, but that’s just how it goes sometimes! You’ll see that my life pretty much revolves around social media (I even talk in #hashtags sometimes) and I love it.

5:30 am

Alarms go off. BLAH. Worst part of the day, IMO. I’m notttt a morning person, but Ben (the boyfriend) has early personal training clients, Cora (the golden retriever pup) wants to go outside and I am on a workout program so I need to get in my workout this morning.

One fun fact about the day, though … it’s Ben’s 29th birthday! 🎉 So I get up, get ready, help with the pup and give him his birthday card (covered in donuts, of course).

Day in the Life: Jessie Deschane

6:00 am

Get to the train. Usually I’m already at the gym, but they’re doing work on my place again today (I haven’t had gas for over a week …) so I help Ben get all of Cora’s stuff packed up and walk back to his place before walking to the train. I listen to a new book on Audible on my walk/train ride.

Day in the Life: Jessie Deschane
6:30 am

Gym time! It’s pretty busy today, so I do my workout out of order (and quickly), but at least I get it in.

Day in the Life: Jessie Deschane
7:30 am

All done with working out and getting ready. Thankfully I didn’t get super sweaty today because I forgot a bra so … strappy sports bra it is!

Day in the Life: Jessie Deschane
I walk to Starbucks, get a coffee and sit down to get a *tiny* bit of work done. My new habit is to be out of the gym by 7:15 so I can get to SB and work for a solid 30-45 minutes before work, but today was a bit rushed. I check Asana and my Google Calendar quick for client work (I have some stuff due for Brittney this week!), make a quick update to my new website (which is ALMOST done!) and then schedule social posts for my San Diego Recommendations blog I published. And, let’s be honest, I also take some time to write a huge, mushy birthday post for the BF on Instagram.

Day in the Life: Jessie Deschane

8:00 am

Work time! I’m a community manager at a local start-up full-time, so I work 8-4:30 M-F for now. It’s a pretty cool gig, although we’re growing SO fast, so we’re all on top of each other. Thankfully we move to another building in August!

I spend the first 45-minutes of work eating, going through emails and digging into the community. Usually, the first hour of my day is managing our Facebook Group that is growing like crazy. Since it’s a user group, I have to look up every person to make sure they have an account. I also approve posts (we get a lot of spammers) and make sure nothing went crazy for the few hours I was asleep. We also have our Marketing Stand-up meeting every day at 8:45, so I get in on that. My colleagues on our general channel on Slack ask for a Cora update, so OBVIOUSLY, I give them what they want.

Day in the Life: Jessie Deschane

Being a Community Manager is interesting – it’s a lot of “hurry up and wait” and a lot of checking in on off hours so sometimes my days run a little slow. It’s a cool place to work and I love my colleagues – but my long-term goal is to work entirely for myself.

9:15 am

Realize I haven’t opened Hootsuite yet (whoops). TBH, I hatttte Hootsuite, but it’s what the company has right now until I convince them to use another product. I also spend some time getting a geo-filter added to Snapchat to be approved for our Boat Bash on Friday. I spend the next couple hours bouncing between Hootsuite, Slack and our FB group.

Day in the Life: Jessie Deschane

11:00 am

It’s storming like CRAZY outside and I’m a little worried about lunch (working out in the AM makes me so hungry). We get free lunch every day (#StartupPerks), but I’m not a fan of what we have today so I’m hoping this rain lets up in the next couple hours. I’m also tweeting back and forth with Freshbooks because one of my payments hasn’t transferred over. I swear, I’m ALWAYS ON SOCIAL. (P.S. Please be nice to brands on social – it’s just people like me behind the computer trying to help you!)

12:00 pm

Meeting with a designer who created new social media images for Twitter and Facebook.

Check out a Day in the Life of Community Manager and Virtual Assistant, @jessiedeschane! #ditl #dayinthelife Click To Tweet

1:00 pm

Right after my meeting, I walked down the street (it stopped raining for a second thankfully!) and grabbed Roti Mediterranean Grill. Fun fact: the last time I was here, I was meeting Brittney in person. 🙂

Day in the Life: Jessie Deschane Day in the Life: Jessie DeschaneOnce back at the office, I popped down at my desk and ate while taking part in #ChatSnap – a tweet chat for Snapchat.

2:00 pm

Jump from #ChatSnap to #SproutSnap. Sprout Social is a local social media management company that I love and go to for all of my social media questions/needs. Today’s tweet chat was on how to brand your business on social. I also take a quick break to post an Instagram post for the company as well as one for my puppy’s Instagram (CAN’T HELP IT).

Day in the Life: Jessie Deschane

3:00 pm

I’m yawning like a crazy person, so I search for another Diet Mountain Dew. I also take part in a small video shoot that’s happening in the kitchen for our party on Friday (slow-mo hair flip for me!)

4:00 pm

New product update blog post is up! We’re currently not working on any type of schedule when it comes to blogs and product updates, so I have to go with the flow with these. I get one from the team and the afternoon is open for social anyway, so I get that out on all our channels.

4:45 pm

Walk to Sprout Social for the #CMXCHI panel on the “ROI of Community.” My friend from a previous job works there, so she took me on a tour prior to the panel.

Day in the Life: Jessie Deschane
7:00 pm

Learned lots of fun stuff, but got out of there a little later than I wanted and was STARVING. Hopped on the train back home, walked to Ben’s apartment while simultaneously ordering Thai food from my app (#multitasking) and helped him grab all of Cora’s stuff to bring BACK to my place. He has a roommate that doesn’t like using the AC, so we tend to stay at my place more often than not.

Day in the Life: Jessie Deschane

8:00 pm

After scarfing down our Thai …

Day in the Life: Jessie Deschane

… we decide to order ice cream from Cone on Postmates because 1) it was Ben’s birthday and 2) he didn’t want to leave the couch. We paid $17 for this …

Day in the Life: Jessie Deschane


We shared the sundae, hung out with Cora and watched three episodes of Parks & Rec.

10:30 pm


Day in the Life: Jessie Deschane

Most nights I work on my blog, my business or my clients’ work, but today was a bit off because of Ben’s birthday so I got it in in the morning before work. That’s the hassle, I guess, of having a side-hustle. Some nights I have hours to work on things and other nights I can’t focus on my work. If you love something, you will get it in when you can, but trust me … I can’t wait until the day I can be full-time in my own business! For the time being, we’ll make it work. 🙂

Day in the Life: Jessie Deschane

Jessie is a community manager by day and solopreneur by night, morning, weekend, lunch hour, etc. She works with her clients to be the organized and creative partner that they need for their businesses. From content creation to creative direction to social media management to brand and business planning/execution, Jessie is here to help you make your dreams a reality!

Follow her: Website | Instagram | Pinterest | Blog | YouTube

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  1. Emma

    August 3rd, 2017 at 8:20 am

    So this is the first blog I’ve read on Brittney’s website and I really loved it! I really like reading “a day in the life” blog posts or watching these types of videos on YouTube, and I love how it’s broken down by hour with plenty of pictures and REAL LIFE thoughts from Jessie. It’s actually inspiring to read these quick posts about you both working together/how you networked and how simply reaching out to people is important and can get you places. I also loved how Jessie really let everyone know what exactly she was doing for work and for her side business. It’s definitely OK to have days that don’t always go as planned or are different than normal, but you sound like you’re “on it” no matter what.

  2. Brittney Lynn

    August 3rd, 2017 at 10:14 am

    Hi Emma, nice to have you here! I totally agree, not every day goes to plan (really does ANY day?!) which is the entire purpose of the series…sharing real days of entrepreneurs, side hustlers and more. Glad you enjoy the series!

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