Trail Markers: How to Reach Out

(Without Feeling Weird About It)

Let’s be honest: the idea of “networking” can make even the most extroverted among us cringe a little. It sounds formal, transactional, maybe even a little fake. But when you reframe it as simply connecting, things get a lot easier.

This post is about reaching out — to potential clients, collaborators, mentors, even peers. And doing it in a way that doesn’t feel pushy, awkward, or fake. You don’t need a script. You just need a bit of strategy, a little courage, and a reminder that people like being seen.

Why Reaching Out Matters

You can do incredible work, have a beautiful portfolio, and still struggle to get traction if no one knows what you do. At some point, you have to step out from behind your website or social feed and make the first move.

Especially when you’re early in your career or shifting into a new space, outreach is how you plant seeds.

Some of those seeds might bloom into clients. Others into collaborators. Some into nothing — and that’s okay too. The point is: if you don’t start the conversation, it often doesn’t happen.

Start Where You Have Shared Ground

It’s a lot easier to reach out when you have something in common. Here are a few ideas to spark that connection:

  • You worked in a similar industry
  • You follow each other on LinkedIn or Instagram
  • You went to the same school or conference
  • You both love the same niche (like public lands or trail advocacy or small town tourism)

You don’t need a deep tie—just enough to make your message feel thoughtful instead of random.

What to Say (and What Not to Say)

Keep it short, relevant, and real. Here’s a structure that works well:

  1. Mention the connection (how you found them, what you liked)
  2. Share what you do (in plain language)
  3. Make an offer or ask (this can be soft!)

Example:

Hi Joe,

I came across your profile while looking at folks who do interpretive planning, and loved your recent project for the state parks system. I do marketing and design for small outdoor organizations and campgrounds, and your work really resonated. If you ever need a creative collaborator or want to bounce ideas around, I’d love to connect.

What not to do:

  • Don’t copy/paste the same message to everyone
  • Don’t immediately ask for a job or referral
  • Don’t oversell yourself. You’re just starting a conversation

But…What If They Don’t Respond?

Totally normal. People are busy. Don’t take silence personally. You can follow up once after a week or two with something like:

Hey again! Just wanted to circle back in case this got buried. Totally understand if now’s not the right time.

If you still don’t hear back? Move on. There are so many people out there who will be excited to talk to you. Don’t waste your energy chasing silence.

Outreach Isn’t Just Cold Emails

There are a ton of ways to connect with people more organically:

  • Reply to a post or story with a genuine comment
  • Tag someone in something you think they’d like
  • Ask a thoughtful question in a community or Slack group
  • Give a shoutout to someone’s work you admire

These light-touch interactions can open doors without the pressure of a formal intro. And over time, they make you recognizable, approachable, and trustworthy.

Reaching Out to the Right People

Not everyone is your audience, and that’s a good thing. Be intentional:

  • Focus on people or organizations whose mission matches yours
  • Prioritize quality over quantity
  • Reach out to both peers and those further ahead of you

Remember: your next opportunity may come from someone who simply knows what you do and likes how you do it.

Practice Makes Less Weird

The more you do it, the easier it gets. You start to recognize what works, what feels good to send, and what kinds of people respond best. Start small. Set a goal to reach out to one new person a week. Or comment meaningfully on three posts. Tiny actions stack up.

You Don’t Need to Be the Expert

If you’re thinking, “Who am I to reach out?” Let me say this: no one expects you to know everything. But your curiosity, creativity, and perspective are valuable. You don’t need to pretend to be more experienced than you are. Just be honest, respectful, and excited to connect.

Final Thoughts

Career building doesn’t happen in a vacuum. Reaching out is one of the most powerful, accessible tools we have—especially in industries where people want to work with people they like.

So treat your outreach like trail markers: small, intentional signs pointing you in the direction of connection, clarity, and confidence. They may not all lead somewhere. But enough of them will, and you’ll be amazed at how far they take you.

Next up: Carry the Right Tools — Legal, Financial, and Emotional Prep.

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