By SGN | 20 Feb 2024
When Karen was an undergraduate in the US, public speaking was an essential component of the curriculum that gave her the jitters. “I’d get comments on my accent that made me feel like an outsider,” she recalls.
While she eventually overcame those barriers and forged deep cross-cultural connections, it also dawned on Karen that inclusion wasn’t just about policies or communication.
“It’s about reciprocating the curiosity towards someone else’s experience, identity and culture that brings dignity to a relationship and system,” she reflects.
Advocating for a more equitable society
This belief in equity would go on to be foundational to Karen across a decade-long civil service career. To date, she has worked in various government ministries in Singapore, and served as a political speechwriter.
“In my career, the common thread is enabling dignity and equity for every person. My life is still unfolding with the open question – what is the most effective way to do this? How am I positioned to do my part in this? The answers to these questions evolve with life stage.”
“My first role was in the Ministry of Finance, where I worked on strategic financing for social programmes.” Karen recalls. A highlight was working directly with then Deputy Prime Minister Tharman Shanmugaratnam, a strong advocate for change.
One of Karen’s and her colleagues’ implemented proposals was a package of reforms to make preschools more equitable and accessible for children from lower and middle-income families. This amounted to a budget of hundreds of millions.
“I was lucky that within months of my joining, there came a window for major structural-level social reforms, backed by staunch support from our leaders,” she says.
Navigating motherhood and Silicon Valley
Towards the tail-end of Karen and her husband’s scholarship bonds, they made the decision to move back to the US to broaden their experience there.
Now based in San Francisco, she is active in the startup scene as a senior executive, talent hacker and coach with a knack for optimising interpersonal growth.
Moving with a five-month-old baby in tow and leaving all social support behind, however, proved to be an uphill task.
“I was very much a trailing spouse even though I was holding down the fort. My husband was pursuing his PhD and had a community he could readily assimilate into and rely on, but I didn’t,” she relates.
Initially still serving in multiple civil service capacities, Karen struggled with a sense of isolation and the demands of parenting while founding the Singapore Tech Forum in Silicon Valley, while she was part of the Singapore Global Network.
“The Tech Forum grew from 700 to 1,200 to 7,000 registrants over three years, 100% over-capacity each year. I remember in the 2020 Tech Forum, I moderated a discussion with PM Lee to a global audience of thousands.
“But that very same month, I burned out and had to take a few months off.”
She realised that many others faced similarly overwhelming situations without adequate support. “It’s only recently become okay to share these types of experiences. There can still be a lot of shame attached to it, but I knew I was not alone.”
As a certified coach, Karen began noticing more peers reaching out to her in confidence about the demands of leadership, workplace trauma and work-life balance. Finding scalable ways to support people through these moments would become her newfound passion.
“In Asian cultures, we are accustomed to being told what to do, think, and feel. In contrast, coaching brings about a sense of agency which unlocks intrinsic motivation,” Karen explains.
Leveraging her experience in strategic talent management, communications and executive coaching in Silicon Valley and Singapore, she founded Threshold Allies in 2021 to support start-up founders & tech leaders in early-stage start-ups or innovation arms.
Helping tech leaders develop resilience and support
“Everyone goes through unsettling periods of transition and adversity. It’s common to feel like you’re alone, because in society we’re better at highlighting victories than supporting each other effectively through challenging times,” says Karen.
While tech leaders are already mentally tough, she observes that they often feel obligated and struggle to be consistently positive outwardly. Maintaining that facade can be incredibly isolating through events like cofounder separations, having to lay off friends, development hiccups and the uncertainty of runway.
One of the biggest obstacles to founder resilience is underestimating the type of support network they need. “Even if you have a great significant other, the demands of start-up life are too much for one person to bear.
“Challenges at work begin to consume your life,” says Karen. “That’s why I always help my mentees build a better support network to help them weather the ups and downs.”
She shares that founders need three areas of support: the first is a ‘second brain’, an objective and non-judgmental brainstorming partner who can look at things from their perspective and values.
