The worst career advice I ever gave was to my brother’s college roommate, Robert Buckley. He was one year out of college when he asked me if he should quit healthcare consulting to become an actor.

I said, No, that’s the dumbest idea I ever heard.

He told me he thought he had talent, and then (like I wasn’t against the idea enough) he told me he was dating some girl he met in Vegas, and she is going to be an actress, and she said that he had talent.

I actually questioned how my brother could be such good friends with someone who was so stupid. I tried to be patient, but mostly I told Rob that everyone in LA has a girlfriend who thinks he has acting talent. I thought maybe his best career move might be to find a girlfriend who was impressed with his healthcare consulting talent.

But really, he did not think he had any future in healthcare consulting. So I became a largely useless advisor to him. And then my brother forwarded me a trailer to Lipstick Jungle and there was Rob: naked, with Kim Raver. And he looked so good. Who knew? And more importantly, who knew I could give such poor career advice?

I think the reason that I gave such poor advice is that I had such strong preconceived notions about the acting career. But I actually don’t know anything about making it big as an actor. I only know that when I played professional beach volleyball in LA we were constantly surrounded by casting agents and entertainment industry types. And I learned that the competition to get anywhere in acting is so tough that you should buy lottery tickets instead.

It’s ironic, though, because I’m a writer, where the odds are not much better. And both actors and writers generally ply their trade because they love it, not because they think the odds are great. If someone asks me if they should become a writer, I repeat the advice I received in graduate school: No. Try anything else first. Writing is too hard.

And I was thinking the same thing with acting: No. Big no. But I needed to adjust my advice. I needed to be able to see when I was looking at someone who could not feel fulfilled if they did not do this type of work.

So every week I watched Lipstick Jungle (I loved it, by the way—for the writing, of course) and I thought about how I could have given such misguided career advice. And I figured out that the hallmark of a bad advisor is to not understand where she is coming from, what preconceived notions she brings to the table.

I didn’t think much more about this until I was in Menlo Park last week for the roundtable organized by Ben Casnocha and Chris Yeh. They posed questions to the group of entrepreneurial types: What makes good advice? What makes bad advice?

The answers were interesting, and each shed more light on why I gave Rob such bad advice. Here are some ideas that came from the group:

1. A good advisor asks good questions. Mostly in order to understand the goals of the advisee. No advice is given in a vacuum. Understand that an advisor can probably give you great tips on how to get to your goals, but really, the hardest part of making any decision in life is understanding your goals in the first place.

So your advisor needs to be very attuned to your goals and where you are in your life. This is why the best advisors ask questions rather than make proclamations. Often a good advisor is more sounding board and less Magic-8 ball.

2. A good advisor is a good listener. Advice is so much about understanding the particular situation that if she is not listening most of the time, then you are probably receiving advice based on incorrect assumptions that actually apply to a different circumstance. But it’s hard to listen when you are a subject matter expert.

In general, all situations sound the same when you give advice to the same types of people all the time. The trick for the advisor is to stop focusing on the similarities, which make her job easier, but to focus instead on the differences, which is more challenging—but makes for better advice.

3. Good advice is not fly-by-night. Advisors are best when they really know you, and they really know the arena where the issues live. So cultivate a relationship with someone who is a subject matter expert, and then he can give you ongoing advice that is relevant to your particular circumstances based on both what you are telling him, and on the relationship that provides a context for your questions.

Wondering how you are going to attract this kind of advisor? Be one yourself. Giving good advice is the same thing as giving a good kiss. You attract what you deserve. Not in a Secret sort of way, but in a way where if you are practicing good behavior then you will attract good behavior.

And, while I hesitate to give advice at the end of the piece about how advice should not be in a vacuum: You usually get in life what you expect to get. So expect good advice. And good kisses. And they will come.

44 replies
  1. Miriam Salpeter
    Miriam Salpeter says:

    Penelope – A timely post, as I have just begun working with a client who wants a job in a very competitive sales field. My first instinct was to question her – maybe re-steer her to a field where it would be less difficult to get a foot in the door. Instead of bursting her bubble, I decided to help her follow her dream, while at the same time coaching her to expand her reach.

