Navigating Real Life And Work

An Interview with the Chief Product & Design Officer of Headspace

I was just six days removed from a second trimester pregnancy loss when I found out the scope of my work, including the project I had just launched, was being transitioned to someone else as part of a broader reorg. My manager couched it in terms of trying to be “helpful during this hard time.” It was not. 

A few months later, still in the bottomless bowels of grief, the world numb around me, I had this cavernous realization this job was not working out. I lacked the support, empathy and engagement to succeed amidst my current reality. I blame no one but the system. But I’m still frustrated that the only way I could figure my way out of that situation was to quit. 

Corporate America and managers are, for the most part, not designed to support the nuance of our lives.

If there’s anything I’ve learned in the last 5 years of my career, it's that it is inordinately difficult to navigate the complexity of real life with an ambitious career. 

Whether that is taking care of an aging or sick parent, going through fertility treatments, planning for parental leave or losing a child. The fact of the matter is there's no roadmap, there are limited protections. And frankly, every company and situation is different. 

Next month I’m hosting a free panel discussion on this topic with the Chief Product & Design Officer of Headspace, Leslie Witt¹ and the VP of Provider Growth and Operations at Lin Health, Shira Butler². 

Shira’s story is so powerful in navigating the challenges of personal and work life with such grace, I figured we should sit down ahead of time to learn from her. Below, our discussion, edited for clarity and brevity.

Key Takeaways:

• Learning to ask for help is key. The advice Shira was given when she decided to become a single mother played into her professional ambitions as she navigated two layoffs while going through fertility treatments and pregnancy.

• Clarifying your life goals can bring courage in how you show up at work. Shira’s vision for the life she wanted played into the manner with which she advocated for raises, promotions and relocations.

• There’s no right way. Every situation Shira encountered, she simply took the information before her and evaluated her options as best she could. It’s humbling and a great reminder that we’re all trying to figure it out.

  

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Cris: How would you define ambition in your life and in your career? How has that evolved over the years, especially as you navigated complex personal demands of your own? 

Shira:  I've worked in healthcare my whole career in Europe, Africa and the United States. Right now, I'm a leader at a company that delivers pain psychology solutions for chronic pain. That in mind, there are three things I’d highlight. 

First, I wanted a job where I felt impactful – where I had access to a lot of information and the pressures of making difficult decisions and where I could positively impact people’s lives. Second, I determined I could find that in product leadership because I love the bridge between what end users need or want and what you can create from technology. Later on I became a general manager because I wanted to lead teams. 

And then third, I've had a longstanding interest in work-life balance. After graduate school I moved to Switzerland for many reasons, but one of them is that I wanted to witness people who worked really, really hard, and then stopped working at the end of the day and didn't work again until the next morning. I wanted exposure and immersion in a culture like that. 

When I came back to the US, my goal was to bring that with me, and to be somewhere people would say with huge respect:

“Shira works really, really hard, and she can solve this problem for you. But you have to catch her before she goes home.”

Cris: That level of clarity and vision is really inspiring, but very hard to make happen. How have you been able to do that, especially in a US corporate work environment?

Shira: Yeah, I mean, it’s about taking a strategic approach and having the willingness to risk my career.

I always earned respect and trust first, and brought in other pieces slowly. I use researched insights that helped [furthering my point] around work-life balance. For example, there was a great Harvard Business Review article about managing your energy instead of your time. And I love that. 

I use that with my teams. We figured out for each individual person on this team what is your highest level of productivity that you can create value for the company. 

With my bosses, I say, here's some norms and things I think we should do. For instance, in a company all hands. If we recognize this person for what they did, we shouldn't say they work nights and weekends to get this done. We should say they worked really hard. They went above and beyond and delivered this really impactful value.

Cris: So that’s the strategic side, what about the willingness to risk your career. Talk me through an example of that. 

Shira: In my mid thirties, I wanted to give myself the option to be a single mom by choice if I didn't find a partner [by a certain age]. I started by freezing my eggs and it was such an incredible out of pocket cost, it was very jarring.

After that, I ended up sitting down with a financial planner. I needed to know how much to save in order to do fertility treatments and buy a house. We mapped out some models and we figured it out it was more than I was saving, living in San Francisco and working at a job that I loved.

That [realization] made me bolder in trying to advocate for myself to get a promotion. I didn’t tell my company I was doing fertility treatments and didn't say that was part of why I wanted a raise. But I did decide to put my job at risk telling my boss I either had to leave this job or leave the Bay Area to reach my goals. There was no precedent for that at the time. But I had a supportive boss that was willing to try, and allowed me to move and [work remote].

