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“Am I allowed to reach out to people?”

Last Updated:

November 27, 2025

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Welcome to Ask Gorick Anything, Edition #50.

This week's question is: “Am I allowed to reach out to people?”

Keep reading to find out.

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ASK GORICK ANYTHING

“Am I allowed to reach out to people?”

💡 The quick answer: Outreach is appropriate and effective when you send highly specific, tailored emails. In the meantime, don’t reject yourself before you give others the chance to say “yes” to you!

THE QUESTION

“I am a young developer who is graduating this December. I am currently in an internship and just got an interview for the full position, everything seems good to go. But at the same time, I feel like I am not really enjoying the work I am doing at this company and I am trying to pivot.

Specifically, the company I am working for does a lot of dev ops type stuff (GitHub CI/CD, Kafka, etc.) but I want to move towards more system engineering, 3D animation, HPC, that you might see with C++ programming. I don’t have a lot of C++ experience (well, my undergrad used C++, but it wasn’t modern C++) so I’ve been building a project and documenting it on Linkedin.

I’ve gotten a lot of connections over the last year in the C++ community, so I believe if I sent the right emails and asked for help, I could get a job elsewhere. But for whatever reason, I keep getting bogged down by imposter syndrome and anxiety.

I keep thinking ‘I don’t have enough C++ experience, no one will want to hire me!’ or ‘Its been so long since I’ve seen that person, they probably won’t want to help me anymore.’ I know these thoughts aren’t helpful and don’t reflect reality, but It’s still impairing me from moving forward.

How can I know when it’s appropriate to reach out to others and when its not? How can I tell when I don’t have enough experience and need more? Does it even matter? Should I just try anyway?”

— “Viv” from Bay Area, CA

GORICK’S RESPONSE

Hi “Viv,”

You’re definitely not alone with this imposter syndrome.

I’ve got a few thoughts on that, but first, I want to answer your questions. Here’s what I heard:

  1. When is it appropriate to do cold outreach as a job seeker?
  2. How can I tell when I don’t have enough experience and need more?
  3. How do I know if reaching out to someone is a waste of time (or not)?

Let’s dive in!

When is it appropriate to do cold outreach as a job seeker?

Here’s the long and short of it: If you can cite a specific reason for reaching out to someone over anyone else, it’s appropriate.

The more of the following criteria you can satisfy, the more likely it is to be appropriate (and effective):

  1. You know them from before (e.g., you used to work together)
  2. You have something in common (e.g., you’re both first gen)
  3. You have someone who can introduce you to them (e.g., a professor)
  4. They are in the role/team/company/geography you’re interested in (e.g., 3D animation at Disney in Burbank, CA)

In an age where everyone can send an email (so all of our inboxes are flooded), the bar for sending a good email has only gotten higher.

So, before you hit “send,” re-read your email and ask yourself: “If I accidentally sent this email to someone else, would this email still make sense?”

If your answer is “yes,” your email isn’t tailored enough and you need to be more specific and personal.

Here’s an email that an executive received the other day and shared with me because it made him face palm so hard (so don’t do this!):

How can I tell when I don’t have enough experience and need more?

In general…

  1. The more well-known the company
  2. The more well-advertised the position
  3. The more attractive the job description
  4. The more attractive the location

…the more applicants you can expect, which is why, if you’re struggling to get into a big, prestigious, attractive company, it helps to start smaller and work your way up.

If you want more specific statistics of your odds…

  1. Get LinkedIn Premium (click here to get a 2-month free trial)
  2. Click on a job posting
  3. Review your job match score, who you can contact, and how you compare to other applicants

Just don’t get too caught up with the data. After all, it’s a human that makes the final decision—and not a machine.

Just because a candidate has all the right keywords in their resume doesn’t mean people will see them as the most competent, committed, and compatible candidate (which is why relationship building is the only way to get a job, especially these days).

How do I know if reaching out to someone is a waste of time (or not)?

Here’s my take: there’s a difference between rejection and self rejection.

  • Rejection is when someone says “no” to you.
  • Self rejection is when others could say “yes” or “no” but you never even let others make a decision, so you’ll never know which it is.

As much as it hurts to get rejected, all you see is a “no” or no reply at all.

What do you not see? The underlying reason—and it could be any of the following:

  1. Your email ended up in their spam or promotions folder (so they never saw it)
  2. Your email got buried in their inbox (so they forgot to reply)
  3. They don’t check their LinkedIn inbox (so your DM went unread)
  4. They got too busy (so prioritized something else over replying to you)
  5. They didn’t think they could help you, whether because their team isn’t hiring, they aren’t a decision maker, or they’re getting laid off themselves (so didn’t reply or said “no”)
  6. Your email was too long-winded or unclear (so they didn’t know what to do)
  7. They didn’t feel enough of a personal connection to reply (i.e., you weren’t compatible)
  8. They didn’t think you were committed to the path or role
  9. They didn’t think you were competent enough to succeed in the path or role

Here’s the thing about this list:

  • Reasons #1-5 are all problems on their side—not yours.
  • Reason #6 is a learnable skill—but still not really a sign that you’re unqualified.
  • Reasons #7-8 are a matter of who you target and how you present yourself.
  • Only reason #9 is because you’re unqualified.

Here’s another thing about this list: You really don’t know which reason it is.

The only thing you can do is (A) keep trying and (B) get feedback from someone you trust on your approach to make sure that you’re targeting the right people and saying the right things.

Hope this helps!

See you Tuesday for our next story and unspoken rule,

Gorick

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WHAT I’M READING

Here are 3 articles that I found interesting recently (no paywalls, although it may depend on your cookies):

  • “Want People to Work Harder? Be Generous” (Inc)
  • “Societal inequality linked to structural brain changes in children” (Medical XPress)
  • “Why Americans don't want to move for jobs anymore” (NPR)

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