Above The Median Newsletter #2: Knowing When To Pivot
Hello to the Above The Median community. We launched in June and the sumptuous response from the first newsletter (here is a link if you missed it!) confirmed our hypothesis that young leaders are hungry for tactical insights immediately applicable to their work situations. This month’s newsletter focuses on the pending question of when one should course correct in their career. My personal journey has been circuitous and I know how mentally taxing it is when debating a move or a totally new career opportunity. Our focus groups have consistently raised this question. Luckily, our Above The Median women have answers on how to navigate the corporate ladder. Let’s dive in!
Newsletter Question 2: “I have been in my job for a while now and I don’t know whether to stick it out or if I should move to something new. How should I think about processing a decision like this?”
Sometimes it’s like trying to move a sofa up the stairwell. If you keep pushing, you may be successful and squeeze that massive couch up the stairs. However, sometimes you need a more subtle approach to make forward progress. While Ross from Friends can yell “PIVAAT”, what does this mean in your career?
For this month’s newsletter, we hear from Aditi Gokhale (Chief Strategy Officer, President of Retail Investments and Head of Institutional Investments at Northwestern Mutual), Katelin Holloway (Managing Partner at 776 Ventures), and Soraya Darabi (Founding Partner of TMV.) These three women have experienced momentous life shifts and teach us about tactical strategies for evaluating both “when” and “if” one should make a change.
Part I: Passion, Value, Timing
Above The Median Spotlight: Aditi Javeri Gokhale
Aditi grew up believing that she could build her own career path. Coming from a middle-class Indian family, Aditi’s parents encouraged her early on to take risks and be resilient. At age 17, Aditi applied to four U.S. universities and was accepted by MIT on a full scholarship. She left Mumbai, got on a plane and came to the United States with $150 in her pocket. Fast forward to today and now Aditi is the Chief Strategy Officer & President, Retail Investments and Head of Institutional Investments at Northwestern Mutual. Aditi has shared with the ATM community the three questions she asks herself when evaluating a major change. Aditi emphasizes that choosing a new opportunity “is not about the interview experience and getting the job, it is about actually performing in the job and being passionate about it.” Oftentimes people jump to a new opportunity and think “new” guarantees success. Do not assume it does.
Tactic: Match Your Passion, Values, and Timing
Aditi’s decision matrix consists of three questions that she has found to be profoundly helpful.
1. Does this opportunity match your passions?
Aditi denotes that if you are good at your job, new roles will come to you. However, it is not about jumping to “anything.” You want to ensure you are passionate about the day-to-day of the next role. Do you intuitively feel excited or inspired when you talk about it?
2. Does this opportunity match your value system? Is there a culture fit?
Aditi’s core value is authenticity. Aditi notes that during new job interviews, she would evaluate if the culture was transparent, honest, and supportive. With limited child support and a 15+ hour flight to see family, she couldn’t work at a place where she had to lie about leaving to be with her child. “I didn’t want to work somewhere where I said I was going to a doctor’s appointment 3x a month when in reality I wanted to attend my son’s school event.” Furthermore, Aditi chose companies like American Express and Northwestern Mutual where she felt her team could be an extension of her family. And, while compensation is important to consider, she always believed that if you match your passions with your job that the money would eventually follow. In addition to a value system, Aditi prioritized opportunities that were not 9 to 5 jobs but were more about results.
3. Is this opportunity right for your current life phase?
Aditi took time off after her role at American Express to be home with her newborn son. When she joined Northwestern Mutual, Aditi established a leadership style that involved transparency and robust communication with her team so that she could thrive as a corporate executive and, more importantly, as a mom. Aditi advises women to not prioritize the job but to prioritize one’s overall life. Consider variables such as health, family planning, ambition level, and external support to guide decisions on whether a specific new job is right for you. Some women may have the opportunity to jump into a startup while others may want a more stable company environment. There is no right answer, but it is important to go through a complete thought process.
Part II: Leave on the Highs and Learn How To Evaluate Your Strengths
Above The Median Spotlight: Katelin Holloway
When Katelin talks about her life, it sounds like she has been reincarnated 9 times. Katelin has been a Substitute Teacher for first grade low income students in Stockton California, a Script Supervisor at Pixar, the VP of People & Culture for Reddit, and now she is running an early stage venture firm, Seven Seven Six, that has raised $750M over two funds with Alexis Ohanian (Serena William’s husband.) To call Katelin a career chameleon would be an understatement. Her successful pivots were by no means easy to do nor easy to discover. Katelin leveraged two tactics that have helped her make decisions on why/when to switch.
