How To Enter a Workplace Through The Side Door

Former consultant turned marketer Maja Wilbrink knew she had struck a serious cultural nerve when her essay “How To Enter Side Doors” gained 2.5 million views online and 7,000 likes on Substack.

Many people, Wilbrink observed, are trained to enter an organisation through the “front door”, which describes moments where companies actively go to market with a hiring push. This traditional route includes job ads, graduate programs, cadetships and postings on social media channels. While the front door offers upfront clarity regarding role expectations, salary and location, Wilbrink thinks applicants seeking to stand out should look beyond standard applications.

For Wilbrink, who has taught hundreds of ambitious students and graduates, that is where the “side door” concept comes into play.

The job market as a search problem

Wilbrink suggests job seekers should think from first principles when approaching hiring. She views the job market as fundamentally a search problem. While starting a job search can feel overwhelming, understanding that employers are simply trying to match the right person to the right role at the right time allows candidates to systematise the process and differentiate themselves.

After aggregating target companies and listings, Wilbrink recommends job seekers refine their approach in three steps.

Jobs are simply a bundle of problems inside an organisation that someone is willing to pay to solve. A job advertisement is an employer’s best attempt to describe those problems, but it rarely captures the full picture.

1. Make your skillset legible before hiring decisions are actually made

Build a personal brand by taking speaking opportunities, publishing writing on platforms like Substack, creating a portfolio website or building projects in public.

2. Have a little audacity

Send a well-crafted email or offer your services through a direct message on social media.

3. Entering through the side door

Wilbrink believes that job seekers must become their own marketers, using tools like personal branding, direct outreach to founders or informal networking conversations to uncover what an employer truly needs.

“I do think many people, especially students, are taught the front door so thoroughly that they do not realise the building has other entrances. It can be easy to miss that careers are often houses you learn to enter through side gates, half-open windows, winding garden paths, basement doors, conversations at parties, public artifacts, warm introductions, cold emails, mutual fascination, visible proof of work and one person willing to take a bet on another person.”

Extending the “side door” thesis, Wilbrink collaborated with filmmaker Linda Zhang to survey business leaders and professionals who secured dream roles. Their research highlights the importance of engaging employers before a job is publicly posted and reflecting on the tasks that make candidates feel most engaged.

Jeston Lu, a marketer at global software company Notion, exemplified this approach when applying from Singapore while still a student.

“The best opportunities don’t come from applying to a job posting; they come from realizing you don’t need to wait for permission to get after it. The door is never locked in the first place. When I wanted to work with Notion, I turned to Twitter. Made a video pitch. Wrote a Twitter thread. Built a landing page within Notion itself, laying out what I could help do for their new storytelling team.”

Lu’s project reached Notion’s executive team, leading to a two-week work trial, a four-week extension and eventually a full-time role.

Danielle Strachman, an educator and investor at the 1517 Fund, advises applicants to identify what energises them during periods of uncertainty.

“The advice I would want to give, especially to any young person right now when we don’t know exactly where things are going, is you have to find what lights you up. That’s going to be the thing that helps people through some rough transitions.”

Strachman draws inspiration from home schooling in her work, citing a transition phase known as “de-schooling” where families unwind from traditional structures before discovering new interests. She noted that career transitions offer similar opportunities for self-reflection.

David Holland, MD, Talent Solutions at Employment Hero, has spent over a decade analysing workplace dynamics for small and midsize enterprises. He says that employers have always wanted great candidates, and while the way they find them keeps changing, what they want doesn’t.

“A CV on its own won’t always get you noticed. But there’s plenty you can do to stand out. Pair your professional skills with a few that sit outside your job. Start a side project or get involved supporting community activities. It’s the easiest way to show what you can do and build the skills your day job doesn’t give you. Spend your time on a profile that gets you in front of the right employers. We work closely with businesses every day, so we know what they’re looking for. Real connections, good skills, hard work and big ambition still put people in the best position to land meaningful work.”