How to Make Connections That Will Actually Matter
Making friends is hard. Sending cold emails to people you admire is harder.
Making friends is hard. Sending cold emails to someone you admire is harder.
As I’ve stumbled into the start of my somewhat professional career, I’ve sent a lot of embarrassing, pointless messages, stuff anyone in their right mind would ignore.
The summer before my senior year, I spent 2–3 hours a day emailing and DMing “cool brands” and marketing/design agencies I found online. With very little experience (and even less understanding of how any of this actually works), I was hopeful that with enough output, I’d land a dream role straight out of college. I thought I had what most people didn’t: a strong work ethic and passion.
I was mistaken.
Those hours and hours of outreach resulted in one freelance photo/design gig that took around 50 hours to complete for a budget of $150.
“Connecting” with people is weird. No matter how far along you are in your career, there’s always someone you think is doing something way cooler than you. There’s always someone you’d love to get coffee with. There’s always another cold email to send.
Here’s a video that describes the exact type of emails I (and so many others) sent.
The biggest mistake I made in college was treating networking like a means to an end. I just wanted to work with someone cool. I wasn’t actually interested in them, their process, their story, how they felt about their own work, or how they got to where they were.
To me, networking used to mean trying to get something out of people. But something changed when I stopped trying to “make connections” and started being genuinely interested in what people were doing.
No matter what your goals are, you’re going to need the help of others: peers, mentors, collaborators, partners.
So the question becomes: how do you build a real network when you haven’t met the right people yet?
I’m still learning this, still navigating the awkward mix of professional relationships online with people I’ve never even been in the same room with. But as I’ve learned and tried new things, I started making friends, connecting with the types of people I wanted to work with, and building relationships that are worth so much more than just an “in” at a company.
As you pursue your creative passions, art, film, design, writing etc. don’t be afraid to reach out to people. Collaboration is one of the best parts of creativity. Finding someone to bounce ideas off of, to share inspiration with, can change everything.
Here’s 5 things I’ve learned about connecting with people online and how it can lead to true creative collaboration.
1. Be honest
This might be the most generic advice you can get about reaching out to people, but it’s still one of the most important.
During college, I spent a lot of time trying to spruce up my resume or portfolio, trying to make my projects look like more than they really were. Then I’d send messages to people, hoping to come across as an “established creative professional.” (I was 19.)
The truth is, everyone’s still figuring it out, even the people at the coolest brands with the biggest budgets. When you approach someone online, it’s tempting to lie a little, to make it seem like you’re working on all these amazing things… when really, you’re just hoping they don’t find out what your day-to-day actually looks like.
It takes humility to say something like:
"Hey, I love [project name] you worked on. It’s been such an inspiration. I hope to create work with a similar style one day. Any chance you’d be open to sharing more on how you came up with it?"
That kind of message is honest: I like what you’re doing, and I want to learn more.
It’s a lot better than pretending you’re cool or accomplished enough to deserve a reply.
2. Be curious
Our interests change all the time. As you navigate creativity and your career, it’s going to take time to find your lane. I’ve started reaching out to people I’m genuinely curious about. Maybe a piece of their work fascinates me, or something they’re building has inspired me. When that curiosity is real, it’s so much easier to send a message that feels authentic… because I actually care.
Those are the kinds of connections you want anyway. You want to talk to people whose work excites you, who ignite your creative energy, not just someone who happens to work at a company you want to join.
3. Don’t tell yourself ghost stories
Being ghosted sucks. It’s frustrating when someone agrees to meet and then never follows up with their availability. But don’t take it personally. These are people too. People with overflowing inboxes, nonstop meetings, and their own list of connections they’re trying to maintain.
Don’t let being ghosted or ignored get you down. Don’t let it make you question your work. Have you looked at your own inbox lately? Chances are, there’s someone waiting on a response from you too. It’s not personal, it’s just life.
4. Find people who have something in common with you
One of the best things I’ve done for my career was finding a Slack channel full of people with similar interests who were working in similar spaces. Suddenly, I wasn’t reaching out to cold, abandoned LinkedIn inboxes anymore. I had joined the Slack community of a small podcast I was listening to, and it was filled with professionals at and far above my level. Because we already had something in common (the podcast) it was so much easier to start conversations and build genuine connections.
Find an online space where people are active and engaged in the topics you care about. Join the conversation. Share your perspective. Talk about what you’ve been learning. You’ll be surprised by the people you meet.
5. Take your time
Don’t go around firing off copy-pasted, ChatGPT-edited DMs to everyone you want to connect with. That approach rarely works. When you want to reach out to someone, don’t rush it. Their inbox isn’t going anywhere. Be deliberate. What are you trying to say? What can you offer? What are you asking them for? How do you want this interaction to feel?
That first message deserves care and intention. Yes, it’s a pain reading it over and over again, but writing something that feels human, (especially through a cold email or DM) is a skill. It’s not easy. It takes time, thought, and attention.
In her article “How to Write a Cold Email,” Carly Ayres writes:
“Cold emailing is fundamentally about making human connections in a digital world. Treat each email as a conversation starter, not a transaction. In a world of constant notifications and fleeting connections, it offers something valuable: a moment of quiet, deliberate outreach. The next time you’re tempted to fire off a quick Slack message or LinkedIn DM, consider the slow email approach. Who knows? You might just get a response that changes everything.”
That’s the mindset to carry into every online connection: you’re starting a conversation, not chasing a transaction.
There are so many people out there to connect with, not just to build your network, but to learn from, create with, inspire, and be inspired by. Finding the right approach will take time. So next time you reach out to someone, remember: that’s a person on the other end. A person you might end up making something great with.
How do you want to start the conversation?
Keep creating and repeating,
- James
🌺 Rosa Sawyers’ Nature-Inspired Animations: Rosa Sawyers transforms everyday natural moments into peaceful, looping animations—capturing the quiet magic of the world around her.
📘 The Vignelli Canon: Outlines design principles like semantics, syntactics, and pragmatics. Stressing discipline, clarity, and timelessness.
🖥️ What Even *Is* a Website?: Carly Ayres explores the evolving nature of websites, creative partnerships, and why we might still be in the silent film era of the web.
🪨 Navigating Career: Designers' Milestones: A collection of personal stories from design leaders reflecting on pivotal moments and lessons learned throughout their careers.
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This week’s advice…
Help! I Have Too Many Ideas!
This week, we’re tackling some of the most common creative struggles, and I’m also sharing a mood board inspired by the muses that have been fueling me lately. It’s a little all over the place, but it’s an honest look at where my head is and where I want to take Create.Repeat next.
This week we are happy to highlight John Thompson, a former men’s lifestyle journalist now menswear copywriter at Huckberry. His Substack, LIVE A LITTLE, is a creative outlet where he shares inspiration and the thinking behind great marketing.
We asked John for a quote that has shaped his creative journey. Here’s what he shared:
“My hero is always 10 years away. I'm never gonna be my hero. I'm not gonna attain that. I know I'm not, and that's just fine with me because that keeps me with somebody to keep on chasing.” – Matthew McConaughey
“I always fall back to this quote when I start comparing myself to others. It reminds me that my art, and my life, must always stay true to me. Authenticity is the key. I don't want to be someone else. I only ever want to be me.”
Check out one of his favorite pieces:
Create.Repeat is a community for creatives.
The Create.Repeat Substack is a project designed to be a weekly diary on creativity. Sharing inspiration for artists to keep creating and repeating.
Written and curated by Zack Evans & James Warren Taylor
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History repeats. Create the future.
Thank you for the feature! Another great issue as always 🔥