Tactic 1: Know When Your Cup Is Full
Katelin has made numerous shifts in her career, but unlike many people who choose to leave “when things are hard,” Katelin instead pursues new opportunities when things are great in her current role. During Katelin’s childhood, her grandmother instilled a strange pearl of wisdom, “It is time to leave when your cup is full.” In practice, this means leaving something when you are at the height of success or happiness. Katelin admits, “It is very counterintuitive. Most people wait to leave when things are hard or broken because they don’t want to feel like they’ve failed.” Katelin expands that it is much better to run towards something than away from something. Additionally, by leaving on a high note, Katelin points out that you maintain a strong reputation.
Katelin used the thought tactic of the “full cup” when she decided to leave Pixar after 5 years with all the perks possible (incredible benefits, name in film credits, access to top celebrities, the annual Disney all inclusive theme park passes to name a few.) But she knew she was on the highest part of the roller coaster and it was time to shift to a new learning and new opportunity. That willingness to jump on a high unlocked an unforeseen growth opportunity to join Reddit in its infancy. She joined Reddit when there were 70 people and most of her friends and family had never heard of the company. At the end of her tenure, Reddit had grown to 750+ people and was the 4th largest website in the United States. Katelin also had built an entire organization deemed “People and Culture”, and she had become best friends with Alexis Ohanian. Again, Katelin points to feeling as though “my cup was full. I had done everything I could and had built a phenomenal organization with Alexis. I woke up one day and left.” After she left Reddit, she built Seven Seven Six as a founding partner. Seven Seven Six has raised over $750M and has quickly built a formidable reputation in the venture world.
Tactic 2 Design Thinking For Your Life:
Katelin admits she wasn’t always the best version of herself throughout her career. One of her biggest lows was when she was working in advertising. “My values were not aligned to the values of what was required to be successful in the role,” says Katelin. The characteristics expressed to be successful cost Katelin friends and her romantic relationship. Her boyfriend at the time (and now husband) called her out in the midst of a breakup. “‘This is not the version of yourself you want to be’ he told me,” says Katelin. Instead of Katelin’s boyfriend bailing on her, he helped her try to identify a new job opportunity. Katelin executed an exercise she terms “Design Thinking For Your Life.” She rolled it out formerly throughout all of Reddit and advises startup founders on the tactic within the Seven Seven Six portfolio.
*Note: ‘Design Thinking’ became omnipresent throughout Silicon Valley in the early 2000s. Stanford Business School teaches a course on the idea for startups.
The goal of the exercise, “Design Thinking For Your Life,” is to “untangle the shit” as Katelin puts it. Or maybe more eloquently articulated, the exercise helps you flush out intentionality. It won’t provide you a new job title to chase but it will provide you clarity on what you need to do to be successful.
Design Thinking Exercise:
Part I: Stream of Thinking
Get a large whiteboard, poster board, and/or something larger than an 8x11 paper
Write down all of your job responsibilities (can be bulleted, can be scattered, however feels good visually for you)
Look through the list and see what is missing…What are things that you would like to be doing? Add these items to the list
Part II: Organize
Circle everything that you are really good at. (If you took a test on it, you would get good marks on this.)
Underline everything that you love to do. (You don’t need to be good at it necessarily. Aspirational ideals can still be underlined.)
Cross out everything that you dislike (even if you are good at it)
Part III: Evaluate the Results:
Circled and underlined = you should lean into as hard as possible. If you don't have those things currently available, you need to build a development plan to get there.
Example: if you are not in HR but you love supporting colleagues then you need to seek that. But if it is in your purview then how do you double down and make that larger in scope.
Circled but crossed out = this means you are really good at it but hate it. Figure out how to delegate this task. Teach somebody else or narrow scope of role to be a specialist
Crossed out and underlined = You are not good at it and you don’t like it. Figure out how to avoid this
Additional Note: Focus on eliminating things. Sometimes we do not have clarity on what we want but it is good to understand what you do want. If you have underlined it, that is your developmental plan, moving towards those things.
Part IV: Apply External Factors
After you have that first round down, you should have a better idea on the scope of the role you might want. It could have twenty different titles at twenty different companies. Ask yourself questions such as:
How much money do you need to make to live the life you need? If you have a roommate and you don't want one, what is the minimum amount for this?
