Sherry and Rob open up about some of the events that have happened with their family in the last couple months. They talk about how the power of entrepreneurship has helped them tackle hard things and how important it can be to have supportive people in your life.

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Episode Transcript

Sherry Walling:

So one of the highlights of my fall was giving a talk at Business of Software in Boston at the middle of September. It was a great talk. I had a lot of fun, went to the speakers’ dinner, stayed up way too late, drank way too much, hanging out with friends and fellow speakers.

 

And I took a really early flight the next day because there was a hurricane supposedly coming in towards Boston. And I was really tired. I hadn’t slept much. But I’m sitting on the plane. I’ve got my laptop open. And I’m sitting next to this woman who’s going on vacation to Las Vegas. And so she’s chit-chatty, and she’s like, “Have you been to Las Vegas?” And I’m like “Yeah, I have. Like every year.” And at some point I just put my headphones on and stopped engaging with her.

 

And I started crying on the plane, pretty hard. Which was very embarrassing and not really my normal MO, but I was crying because I was writing this document, writing about our family. And writing about all of the things that I love about you and our two boys. And writing about all the things that we would change, or we would lose if I made a decision that I had to make, or that we had to make together.

 

So I’m on the plane, I’ve just given this great talk. And I’m descending into this mess of tears and fear and worry about the future. That was, I think, a Tuesday. I came home on Tuesday, and I turned around, and on Friday I got on a plane, and I flew to California with a question in my mind of whether or not I would return home with two more children.

 

And I think the plane ride after BOS, the plane ride home from Boston, crying on the plane, writing, trying to just put everything out into words, get it out on a piece of paper, so I could sort of sort through how I felt about this decision. That was one of the most sort of pivotal moments for me in the last couple of months.

Rob Walling:

And so today we wanted to talk through what that experience has been like. And I wanted to frame it and structure it around a talk. Actually really a non-talk. It was more of a conversation that I had from the stage of MicroConf Europe that was in Lisbon a few weeks ago and kind of want to talk through, not only that process, but just dive into the power that we have as entrepreneurs and I think a lot of things that we take for granted, and things that we don’t talk about in our space, are things like once you’ve achieved freedom and you run a business, what next?

 

Like that’s the goal for so many people, but what else is there, and what other moral imperative should we feel, both for our families and colleagues, friends, and to the broader world.

Sherry Walling:

I think when I say also that today episode’s sort of intensely personal. You used the term moral imperative, and I think that’s a good term to use. But it’s also one that is personal, like one that really reflects one’s own individual values and approach to life. So we’re going to talk about what has happened in us and in our family in the last couple of months. But this is us talking about this family situation a