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A Survival Guide to Balancing Pregnancy and Your Career

The fact that women can grow human beings is literally a miracle. Women are incredible, and I’m so glad I was able to experience being pregnant. But if we’re being real, pregnancy was also one of the most difficult experiences in my life. Balancing growing two babies at once while going through a worldwide pandemic was stressful to say the least. I’ve put together some tips below to help pregnant women balance their career while also embracing this exciting time in their lives.

Members of the CloudApp team skiing
Skiing with the CloudApp crew while Iwas 5 weeks pregnant

GIF of my parents finding out I was pregnant
Telling my parents Iwas pregnant

Embrace remote work

Almost immediately after getting a positive pregnancy test, severe morning sickness kicked in and I was miserable. If remote work is an option, I would highly suggest taking advantage of it on the days when the first (or second or third) trimesters are overwhelming.

Picture of Maile Waite working from home
Working from home during my first trimester

Minimize meetings

We could all use less meetings in our lives. Our motto at CloudApp is “Skip the meeting, send a video instead”. But especially when pregnant, it is important to maintain energy and be as efficient with work as possible. Try blocking out chunks of time on your calendar to focus on projects. You can also encourage coworkers to send screen recordings or screenshots instead of booking meetings on your calendar.

Maile Waite ultrasound picture of twins
My first ultrasound- we were shocked to see twins!
screenshot of gender reveal balloon popping
Baby A is a girl!
screenshot of gender reveal balloon popping
Baby B is a girl!

Optimize your calendar

After finding out I was pregnant, one of the first things I did was add key dates and to-do items to my calendar. I marked down a tentative date for my baby shower, the time frame for completing my baby registry, my 20 week mark, when to start taking a sleep training course, when to get CPR certification, and a tentative date for starting maternity leave. This may seem too in-depth, but I wanted to make sure I wasn’t letting anything fall through the cracks. Your future self will thank you for the planning!

Maile Waite working from home while on bedrest
On bedrest and working remotely- at this point Iwas getting daily IV fluids and was DONEbeing pregnant

Prepare early for maternity leave

One of the most important ways to balance pregnancy and your career is to focus on preparing for maternity leave. After I found out I was having twins, I started preparing for the possibility of an early exit due to preterm birth. Here are my top tips for preparing for maternity leave:

Document processes using video

The number one tip I have is to document your processes with a screen recorder. It helped me save a ton of time that would have otherwise been spent typing out processes. I was able to quickly record videos while I completed my daily processes and save them in a document for other team members to reference or use for employee onboarding.

Meet with your boss about maternity leave logistics

One of the first things I did after finding out I was pregnant was to sit down with my boss and make a plan. I told him the ideal date I would start maternity leave, as well as the contingency plan in case of preterm labor. We also discussed benefits and the company maternity policy (a good rule of thumb is to make sure to get this in writing). It gave me peace-of-mind to know that we were on the same page.

Make a to-do list

I had a lot of projects I wanted to complete before I left on maternity leave, but I made a list of the most crucial ones in our project management software. This helped me stay prioritized and focused.

I went in for a routine ultrasound at around 33 weeks and was told I needed to have an emergency c-section that day. Because of my upfront planning, I was able to focus on my health and babies instead of stressing about leaving work so much sooner than I anticipated. In fact, I was able to get my work to-do list completed literally within a couple of days of going into preterm labor.

Maile Waite in a mask in the hospital
A selfie in the hospital to document pregnancy during the pandemic
Maile Waite's baby Hailey in the NICU
Hailey Waite
Maile Waite's baby Madison in the NICU
Madison Waite

Document the experience

Though I was miserable for most of my pregnancy, I am so glad that I took the time to document. It’s a life-changing experience that I will never forget and I cherish the memories, even the difficult ones. My girls were in the NICU for nearly a month and it’s amazing to look back and see how much they changed during that time. I recommend snapping pictures or taking videos often!

Maile Waite pregnancy announcement
Babies Madison and Hailey Waite

Build a community

One of my favorite parts of being pregnant was building friendships with other women who were moms or expecting mothers. I found a specific group of incredible women on Twitter who also had twins and were in marketing. I reached out to them and received amazing advice and words of encouragement. If you don’t know where to start, try looking for a local group for moms on Facebook.

Maile Waite with her cats recovering from a c-section
Taking a nap with my cats between pumping sessions

Utilize tools

I am super grateful for all the helpful tools I was able to use to make both my work and personal life easier. Here are some of my favorite tools:


Decrease meetings and create processes much more quickly


Easily create, organize, and assign tasks to coworkers in one place

Google Photos

Store, access, and share photos easily

Google Calendar

Keep track of meetings, events, and important dates

Google Tasks

Create to-do items with due dates

Command E

Easily find G Suite documents, Asana tasks, and more


Maintain sanity by finding the perfect playlist to have in the background


Virtually attend meetings from your couch

Marco Polo

Keep friends and family in the loop during pregnancy, even while social distancing

Maile Waite with twin girls

What’s next for me

Mom guilt is a real thing. If you return to work full-time, you feel guilty. If you return to work part-time, you feel guilty. If you stay at home full-time, you feel guilty. Sometimes it feels like a lose-lose situation. But I really believe that whatever is best for you is best for your kids. I know plenty of women who have decided to do any combination of those choices and they are all amazing moms.

CloudApp was incredibly supportive of whatever decision I chose to make, and they were very clear about that from the beginning. I always planned on coming back because of the awesome company culture, the amazing people, and the fact that I love my job. Because of the pandemic, I was planning on working remotely and having my mom help out with the babies. But a couple of weeks into work after maternity leave, I realized that right now I need to focus on my babies full-time. It was one of the toughest decisions I’ve ever made, and I am going to miss CloudApp so much.

I will still be using CloudApp on the daily because I’m low-key addicted to screen recording and taking screenshots, and I hope to be a regular contributor to the blog in the future. I will also continue to provoke Michael and Joe on Twitter because old habits die hard.

Screenshot of CloudApp team meeting on Zoom with Maile, Joe, and Michael
Marketing team meeting with our newest (tiny) team member

GIF of a CloudApp team meeting featuring Maile's baby
Distracting coworkers with cute babies since 2021

GIF of CloudApp screen recording featuring Maile kissing her baby
When you work remotely, every day is bring your daughter to work day!

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