If you want to start a family will you want something more inherently stable?
Does geography matter to you?
Do you want to be in a big company or a small company?
Your list should begin to dwindle while clarity regarding jobs you actually want should become more explicit.
Now, it's time to start having conversations on what supports what you want. Katelin suggests reaching out to people for informational interviews based on what you think you want to do. People will respond very differently if you ask to learn about their jobs rather than say you want to apply for a role. “People love talking about themselves,” says Katelin. When Katelin went through her own design thinking experience to get to Pixar, she reached out to 10 people. 8 of the 10 responded and got coffee with her. A few are still considered mentors for her decades later.
Part III: Ask Yourself Questions Annually and Filter Advice
Soraya Darabi
Soraya Darabi’s life story highlights the power of risk-taking, and is an inspiring example of how charting one’s own path results is a better metaphorical ROI (return on investment) versus blindly following the “status quo”. In less than half a decade, Soraya went from spending the majority of her capital on her startups and angel investments to raising over $100M+ for her venture fund TMV.
In her New York City office near Gramercy Park, she has a framed post it note that reads “No more blueprints!” The statement serves as a testament to her innate sense of creativity that has guided her personal and professional life: While Soraya lives and breathes the world of investment and finance, her approach to life is imbued with a deep, almost artistic sense of innovation rather than the mathematical rigidity of many other successful investment professionals. She defies what she is “supposed” to do and leans into intuition to succeed.
Soraya’s early career started at The New York Times where she managed Digital Partnerships and Social media during the onset of the web 2.0 era. She left The New York Times in 2009 to become a co-founder of Foodspotting (a visual geo-local guide that highlighted dishes over restaurants, which later sold to OpenTable). Post exit, Soraya aimed to repeat her success in the world of sustainable fashion. Soraya raised capital from some of the top Venture Capital firms known throughout the world. She also put her own capital, most of her life savings in fact, into the Company because she believed so firmly in the opportunity. Unfortunately, market timing was not on Soraya’s side and the Company failed to grow for many reasons, timing being one. That loss took its toll on Soraya’s mental health and she needed time to recalibrate before embarking on something new.
But this isn’t a sob story. Soraya flipped the script and found the silver lining. Through her experiences as an operator and an investor / advisor, she learned what she valued most in early stage investors. So she pivoted to the other side of the proverbial table and began to invest. “I saw how early stage investing worked, and I also saw an opportunity to approach it differently and support Founders in a way I thought was uniquely helpful, hopefully transformative.”
Soraya created an investment philosophy that channels a mixed energy of Erin Brockovich, Mr. Rodgers and Jerry McGuire. “I believed I could source and win Founders by being empathetic with the right mix of hustle and grind. I want to be perceived as a Founder's agent, and our team at TMV will not stop until we reach a shared goal.”
In 2016, Soraya and her Co-Founder, Marina Hadjipateras, launched Trailmix Ventures (TMV), with an inaugural $11M fund. The firm has been so successful that their recent second fund, announced earlier this year, is 6x larger at $64M, oversubscribed, and includes impressive backers such as Bank of America and JP Morgan Asset Management. Additionally they have raised a great sum of capital through direct deals, so the firm has ~100M AUM to-date.
Beyond the obvious “grit” Soraya possesses (note: highly recommend reading Angela Duckworth’s book Grit to dive further into this quality), thoughtfulness and humility pulse through her veins. Soraya acknowledges that she does not know everything, but she believes that constant exploration of the unknown is the key to success. You can find her favorite reads on the homepage of the Blinkist App this month for more on her approach to learning.
Tactic 1: Annual Check-In: What Am I Learning? What Am I Teaching? What Do I Want to Learn?
Soraya does an annual reflection on her life to understand if she is on the right track. Inspired by Wally Olins, she asks herself three questions each year: What am I learning? What am I teaching? What do I want to learn?
(In fact it was her friend and TMV LP Georg Petschnigg who leads Product and Design at The New York Times who taught her the framework.)
Soraya elaborates with follow-on questions under these three headers in her own words:
What am I learning?
“You should learn on a DAILY basis, no matter what job you are in. In your 20’s the goal is to be learning on someone else’s dime.” This is why she is not a fan of starting a company until you’ve had a few years of corporate experience first.
What am I teaching?