    I agree that a good advisor has all of the qualities you mentioned. He or she must be willing to both challenge and support the advisee and remember that the advice needs to be about the person seeking the advice, not about the person giving it!

    Thanks for the great food for thought!

  2. Taisha
    Taisha says:

    Good advice is all about the questions. I happen to be one of those people who trusts that most people do actually know what is best for them. Unfortunately, many advisers give advice to shore up their own egos (not that you were doing that with Rob, of course). :-) The Vegas girlfriend’s opinion would have made me somewhat suspect as well. But, in truth, if you know the right questions to ask, the person you advise will reach the right conclusion for himself.

  3. Jon Snitz
    Jon Snitz says:

    I once followed PT’s advice on doing yoga in the bathroom at work. I was getting in the downward facing dog position when the CEO walked in. Next thing you know, I was offered a huge raise and a promotion. Great advice, PT!!

  4. Duncan W.
    Duncan W. says:

    PT,

    I’ve been reading your blog now for awhile, mostly for the comical aspects. I think you are the last person on the Internet who should be giving career advice to anyone.

  5. chris
    chris says:

    I would argue that all advice is good advice, depending on what you do with it. When someone gives you advice that just doesn’t sit right, that you choose to reject, you are forced to think for yourself about why the advice is wrong for YOU. When you reject someone’s advice, you make a choice to trust your own internal adviser. And the more practice you give your internal adviser, the better it gets. I think. I better check with my adviser about that. So maybe you gave Robert just the advice he needed to hear in order to get to where he needed to get. How can that be bad advice?

  6. Joselle Palacios
    Joselle Palacios says:

    This post is good advice.

    I’d also add that if the advice is aggressively unsolicited, it may be bad advice. The best advice I’ve received is from, as you state, people who ask questions and help me to think of the solution. Not from know-it-all busybodies.

    By the way, I do yoga in my work bathroom all the time. I didn’t know this was Penelope-approved!

  7. Norris Krueger
    Norris Krueger says:

    In the entrepreneurial world, good advice is a function of the Three “Cons” — Content, Context & (for lack of a better term) Con Brio!

    Some people really know content – but have no clue about what it takes to be an entrepreneur (they make think so, but… LOL). There are those who really know the context- they get it about being entrepreneurial (and usually have content knowledge too – or can find it).

    Markers for context: A small biz is not a little big biz… nor is a new biz only younger. And if you’ve never been immersed in an explosive-growth gazelle, you have NO idea. But it’s easy to ask.

    However, what you really want to find are advisors who are themselves passionate – about the topic and about seeing you succeed. “Con Brio” indeed!

    p.s. Penelope – don’t expect good kisses.. expect GREAT kisses. You’ve earned them!
    nk

  8. Alice Bachini-Smith
    Alice Bachini-Smith says:

    I really like how you conclude that the advice you gave to Robert Buckley was bad advice, because it turned out retrospectively not to have been right for him. A lot of times we put mistakes down to statistical chance or inevitable failure-rates, even arguing that what we did was right, it just didn’t turn out for the best because of unpredictable factors. And maybe that’s true sometimes, but you can’t learn from it as a general approach, whereas you did and then shared the learning.

  9. Tiffany Monhollon
    Tiffany Monhollon says:

    When I was reading this, I kept thinking, this is great advice, and not just for career-minded individuals It’s good advice for businesses, managers, trainers.

    In fact, twist this post around a little, and it could take on a different form all together. Three reasons most people don’t make great managers – because they don’t naturally do these things. Or three reasons most companies fail to evolve – because they don’t train and empower people do do these things.

    Organizationally, there should be so much more emphasis on these three core ideas: questioning, listening, and building relationships – internally and externally, up and down. Instead, why is it that so many companies seem to spend all their time doing anything but these things?

