Lifelong Tips for Creating a Fulfilling Career with Tech Entrepreneur and Philanthropist, Jessica Lui


Many students come out of high school or University, bright-eyed about the future and with ideas about changing the world. And although there is a small percentage of post-grads that are lucky enough to snatch their dream jobs, the majority of graduates are faced with a disappointing reality.

The first entry job is not as glamorous or exciting as most envision for themselves. Many begin to feel disempowered, perhaps even cynical about what the future holds.

Simultaneously, there are plenty of mid-stage career professionals that question their current career path. Reports show that even two years after the global pandemic, workers are still leaving in the millions every month despite ample work opportunities, indicating high levels of work dissatisfaction amongst the U.S. population. In a Gallup study, there were concerningly high rates of disengagement from the general workforce, with 60% of workers reporting detachment from work, and 19% feeling miserable.

Letting go of a career you’ve worked hard for, in order to transition or explore a new path can be incredibly nerve wracking. However, sometimes taking this leap of faith is necessary for individual growth and fulfillment. Whereas, staying at a job that fails to challenge you or helps you learn continuously, can become more of a deadweight than anything else.

Jessica Lui has a lot to say when it comes to empowering young people to pursue ‘unconventional’ paths or opportunities. As a multi-faceted tech entrepreneur, philanthropist, and public speaker, Jessica has held numerous roles in both public service, including being a youth ambassador for the UN and working extensively on the data and strategy side, at her day job with Deloitte.

We explored her golden tips for helping young people navigate the tough career landscape, and how to break through into different industries.

Interviewer: How were you able to connect the dots between two vastly different fields: tech and philanthropy and what inspired you to bring these different communities together for your initiatives?

Jessica: I’ve always had a long-held interest in public service. Regardless of the title that I hold or where I work, I believe it’s important to give back to the communities that we belong to, whether it’s local or global, and to work together to be able to strengthen our collective well-being.

I think great leaders have always been the people who can rally or inspire others to lift other people up. One of the philanthropic areas that I’ve always been passionate about is supporting access to education. I don’t think there’s a single industry or field that hasn’t been impacted by the growth in technology. However, I think the landscape of education is increasingly virtual. Technology can be a great equalizer.

For example, it grants democratic access to educational resources available through the web. No matter where you are in the world, if you’ve got an internet connection, you can check out a lecture at Harvard, or you can take a virtual philosophy class at Columbia. 

It gives us broad access to so many great educators. A good example of this is, recently, I was the founding member of a program called Citizen Girls. The program which was ran both in Canada and Nigeria focuses on educating participants on building civic leadership skills.

What was interesting was that the entire program was created through virtual collaboration. From writing grants to building partners, hiring, and the delivery of the program, was all done entirely online.

This allowed us to get a hundred young women to participate in the initial launch of the program from both Canada and Nigeria, in collaborative learning sessions across both countries. It was inspiring to see folks who had been impacted by Covid and couldn’t leave their homes to still be able to have access to great speakers, and classes from the other side of the world.

My point here is, effective philanthropy benefits profoundly from digital tech. It can be used to develop partnerships or to rapidly scale projects and programs globally. 

Interviewer: Do you think women still face barriers in the world of tech? How do you think we can help them overcome these barriers?

Women standing behind lines of code

Jessica: Women in general are still underrepresented in tech and it’s particularly evident in senior leadership positions. There was a study released by McKinsey last year which showed that one of the big challenges in getting women to senior leadership positions is that they face what is called a “broken rung” at the first step up to manager. 

In other words, if you don’t get a promotion earlier on in your career, it slows you down from continued career growth and limits the opportunities you’ll have going forward. Conversely, if you get a promotion earlier on, you’re more likely to be visible, recognized, and promoted within your organization.

McKinsey showed that for every 100 men that are promoted, only 86 women are. That makes it difficult to establish a foundation for career growth. When it comes to a company perspective, addressing the diversity opportunity in tech should be an integral part of talent strategy.

It’s also positive that companies with diverse senior leadership are shown to outperform competitors and attract top talent. I think companies can help by ensuring that DEI (Diversity, Equity, and Inclusion) programs are integrated into overall talent programs. 

Coming in from a tech perspective and as a data nerd, I think we can really use data to identify what those issues are in order to set specific goals and attract and retain women in tech. 

As individual leaders at any level of organization, you can help by supporting affinity groups and in particular, mentorship programs. Whether that’s in terms of funding or in terms of becoming a mentor yourself. 

This is because I believe women in tech benefit enormously from mentorship programs and in growing their network because it allows them to connect with leaders who can help them succeed. It helps them to identify opportunities for growth. A lot of the time, it helps them to become more visible in their organizations because they have someone to advocate for their growth and sustained success.

