Why I'm Tapping Out

Why I'm Tapping Out

Upfront Work sits down with Chicagoland’s brightest product leaders to discuss, what made you quit your job (without a job lined up)?  What lessons did you learn? Was it worth the risk?

It was a raining Tuesday evening at the The Robey Hotel in Chicago’s Wicker Park area while bar sounds quietly sing in the background and the smell of fresh bread and cheese fill the air.  The three senior product leaders Margaret Jastrebski, Cat de Merode and Colleen Wilson walk into the ceramic tiled restaurant with friendly smiles and warm greetings. Each equipped with their own story to tell and vulnerability bubbling at the surface. Wine and drinks are quickly poured and small bites are ordered for a relaxing conversation among cohorts.

Margaret Jastrebski, former senior vice president at ShopRunner is one of the most well-known product leaders in Chicago.  She recently left her job to create enough time and bandwidth to focus on her personal life. After seven years of trying to get pregnant through multiple rounds of IVF, Margaret (known as “MJ”) knew the time was right to prioritize herself and her needs.

Cat de Merode, head of product at Pixavo, is best known as GrubHub employee #9.  One of her best memories is standing on the floor of the New York Stock Exchange the day GrubHub went public with her now husband (GrubHub employee #1) in 2014. Despite happy beginnings, she knew staying at a company she loved, under a boss she didn’t, would not serve her or the company well and decided to part ways.

Colleen Wilson, vice president of Product at Blueleaf, has had a long career at various companies like Square and Edward Jones. While working long hours,, her health continued to take a back seat and the extra 90 lbs she was carrying around left her feeling like her life was off balance.  After tapping out at different stages in her career, she now has clarity in what she wants and doesn’t hesitate to go after it.

Upfront Work, is a strategic product development consultancy, passionate about highlighting female product leaders with fresh, product content.  Partners, Jess Mean and Bridget McMullan, wanted to highlight the importance of “tapping out” and why, especially for women trying to do it all, companies, hiring managers and product managers struggling to decide if they should, can learn from these bright and driven leaders who say, “Go for it.”

In 2018, product management continues to struggle with clearly defined roles or responsibilities.  Leaving it up to companies to fill in the gaps that best fits their needs. While the expert generalists can gracefully adapt, it is no question taking a toll on the talent that enters and grows in this industry.  With an open and honest dialogue, product leaders Margaret Jastrebski, Cat de Merode and Colleen Wilson tell their stories with strength and vulnerability. While all different, one can’t help but ask, why isn’t everyone  finding a time in their career to tap out?

After drinks are ordered and everyone settles the main question gets asked, so what inspired you to tap out? All three women looked at each other to politely and respectfully let the other speak.    Colleen jumps in first to share her story.

“The first time I tapped out was when I was with Edward Jones.  The culture had an average employee working there for nearly 20 years.  So they were surprised when I left after 10 years because my husband got a job opportunity in California. We were really excited to do something different, but some of  my cohorts and advisors thought I was nuts.

The second time I decided to tap out was because my life was out of balance. I had been working at Square and truly loved it – the company was on fire, but my health was out of control. I had been heavier most of my life, but I had just hit my heaviest. Realizing this was not working for me, I had confidence from the first time and I tapped out to make a change and move to Chicago.  Since then, I can pull from my previous experience to know what I need; if a situation is not working for me, I take action to correct it,” Colleen unapologetically states.

With many questions asked back and forth, Colleen suddenly feels like an expert in tapping out and looks to MJ, the most recent to leave the workforce, to hear her story.     

“After working in Chicago tech for 18 years, I felt like my career had become oriented on external validation.  Each new title or name-brand company was another scout badge, with LinkedIn serving as my sash. I loved working for Shoprunner and was proud of what I accomplished there, but operating in high stress and high risk early stage environments for many years had caused me to lose my perspective.  I began to ask myself, how much do I want to work nights and weekends vs have a family?

My husband and I have dealt with infertility for almost 8 years.  I hoped my professional life would stabilize to the point where I could pursue IVF again.  I am 41 and have limited time left. I chose to walk away from the external “stuff” like a great title and a strong company, so I could make having a child my top priority” says MJ.

You can’t help but feel like you are at a slam poetry reading hearing these gutsy leaders share their stories so vulnerably.  With a high sense of self reflection, Cat begins to share her story.

“I started at GrubHub in 2008 as their ninth employee.  I met my husband there who was their first employee.  It was incredible over those eight years to shift into multiple roles,  move to different cities and even stand on the floor of the New York Stock Exchange the day we went public. Over the course of eight years working there, I must have had 12 different bosses. In 2015, while I loved the company, for the first time I absolutely did not love my boss. I knew it was best for me to quit that boss than to stick it out and lose my mind.”

The conversation goes back and forth as each leader asks the other what they did next, how long they tapped out and who they connected with along the way.  With the supportive and curious environment, each leader naturally shifts into what they learned.

MJ talks about how much she realized how important her network was after tapping out.  

