Direction Unknown: Ask a Stranger

Elizabeth Scott // Columnist 

As a socially anxious introvert with a rather modest social circle, “it’s all about who you know” is one of the most terrifying pieces of advice I’ve heard—and I think I heard it six times last week alone. To make matters worse, it’s incredibly accurate.  

We’re continually reminded to make professional connections and build a solid network throughout our time in university. Do people actually? Sure, maybe. Did I? Definitely not.  

I envy people with the tenacity to casually and confidently engage with strangers. Whether it’s in person or online (with the added bonus of anonymity and unlimited revision to your opening lines), connecting with people you don’t know is challenging. It is for me, at least. Finding the confidence to make connections is something I’ve struggled with for years. But as a wildly lost graduate with a measly network, I was in desperate need of guidance and connections. And seeking those things meant talking to other humans.   

Something I’ve discovered since graduating is the masterful art of sliding into a stranger’s DMs, and most importantly, the opportunities to be gained from such a bold move. The act of sliding into DMs is generally associated with messages powered by horniness and desperation rather than professionalism (although, my messages definitely oozed desperation, too). But let me tell you, it can be an incredibly valuable skill if you do it right. 

We’re digitally connected to hundreds if not thousands of people, many of whom we’ve never met in person. But how often do we actually take the opportunity to connect with these pseudo-friends on a deeper level than just dropping a few emojis under their latest updates?  

Finally, I decided to say “fuck it” and take advantage of the easy access social media grants us to influential folks, story-tellers, changemakers, artists and icons. 

The first time I decided to craft an unsolicited message was when I desperately needed insight and direction while trying to figure out the next steps in my post-graduation journey. Naturally, my irrational fears took over. What if this person thinks I’m a complete fucking idiot? What if they feel like I’ve wasted their time? What if they burst into laughter at my pathetic attempt to make a connection? I took two hours to write, rewrite, and vigorously revise an Instagram DM (which has a limit of 500 characters, FYI. I had to pare down my initial novel by about 7.5 million words).  

I hesitantly pushed send after finalizing my masterpiece, launching my words into the digital sphere with no going back. Then I waited.  

I sent the message to Abby Mills, a renowned fashion influencer who also happens to be an incredibly successful digital product designer (otherwise known as UX design or user experience design) for one of the world’s leaders in technology and design. That’s right, I’m talking about Apple. Her career path is one I marvel at and aim to pursue. Abby of @clothesandpizza is a living legend, my style icon, and newfound career guru.  

She responded. She requested my email because her wisdom was far too colossal to fit in an Instagram DM. A few hours later, I received her email and sobbed into my keyboard.  

Abby had taken the time out of her hectic Silicon Valley life to provide me with her UX design resources, blogs, podcasts, personal anecdotes, online courses and general advice based on her own experiences. Unaware of my location, she even mentioned that she’d get coffee with me. You bet I immediately looked up the cost of flights to San Francisco. Our conversation expanded into vintage clothing, travels and tattoos. Now she’s a powerful connection I can confidently message at any time. Maybe she’ll vouch for me as a potential Apple intern one day… who knows?! Or maybe we’ll share a pizza and get matching tattoos.   

The next time I reached out to strangers, I had a certain level of confidence that didn’t exist before. I chose to post publicly in Girl Gang, a Facebook group for Vancouver-based women working in technology, design and marketing. Again, I relentlessly revised the short message before posting it, then panicked and overanalyzed the lack of responses for hours afterwards.  

I asked for advice from anybody who had landed a UX design role without a formal education in related fields. I received some responses, struck up some conversations, and took some brilliant ladies for coffee. Now I’ve got a mentor I meet with monthly. Mara used to be the lead UX designer for a cybersecurity company and is now the Director of Strategy and Editorial at a local marketing agency. She’s cool as fuck and loves offering her guidance.  

I discovered a few things from pushing through my anxieties and reaching out to strangers. First of all, I learned that people really want to engage and enjoy sharing their stories. Who doesn’t love to talk about themselves? It’s probably pretty flattering to be considered someone with valuable advice, too. Each time I send a message of praise, curiosity and eagerness to connect, the responses are overwhelmingly friendly and willing. I also discovered the benefits of connecting with the people who inspire you, and the immensely fulfilling feeling of having idols within your network.  

You better believe I message people all the time now. My once-foreign ability to start conversations even leaked its way into my day-to-day life. It has allowed me to discover things about myself and about the people I admire. Conversations and connections have helped me visualise my ideal career path and how to go after it. Through connecting, I’ve been granted writing gigs, offered side hustles, and recommended for work opportunities. Plus, it just feels damn good to have a growing number of people on my team while I try to navigate this wild journey. I hate that it’s true, but it really is all about who you know. But the good news is, if you just try, you can know anybody you damn well want to. 

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