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4 execs share their best strategies for getting out of a career rut

Need a reset? Try what has worked for these leaders (and moms).

4 execs share their best strategies for getting out of a career rut
[Source photo: Nigel Tadyanehondo/Unsplash]

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If you are feeling stuck, Anne Raimondi, COO of Asana, has a reassuring reminder: It’s totally normal. Raimondi, who previously worked as an executive at Guru, ZenDesk, and TaskRabbit, views ruts as situations in which you simply aren’t thriving. She says it’s valuable to acknowledge that such periods are a to-be-expected part of any high-growth career—and that it’s important to be intentional about navigating them. 

Here, Raimondi and three other seasoned executives, all of them mothers, open up about practices they’ve used to help ground themselves and determine the path forward during some of their most challenging periods.

1. Use a decision-making framework

Early in her tech career, Raimondi found herself coming home to her young kids with an uneasy feeling: Months into a job at a promising, well-funded startup, she was realizing that she didn’t like the company’s leadership style, especially with regard to the way decisions were made, and unacceptable behaviors rewarded. “It was very incongruent with the things I was teaching my children to do—treating people well and using your words in a constructive way,” says the mother of three. 

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To make sense of her assessment and troubleshoot, she walked herself through a decision-making framework she still uses today. Inspired by Stanford professors Bill Burnett and Dave Evans’ book Designing Your Life, it helps her assess her situation, in relation to three dimensions she prioritizes, by asking herself the following:

  1. Purpose: a) Do I believe in the problem being solved? And b) Am I excited to spend time helping to solve that problem and serve customers with that pain point?
  2. Impact: a) Can my experiences and strengths make a difference in the role? And b) Will I learn and grow?
  3. People: a) Do the people inspire me? And b) Do they make me better? 

Answering those questions helped Raimondi channel the courage to quit her job within six months of starting it. She thought there might be a cost to her decision. To her surprise, after speaking honestly with an investor about why she chose to leave a seemingly successful company whose values and culture conflicted with her framework, the investor helped her find her next opportunity. She’d learned another important lesson: that removing yourself from a toxic situation can sometimes open more doors. 

Now, as a veteran people manager and a lecturer in management at Stanford Graduate School of Business, she reminds her employees, mentees, and students to zoom out and think creatively about their options. “We tend to think we’re stuck or that a single decision or move is going to dictate the rest of our career,” she says. “We think about things as, ‘What if I make a mistake?’ In the moment, these decisions are really big. But our ability to learn and grow and reflect on our decision-making choices is really important.” Raimondi references her dog-eared copy of Designing Your Life again and again.

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2. Visualize your next steps, and stay positive 

After beginning her career in the public sector, including as the youngest deputy chief of staff to the then-mayor of Los Angeles James Hahn, Nathalie Rayes rose the ranks as a communications executive at the Mexican conglomerate Grupo Salinas. Fourteen years into the job, she was vice president of public affairs. She also sat on the board of directors for the Hispanic Federation and the Planned Parenthood Action Fund. The mother of two felt comfortable. 

Then came March 2020. As the first wave of COVID-19 forced the U.S into lockdown and the presidential election gripped the nation, Rayes was home with her two preteen sons feeling a personal calling to “move from the sidelines to the frontlines.” “It was the tipping point in our country,” she says. “I wanted to show up. There needed to be a shift.” So began the conversations—first with her family, and then with friends and mentors. 

To grasp what change could look like, Rayes used visualization and affirmation exercises. “I visualize a chalkboard and me taking an eraser and erasing that chalkboard,” she says. “I blow away the cobwebs from my mind.” She says she also kept repeating aloud to herself an encouraging Spanish mantra her aunt constantly cheered her on with growing up: “Pa’lante. Tú, sí puedes,” or, “Forward. You can.” 

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Rayes believes it’s critical to find effective ways to tune out the fear and noise pollution you feel in trying moments. 

As her vision of what she was seeking became more clear, Rayes turned to organizations she was already involved with—including the one she now leads. She had already spent years as a board member of Latino Victory, a progressive political organization focused on increasing Latino representation across all levels of government. She’d even chaired the committee and hired the headhunter to find a successor when the previous CEO left. As she continued visualizing what she wanted her next opportunity to look like and speaking with trusted friends, it became clear that putting herself in the running for the CEO opportunity was what she wanted. Her sons have come to expect seeing her standing in the mirror saying aloud to herself: “Focus, Nathalie Rayes. Pa’lante. Tú, sí puedes.”

3. Reclaim 30 minutes of your day to look inward

Anne Fulenwider used to think she’d work in magazines forever. One of the things the former Marie Claire editor-in-chief loved most about her media career was that the subject matter was always changing. But with constant change came a busyness that, starting about five years ago, felt increasingly unproductive. Then her mother died. Fulenwider went to Boston for the funeral, unplugging from her usual day-to-day and staying for nearly a month. Sitting with the many different people who’d been part of her mother’s life made her want to feel more present in her own life, with more introspection and less emphasis on rushing from point A to point B. 

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At the suggestion of a friend, Fulenwider started a short morning yoga and meditation practice to train herself to be more present and look inward. She’s not a “natural meditator,” but she began setting her alarm 30 minutes earlier. Rising before her two kids, she’d go straight from her bed to her basement and do a five-minute Headspace meditation, along with 25 minutes of yoga on the app Down Dog.

By making more space for herself, she began realizing that she’d been approaching work with a scarcity mindset, constantly thinking of all the stories she had to say no to. “I started looking at my life in total instead of the day to day,” she says. “You really have to decide, ‘Do I want to be intentional about how I spend my days, or do I want to just let my days happen to me?'”

Fulenwider’s mindfulness and movement practice also helped her hone in on a topic that’s at the forefront of her work today: women’s health. She left Marie Claire to cofound Alloy Women’s Health, a newly launched telehealth startup focused on the needs of women over 40.

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4. Identify options, along with pros and cons

When Eileen O’Connor is at a professional crossroads, she sits at her table and jots down a good old-fashioned pros and cons list. From deciding to leave a prestigious TV journalism career for corporate law, to going from an Obama administration role in Afghanistan to Yale University’s VP for Communications, O’Connor has found pen and paper to be critical, clarifying tools. 

Before mapping out specific pros and cons of her potential next steps, she runs through questions like: Where would I like to go? What’s the culture? What’s the environment? What are the things I really want to do and accomplish?

Then she asks herself: What would it mean for me to go pursue that?

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O’Connor, who is now senior VP for communications, policy, and advocacy at the Rockefeller Foundation, encourages her five daughters to go through similar list-making exercises when assessing their own opportunities. She also stresses the importance of answering the question, What do you really like to do? “Dream it,” she says. “It’s not always going to work. But you always learn something from even trying. And if you don’t try, someone else will.” 

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