Ask Lindsey -Working at The DIY Playbook, Life As A Mom of Three, & More


Every month, I answer your questions right here on the blog with my “Ask Casey” series. You can find all of my past posts right here.

Today, I thought it might be fun to change things up and have my assistant, Lindsey, answer your questions! She has been working for The DIY Playbook for almost two years now and she is such a force behind the scenes. I’m so grateful for her hard work and also her friendship.

I asked for your questions over on Instagram a few weeks ago and you sent in some really great ones. Lindsey picked her faves and is here to share a bit more about herself.

Working at The DIY Playbook

Lindsey helping out with our makeover

How did you and Casey connect? What is your favorite part about working for Casey?

It didn’t surprise me at all that so many questions I received were asking about what it was like working at The DIY Playbook. It would be my first question too, give me all the behind-the-scenes scoop! I have been following the blog since almost the beginning, I used to call Bridget and Casey my Chicago besties to my husband, so he knew who I was talking about.

When Casey posted in the Summer of 2021 that she was looking for a virtual assistant, I immediately got my resume ready and sent it over as fast as I could. I don’t think I have ever been more excited about a job than I was about this one. (Note from Casey: Lindsey was the first submission I received. Less than 30 minutes after I posted about the job. Ha!)

Working for Casey is honestly a dream. It was definitely intimidating at first because I have followed and looked up to her for so long. What if she was this awful person in real life? They always say you never meet the people you look up to because then your heart will be broken learning who they really are, but I can say, without a doubt, Casey is even better IRL. She is supportive of being a working mom of three, cares about what I enjoy doing, and pushes me outside my comfort zone to do hard things, like writing today’s blog post!

It is so fun learning and watching Casey be a businesswoman and follow her dream. She has definitely inspired me to be more confident in my work and push my boundaries on what I thought I was capable of. I also have gotten the chance to do some amazing work, like helping with the Feel Good Makeover and I will be heading to Italy with Casey in April. Tyler, my husband, has worked with us a bit on SEO and he always comments on how awesome she is, so clearly, we are big Casey fans around here! Also, it doesn’t hurt that part of my job is online shopping for house decor!

Kansas City, Born & Raised

Kansas City favorites

What is life in Kansas City like? Sounds like it would be SO different from the Finn’s city life! Any favorite neighborhoods and spots in Kansas City?

We love Kansas City! It is definitely a hidden gem that is starting to get more and more popular with its affordability and culture, and it is great for both families and singles. We live in the burbs, but it is easy to get downtown and to different areas of KC. The traffic is nothing compared to larger cities. I love the cozy feel, because while it has the big city amenities, it also isn’t unusual to see people you know out and about. It feels like the city is one big club, we all support the same teams (Go Chiefs!) and midwest politeness is everywhere.

Kansas City is actually one city in 2 states, something that confuses most people. The city sits right on the Kansas and Missouri state line. If you see pictures of downtown Kansas City, that is actually the Missouri side. It isn’t abnormal for people to live on one side of the state line and work in the other, although it does make taxes a bit more complicated! While there is friendly banter back and forth on what side is better KS or MO, it doesn’t change the feel of it being one city.

As I mentioned we live in the burbs, specifically in the Northland on the Missouri side, which is growing more and more every time you turn around. We love to go down to North Kansas City on a nice weekend to hit up the parks, Chicken N’ Pickle, and the local breweries. If I am heading downtown I am typically heading to River Market to the weekend farmers market and I always make a much-needed stop at Bloom Bakery for a quiche lorraine.

For date nights, we usually end up in the Crossroads or Westport. They both have amazing restaurants and good nightlife – not that we do that too much anymore; 10 pm is my bedtime. If you haven’t tried Chewology yet I highly recommend it. You also can’t go wrong with having a group outing to Boulevard Beer Hall. If you like hole-in-the-wall bars, Jim’s is a great stop for an affordable beer.

Family Life As A Mom of Three

Sharing life as a working mom of three

How did you know you wanted three kids? Hardest transition 0-1, 1-2, 2-3?

Before having kids we wanted four children. Tyler comes from a big family and I have always wanted a house full of kids. Well, wouldn’t you know, kids are hard! After having our first we said, “Okay, maybe just three kids”. Then we had our second, and said “Yep, I think we are done.” We were then surprised with our third! Our kids are also pretty close in age. Our boys are 19 months apart and our youngest kids are two years apart. Yes, I had three kids in diapers of some sort at one point!

I personally would say the transition from two to three kids was the hardest for us. Our daughter is a 2020 baby, so not only was the pregnancy and birth experience completely different than my other two but also bringing her home was extremely isolating.

We had a newborn and two young kids, and a worldwide pandemic happening, and didn’t know how it would affect our babies if they were to get sick. We come from a large family (and an even larger support group), so not being able to have everyone around was difficult. Also, you are going from man to man to zone defense, and it pulls you in so many different directions! Life as a mom of three can be tough.

I ended up getting diagnosed with PPA and PPD three months after our daughter was born and got on meds right away. I am so happy that taking meds is becoming more normalized, but we still have so far to go in terms of support for moms after birth.

I was a full-time stay-at-home mom before having our daughter, but knew it wasn’t something I could continue for my own mental health and what was best for my family. That is part of what made me so excited to see Casey’s job posting because I knew it would be perfect for me! I am able to have a flexible schedule for my family, while also having something for me to pour into besides my kids, husband, and home.

Family Photographer

Lindsey's and life as a mom of three

How do I find a good family photographer in my area?

I have been doing photography on the side since high school and specialize in family photography. Photographers might be the best and worst clients to have. They understand the reality of trying to get a good photo, but they also have high expectations. When it comes to finding a photographer in my area, I always start with two methods. The best is to check out your friends and who you follow on social media for their photos. If you like someone’s photos, check out who took them and see if they fit your style and budget. If you still aren’t finding what you want head over to Instagram and search the hashtags in your area (Example: #kansascityfamilyphotography, #kansascityphotography).

I have to add this snippet for photographers everywhere: When you hire a photographer, you are hiring someone for their skill and art style. If you like light and airy photos, don’t hire someone whose portfolio is dark and moody, and expect them to change their style to meet your expectations. Also, realize that this is their business. They are charging for not only their time spent with you at the shoot, but also the time it takes to edit the photos, which typically takes longer than the actual shoot. If you see someone whose work you love, but you can’t afford them, keep looking. The price you pay for a photographer is seen directly in the work they produce!

Get out and start shooting!

Side Note from Casey: Lindsey wrote this blog post last spring with tips on how to take better photos using your phone. It has lots of details to improve your photography skills if you want to take your own.

Thank You, Lindsey!

A big thank you to Lindsey for writing today’s blog post. I’m so happy the Playbook community got to learn a bit more about her. Also, does anyone else want to visit Kansas City after those details she shared?! I think I need to plan a visit soon…

More Questions? Ask Away!

Next month, I’ll be back to answering your questions. You can submit yours using the form below.


The Year of Casey

Hey there!

I’m Casey Finn, the voice behind The DIY Playbook. I’m married to Finn & mom to Rory and Ellis. Together we’re creating our dream home in Chicago, one DIY project at a time.