Soraya thinks a job should incorporate an opportunity to teach others. Teaching can be the best form of demonstrating mastery. Are you literally teaching a class? Are you presenting internally or externally? Are you leading Twitter tutorials or something more formal? Anything counts.
“Think about how you can communicate what you learn into palatable sound bites. You will retain the knowledge and grow your own brand in your career.”
What do I want to learn next?
“I ask myself this question a minimum of one time a year (with my therapist, ha!) I believe I possess unbridled curiosity. If you don’t know what you want to learn next then you will be stagnant.”
Tactic 2: Filter Advice
Another aspect of making decisions in your career is knowing how and when to filter advice.
“People will also have their own opinions and want to give you opinions. But opinions are just opinions unless supported with facts,” says Soraya.
Throughout Soraya’s life, she has filtered people’s opinions to pursue what felt most authentic to her own self.
Right as she launched TMV in 2016, AI/Blockchain/ Web3 /Crypto were the “hot industries” for early stage investment. LPs of TMV, a firm initially focused on healthcare/well-being at work, encouraged Soraya and her Co-Founder to invest in those topics occasionally. However, Soraya had conviction and listened to her intuition. Her conviction proved correct and the Zeitgeist bullseye inevitably aligned to where TMV had been aiming from the get-go: Healthcare, The Future of Work, and Tech-Enabled Sustainable Solutions. If Soraya had shifted her focus, TMV probably would not have gained the traction that it did.
“Trust your instincts and never let someone else tell you who you want to be,” says Soraya.
Aditi, Katelin, and Soraya are three spotlights of women whose careers have been non-linear. What’s fascinating is that the majority of women I spoke with for Above The Median all had significant role diversity and all hold executive roles.
I did ancillary research to see if there is scientific evidence to support the benefits of shifting roles and learned about “CEO Sprinters.” “CEO sprinters,” is a term to describe people who reach a CEO role faster than the average of 24 years from one’s first job. Elena L. Botelho and Kim R. Powella coined the term as they studied 17,000 CEOs and C-suite executive assessments with 13,000 hours of interviews to better understand how someone moves quickly into the C-suite. With their research, Botelho and Powella found that rarely do CEO sprinters have a perfect pedigree or move up the ladder. Rather, CEO sprinters zig zag in their career. 97% of CEO sprinters undertook at least one catapult experience and the average was three catapult experiences. Botelho and Powella describe a catapult as being caused by a “bold career move.” Even more interesting, sometimes these catapults were taking a role that was smaller or horizontal to a person’s current trajectory. More than 60% of sprinters took a smaller role at some point in their career. What is the lesson here? The corporate ladder is hyperbole. The corporate zig zag is reality and in fact, conducive to moving into bigger opportunities.
A career is a journey. How to choose when to alter the direction of that journey can be difficult. However, based on research, altering directions and being fluid in your career is more important than ever before. Be confident in your decision to jump when you know the time is right.
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Some additional quotes from our guests along with a few additional reading/listening recommendations:
Aditi Javeri Gokhale: “So often women talk themselves out of situations – attending social events, applying for jobs, etc. because they lack confidence. When I mentor women, I remind them that we need to talk ourselves into these situations -- because if not, we will never know what incredible opportunities are around the corner when we put ourselves out there.”
Aditi’s Book Recommendation: The Autobiography, by Margaret Thatcher
Katelin Holloway: “Run towards something as opposed to away from it.”
Katelin’s Book Recommendation: Alpha Girls, by Julian Guthrie
Soraya Darabi: “Stop caring about what people think. Care only about what specific people think…the people that actually matter in your life.”
Soraya’s Book Recommendation: Give yourself a break this Summer and re-read a favorite from your youth. She just re-read some of her favorite trashy Christopher Pike novels from the 7th grade.
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What’s inspiring us this month:
Instagram of the month, by @still.life:
Video: Handling Difficulty from Kara Lawson, Head Basketball Coach at Duke University: “Handle Hard Better”
Tweet of the Month:
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See you all next month!
Special thanks to…
Kendall Warson for all of her design work that helps breathe life into the vision
Jocelyn Teece for deep diving and contributing to the project (all while simultaneously attending Tuck Business School and navigating the pandemic)
Adam Grosser, my mentor, business partner, and chief editor
All the amazing women who were interviewed and who opened up to share their stories
Everyone who participated in a focus group that inspired the questions for the interviews