“I wanted to write a book that would help other women avoid the terrible experience I’d had.” —Allyson Downey, founder and CEO of weeSpring and author of Here’s The Plan (Photo credit: Allison Hooban)

CEO Dishes On The Pregnancy (And Work) Advice No One Tells You

Marie E. Oliver
PowerToFly
Published in
7 min readApr 11, 2016

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Allyson Downey dreamed up the idea for her fast-growing startup weeSpring — a social shopping website that gives honest advice on baby products — after a particularly stressful trip to Babies R Us before the birth of her first child. Now, the CEO and mom-of-two has created something new for moms to cheer about. Her book, Here’s the Plan: Your Practical, Tactical Guide to Advancing Your Career During Pregnancy and Parenthood, covers everything from how to announce your pregnancy at work to hiring quality childcare. We asked Allyson to give us a sneak peek into some of her best tips before the book debuts at the end of this month.

At the start of your book, you talk about how in your early 20s “pregnancy and parenthood seemed a million years away.” If you could go back in time, what’s one piece of career advice you would give yourself?

In all honesty, I feel like I got some pretty great early career advice from the women who were around me — and it’s a big part of why I landed on my feet after getting nudged out of my job. [Editor’s Note: Read Allyson’s book for more details on how her Wall Street investment firm reacted when she requested to work from home for medical reasons during her first pregnancy.] I’ve always been a relentless networker; I love building relationships and making new connections. What would probably surprise most people who know me is that I’m a little bit of an introvert, so “networking events” aren’t my thing at all. (I hate them, in fact.) I’ve built up my own network simply by connecting people with each other. At this point, I almost feel like I have muscle memory for it: when I meet someone new, one of the first things I think about is whether I know anyone who could be helpful to them.

And because I’ve invested so much time and energy and effort into helping make connections for other people, a ton of new connections come my way too.

So that’s my best advice for women early in their careers: be generous with your relationships. (And keep track of who you know!)

You mention “little things you can do to smooth your path” prior to the birth of your baby. Can you share some of your top examples?

One really simple one: write down what you’ve accomplished. Do this every week; schedule 15 minutes toward the end of the day on Friday. Women spend so much time worrying about what we haven’t done that we forget to celebrate what we have done.

And while part of this exercise is about acknowledging your successes, it’s always a powerful record to have when it comes time for your performance reviews. You’ll have a list at your fingertips of all your contributions to your company’s success.

You write a lot about the lack of adequate paid leave in our country. Why do you think it’s not a bigger issue in the upcoming presidential election?

While I wish it was a bigger issue, I’m not discouraged. I have a theory that we’ll see a lot of parallels in the path to paid family leave with the country’s legalization of gay marriage. It’s already started with a handful of states, New York being the most recent. I also believe that private industry will be a major driver, signaling to elected officials that attracting and retaining women is good for their bottom line — not a drain on it. We’re seeing a virtual arms race right now, with companies trying to outdo each other to become the most family friendly workplace. Just in the past year, we’ve seen Netflix, Vodaphone, Etsy, and almost countless others trumpet the generosity of their paid leave packages in news releases.

As a founder and business owner, can you give some examples of how you ensure your company culture and policies support mothers before, during, and after their pregnancies?

Our team is 100% virtual (including two PowerToFly team members), and we really keep meetings to a minimum. I hired people that I knew were self-starters — motivated, driven women who were personally invested in doing great work.

And because we have that culture, I don’t spend a lot of time worrying about whether someone is getting her job done; I just trust that she is.

So everyone works on her own schedule. We have a couple of regularly scheduled meetings that everyone comes to, but otherwise, everyone has full freedom to do their jobs when and how they want.

You included a personal story about how you were treated during your pregnancy while working on Wall Street. Do you think a lack of diversity, especially in leadership, contributes to a cycle of discrimination?

I’m not sure you can draw a clear line between a lack of diversity and discrimination, but I think that if you aren’t focused as a company on inclusion, you’re going to wind up losing a lot of really talented people. I heard someone say recently, “Diversity is being invited to the party. Inclusion is being asked to dance.” I just think that analogy is so illuminating.

And that culture of inclusion needs to start from the top: it isn’t enough to hire a pool of people who might look different from one another. I’ll keep beating at this analogy: if you’re the host of the party, it’s your job to make sure everyone is having a good time.

If you’re leading a company, it’s your job to make sure everyone is empowered to succeed.

What is your advice for women who are trying to decide whether or not to stay in the workforce after having kids?

This is such a prickly one, because I by no means want to discount the choices made by women who want to focus on their children. Every choice is a valid choice.

That said: while your tiny newborn baby needs you tremendously, by the time your kid is five, she’s going to have her own full time job. (Elementary school.) Hiring a caregiver or paying for daycare can be cripplingly expensive, but if the financial impact is the biggest factor in your decision making, know that it’s probably more expensive to miss out on five years worth of promotions and raises. And if you do decide to take time off, keep your foot in the door. Try and take on a little consulting work to stay connected with old colleagues, stay abreast of what’s going on in your industry, attend conferences. Make sure that you don’t disappear fully, because it’s so hard to reclaim your old relevance.

There are a lot of misconceptions about women who work from home with kids. How has remote work allowed you to work smarter?

For me, it’s really more about flexibility. I have an office in downtown Boulder, and I go there most days. But that’s a personal choice, since I’m the only person from weeSpring who goes to that office — and on the days that I know I’ll be more productive at home, that’s where I work.

When I lived in New York City, I was losing at least an hour of my day every day to my commute. That’s basically two extra workdays a month! I also love being able to structure my days according to where I do my best work: I’ll often schedule calls for the morning and do those at home (while occasionally doing mundane household tasks, like prepping veggies for dinner). I go into my office when I want to be 100% focused on my computer — when I’m writing, or answering email, or pulling together a proposal.

I think if more companies embraced that flexibility and empowered people to work (with accountability, of course) on their own terms, they’d see a surge in productivity.

Isolation in new motherhood is something you mention again and again. Can you talk about the community you hope build with the launch of this book?

Isolation is such a big issue for new mothers, particularly new mothers on maternity leave. There’s a real loneliness that too few women speak up about, which leaves the women who are feeling lonely even more isolated. And early on in pregnancy, you’re not supposed to tell anyone that you’re pregnant, so that can leave you feeling really alone as well.

What I set out to do with my book is give women a sense of community by showcasing just how common these feelings and experiences are. So if you’re feeling guilty about leaving work at 5pm, or you’re not sure when to talk to your colleagues about your maternity leave, you can turn to the 50+ women I interviewed for the book to hear their wisdom and stories.

What inspired you to write this book? Was it something you always wanted to do? Or was there an ah ha moment?

It’s a little of both: I got my MFA in fiction writing from Columbia right after college, so I always thought I had a book in me, though I would have guessed then that it would be a novel. But when I had my first baby, I had a horrible experience with pregnancy discrimination. I had always prided myself on being tenacious and unstoppable, so I was the last person I would have thought would find herself sidelined.

The “ah ha” moment came a couple years later, after I started weeSpring. We had this thriving community of new and expecting parents, and a friend who works in publishing suggested that I write a book. And it almost came to me then like a lightning bolt:

I wanted to write a book that would help other women avoid the terrible experience I’d had.

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Marie E. Oliver
PowerToFly

Editor, writer, freelance journalist, mom x 2, living the dream in LA (not L.A.)