First up, he's a long time friend of mine, but not someone I ever will get along with in the same room for more than an hour. In the past, I've had a lots of insecurities and he used to be the proverbial pack leader that you always obey and don't piss off, because he could easily turn the other members of the pack (who are also extremely close to me, I like the others more than I like the pack leader) against you. This is the sort of relationship it used to be when we're 12-17.

We drifted off our own paths after 18. He's doing his thing, I'm doing mine. But the patronizing attitude of his really rubs me the wrong way every time he talks to this date. We're both 23 now.

I'm studying for an advanced degree (Masters) and he is not, but he always acts like a father-figure type of person who knows it all, except that he doesn't, and he's not a father figure. He just wants to let you know that he's better than you. I'm saying this not because I'm insecure, but because this has been made apparent in multiple conversations. He's an entrepreneur. I don't know what he's doing with his company. Whatever the progress maybe, I honestly, don't care. He could be a billionaire one day, or not accomplish much.

But he says something along the lines of 'We can hire you if you finish a post doc and an MBA'. Now I try to stay humble, by saying 'Thanks for the motivation man, I'll work super hard', when in actuality I have zero interest working for him because it feels like he doesn't know what he's doing with his company. He's still working on the idea! Inside my head, I really want to tell him 'Bro! Why on earth would I want to work for your company when, with those credentials, I could either start my own or end up in a place like Google?' I either ALWAYS come off as too rude, or too soft.

He's the sort of guy that would say something like 'I want you to implement this thing that only a post-doc researcher can do. We'll split the profits 70-30, I take 70 because I'm the CEO'.

I need to be able to tell him to not tell me what to do and not sound arrogant while doing so. Because he's continuing to send me actual images of his conversations where his advisors/HR consultants give him a salary quote for a position in his company and he can send it to me to 'motivate' me.

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    Is the only reason this person is still in your life your mutal friends?
    – apaul
    Commented Jun 26, 2018 at 20:54
  • @apaul It used to be the case! But that's no longer the case now! I'm just being polite and we've always tagged along as 4 people, so him, 2 others and myself have almost ALWAYS been together no matter what. Commented Jun 26, 2018 at 21:53

2 Answers 2


To specifically address the scenario you mention about working for his company, you could say something like:

I'm actually considering a different career path. Currently, working for a large, established company is more interesting to me than a startup.

This can be a general template for dealing with his unwanted suggestions: politely and clearly say something that makes it obvious that the advice is irrelevant. If he persists, you could consider saying something like:

You know, I've actually got my own ideas on my career direction. Your advice is no longer needed.

You could consider being direct in stating he lacks qualifications as well:

I've actually decided to discuss my career direction with others who have more experience with the job market for people with graduate degrees in my field.


You could just slowly scale back your responses, gradually making them shorter and further apart. It's not the most direct, or the most honest thing to do, but it works.

When they send you a message, wait a while before responding, you're not all that interested in the interaction and a slow reply is a way to demonstrate that. When you write your response don't invest as much time and energy into it, this sends a similar message as the slow response.

Your "friend" has taken to this mentor role because they've gotten away with it for a long time. You've always responded politely, so they likely assume that you appreciate their mentorship. Slowly breaking the pattern will probably be enough to get them to quit sending these sorts of messages.

I've had aquaintences that tried this sort of thing with me, I wouldn't call them friends, because they really weren't. Some people seem to need to assert hierarchies into their relationships, I have very little patience for this sort of thing and I'm not a fan of hierarchies in any case, so I usually end these relationships quickly.

If you'd prefer a more direct and honest approach, you could just be, ya'know direct and honest. Tell them that you don't appreciate the way they tend to talk down to you, and that you're really not interested in working for them.

This is my preferred approach, but be warned that this will typically burn bridges. Folks that need to feel superior don't usually respond well to insurrection. On the rare occasion you'll encounter people who didn't realize that they were coming across that way and will adjust their behavior, but these people are rare.

  • You are absolutely correct in that, I have allowed him to play the 'mentor' role for far too long in that he's used that freedom to promote 'I know a lot more than you, and it would be good for you to follow my advice, and I will always keep reminding you that I'm better than by trying to mentor you!' Commented Jun 26, 2018 at 22:41

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