Rhea Drysdale
10 min readMar 15, 2016

Over the summer I visited my grandmother for the first time with my 2-year-old son. She was happy to see him. While there I could barely stomach lunch, so I decided to share the news, “I’m pregnant.”

Her response was unforgettable, “What are you going to do with that?”

After my initial shock, I pointed out that she was the mother of six children to which she said, “yeah, but I was a stay-at-home mom. You have a business.”

Her honesty was refreshing.

I’m a 33-year-old CEO of an internationally recognized digital marketing agency, and I just had my second child. Like most parents, I soon realized not to expect congratulations when announcing your second. When I shared the news this time, replies included, “wow, did you want to have another?” “I don’t how you balance everything, that’s why I chose to stay home and be there for our children.” And, “Oh… Congratulations, I guess.” (The latter was my mom — thanks Mom! At least she now has the granddaughter she’s been requesting since before I graduated college.)

With my first pregnancy, in true CEO fashion, I discussed the decision with my team and potential hires knowing this would be a company-wide commitment with just four employees at the time. I didn’t expect to get pregnant the first month my husband and I tried and neither did my team. We did.

I knew it was going to be hard, but Marissa Mayer, had just announced her pregnancy and started her new position as Yahoo’s CEO. If she could run a Fortune 500 as a pregnant CEO, certainly I could with a much smaller team and on my terms. Sure it’d be rare, simply being a woman CEO in 2012 put Marissa in a group with just 19 others — there are only 23 today. Unbeknownst to me at the time though, it was also about to be the season for leaning in, so I was on trend. (In reality I was just a workaholic entrepreneur who wanted to show my kids the value of work.)

Six weeks into my new “condition,” the reality of being a pregnant CEO hit. I was nauseous all the time and exhausted on a level I’d never felt before. Gone were the late nights networking in hotel bars after a conference and all-nighters to polish a client deliverable; my body demanded that I pass out by 9pm or suffer the consequences. To make matters worse, I couldn’t breathe! I’m known for being outspoken and talking fast, but I’d find myself gasping for oxygen a minute into a presentation. Words would fail me; I’d motion to my laptop and forget the word opting instead for, “rectangle, grey thing.” I was clumsy and frequently injured myself, once I dumped an entire cup of tea in my lap at the office.

This was not the picture I’d had of a strong, capable pregnant CEO tackling the world. It wasn’t what my team had imagined either. Fast forward a year and during one employee’s exit interview, he told me that he wished he’d had a chance to work with Rhea before kids. This new Rhea was somehow less than — not a full professional, not fully entrenched in the industry, not fully attentive to my marriage, not fully attentive to my pregnancy, and certainly not attentive to myself.

I felt lied to.

How come no one talked about this? There were jokes and movies scenes, but the reality of pregnancy (and parenthood!)… it was like a giant conspiracy; everyone had left so much out! I needed to apologize to every pregnant woman I’d ever known.

I decided not to let up on my schedule in part due to the understanding that many women leave their jobs or are pushed out during pregnancy. The rest of the reason is that I love to work.

I traveled to conferences, grew our team, rebranded the company, moved offices, and was honored as part of 40 Under 40 just three months into my thirties. Somewhere in there we bought our first home, got a new car, and took pregnancy classes. We rallied and got things done and it was only possible through the teamwork and support of my colleagues, family, mentors, and friends.

Mistakes were made along the way of course — I cancelled more morning meetings than I’d like to admit and I still worked late nights. But, I was proud of how much I’d done and simply regretted not doing more.

Then my son came three weeks early and I learned a humble lesson — I wasn’t in control. I couldn’t control my traumatic labor, my son’s hospitalization in the NICU, the blood infection that put me in the hospital nearly sepsis, the oversupply during breastfeeding that left him screaming in pain, the five weeks of recovery I needed to walk without discomfort, and the post-partum anxiety (PPA) that made me fear for my child’s safety at all hours.

No one and no research had prepared me for that.

Once we made it through those first couple of months the realization of how much support we needed sunk in. We had no family in the area and few local friends in a similar stage of life.

My son went to daycare early, because I had to return to work. We tried a flexible schedule at first, but the thing about owning a business is, the company needed me. Our marriage was strained when we had to question, which one of us would stay home with a sick baby (an infant’s immune system in a child care environment bring colds and flus home monthly for the first year and wracks up untold costs in healthcare and missed work).

I still traveled, but it wasn’t like before — I was hauling bags of pump parts, bottles of milk, ice packs, and sterilization bags with me. I pumped in Penn Station, conference closets, airplane bathrooms, and offices. I did what I had to, no matter how difficult, and I cannot begin to describe how rewarding it was. Thank you to the conference organizers, flight attendants, airport employees and TSA agents, hotel clerks, conference facilities, waiters, clients, and fellow travelers who gave me ice, travel tips, refrigerators, and a smile that said knowingly, “you’re an amazing mom, do your thing, I’ve got your back.” I’d survived the first year as a breastfeeding CEO through the kindness of strangers.

That year was a blur of sleep deprivation, sickness, and testing our personal limits.

And then there were two…

Somehow, we decided to do it all over again!

