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Send The Awkward DM

Most people aren't stuck due to a lack of talent. They're stuck because they won't press send.

That next opportunity you want, the one you've been talking about, thinking about, journaling about, is likely sitting in someone else's inbox. You never sent the message. It felt awkward. It felt like a reach. You didn't want to be that person.

I can't tell you the number of times over the course of a month I say to people, "Yes, press send, do it!"

The fear we create around putting a note in someone's inbox is wild to me. So what's the worst that happens? They don't respond? Who the fuck cares.

Nobody is going to print your message and buy a billboard in Times Square to shame you. You're not going to see your message on a LinkedIn post showcasing how big of an idiot you were for trying to get seen. It doesn't happen that way I promise you.

The people who win aren't always the most qualified. They are the ones who ask. They are the ones who shoot their shot, even if it makes their palms sweat. Networking isn't beneath you, and you're not above sending a cold DM. If you're serious about your growth, you have to get over the fear of looking foolish.

Let me be clear before I go forward, though, this article isn't just about networking. It's also about being aggressive in your job search, being active in connecting with high value individuals, and being vocal in your current role.

Networking isn't about sounding perfect or pretending to have it all figured out. It's about being bold enough to initiate. That's the whole game. The person you're nervous to message is just a human. They aren't sitting around critiquing your tone. They're busy. If they don't reply, it's not personal.

Move on and message someone else.

The real cringe isn't in the DM. It's in staying stuck at a job you've outgrown, while someone else lands the role you wanted because they had the guts to reach out. People fear rejection so much that they reject themselves before anyone else gets the chance.

The idea of "building relationships" has been romanticized. Many think it's supposed to happen organically or take years. Most connections start with one risk. One sentence. One compliment. One simple ask. Waiting for the perfect conditions kills more opportunities than failure ever will.

I have had people build a relationship with me over one call. Boom. Done. You have my number. Call again anytime.

I've seen people land clients, jobs, speaking gigs, and partnerships off one message. Was it smooth? Probably not. Was it worth it? Always. You don't need a perfect hook or polished pitch. You need honesty and initiative. Something as simple as, "Hi, I've followed your work and really admire what you're building. I'd love to connect or ask a quick question if you're open to it," can open the door.

There's no need to fake friendship. Just be respectful and clear. That's enough. Even if it feels uncomfortable, even if you stumble through it, the act of trying already separates you from 99 percent of others.

Confidence doesn't show up before the message is sent. It shows up after. Every DM you send builds your tolerance for discomfort. The more you put yourself out there, the easier it gets. The worst outcome is silence. If you're already staying quiet, you've already experienced that result.

Your next chapter doesn't begin with a new resume. It begins with one message. One you're probably afraid to send. Write it anyway. Most opportunity hides behind discomfort. It is rarely wrapped in clarity. It's often hidden in that one awkward DM you still haven't sent.

So press send.

Stop overthinking it.

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