Why We All Need A Space To Speak Honestly—About All Of It

Last night I was chatting on Twitter with one of the new partners at First Round. He shared his philosophy for what makes a great business and how to vet a running list of business ideas to see what’s going to be a success. I looked through the criteria and realized that I am potentially on track, according to his criteria.

Here’s the thread, and I was floored by his response to our business model and the questions he asked about the experience we’re building.

What we’re building with The Wise Women’s Council here at Startup Pregnant is pretty special. But sometimes I struggle to explain what it is.

It was useful to chat with a VC. We riffed back about forth about Startup Pregnant and The Wise Women’s Council and the experience of joining our community platform, and the business model behind it.

It was late for me—9:54pm. I woke up today feeling like I didn’t explain the business model and the benefit that clearly. It’s something I think about a lot, because I spend so much time trying to figure out how to subtly tweak the experience so that it really meets parents where they are, not in some mythical land where kids never get sick and your calendar actually works.

This is one of my struggles: how do you explain the value proposition and idea of The Wise Women’s Council clearly? Sometimes I describe it like a conference. Sometimes I describe it like a retreat. Sometimes I describe it like a group coaching program.

If you haven’t done coaching before, or you’re wary of the virtual-online-business stuff, I get it. It can be hard to buy into. I’m that way, too.

Then I realized one of the ways I’ve been describing it is wrong. I keep relying on describing what it is rather than describing the benefits and outcomes that people get. I’ve forgotten to focus enough attention on the reason why we made the program, and why it’s so important and impactful for working parents.

In describing your product or project what it is and what it’s for are two different questions.

With The Wise Women’s Council as a case study, you read all about what it is here. It’s a nine-month community mastermind and group coaching program for women at the intersection of work and parenting. It’s a place for women to gather and find community around these crazy hard years of our lives and all the challenges that come up when career and family collide.

But I don’t think I’ve fully addressed why we do it. Why is it needed? Why build something like this? Beyond what it is, I thought I’d talk about what it’s for and what my goals are for the women who join the program.

Goal #1: I want you to find a space where you can speak honestly and openly with other women about what’s happening across all of the areas of your life.

At work, we don’t always want to share transparently about our personal things—not everyone heads to work and says, “Hey, we’ve been trying to get pregnant for the last year and it’s really stressing me out.”

So we don’t talk about it.

With our local community group, we might not share everything that’s going on in our home life, because it feels too awkward to unload about all the partnership stresses you have to the people you run into every day. “Hey, so, I see you at the coffee shop every day and I just need to blurt out that I think my marriage is really struggling and I don’t love my kids right now and I wish I could leave my job.”

It’s too overwhelming. So we don’t talk about it.

And then, when it comes to our sacred partnerships and friendships—like our spouse, or boyfriend, or girlfriend, or dear one—we might not have enough bandwidth to have the rich conversations we’re so longing for, because nighttime becomes a tangle of a too-long commute home, a landslide of logistics, emptying the dishwasher, convincing the four year old with unrealistic bribes to go the F to sleep, rocking the baby to sleep, getting up at 3am to solve someone’s vomit, and texting work to let them know that you’re going to be late again…fuck. Sorry.

So we don’t talk to our partners.

For founders, too, I find being at the helm of a business to be exceptionally lonely as well. Who do you talk to about the very real hiring problems you have, or the staffing issues? What if you need a place to unpack the strategy you’re working on, and the fact that the risks to the strategy mean you might have to lay off two of your team members as you pivot to a new direction? You don’t talk to them about it, that’s for sure. Any conversation that goes, “Hey, you might be fired, but keep doing a great job in the interim” isn’t going to be effective. It’s going to send them scrambling to find a new gig.

I write this because I know how hard it is, and how much of a whirlwind it can be for working parents to have lost touch with people because the combination of working and pregnancy and parenting can be so much.

So—how does an online program solve for this?

What I’ve found that so remarkable and incredible is that joining a group of people you don’t already know (for the most part) can be liberating and freeing when it comes to sharing your inner world.

When other business owners are in different segments or industries, and they don’t live in your home town, and they don’t know your partner, there’s something amazing that happens when you can show up and say:

“Hey. I had a miscarriage this weekend, and it’s been rough. I have a huge deadline at my work and we’re still launching a project, but I’m going to take some time off Thursday and Friday afternoon to get a massage and go on a walk through the forest. I don’t know if I want to talk about it more, but I just want you to know that this is all of me right now. Feel free to check in with me this weekend.”

When you can show up and say:

“My partnership is really rough right now. I need my spouse to take on more of the home responsibilities and he seems totally clueless. How do I get them to understand that this is making me not just deeply resentful but I’m also exhausted?”

