Advice to a Young Man Hoping to Go Somewhere (Or Get Something From Someone Successful)

September 5, 2011 — 86 Comments

When I dropped out of school at 19 to start my first job in Hollywood, I didn’t know anything and I had no idea where I’d end up. Thankfully, I was attached to some smart and forgiving people who let me learn under them. I suppose I also had good instincts. Within a few short years, I’d become a bestselling author, the director of marketing for a publicly traded company and got to work on a ton of cool projects. I’ve hired my fair share of people now (fired them too) and having been through the ringer of young-person-just-starting-out-in-a-new-field close to a half dozen times, I figure I know it well enough to talk about it.

It goes like this: You’re scared but overconfident, clueless but eager to learn, just glad to be given a shot and you don’t want to screw it up. I tried to think of a few things I wish I’d been told when I was just starting, things that would have saved me some tough lessons. These are the things I still tell myself.

They are:

-Calm down.

-Assess the terrain. Sit there and observe. Figure out who the dominant personality types are, what makes them tick and how things really work. Don’t act, don’t give your opinion, don’t do anything until this has been done. When you understand the people, politics and the business (eg, the terrain) then you can begin to get to work.

-Always say less than necessary.

-The point isn’t just to prove that you’re capable, but also that you’re sane. In fact, if you had to pick between the two, being well-adjusted the better one. You can teach people how to do things. You can’t make them normal. In other words, leave your crazy at home.

-Stay on the radar. Your excuses need to be just not-flimsy enough that they don’t seem completely full of shit. If it passes that test, then any question, any update, any offer to worth using to stay in the frame.

-Don’t be too good at being an assistant (or an intern). In fact, the whole point is to be too good to be wasting your time and other people’s time at administrative shit that you mess up anyway.

-Remember, most people on the internet are losers and outsiders. “Don’t go expecting Plato’s Republic,” Marcus Aurelius would remind himself. Don’t go expecting Seth Godin, Jeff Jarvis or [insert industry blogger here]. Whatever you do, don’t quote them. Your job is to successfully mitigate their vision of how the World Magically Should Be with how it Realistically Is. If you can do that, you’re more revolutionary than they will ever be.

-If you’re working all the time—that is, if you don’t get to leave the office until midnight and got there at 5am—you’re doing something wrong. You’re either working for an idiot who is going to burn you out, or you’re the idiot and you haven’t figured out the short cuts. For a while I had 3 full time jobs (ones you’d have killed for) at the same time. I wasn’t working all hours of the same, I just did them simultaneously.

-Steer clear of the charlatans, lifers, and the toxic. You become who you know.

-On the same note, you can probably skip most of the “social” activities the job requires. Introductory calls, lunch meetings, parties and conferences are usually a waste. Don’t be friendless and don’t be rude, but these things are mostly collective effort to waste time and forget how unhappy everyone is. Besides, being the conspicuous absence can help build your reputation, if done right.

-Ask yourself: “Am I saying this because I want to prove how smart I am or am I saying this because it needs to be said?” When you’re just getting started, it’s usually the former.

-Forget credit. Fucking forget it so hard you’re glad when other people get it instead of you. After all, that’s your job—to make other people look better.

-Save your money. The smaller your nut each month, the less pressure you’ll feel to put up with stupid shit. It gives you the luxury of not being dependent on the system. It lets you see through it. (see: The Dress Suit Bribe)

-Write your own rules. Forget the bullshit ones (dress code, hours, hierarchy etc), follow the critical ones (getting results, never offend the wrong person) and do whatever you want. Seriously.

-Educate yourself. No one is ever going to teach you enough or hand it to you on a platter. Books and articles, and ask questions—an endless amount of them. People love to give advice and they love people who they don’t feel they have to drag to the next level.

-Make it happen. Nobody cares what it will take, what problems this causes for you, what personal stuff you have going on. Just get it done. You can tell us what you went through…after.

-Have an exit strategy. Know how this all fits into your grand strategy, this is the Start-Up of You. But also have the easily explainable, non-threatening goal that you tell people so you can maneuver in peace. If you’re working at a management company, don’t tell everyone your goal is to be a stand up comedian. The grand strategy is just for you.

-Don’t expect anyone else to understand. It’s your job to find a release and an outlet for the stress and the feelings. Never forget: the crazy stays at home.


