To Find a New Career Path, Get a Little Lost

In my early 20s, my dad told me you can't find a new path without getting lost a little first. That was back when I felt more than a little lost, long before I realized I'd spend my whole life trying to forge new paths. 

Something you should know about me is that I'm curious. Depending on who you ask, that either makes me creative or extremely stubborn. I ask "why," not necessarily to the point of agreement but until I understand. 

So, when it came to my career, I found myself veering off the "normal" (corporate) path because I was never able to get reasonable (or any) answers to my questions. I remember the first month in a new role, I asked a colleague why a report was structured a certain way. I shared suggestions on how it could provide more value and asked questions to make sure I had the proper context. By the fourth or fifth time I shared my thoughts, this colleague snapped and said, "It's just how it's always been done."

It turns out that this was not an uncommon sentiment. As I continued to try creating new ways of doing things and shared ideas with different teams in the company, I kept getting shot down with some version of "stay in your lane."

So, I swerved and started down a new path.

I started my first business in 2016 when I noticed that telling myself and others that "I don't read the news because it's boring" was not really an acceptable answer. There was a problem with the news—it was boring, filled with jargon for no reason, and biased—so I decided to solve that problem for myself and then share the solution with the world.

The next four years of building Pressed were chaotic. 

The first time a stranger signed up for our newsletter, I cried tears of joy. A few months later, one of our competitors (a female founder, ugh) bought "Pressed" as a Google Ad Word and pretended to be us. About a year later, we raised our first round of funding. Around the same time, I noticed I was getting under five hours of sleep a night. So, you get it… building something new is rewarding, but mostly, it's hard. 

Starting anything new is hard, whether you're trying to make changes within a corporate setting or building something from scratch. New ideas don't come with a roadmap, so you're constantly getting things wrong, making mistakes, and trying again. Not to mention the self-doubt… oh, there is so much self-doubt.

Layer on top of all that, being a woman in a world where we're constantly told we can't. 

I started Pressed eight years ago. Back then, I was often the only woman of colour at events that weren't branded "ladies' night" or the token woman on a startup founders panel. 

Things have improved, with companies like Hard Copy and communities like Monday Girl carving out space for women to be whoever the f*ck they want to be. However, when I open the homepage of major news publications, nearly every funding announcement (celebration) is still accompanied by a photo of Steve, John, and Mike.  

The other day, I was doing some research for a client in the investment space when I landed on a company page with a woman right at the top. I thought, "That's what I'm talking about!" until I looked closer. The female employee was a junior-level assistant placed at the top of the page beside her male executives, presumably to showcase diversity. 

Alongside news of basketball superstar Caitlin Clark landing a historic endorsement deal are still stories of men like Harrison Butker telling women that no matter what they achieve, they'll be happiest when they become wives and mothers. To be clear, the issue here is not what makes women happy—their careers, their babies, whatever—the issue is that he (a privileged white man) is telling women what should make them happy. 

So, we still have a long way to go. 

Two of my best friends are startup founders, both women of colour. They've been running successful tech businesses for many years, but neither has ever pitched for meaningful funding. Not because they don't need it, but because "what's the point," or "we haven't proven ourselves enough." Translation: we don't look, sound, or do things like the people (men) who raise the big rounds.

We shouldn't have to. Women succeed in business because we bring different strengths to the table. Despite limited access to financing and societal biases, women-owned SMEs in Canada have created over 1.5 million jobs and contributed more than $150 billion to the economy. Women-owned businesses are often more sustainable because we set realistic, not overly aggressive, goals, and our empathetic, gentle approach brings communities together. 

But we can't walk these new paths alone. We need advocates to push us to do things we've been trained to think we can't. We need examples of women before us, women who will open doors and welcome us as we are. 

While I wait for the scales to balance, you'll find me continuing to choose the path of most resistance. I recently started a new business venture, and my co-founder and I are on a mission to simplify DIY home projects from start to finish. 

Social media makes DIY projects look fun and easy in 60-second reels. The reality is that instructions to complete a project are fragmented across multiple online and offline channels. Our goal is to provide a space for women to hone new skills while making their home decor visions come to life.

I know the path to success won't be easy, but with two failed startups behind me, years of hard-earned experience, and an army of women blazing new trails by my side, I'm ready for the challenge. Getting a little lost is just part of the journey.

Jacqueline Loganathan is the co-founder of Hone