In the post, the Guelph, Ont.-native shared two side-by-side photos of her and her one-year-old daughter, Lemmie Lynn.
On the left side, the body positive advocate cradled newborn Lemmie in a grey sports bra and shorts set. On the right, Landry shared a recent photo of her kissing her youngest on the forehead as she got Lemmie ready for daycare.
On the second slide, the influencer posted an adorable photo of Lemmie in pink and white checkered pants and a denim jacket. She smiled for the camera beside a purple backpack with a citrus fruit print.
In the caption, the "Papaya Podcast" host opened up about the "guilt" she feels when sending Lemmie to daycare.
"I don’t have a beautiful caption to go with this but I’m going to give an honest one. This is hard. This is exciting. And it’s brutal and filled with guilt and self-questioning," she began.
The social media star also revealed that she often doesn't know what to as a parent.
"It’s going with and against my gut at the same time. I don’t know if this is the right thing. I miss her already. I want her to have friends and social time. I also just want her with me. I thought when we signed her up it would feel like she was a big kid ready to go but she feels like a newborn in my arms right now. She feels so new and so little and yet so big and so eager," Landry wrote.
The self-love advocate finished her caption with explaining how the first drop off went, and that as a parent you have to trust your instincts.
"She didn’t cry. I did. She just blew me a kiss and walked away. (I am both relieved and devastated by that). Nobody writes books for this stuff. Maybe they did. I don’t know. We need words for the absolute silliness of trying to figure out what the right thing to do is and having like 45 different ways to do the right things," Landry concluded. "I guess we never really know. So we just have to assume we did alright."
In the comments, fans sympathized with Landry's feelings and tried to virtually comfort her.
"Oh my heart Sarah. This. I felt this so hard. Hugs mama," commented a follower.
"She is just so sweet. Sending a big hug to you both. I started back at work full on last week - it’s never easy to be apart from them," wrote a fellow mother.
"Ah mama I feel you! How is she old enough to wear a backpack?! Precious thing!" shared someone else.
"My heart! Happy first day Lemmie and Sarah!" added a fan.
"Aw where does the time go?" an Instagram user asked Landry.