If only real life could be as simple and curated as this Dall-e created image….

Cris: That’s wild, that a decision you made for your personal life played into the courage and boldness with which you were able to show up at work. Can you dig into that a little bit more?

Shira: In my twenties, I chose to go work abroad because it was an important experience I wanted to have, even though it wasn't clear that it would be good for my career. In fact, many of my mentors told me it would be bad for my career.

So early on, I decided that I wasn't going to only maximize my ability to move up in the world or my salary. Those things were important, but even more important, was making sure that I liked the life that I was living and did things that were really important to me.

Cris: What happened next, after you risked your career by moving to a place you could afford to raise a family?

Shira: One thing I did was get to know women who had decided to have kids alone. They were super badass and one of the best pieces of advice they gave me was to practice asking for help because that would be the key skill to succeeding.

Cris: I feel like that advice is transferable professionally too!

Shira: Yeah, it was. I ended up being part of two layoffs during this journey to motherhood. The first, was right after I’d moved to the new city and was in the process of putting bids on a home and in the middle of my fertility treatment.

Then, I succeeded in getting pregnant and when I was 6 months pregnant, I found out that the child I was carrying had a very serious medical condition and a couple weeks later I was laid off from my new job as part of a larger layoff. That was the scariest layoff of my life.

After a couple of weeks of emotional processing, I reached out to a small circle of people I trusted and I told them what my situation was. Two of those people offered me contract work until I gave birth, knowing what my limitations were, but also knowing how hard I worked and how good a job I could do. That was really really impactful.

I had built the right kind of respect, community and self-confidence to be able to ask for help. And it worked out. I didn't end up getting a full time job until after my daughter was born. I'm still annoyed about the loss of income from not being paid for my maternity leave. But I'm also very grateful for the time I got to spend with my kid.

Cris: Can you tell me more about that resentment? 

Shira: First of all, I had met a partner during this process, but I was still the primary income earner for my family. I held the mortgage on my house and I was terrified of what the costs would be for my daughter because of her medical condition.

I also knew that I had the ability to find jobs, I had done it before. I wasn't angry at my company that had laid me off. They hadn't known I was pregnant because I hadn't told them. They were people like me who were trying to run a business, who were trying to help the world, who were trying to do the best they could. 

So I couldn't direct my resentment or my anger at a person or at the company. But I still feel upset at the situation and system. I made the best decisions that I could at the time.

Cris: What have you learned, overall, about managing this ambitious career and a rich personal life? 

Shira: It's on my shoulders to have discipline around when I work, and when I don't work. I am a high achiever and I contribute a lot and I make my boundaries very clear. I think as long as we are delivering value and delivering results, it doesn’t matter what hours you work. 

I also think it’s important to say, in most of my jobs I did not feel comfortable advocating for things like fertility benefits, or making it clear upfront that I was pregnant while interviewing or that I wanted to control my hours. I worried that I would not be treated with the same level of respect if I said those things upfront and was afraid that would lead my bosses to pass me over for promotions or opportunities. 

So I want people to hear the ways that I DO advocate for myself and the things that are important to me, but to also say that I don't think everybody is in a work environment where you can just be comfortable saying those things out loud and not think that they'll have an impact on you. 

We have to be really careful about what we tell our managers. I think being sensitive to that as a community, and knowing that there's definitely still risk associated with all of those things is important.

I don't have an answer, except that when we are the ones in positions of power, we should make sure that we act and advocate with a lot of integrity.

Cris: Someday your little girl will bring the full force of her ambitions into this world. What do you want that experience to look like for her? 

Shira: I hope that she's able to enter a workforce where we care about what the individual does, and not about the group to which they are attached. I want her to define who she is and what she does and I hope that she has the respect and the trust of the people around her to decide how she works best and what she needs in order to achieve her dreams.

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Thanks again to Shira Butler for her willingness to share her story.

We don’t talk about navigating the complexity of real life with a career very often because it’s messy and there’s no right or wrong answers and people aren’t comfortable talking about things with those attributes. But I think we have to start somewhere.  

In that vein, I’d love to have you join our panel discussion next month. It can feel very lonely, at times. At the very least, we have each other.

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With thanks to

Emma Dorge

Becky Isjwara

Maria

for the edits and support on this week’s essay.

1. https://www.linkedin.com/in/leslie-witt-582a472/

2. https://www.linkedin.com/in/shiramlee/