Most importantly, remember that you are not special. There were a million other kids on this path before you and there will be another million after. Most of them either went nowhere or turned out to be nothing. Even the successful ones might still flame out or be assholes. What does this mean? It means don’t get high on yourself. Don’t tell yourself a story. Be quiet, work hard, and stay healthy. It’s not ambition or skill that is going to set you apart—notice I didn’t mention those things a single time. It’s safe to assume you’ve already got them covered. What will set you apart, what is rare, is humility, diligence and self-awareness.

One last thing. You can always email me (as many of you have taken it upon yourself to do). I’ve been there. I’m still there in some ways. But like I said, I’ve been through this ringer more times and with more riding on it than most people. I’m happy to help.

Ryan Holiday

I'm a strategist for bestselling authors and billion dollar brands like American Apparel, Tucker Max and Robert Greene. My work has been used as case studies by Twitter, YouTube and Google and has been written about in AdAge, the New York Times, Gawker and Fast Company.

86 responses to Advice to a Young Man Hoping to Go Somewhere (Or Get Something From Someone Successful)

  1. Ryan this is some of your best work. Well done.

  2. Ryan,

    I’m pretty new to your site and just wanted to say thanks. You are wise beyond your years and your advice/outlooks are truly inspirational. I’ve just recently accepted the time I’ve wasted thus far and have decided (with a little push from you) to start using my time for more meaningful endeavors. Like you said in a different post, I’ve gotta lot of reading to do ><. And yea, I too was linked from Tim's site.

    Thanks again.

  3. Hey Ryan,

    Good post. However, I’m not totally sure of what you’re trying to say with this:

    “-Stay on the radar. Your excuses need to just not-flimsy enough that they don’t seem completely full of shit. If it passes that test, then any question, any update, any offer to worth using to stay in the frame”

    Could you expand upon that? What are the excuses for?

    • Let’s say you’re working for me or I am trying you out to work for me. I’m going to be too busy to babysit you or monitor your progress every second. In order for you to get the most out of the opportunity, you need to stay on my radar constantly (in a good way). “Hey Ryan, I have a question…” “Hey Ryan, I finished doing what you asked me to do…” “Hey Ryan, is there anything else I can help with..” “Hey Ryan, here is an article you might like…”

      This is especially critical in remote gigs. It’s obviously a little bit different if I have you on a desk in front of me, but still the radar is important. For all I know you’re sitting around on iChat all day.

  4. thanks for this.

  5. A corollary of “save your money” is : Try not to buy a house, have a kid or get married too young.

    A final one is don’t depend on approbation from your parents.

  6. You make good points. I have learned many of the lessons the hard way. Practice makes perfect, eh?

  7. I feel like this is the culmination of every previous post you’ve written on this site. Great work.

  8. I’d be interested to hear what your opinions on college are..

  9. Would your advice be any different for a young woman hoping to go somewhere?

    • Not significantly.

      I would add some stuff about keeping your distance socially from people in the office. Girls make friends in offices quicker than men in my experience, but you’re not there to make friends. You’re there to prove yourself. Stay above the fray. Don’t get involved in drama.

      But I said man because I hate that he/she bullshit

  10. “-Steer clear of the charlatans, lifers, and the toxic. You become who you know.”

    Love this one. But could you explain what you mean by “lifers” a bit?

  11. Like Andrew said, this is a solid list that serves as a good culmination of some of your older content.

    The only thing I would add is that confidence is so crucial to co-workers perception of you. If there’s doubt in your voice they won’t trust you. Most people don’t actively want to make decisions, which is why they enlist many other people’s opinions (meetings and such). This stalls the decision, while effectively not making them solely responsible for the results.

    If you can confidently make recommendations/decisions and follow through with solid results the rest will often take care of itself. (At least in my experience).

  12. your view on pursuing women at work? I think I can do this without bringing out the crazy and I produce enough so that I’m above average

  13. -Save your money. The smaller your nut each month, the less pressure you’ll feel to put up with stupid shit. It gives you the luxury of not being dependent on the system. It lets you see through it. (see: The Dress Suit Bribe)’

    Qns 1: What do you mean by ‘the smaller your nut’? I think i get the gist of this bit of advice: Be as self reliant as possible: since the greatest shackle a job can have on you is that of money, by reducing your dependence on your job as a means of survival, you become more emotionally liberated, and hence more clear-eyed to see the truth of situations. But does nut in this case mean ‘ego’? or something else entirely?