“I reached out to Colleen (Wilson), who was amazing.  She shared her experience and lessons along the way. It gave me such comfort to know that I can leverage my network like that.  Women tend to play small. Because of my connections, when I’m ready, I know I can make something happen quickly and go big.”


Colleen jumps in to say, “Of course I would help you, I’ve been there and it can be terrifying.”  She takes a pause to reflect on her learnings.

“Tapping out has changed who I am and how I work.  When I was in MJ’s situation, I had a kind woman give me free advice.  She helped me tremendously. I felt like I used to wait for someone to tell me what to do.  Now, I trust any problem I am solving and can apply that to my life,” says Colleen.

Different names are thrown around as each leader discusses a multitude of  individuals in their network. With discussions circling around stories of endless coffee meet ups, the value of social capital and great networking groups to join (Women in Product Chicago Chapter).  Each lesson ties back to their experience in product.

“Being a leader in product, means you have to be comfortable in the abyss,” says Cat.  Colleen jumps in agreement with, “Exactly. When I would talk to the product team about the product vision, people tend to look at you like you are from Mars.  After some practice, it makes you much calmer about moving forward despite uncertainty and ambiguity which you can apply to your life.”

Adding to ambiguity, talk shifts to change.  With the understanding that notnot everyone can afford to leave their jobs, what lessons on how to cope can be shared for others not as financially able to tap out?

Like any good leader, each person takes a minute to reflect.  MJ digs into change. “Life always changes.  The context you are in now will be different in the future.  Even though it might not feel like it at the time, bad situations don’t stay bad forever.  Don’t try to fix everything at once. Identify the one thing you want to learn (even if you suck at it) and find a way to practice it in your current situation. Make your job work for you. Ignore everything else.“

Colleen and Cat agree that where you are now is not where you have to end up.  Colleen digs into how dangerous it can be making work your identity.

“I think putting protective bumpers around work is important.  In a way, figure out how to be passionate about your work but still have perspective.  In the long run, none of this matters because everything can fall by the wayside.”

Cat shakes her head in agreement and focuses on honesty. “I believe if you do not have the financial means to quit, be brutally honest with yourself and the people around you. Acknowledge that you can’t future-proof anything, and few decisions are truly permanent - with a little self-reflection, you can find a good direction. It’s what I tell people who are stressing about picking their college major: Stay in the present and you’ll carve a good path.”

Listening to the confident input and smiling faces, pride permeates the restaurant.  After all is said and done, was it worth the risk?  Colleen starts off.

“Yes, I can choose to change my entire career if I want. Now knowing I can survive, I make better decisions for myself.   It has paid off in my career and in my personal life in manifold ways.”

Cat follows with, “Yes, I have learned that now I do not have to do things strictly for my resume. I’ve proven to myself I’m capable of finding a good job when I need to, so I feel liberated that I can leave one if I’m unhappy. I believe it becomes harder to extricate yourself if you only make decisions for your resume.  Like having a gap in your resume or worrying what other people think - do it for yourself and it will pay off.”

Quietly in the corner, you can see MJ wishing for a crystal ball to be able to validate her decision like Colleen and Cat’s, but for her, it is too early to know.  She follows with, “I don’t know the specifics on what’s next for my career.  I do know I am going to work on an organic farm in Michigan tomorrow. After that, I am headed to sleep in a camper under the stars and then to a 10 day silent meditation retreat. I am now able to make choices wholly in service of my mental and physical health.   

Interesting people live interesting lives and that’s what I plan to do. For work, I can find a job at any point if I choose, but that is not what I want. I trust my future will be even better than my past, because I believe whatever you put into the world comes back to you. Right now, it’s unclear where I will take my career next, and I am very comfortable with that. I’m enjoying living in the ambiguity.”

The night wraps up as the last sips of Pinot Noir are taken. As each woman leaves, a kind goodbye is said and future plans are scheduled to stay in touch.

One starts to think, what about someone who didn't feel “tapping out” worked for them?  Does that person exist? The thing is, that person has been talked about relentlessly and many still feel that there are loads of industries, companies and cultures that believe “tapping out” is irresponsible or weak (even in 2018).

While we know that quitting a job without another isn’t ideal (especially if you live paycheck to paycheck), but is it worth staying if it means putting off having a family, losing your sanity or ruining your health?

When it comes to female product leaders, we have more to think about than men.  With the pressure to do it all and lean in, how should women lead differently?

Or, should the responsibility be on companies, industries and cultures to adapt?

One thing is certain, times are changing and brave women like Margaret Jastrebski, Cat de Merode and Colleen Wilson know it is up to them to own their destiny.  

For companies that want to hire impressive employees like these, flexibility is the future.  Whether offering longer maternity and paternity leave, offering remote work or offering flexible work hours, the companies that adopt these practices earlier will be ahead.

No matter what situation you are in, is it time to ask yourself, “should I tap out?”  If you are on the fence, we hope stories like these will be a strong guide to determine the best solution that is right for you.








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