Breaking the Comparison Trap: Jessie Leong on Why Your Financial Journey Is Never “Apples to Apples”

For writer and How I Fund This founder Jessie Leong, the hardest step wasn’t learning the jargon, it was finding the confidence to start. Now she’s demanding equal access to financial education and teaching women how to quit comparing their portfolios.

The feeling of anxiety was quickly overshadowed by triumph. Jessie Leong recalls the fear that gripped her before making her first investment: “Was I going to lose all my money? What was going to happen next?” Yet, the moment she put that first £20 into the market, everything changed. “There was this feeling, this sense of this baby step had happened,” she recalls. “I was like, okay, this is it. I’m an investor now.”

Jessie, a personal finance content creator, writer, and speaker, is an advocate for equal access to financial education for all. Her mission stems from a deeply personal void. While her parents instilled the importance of hard work and saving for a “rainy day fund,” the conversation always stopped short of investing.

“Investing wasn’t something that they did,” she notes. “And for me, that meant that I never felt comfortable with investing when I grew up… It wasn’t something that I was privy to or felt that I was part of that club.”

The spark that finally ignited her interest came, as it often does for this generation, via social media. Seeing people her age and gender investing online shattered the image she had held, that the club was reserved only for those who were “older, richer, [and] looked different.”

The Cost of Comparison

For Jessie, the psychological barrier to wealth creation is often rooted in the media and the toxic cycle of comparison.

She points out that women are frequently characterised in media as “spenders” with “bad money habits.” This portrayal signals to women that if they recognise any of those habits in themselves, they are intrinsically “bad with money.” This lack of financial confidence is corrosive.

“If you don’t feel confident making financial decisions,” she asserts, “then you’re less likely, or you’re going to feel restricted in the opportunities that are available for you.”

This lack of self-trust was compounded by her own early investing mistake: “My biggest mistake in investing was trying to follow too much of what other people are doing, and not focusing on what are my priorities.”

Her remedy is simple but powerful: recognising that comparison really is the thief of joy. “I don’t need to keep up with the Joneses,” she explains, “because the Joneses are on a very different journey to me, and they have very different priorities to me, and I can’t see all of their finances.”

Nuance, Culture, and the Next Generation

For Jessie, understanding personal finance requires looking beyond the numbers to include the deep, often unspoken, nuances of culture and background.

She highlights how her own cultural obligation to financially support her retired parents often confuses her peers, a clear illustration that no two financial journeys are alike.

“Finance spans across so many different nuances. It’s your gender, it’s your background, it’s your culture, it’s how you identify as yourself. That’s what I find interesting because you are never comparing apples to apples.”

It’s this realisation that powers her next crusade: demanding comprehensive financial education, particularly for the 5 to 18 age bracket. With young people becoming increasingly anxious about money, Jessie is adamant that education is the ultimate tool for empowerment.

“Money dictates almost everything we do,” she states, whether it’s “what we eat, where we live, the job we have, the opportunities we have as well.” By giving young people this vital knowledge, she believes they can use those tools to better themselves and break free from the anxiety that plagued her own generation.

Jessie’s message to those still waiting on the sidelines is one of urgency and grace. “I would say that it’s not too late to start. Don’t think that because your particular age or you have a particular salary, that actually investing is not for you, because it is for everybody.”

She encapsulates her mission, joining a powerful movement of women using their platforms to bring visibility to the historically quiet world of wealth creation.

“I invest largely because I want others to see that investing is accessible to them.”

Watch Jessie’s full chat with us below:

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