Founder of The Giving Keys, Caitlin Crosby On Pregnancy, Going From Musician to Entrepreneur & Working Towards Solving Homelessness

Bright and vivacious (also, THE warmest human, not to mention a total badass) Caitlin, the founder of The Giving Keys (a company that employs people transitioning out of homelessness), is following open doors! From singer-songwriter to entrepreneur (plus philanthropist and mom too!) she chats about pregnancy with her second (literally days before she gave birth to Love Sheridan Benward), growing up with ‘female’ health issues, plus her mission to spread positivity & passion for ending homelessness. @caitlincrosby @thegivingkeys

Current state of mind?

Glad I made time to journal yesterday to get my mind straight before giving birth this weekend. I am intentionally trying to stay positive & faith-filled.

How are you feeling on your due date?!?

Exhausted and run down. Working to fight off getting sick (again).

What was your path to pregnancy?

I had dealt with a lot of ‘female’ health issues growing up, so much so, that I’m writing a book about it (stay tuned!) Therefore, based on my experience, I thought it would be extremely challenging to get pregnant, but fortunately, it only took us a few months of trying.

As an entrepreneur, how do you anticipate taking maternity leave given your important role at Giving Keys — what will the day to day look like?

Though I’m technically giving myself three months maternity leave, I’m likely going to check in with the team over email at least once a day. It’s hard not to worry about stepping away, but I will have to force myself once the baby comes. Also, I’m planning to delete the email option off my phone, so I won’t be tempted to check them on the regular and instead create dedicated time for email.

Do you think it’s important for your kids to grow up with their mom working and running her own business? Do you think this will positively impact them?

It’s a concept I think about often. While I am proud of the work I do with The Giving Keys in spreading positivity and fighting for an end to homelessness, I have seen how the time away (and the mental distraction) has negatively affected my son. I’m working on shifting more of my time & focus on him and the upcoming baby. I don’t want to look back and regret missing so much.

What has been your experience with the community both online and off in motherhood + pregnancy?

Oh! Honestly, it’s one of the perks of motherhood! The bonding with other mothers is SO deep and beautiful. To be able to have this unspoken connection through our shared experiences is priceless.

How do you manage running your company and momming?

With nearly three years of trial and error, I still feel “off balance.” However, I plan to continue fine-tuning and trying new schedules to better meet my responsibilities on both ends.

On how you launched Giving Keys and what’s next for the company?

Ten years ago, in another lifetime, I launched the company accidentally while on tour as a singer-songwriter. I started making the key necklaces engraved with empowering words and selling them on tour. When the necklaces began selling out more than my CDs, I took notice. Meanwhile, I met this young couple, living on the streets inside a dumpster and had my “aha moment” to hire them to engrave the inspirational words on the keys. Within a short period, they saved up enough money to get their own apartment. Since that first hire, we’ve been able to hire over 120 people who are working to transition out of homelessness. It’s powerful to work towards real change. Next, we’re designing and launching additional products while trying to sell as many necklaces as possible to get people off the streets!

Any rituals you’ve had throughout pregnancy?

I go to prenatal yoga twice a week at Wellbourne Lifestyles, bounce on a birth ball, plus, I use an obscene amount of lavender essential oil.

Oh, and because of my insomnia, it’s become a “ritual” of mine to beg my husband to wake up with our toddler in the morning. As life would have it, I almost always fall asleep just as he needs to get up!

What does a regular day of eating (plus, any cravings) look like to you?

In short, I eat like a toddler because often it’s easiest to eat whatever my son is having. This includes an unhealthy amount of his goldfish, plus cauliflower pizza, and endless Ceaser salads (mainly for the croutons).

What’s the first thing you want to eat post pregnancy?

Sugarfish raw sushi and spicy tuna crunchy rice!

What’s one thing you do every day no matter how short on time you are?

Cover my son Brave in kisses. Plus, check my email an ungodly amount of times.

Your go-to pregnancy style?

Not maternity clothes. Because other than Hatch, most maternity clothes are neither fashionable or cool. Therefore, I mostly bought Larges or XLs in cute dresses and hope that I’ll want to wear them post-pregnancy…the verdict’s out on whether that will actually happen or not!

If your pregnancy were a song what would it be?

How Sweet It Is To Be Loved By You

How are you planning to recover or care for yourself after birth?

I’m trying for a V-BAC but obviously will go for a C-section if need be. In which case, my husband will have to be extra hands-on with my toddler as I likely won’t be able to pick him up for a while (which makes me sad!). I plan on going for tons of massages at this place near my house called Spa Le La. It’s brilliant, they watch your kids while you get pampered!

Do you think it’s essential for women/moms to take time for self-care?

100% or else you’re taking care of your kids while running on empty — that inevitably will lead to burn out. It’s essential to know your limits and take time to recharge.

Sex while pregnant?

Well, truth be told, it’s not my favorite, but my husband still wants to, so I rally! Although I have to say, I’m more keen as of late since it’s known to be a labor inducer.

What is one tip you have to share for keeping it all together?

Journaling, taking walks, praying, and giving yourself the grace to be imperfect and messy.

Advice for women who are embarking and motherhood and running a business?

Make sure you’re clear on your priorities. Plus, ask yourself what you’re willing to miss out on, from all sides.