Interviewer: You have a TedTalk based on the principle of success. Has your definition evolved over the years— and what is the current one?

Jessica: Maya Angela said it best, “Success is liking yourself, liking what you do, and liking how you do it.” The gist of my TED talk is that you find success by defining what matters to you. What brings you fulfillment, and joy, and sparks your interest? Ultimately I think success is meaningful and enjoyable only when it feels like your own. Everyone has the right to write their own definition of success.

Interviewer: To have a multi-faceted career that you have (ie. consulting for Deloitte, speaking, maintaining different initiatives), do you think there was a certain point where every acclimatized at the same time, or did you gradually adopt each of these roles over time? 

Jessica: In my career, I’ve chosen to focus on the opportunities that I have in front of me at that particular point in time and make the most of them. I haven’t adopted all of those roles at one time. 

 “You can have it all, but just not all at once.”

 It’s important to focus on what you value most and what skills you want to develop. From there, you can start thinking about the opportunities you want to pursue and how you’re going to allocate your time.

It’s better to have consistent, focused effort in one area than to be overextended and failing in several. Over time I’ve adopted each of these roles and explored each of the different areas that I’m passionate about. It’s allowed me to continue to build on my skill set. In particular, problem-solving skills are useful no matter where you go. I’ve been able to bring a really diverse perspective, as a result of the different facets of my career.

Interviewer: Do you believe young people should pursue their passions?

Jessica: Finding out what you’re passionate about is part of the process too. You might try things and find that you love it, or you might discover you don’t like it. 

“I think particularly for young people, there’s a lot of pressure to only pursue your passion and to know what that entails.”

 I tend to think of a passion as something that has been developed over time. If you enjoy things, pursue them, and the things that you stick with and continue to enjoy over time, they become your passions. If you don’t know what you love doing, you’ll find out over time.

There’s also more room for risk taking when you’re out of school. In school, how you progress is very black and white, you either pass or you have to retake the course until you get a passing grade. Conversely, your career will likely be less linear: setbacks, disappointment and failure are common on the path to success.

When you experience a tough patch, having self-compassion is really crucial because you can’t control everything that happens in your career. There’s going to be unforeseen circumstances (like COVID) that happen along the way. However, if you’re compassionate to yourself, you’re able pick yourself up, dust yourself off, and get ready to move forward.

Interviewer: What’s your advice to younger girls who are interested in more career avenues than one?

Jessica: My first piece of advice is to be realistic about your capacity. Remember, that you have a lot of time in your career. The average undergraduate finishes in their twenties and the average person retires in their sixties. That means you have 40 years to do all of the things you want. There’s no rush. Choose one or two things to focus on at a time, and do them well.

My second piece of advice is to focus on the opportunities that stand out the most to your interests right now, and then take it from there. If you’re interested in multiple career opportunities, a lot of the times that will mean taking a leap of faith as you transition from one career path to another. You’ll come to a fork in the road when you have to decide if you’re going to continue where you’re going, or if you’re going to start something new. When you get to that fork in the road, even if you don’t feel ready, take a leap of faith anyway. Believe in yourself enough to know that if you fail or encounter a bump in the road, you will probably have the capacity and the resilience to find a path forward.

Interviewer: What’s your thoughts on failure?

Failure is an important part of growth in developing resilience, and it’s okay to take smart risks. Especially early on in your career, you won’t be afraid to try out some new things, even if you’re not entirely sure whether it will work out at that point in time. I think the best safety net that we can have when we’re overwhelmed or if we think that we’re going to need support, is to ask for help. 

“Because if you’re ambitious and you want to accomplish big things, you cannot do it alone. You need a community.”

It’s important for us to choose people whose presence in our lives will make us better people. I think we owe it to ourselves if we want to take that leap of faith, or want to explore a new area to ask for help, or to talk to the experts or mentors who are going to help you navigate the path ahead, especially if it’s unclear. You never know when these connections might just change your life. 

Conclusion: Becoming a Student of Life

There are bound to be times of uncertainty, fear, and self-doubt in the course of one’s career, regardless of what stage they’re in. However, looking at a career and life through an opportunistic lens can offer a lot of potential, especially in the transitionary phases.

Often, this requires putting ourselves out there again, reaching out to connections, mentors, peers, and strangers.

If it doesn’t feel a little scary, it’s most likely because you’re not taking any risks. Taking risks and pursuing opportunities to fail is sometimes the biggest source of learning and growth, which can propel you further if you act on changing and optimizing your actions.

When you become a student of life, every opportunity, curveball, and mistake becomes a chance to learn and develop a career you wouldn’t have otherwise dreamed of.

Naomi Peng
Naomi Peng
Naomi is a business journalist who specializes in crafting the most inspiring stories about entrepreneurs, the startup world, and investment trends.