Three different ways self-awareness can inform a leap

Our next article in our series is a summary of our takeaways from our conversation with Sarah Bishop (she/her). Read on to learn about how Sarah highlighted risk, strengths, and commitment as key aspects of self-awareness.


Last week WERKIN hosted an interview with Sarah Bishop, Head of Platform Products at Tractable, a fast-growing AI company. Sarah has made relatively risky leaps ranging from putting her salary ‘at-risk’ while she went and helped a non-profit expand and fundraise, co-founding a company, and working at other start ups and scale ups. Three key themes emerged that guided Sarah’s path and can inform how to think about which leaps to take represent different aspects of self-awareness –

1.      Know your risk tolerance and leap accordingly

2.      Explore your strengths in different contexts

3.      Go all in and be honest when you aren’t

Know your risk tolerance and leap accordingly

As a very risk tolerant person, Sarah took risks accordingly – such as joining a nonprofit doing unpaid work with the intent of fundraising her salary. When she felt like she wasn’t ‘employable’ and had never worked in a corporate environment, she took the risk of founding her own company. And when she decided to pursue a role in a corporate environment and take charge of opening her company’s London office, she took on another huge risk. That’s not to say that everything always worked out perfectly or was without challenge, but that she had the self-awareness to know what level of risk she was and wasn’t comfortable with, which was a guiding force in her decision-making about different leaps that she took.

Explore your strengths in different contexts

Sarah is extremely entrepreneurial and described her ‘scrappiness’ and willing to roll up her sleeves and make something work as a personality trait. She knew that thinking creatively about challenges and building on her ideas was something she was good at and saw she could be successful after earning her own salary, then saw how that strength applied to co-founding a company, and how it relates to her work today as Head of Platform Products in thinking through different applications of Tractable’s technology. It is easy to assume that being entrepreneurial must only ever involve starting companies, but Sarah’s journey shows how she’s been able to apply this strength in a range of contexts as she’s built out her own learning around different sectors, industries, and sizes and stages of companies.

Go all in

For Sarah, realizing she wasn’t all in about her startup was the litmus test of whether to continue with it or not. By knowing what it felt like to not be all-in, Sarah was better able to recognize and distinguish between the times that she was all-in, such as when she went to work for a non-profit understanding and with full buy in on their model. To go all-in is committing to something fully, which requires personal accountability and buy-in. This creates a level of commitment and energy that is sustaining and drives engagement in work. That’s not to say that being all-in is a requirement or pre-requisite to every leap, but understanding your personal level of buy-in before taking a leap can be a good indicator of whether you are taking a leap versus a step in a direction. That isn’t to say one is better or worse, but it can be clarifying to know the difference and evaluate opportunities accordingly.

These three findings from our conversation with Sarah can be extended broadly to inform leaps. A measure of self-awareness is key, both to understand your risk tolerance, strengths, and personal buy-in. That awareness is built over time, through exploring and trying different opportunities and taking different leaps. While it feels like a chicken-and-egg problem, leaps help identify these traits and yet these traits inform leaps, it does require a bit of curiosity and exploration. Leaps come in all different shapes and sizes for individuals. While we might not follow Sarah’s path, her learnings might inform our own individual journeys.

Photo by Varun Gaba on Unsplash

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How to manage natural tensions throughout leaps in your career

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Reflections on perspective, power, and place from our conversation with Joanna Kuang