How work happens now.

I’d like to admit that pregnancy was easier the second time, but it wasn’t. The second pregnancy was much worse physically and has come with a slow recovery. The birth itself was much more rewarding, which I needed for my own mental health (something anyone who has been through a traumatic birth can attest to).

It’s been a little over four weeks since I gave birth to our baby girl and I’m back from leave, working an almost full-time schedule. We’d planned on a longer leave and even hired an interim CEO, but after just four weeks it feels like I was gone too long. There were pre-existing factors that came to a head in strained, remote communication damaging the business, company morale, cash flow, and our growth plans. While it’s been stressful and not what I’d had in mind, I learned one key lesson — my company needs the best of and a more accountable me.

The biggest difference between being a pregnant CEO and a pregnant employee is that you don’t really get leave as the CEO. Perhaps some have figured out how to take it, but two births in and I’m still nowhere near figuring it out. The team is twice as large with much more complexity and many more needs. Maybe if we’d not grown so much I could’ve handled it better, but I’ve never been very reasonable in that sense. Taking leave from an eleven-person team proved to be much different than one half its size.

While things didn’t turn out as planned, leave always provides an invaluable opportunity to take a deep look at the company, our culture, and my own accountability with lessons I’ll be growing from for the rest of my life. There’s something to be said for preparing for your departure and seeing how things operate or how quickly they breakdown in that absence.

Leave Lessons

Here are the top lessons learned from this pregnant CEO’s leave, which can be applied to any owner or manager preparing for an extended leave of absence from their business:

Question your culture. Company culture will show in your absence and if there are holes, negativity, a lack of accountability, or other, it will shine through. What you think you’ve built versus what has actually been built will soon become apparent. Try to have a clear understanding of this in advance and work to make company-wide and personal corrections if your perception of your company’s culture differs from reality.

Make sure everyone knows when and how to come to you. I failed miserably at this. Part of the reason was suddenly needing to be back in the business for financial reasons, but also because I was frequently switching devices, apps, and hands based on our breastfeeding and bedrest situation. I couldn’t work from the laptop easily so I relied on email or social media for communication, but my team worked best in Basecamp and Slack. Email felt too formal and social media was too casual. I personally didn’t want to put Basecamp or Slack on my phone for fear of being brought into too much. It was a cluster of terrible communication.

Put a system in place to receive positive news, not just the fires. You will quickly find yourself in a mind space of putting out fires rather than feeling confident and excited by your team’s ability to handle things. If you have a system in place to receive positive news about your team and the work, you will feel much calmer and happy. So will others.

Ensure you have solid cash flow. (And make sure you don’t have a change in CFO responsibilities during your leave!) Make sure your accounts receivable look solid and there’s good business in the pipeline. In fact, personally check your recurring transactions to make sure every invoice is scheduled, every payment will be processed, and all of the accounts look good.

Grow your team with sufficient time to onboard them. Working hard to staff the team in preparation for leave is fine, but every new team member will change the dynamic of the group and each hire comes with their own training needs. Give yourself a cut off, so this doesn’t happen too close to or during your actual leave.

Take your leave. If you’re going to be “on leave” commit to it fully or your team will be very confused and possibly freaked out, especially when you suddenly stop by. It’s very disconcerting if you start appearing, but everyone is working hard to honor your absence.

Don’t return to the same role. This is an opportunity to take a close look at what you enjoy and excel at as well as what you detest and should probably have never managed in the first place. Accept this gift and make a change, your team will thank you for it and the company will grow from it.

Having a child is a choice, but it’s also vital to the future of the human race, our country, and our own geriatric needs. Putting my decision on my team wasn’t easy, but I saw it as part of life and they know I’d do the same for them (and have). Every other developed country in the world understands the importance of children and honors and mandates this special time with good benefits and leave policies for parents. Many companies are starting to embrace better benefits and policies leading the way when our government has failed to simply keep pace.

At Outspoken Media, we decided we weren’t going to wait for the US government to catch up; we needed to offer better benefits today. We worked to intentionally shift our digital marketing agency away from a predominantly young team (the oldest employee at a similar agency was 28) to a lifestyle-driven, high-performance agency made up of experienced professionals. We needed to attract more qualified professionals, regardless of age, and while we couldn’t compete with big city salaries, we could offer great benefits — benefits, I wanted to use, too!

So far our little team of eleven has been able to return three mothers to work after the birth of their children where 43% percent of moms leave their jobs after birth. Perhaps the most absurd and common question I received as a pregnant CEO (both times) was, “what would I do with the company after the birth of my kids?” While I understand that leaving the business was an option, it never entered my mind. My business was not as casual as my unhealthy Sunday brunch and Netflix binge habit. The company wasn’t something my team or I could afford to lose and I may not be the person I was before birth, but I know I’m a much harder worker today and significantly wiser.

For the women reading this who don’t know whether you want to have children, but aspire to be in a position of leadership, please know that it’s possible. It’s hard and you will lose a lot in the process, but you can still hold onto the things you value most.

Rhea Drysdale

Outspoken Media, CEO; addicted to growing things like companies and humans