The second is emotional support, a safe space where they can be candid about challenges and feel safe. It’s easiest to get this among peers at a similar stage. This is why Karen runs highly curated, intimate workshops for tech leaders and mid-career women where they can pick up skills and find a peer support network.
“You feel empowered when you realize everyone is facing similar challenges and learning.”
Finally, you need trusted specialists like lawyers, therapists, HR and finance leaders who can help the founder problem-solve for their stage.
“Elite athletes will tell you that regulating emotions is the largest factor influencing performance,” says Karen.
Likewise, the most successful leaders are those who learn to manage the emotional ups and downs. They become a stabilizing force, rather than adding to the chaos.
“Leaders in high pressure environments cannot avoid being triggered by stress and anxiety. Your response in turn triggers your team into their own threat responses, such as freezing (complying mindlessly), fighting (attacking), flight (switching off),” she explains.
“Effective leaders learn to be the first to recognise and remove themselves from the threat cycle. You acknowledge that you too are human, and that there are stressors that can make you behave in unintended ways. It’s ok to recognise this, step out of it, and invite your team back into safety,” says Karen.
“This goes against the concept of a leader who is just ‘strong’ and ‘unshakeable’.”
Bridging the gender gap in leadership
Motivated by the growth and breakthrough she saw in her clients and mentees at Threshold Allies, and driven to fill the gaps she’d continue to identify for women, Karen and her co-founder Cyrena launched Her Life Ally.
Their goal? To address the adversities women faced with their wellbeing and confidentiality at the heart of it.
By matching allies with women who have been through similar circumstances 1:1 and curating hyper-local resources for women navigating workplace challenges, they aim to be the first responder, peer support network for resolving professional adversity.
She elaborates, “Women need support from other women with lived experiences. There’s immediate empathy and practical guidance. Our allies are all senior women who are skilled in pattern recognition, can triage your situation, and help you feel seen and heard because we understand what it’s like.”
Having worked with hundreds of women globally, Karen advises them to proactively prepare for career transitions. “When you enter mid-career, the ground shifts beneath you – expectations of your role, how people perceive you, and your life circumstances, they change.” Karen says.
“You have to refresh your mindsets and pick up new skills to navigate mid-career successfully.”
Beyond that, support networks need to be enhanced. “If you start to feel like something is ‘off’ at work, you don’t want to shout about your experience on the rooftops, but neither should you minimize it. Instead, ask for perspective and practical advice from other senior women who you trust.”
All too often, Karen has seen women in their 30s rising up the ladder, only to drop out.
“Corporate and societal structures are not designed for women to flourish professionally. Many are still expected to be main caregivers at home, especially at mid-career. Pregnancies, children with special needs, family with critical illnesses – it’s a relentless obstacle course.”
Karen believes that programs like Her Life Ally fill an important gap in helping women confidentially resolve their workplace adversity with their wellbeing in the center, so that they can continue thriving both professionally and personally.
“One of my mentors put it this way: When you think about women in their 30s and 40s still pursuing professional careers, you’ve invested a whole lot in their education and opportunities. The cost of one dropping out of the leadership pipeline is huge.”
She asserts, “We need to strengthen support as they move up the ladder. Imagine climbing a steep rock wall. Programs like Her Life Ally are like ‘climbing holds’ and ‘safety ropes’ which make it easier to keep ascending. It’s going to be tough, but we can make it easier for women.”
Thriving Under Pressure: Practical Tools for Tech Leaders
Looking for tools and tips to grow as a tech founder? Discover how you can better triumph over the rollercoaster of start-up leadership in this interactive workshop and dinner curated by Karen for the SGN community!
HerPath: Navigating and Thriving in your Mid-Career Journey
Meet like-minded women and pick up actionable strategies for the workplace in this workshop led by Karen and Minli, who bring a wealth of experience in both Asian and American contexts.
Unlock a 20% discount and other perks!
About Karen
Karen has held senior leaderships positions across technology startups and government bodies in Singapore, advising locally and globally on talent, social reforms and organisational behaviour. She is currently the Founder of Threshold Allies and Her Life Ally, and a coach to senior executives in the US and Singapore.
Connect with her here or at karen@threshold-allies.com.
