Getting Pregnant Was the Best Thing I Ever Did For My Company

The WITS ’17 Planning Team. Photo by the amazing Jason Seagle of Vayando.

Not long ago, I spoke at the Boston GLOW Career and Empowerment Conference in a session called “Startup Mama: How Motherhood Can Enhance (Rather Than Hurt) Your Entrepreneurial Career.” It was a session that I had pitched months ago when I had a three-month-old daughter. Yet even three months into parenting I knew it would be an important (and unpopular) opinion.

Just before I started my session, a woman came up to me and said, “This session is the reason I came to this conference.”

I was floored.

She went on to explain that the positive side of parenting while being an entrepreneur was almost never talked about. That all she heard was how awful it was — the gender gap, the sleepless nights, the risk.

Then, for Mother’s Day, the New York Post published an article that cited that 62% of moms report that flexible working hours was one of the top reasons for starting their own business. One commenter on Twitter pointed out that that number is likely far less for tech founders. I couldn’t disagree more.

I have preached a couple of times now about how the flexibility of entrepreneurship (and I will continue to defend this; if you run your own company you absolutely have more flexibility than if you are working for someone else in an office) makes parenthood not only easier, but more fulfilling.

But there’s one other reason why entrepreneurship is a game-changer for parents. And it has nothing to do with being more flexible.

It’s actually about being less flexible.

Attendees at the Women in Travel Summit, created and run by Wanderful. Photo by Jason Seagle.

As you may know, every year Wanderful runs the annual Women in Travel Summit (WITS). It’s a fantastic event with over 400 attendees in travel media, entrepreneurship, and industry who gather to talk about the future of travel and how we can use our collective voices to change travel for the better.

Last year, our event was held in the gorgeous Hilton Milwaukee City Center in Milwaukee, Wisconsin. It was our fourth year running the summit, and as we got the organizing underway we had just started to reach our stride.

That was until August of 2016, anyway, just a few months before our April summit would take place.

That’s when I found out: I was pregnant.

Not only was I pregnant, but my due date was the exact same week as WITS.

I still remember taking that pregnancy test and immediately running to my computer to calculate my due date. Then, with a weird mix of joy and panic, I began to map out all the ways I could make this work. I could rent an apartment in Milwaukee for a month and stay there in case I had the baby early. I could drive with my husband, plotting all of the hospitals along the journey from Massachusetts to Wisconsin. I could lead the entire conference virtually.

For the last three years of WITS, not only was I the head organizer and creator, but I was also the emcee, the key sponsor contact, the figurehead, and the woman who made sure the PowerPoints were working.

And now, I would be none of those things.

There was absolutely no way that I could travel to Milwaukee to be there.

I called the WITS Advisory Board, afraid of what they might say. Would they berate me for not having planned this better? Would they express concern on my behalf about what our sponsors might think?

When I told them my news, there was a brief pause. Then one of my advisors spoke. Here’s what she said: “Congratulations! Now you will know if your business can survive on its own.”

My advisory board was overjoyed — and not worried a bit. They said an entrepreneur’s best accomplishment was for their business to thrive without needing them, and this was my chance to see if that was the case for what I had built. They encouraged me to start thinking about what my team would need in order to run this conference, and highlighted the fact that I would be able to spend the entire year preparing them for what was to come. The only thing I wouldn’t be there for was the execution of the event itself.

The response from my team was less jubilant.

A very pregnant me + the WITS Planning Team having an early team retreat in March 2017. That team retreat set the stage for many more early team retreats to come, which resulted in much less stressful and much more enjoyable summits!

Of course they all sounded extremely happy for me, but it was easy to understand that they were masking a feeling of sheer terror. What would you do if your boss basically said to you, “hey, I’m out, good luck running this thing yourself”? What if that “thing” were a 400-person conference with some of the top voices in the industry?

I asked Marissa, who had had nearly every role on the WITS planning team since she started with us, to take over as our WITS ’17 conference director. I brought on Erin, who had been working as our brand relationships manager at Wanderful, to assume a supporting role to make sure we had enough hands on deck. And for the rest of the team, I asked them to step up. I have to hand it them — not once did they convey anything but confidence to me throughout the entire course of my pregnancy.

And you may not believe it unless you were there yourself, but this conference was outstanding.

At 40 weeks pregnant, I watched as the conference I had created three years prior ran itself. I stalked just about everyone on Twitter. I watched every single Facebook Live session. I was glued to my email, and every time my phone rang I leapt to it, wondering (hoping) if it was a member of our team needing me.

They hardly called me.

The WITS Planning Team taking charge at WITS ’17 in Milwaukee, Wisconsin. Photo by Jason Seagle.

The conference went off without a hitch. Attendees messaged me saying, “No offense, but this was the best conference yet.”

It was in that moment that I knew — we really had something.

We were more than fine. In my absence, the conference excelled. The team, initially wondering how they were going to pull this off, discovered a new-found confidence. They really could run this thing.

After WITS ’17 ended, I looked at them and said, “Why don’t you just do the same thing again next year?”

That’s how Marissa became our WITS ’18 conference director, our team became comfortable in their own skin, and how I ended up in an empty conference room in Quebec City just one day before our conference began. My job was to put up banners, get coffee for people, swipe my credit card and sometimes talk on stage. I was no longer needed for the big stuff.

It was a dream come true.

The WITS Planning Team back together again for WITS ’18 in Quebec City, Canada.

There are few occasions in the world when you can throw your hands up in the air, tell your team, “Sorry, but I can’t do this — you’re on your own,” and have them understand and support you. Pregnancy is one of those occasions. It forced me to optimize processes, think long-term, and strategize for growth.

Though I believe one of my key strengths as a leader is in delegation, this was a whole new level of delegation that I had never experienced before — essentially throwing your team out a window and hoping they spread their wings. It taught me incredible lessons in trust and management. It also taught me that the foundation of what I had created was sturdy — and that it was going to be just fine.

I feel like my words fall short when I express how grateful I am for the team who made the Women in Travel Summit happen in 2017 and again this year in 2018.

As a sole founder, I think often about what would become of my business if something happened to me. Would Wanderful die if I were no longer able to run it?

One of the greatest joys of entrepreneurship may just be seeing your vision executed flawlessly without you. It brings me hope to know that something I have built can go on in the long term. I am constantly inspired and awed when I think about it.

Where would I be if I didn’t get pregnant? Probably emceeing a conference and stressed out of my eyeballs for the fifth time scrambling to manage details while also keep a calm face for attendees. Probably so focused on building and executing WITS that I wouldn’t have been able to take that vision and expand it to other events like Wanderfest and WITSx, a WITS spin-off in five cities this fall. Probably a little bit more rested, to be honest.

Nora makes her appearance at her very first WITS in 2018.

Pregnancy allowed me to test my limits, as well as the limits of my team. It allowed me to take a birds-eye view of my business when previously I had spent most of that time at ground level. It allowed my team to create their own bonds and their own systems. And it helped me build a new vision of growth that I hadn’t had before.

Pregnancy made me less flexible.

And in that inflexibility, it taught me that being a great entrepreneur is not at all about doing everything. In fact, great entrepreneurs can’t do everything. Pregnancy forced me to work smarter when I could no longer work harder. It forced me to find people who were better than me at doing things, and to let them take the reins. It forced me to see the company not as an extension of myself, but as its own living being.

My company — and I — thrived.

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