    Qns 2: Also, I’d like to have your opinion on college, and its value. I’m turning 20 this year, finishing my mandatory military service in my country, and I’m going to study English Literature in a local college.
    I have struggled with guilt over this choice (‘because Literature is ‘fucking useless’, because I feel like I’m signing up for 4 years of something I have no idea what I’m in for, and because my parents are paying for me. Especially because of the last part.) But at the same time, there’s enormous social pressure to go to college in my country, regardless of whether or not you know what you’re going to do with your qualifications or what you learned from your time there. And i don’t particularly know which direction to turn to if I wanted to do otherwise.

    Even if there’s so clear cut solution, would you give me your 2-cents regarding this? I would deeply appreciate it.

    Lastly; and this is out of a curiosity derived from admiration: Are you yourself clear about what you intend to achieve in your lifetime, or on a less ambitious scale, over a long term period. and more importantly, do you know why? And if you do, how would you advise someone to go about finding out?

  14. Ryan

    Thanks for such great words of wisdom.

    I have been working almost 20 years and this stuff applies every day in the corporate jungle. It is too easy to get sucked into the vortex that is the daily swirl of drama in the office. We all need to rise above it and keep an eye on our personal end game.

  15. Ryan, I enjoy your blog because you write thoughtfully about using philosophy (or any real knowledge) in everyday life. I studied political science and philosophy in college as well. Though I got a great deal of personal satisfaction from my studies, I found that they didn’t really qualify me do do anything.

    You regularly allude to your working life, but give few details. What is it exactly that you do for work? Or more importantly, how did you acquire the knowledge and skills to get these jobs “you’d have kill for?”

  16. Advice, like youth, probably just wasted on the young.

  17. Ryan,
    Thank you for posting this – it’s fantastic.
    Can you please shed some more light on, “Always say less than necessary.”
    I’m currently in law school which tends to advocate an idea of ‘over communicating’ and explaining yourself to the point where there is absolutely no question as to what you are attempting to communicate…
    Like everything, there is probably a gray area somewhere in the middle – I’m interested to hear your insight on this.


    • Law 13, my friend. I’m quoting someone smarter than me.

    • Or the gray area J, could be thinking about what u have to explain very thoroughly and condensing it down into such few words that they have very heavy impact.

      Almost like a quote that just makes someone stop and think. That might differentiate u from ur peers. U’ll probably need to learn some copywriting to master this skill, I suggest the works of Joseph Sugarman.

      G’luck in ur career!

  18. Thank you for making this post. This was honest and refreshing advice compared to the boilerplate tripe you usually hear from most blogs on the internet.

  19. Richard Nixon, an anti-semite, employed Henry Kissinger as one of his closest advisers. When asked why he valued Kissinger so highly, Nixon replied:

    “He always knew what to do without being told. I could trust him to handle issues.”

    Nixon, completely paranoid of what everyone around him was thinking/doing, somehow managed to instil his complete trust in a machivilian Jewish man.

    There’s something profound here. If you want to earn someone’s respect, bring up the right issues without being told. Research something new and innovative before they tell that it’s new and innovative. Be ahead of them.

    There’s no one we trust more than others who seem to know what we’re thinking before we ourselves think. Nor someone we consider more intelligent. The ultimate in impressing and standing apart.

  20. Bonjour Ryan,
    Just found this site. *Love* this post. Explains alot about why I have a hard time finding people to work for/with me. My tolorance for crazy and drama, etc. is zilch. I find most artist types to be unbearable to work with. Maybe I will hand prospects a copy of this post. Wish I could hand it to some clients too!

    Was great to have a few miutes to chat at OTK, by the way. :)
    I am now off to read some older posts… Ciao!

  21. Would your advice on skipping office social activities be different for someone that is hired to network and fundraise? I fundraise for a living (some of it is employee fundraising) and I try to hit as many employee functions as possible to improve relationships.

  22. Really good post. A couple quick things I’d add, just to expand upon the “leave your crazy at home” point:

    1- No idolization. People feel uncomfortable if you gush like they’re your savior. Do it enough and they’ll resent you. It’s the same underlying sense of desperation that creepy guys show when they’re in the presence of attractive girls. You can show respect and appreciation for someone’s work, but do not worship that person. (A good example of doing this the right way is that first essay you sent to Tucker).

    2- Be energy-neutral or -positive. Don’t complain, don’t put your emotional instability on display, etc. Your mood affects others. Avoid bringing people down with you.

    • These are all very true. I think it’s best put as: Have your shit together and be comfortable with yourself so other people are comfortable being around you

  23. The law ‘Always say less than necessary’ fits in well with ‘Brevity is the soul of wit’ (Shakespeare) and ‘Less is more’ (fuck if I know).

