FlipMyFunnel Post, Other

The Dark Side of the Word “Hustle”

Jill Rowley has been exceptionally vulnerable on social media about her work/life balance.

Work is her great passion in life, and her career has taken a high percentage of her time and energy. But now, stepping into a new space as a Partner at Stage 2 Capital, she’s working on changing her lifestyle to achieve more balance in her life.

One major way she’s doing it is becoming allergic to the word “hustle,” the idea of the never-stopping, never-slowing grind that can easily become an addiction for professionals.

She’s got an amazingly vulnerable story of how she’s learning what actually matters in life and work, and she was kind enough to share it on the FlipMyFunnel podcast. We’re covering most of what she shared in this article.

What We’re Covering in This Article

  • The Awful Statistics Around Venture Capital and Female Founders
  • Stopping the Hustle Mentality
  • The Changes She Made to “Hold the Hustle”
  • Reverting Back to Old Habits
  • Alcohol/Workaholism
  • Advice to a Jill Rowley of 20 Years Ago

This post is based on a podcast with Jill Rowley. If you’d like to listen to the full episode, you can check it out here and below.

The Awful Statistics Around Venture Capital and Female Founders

Of the $130 billion of venture capital deployed in 2018, only 2% of those dollars went to female founders.

It’s a shocking and sad statistic. It also had a lot to do with Jill’s recent pivot in her career, from MarTech to venture capital.

Once she saw the data about how few women there are in the industry, she sensed an opportunity to come into a newer market and do what she’s always done in her career: disrupt. To highlight the amazing female founders out there and potentially move 2% to 5%, 10%, 15%, 20%, 25% . . . it was too good to pass up.

But her new career path also coincides with a new mentality she’s been developing in her personal life.

Stopping the Hustle Mentality

Jill just celebrated her 15th wedding anniversary with her husband—and the 20th anniversary of their first kiss. Her husband has been a grounding force to her in a career driven by an internal fire and what some would call a “chip on her shoulder.”

At one point, while they were living in the Bay Area, Jill woke up and realized how all-consuming her career had become. There was nothing outside of her career that she really enjoyed. Her husband plays golf. But she didn’t have any hobbies herself.

She enjoyed reading books—but they were books about growth, being a great marketing leader, sales acceleration formulas, and conversational marketing. They were as close to a “hobby” as she could find in her life.

Things were out of balance, and something needed to change. And it did.

The word “hustle” is a trigger to her now. It’s not that she’s not going to work hard in her new role: she’s just not buying into the often-addicting concept of “the grind.” She even worked to develop a campaign against the word.

“More” in and of itself, Jill says, is not better. Instead, work should be more relevant, more specific, more intentional, more helpful, more personal, more contextual. As for the name of the campaign, her first idea was f_@% the hustle, but ultimately they landed on #HoldTheHustle” instead.

“Hold the hustle,” she said. “The hustle will lead you down a path that it led me down. December of 2014, I woke up and I knew that was the beginning of a very severe case of burnout and depression. It was one of the hardest periods of my life, realizing that all of this success that was so important to me—meant nothing.”

The Changes She Made to “Hold the Hustle”

She made some changes almost overnight.

She didn’t have travel on her calendar for six weeks, so she finished a speaking engagement and then simply broke down. Her husband went with her to doctors. She was so torn up inside that she expected to be diagnosed some kind of serious or terminal illness.

Talking to the doctor helped her clearly realize that she was suffering from depression and severe burnout. She needed to be on medication and in therapy. So she made those changes.

Underneath it all seemed to be an addiction to being recognized, to being acknowledged. She’s built an incredible personal brand; social media is a big part of that. But it only fed the addiction, so she stopped having her phone on her. When she would get in the car to drive somewhere she would put the phone in the trunk. The clinical term is “conscious uncoupling.”

One day, while walking by a Starbucks without having her phone on her, she met a woman who looked lost. Jill helped the woman find the Starbucks nearby and bought her a tea. They sat and chatted for a while. It was a profound moment for Jill. What if she’d had her phone on her?

“I remember thinking, ‘Oh, my God, this never would have happened.’”

Reverting Back to Old Habits

Addictive habits can strike anyone, regardless of geography, gender, or socio-economic status. They are difficult to stay away from for long periods of time. Jill talked about how her husband helps her talk honestly when she’s getting “out of bounds,” which unsurprisingly seems to happen most when she tries something new in her career.

Before she started working at Marketo, they had moved across the country to Charleston. Jill was ready to have a life outside of Silicon Valley and work. The slower pace helped her adjust to life outside of work, but that was disrupted when she took the job at Marketo.

For a year, she technically lived in Charleston, but she was hardly there. She was definitely going against what she’d said was important to her.

But her husband’s support never wavered. They knew it was for a period of time and that it was a career opportunity of a lifetime.

When she wound things down at Marketo, and wound things up at Stage 2, she once again started to see herself doing the exact same thing. It made sense: she was entering a new category that she had to figure out. Her husband called her out.

“Look, it is a constant struggle,” she said, “but I’m much more aware of it. I’m willing to talk about it. I don’t want to be that person who works on weekends anymore. I don’t want to be that person who, anytime any day, any channel you call me baby, I got your back. I’ve got four kids. Now they’re 25, 24, 20, and 14, and my kids couldn’t get my attention, but some random person on Twitter could.”


“Anyone who knows me knows I could party like the best of them,” Jill said.

But there was an interesting thing she learned about depression and burnout: alcohol doesn’t help.

Her therapist kept wanting to diagnose her as an alcoholic. But while she knew she was reliant on alcohol, she’d seen true alcoholism, and this wasn’t it. She cut out drinking completely so she could get a truer diagnosis of what was going on with her.

She discovered the work of Dr. Sherry Turkle, a leading expert at MIT in the discussion about the impact that technology has on humans. She even got to meet her and tell her that her work had helped to get Jill to the other side of workaholism.

Jill hasn’t had a drink in over four years.

Advice to a Jill Rowley of 20 Years Ago

If you’re in a position similar to Jill, here’s her advice:

Be more intentional. Think long-term, rather than just what’s in front of you today. Relationships are everything. Porter Gale wrote the book, Your Network, Is Your Net Worth. There’s a lot of wisdom in the name of that book.

Build relationships intentionally; give more than you take. Make deposits before asking for withdrawals. Always look for ways to help other people.

Build an advisory, a group of folks who can check you at the door. People who can say, “You’re a little out of bounds here.” Be open to their honesty. They can see the warning signs.

“You don’t know how much time you have on this earth,” Jill said. “You can’t wait until you’re 60 or 55 or 50 or some other number to say, “OK. Well, now I’m going to breathe. Now I’m going to take the weekend off. Now I’m going to…

“You might not ever get there.”