When you can show up and say:

“I’m working every night in our back office for the next two weeks because we’ve got a $2.5million contract on the line and I really really REALLY want to win this proposal, please encourage me to keep going because this would let me hire 20 more people over the coming years!”

These are the conversations we get to have.

Goal #2: I want to add as few things as possible to your calendar.

One of the biggest problems for working parents is the chaos of the calendar. You’re already managing the schedules of you, your spouse, your nanny, your daycare, your children, and your work colleagues and team. Honestly, one of the biggest blockers in my life is scheduling. If it has to be scheduled, sometimes it takes FIVE WEEKS for me to reply to an email. Plus, who knows if your child will be sick or if your work meetings will be cancelled last minute? Yup. Scheduling is a pain in the … You know.

More meetings is not helpful.

That’s why the Wise Women’s Council is as asynchronous as possible.

What I do know is that we often have tiny pockets of time that are hard to use effectively. Time like… driving across town to pick-up your kid and then waiting in the queuing line at the kindergarten pick-up. Yup, 20 minutes where you blast the radio or listen to a podcast.

Time like… those 20 minutes of loading the dishwasher at night and folding the laundry and picking up toys. (None of which requires a ton of brainpower, but for some reason they have to keep being done.)

Time like… being on the sidelines watching your kids’ soccer team swirl like buzzing bees around the ball and then kicking to pass it to each other and missing completely.

… Or prepping bottles in the morning, or packing lunches.

There are little stitches of seven minutes of time here and there, and it’s—I don’t know how you feel, but it can be meditative and it can also be, frankly, boring.

So I designed for this.

There are only two calls each month that need to be on your calendar—four if you’re joining the group coaching program. Once a week. And even if you’re joining the group coaching program, there’s really only one thing you absolutely have to make, and that’s your own coaching session. ONE THING A MONTH.

Last year, the participants said one of their favorite parts was getting to listen back to the coaching sessions, the group calls, and the guest teachers. There’s one new thing each week, about an hour long, and you can download the session. (We use Teachable which has an iOS app that lets you download and save the sessions offline if you want to listen to them without streaming charges on your phone.) You can play the recordings at double speed.

Yup, it’s like a private community podcast that you can go deep with and hear other people’s stories once a week for the next year.

So… why do I do this?

The reason I do this is to facilitate connection between you and all the other women in the group. Listening to women share opening and honestly, and hearing their voices, is a way to facilitate intimacy and connection.

If you’ve ever listened to a podcast and loved meeting and hearing the stories of other women, this is like a podcast with all of the other women in the group AND YOU GET TO HANG OUT WITH THEM ON SLACK AND IN THE GROUP CALLS LATER.

I want you to be able to make connections that last far longer than this program. It takes us a full nine months to really get to know everyone and truly listen to what they’re going through and see them in action. It takes a while to build the cadence and rhythm and connections we need to sustain our village.

I want to help build the constellation of women and parents that you need to make it through this crazy tough time in your life. Beyond business, beyond money, beyond success metrics, beyond goals—what makes us happy in life are the quality of our connections and the depth to which we feel integrated into communities that matter to us. The more communities we are a part of, the happier we typically are.

Your promotion isn’t going to solve your problem. Having people around to help get you through the rough patches is what makes this difference.

Goal #3: My aim with this space is to create the type of connections that can happen when you spend a weekend in retreat with other women, and to leave you with long-lasting connections, friendships, and support even after the program wraps at the end of the year.

Back when we were in college, we made lifelong friendships that we still cherish to this day.

I miss college, frankly (at least parts of it—I don’t need any more frat parties next door and I definitely don’t need any more sleepless nights). But I miss the connections and the serendipity of seeing other people on a regular basis. One of the best ways to support your growth and happiness is to find and be in communities with other people. This is a community of women entrepreneurs that are navigating pregnancy, parenting, and business.

That’s why we’re building this. That’s what it’s for.

If you want to come join us this year, put in your application. I read them all as they come in and I’ll reach out to you within 2-3 days about setting up an interview and the next-steps for joining us. I’m looking forward to meeting you—we all are.

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PS: Here’s the Twitter thread about the four things you need to make a great business idea. Would love to hear your thoughts in the comments and give a shout-out if you’ve been in The Wise Women’s Council before.

PPS: This idea of distinguishing “What it is” and “What it’s for” I learned from Seth Godin. Often we focus a ton of time on telling people what our product IS (“A group coaching program that meets four times per month,”) and forget to tell people what it’s FOR (“To help working parents navigate the loneliness and overwhelm of early parenting and forge potentially lifelong connections with other business owners so they can find happiness, joy, and laughter again in their lives.”).