  24. I see that people in pursuit of power either take an aggressive, charismatic route, or the other extreme: silent and fluid. The former seem to understand what people want, playing on their emotions, giving them a character, must like what Tucker Max did; the latter seem much more detached, objective, focusing on the learning experiences. Each day, I’m conflicted with my desire to be both. I’m more inclined to be the latter, observing others as a backdrop, but being former is too much fun. The inconsistency, however, seems more damaging than just committing to one.

    I’m curious as to what your thoughts are on either archetype. You are obviously the latter: was that a conscious decision or something that was shaped naturally by your experiences?

  25. 1-I like be young man and young adult man date women sex

  26. I read this entire post and every single comment posted below it and I really enjoyed it! Good job!

  27. Fuck it, I’ve been reading you for years, but I don’t think I’ve ever commented. Will start doing that frequently now.

    One of your best posts for sure. Stopped by to re-read it after seeing a link to it on your recent interview with Andrew.

    I’d add this to the list: learn from mistakes, and implement a system to show it. Systems are the compounding key of progress. Like Scott Adams likes to say: “Losers have goals and winners have systems.”

  28. awesome. i’m def gonna be rereading this for a while. thanks Ryan

  29. Fantastic post Ryan, I’ve found that I had to learn most of these lessons the hard way. To my chagrin I’m still learning and re-learning a few of them. Great tips.

    The one I’d be curious on hearing your thoughts in greater depth on is your comment about lunch. I’ve found it to be incredibly helpful and informative, but that depended heavily on who it was with. If it was lunch for lunch’s sake, or with immediate co-workers the benefit was limited. If it was a regular lunch outing with my bosses and senior members of the small company I worked for, it led to some of the best business wisdom I’ve ever been exposed to. How do you think this differs based on company size and management style?

  30. Havent even finished reading the article but I just had to stop and say Ryan, thank you man. especially for this paragraph -Have an exit strategy.

    That one and the rest of the preceding content felt like my older self talking to me!

    Once again, thanks man!

  31. What did you mean by:

    -Don’t be too good at being an assistant (or an intern). In fact, the whole point is to be too good to be wasting your time and other people’s time at administrative shit that you mess up anyway.

    I started my own company when i was still in college (19), hence i was too ambitious and failed after a year… Thanks for the advice, now that i foresee what i have to do! overlooking the Terrain is something obvious when thought of, a not rushing into these kind of things. Its an eye opening!

    Now that I’m 24, i feel stuck and not motivated, (ups and downs that is) my ambition and pride got the best out of me…


    • If you’re too good at it, you won’t be promoted. Good assistants are hard to find. You want to be just bad enough that you don’t get fired and just good enough to warrant a promotion.

  32. I’ve skipped a few social events since reading this blog post.
    Actually kept me out of trouble.

    “Most people on the internet are losers and outsiders”… good one to remember

  33. This is awesome stuff. I just wanna read everything you’ve written and posted on this blog. I want to re-post some of your stuff on my blog, is that okay?
    I also want to subscribe to your blog so that I can get a notification when you post another. How do I do this?
    Well done man. Well done.

  34. To any young man reading this…
    Read it again and again until it makes sense
    Then read it some more
    Then read it until you have it burned in your memory
    It’s that important and will save you years

    “For all his blithering on, a man only needs two things in life. A reason to get out of bed every day and a reason to get back in bed every night. Everything else is crap.” -@ArtGow

  35. Ryan dynamite stuff!

  36. Hi,
    I like your stuff. We won a national competition and are going to Sunywalle Plug and Play tech centre. Would you like to have a cup of coffee with us/me? We will bring some European spirit:)

  37. Hey Ryan,

    Cheers for the insight. This is valuable for the rosy-faced interns like myself.

  38. Hi Ryan,
    I just wanted to thank you for this post and the value your blog delivers and this post specifically. I find myself revisiting it often when I am looking for some guidance, or office politics come up. It is like a playbook on how to keep your head on straight.

    Do you have any posts or advice on how to transition when you have learned as much as can? I have gotten to that point and am beginning to feel “stuck.” Thanks again.

  39. Thanks for the Good advice.
    I used to think, I wish someone told me so!
    Until I realized that most of the times learning by experiencing is the only way. So referring to your post: “Calm Down” and experience it all.

  40. I just came across your blog after watching your interview on Chase Jarvis Live. I just started a new job and you have no idea how helpful this is. Thank you for writing it.

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