  10. prklypr
    prklypr says:

    One look at Rob Buckley and you can see that talent isn’t the only thing he’s got going for him…

  11. Diana
    Diana says:

    I can only imagine what you thought when you saw that trailer. And by the way, WOW he is hot, and I also enjoy watching Lipstick Jungle – especially the steamy parts! Giving advice is easier (maybe better?) if you were once in a similar situation. If not, all you can do is listen, which is sometimes all someone needs. They need to voice their concerns out loud, listen to themselves say it, and then have it be heard.

  12. Jennifer Lynn
    Jennifer Lynn says:

    Interesting post. I think point #3 is especially wise (Good advice is not fly-by-night; advisors are best when they know you) because if the advisor knows you pretty well, then you probably know her pretty well. That way, you’ll know when a particularly strong opinion is sound advice, and when it’s an (albeit unintentional) attempt to justify her own life choices by convincing you to make the same ones.

    This is something I learned about an hour ago.

  13. Rob
    Rob says:

    Sounds familiar. Eeeearily familiar. Now, taking into consideration what you’ve just said, why is it that you hold yourself out as advisor om virtually every subject?

  14. Jessica Bond
    Jessica Bond says:

    Very interesting post…from healthcare to hollywood. I like it!

    Getting advice in a “360 degree fashion” seems to work for me. In other words, seek multiple, different perspectives from the wisest, most trusted people you can find.

    All the best,
    Jessica Bond
    Medical Careerist

  15. Bill
    Bill says:

    Your advice to Rob was correct, from any practical standpoint. But it was also irrelevant. He was only looking for validation to a decision he had already made. If he wasn’t on TV he’d be doing dinner theatre somewhere.

  16. Mark
    Mark says:

    The best career advice I’ve received as basically been people who just ask questions and keep drilling down until I reach the point where I’ve made a decision by using their help to figure out what I knew if I just could clear the clutter.

    I’m going through that process right now. I just took a job in a field I don’t know a great deal about but for some reason the management thought I’d not only be good at it but could be trusted managing 15 people (my staff is less than thrilled none of them were selected over the ignorant outsider). To put it mildly its a fun challenge because I am learning a new field and helping the organization by challenging old habits. Plus opening good future career doors.

    Now after six weeks I’ve got a chance to head to a totally different field. I’d have to take a small pay cut but with overtime (guaranteed I can take up to 16 hours once I’ve been there six months) the pay would be better and instead of keeping a strict schedule I’d have wide latitude to work basically any hours between 6:00 am and 8:00 pm. Could work as few as four days or as many as 7. After six months I could even telecommute two days a week. The big downside is that it would close a lot of career doors.

    Now I’m working the process I’ve learned from others figuring out what is important and examining myself to learn whether control of my time and more money short-term is worth closing so many doors.

  17. d'gou
    d'gou says:

    This part of The Fellowship of the Ring seems salient, esp. the very last part quoted:

    ‘And it is also said,’ answered Frodo: ‘Go not to the Elves for counsel, for they will say both no and yes.’

    ‘Is it indeed?’ laughed Gildor. ‘Elves seldom give unguarded advice, for advice is a dangerous gift, even from the wise to the wise, and all courses may run ill. But what would you? You have not told me all concerning yourself; and how then shall I choose better than you?’

  18. Kimmy
    Kimmy says:

    Yep, Buckley is hot.
    But I kinda got stuck on the eyebrows… Hmmmm.
    Easily distracted from reading good career advice!

  19. Christine
    Christine says:

    I agree with points number 1 & 2 – Good advisers should ask questions and be an active listener. But I’ve also gained valuable insight and input from people who work in a different field.

  20. Mark W.
    Mark W. says:

    Penelope,

    You didn’t include in this post any dates or your experience in dispensing career advice at the time you gave advice to Buckley. This information would be helpful.

    Mark

  21. AmarilloSlim
    AmarilloSlim says:

    Look, you told the kid not to draw to an inside straight with three aces showing across the table. Who would have thought he would have drawn the right card?

    Look on the bright side. Now that he’s a big star, maybe he will invest in BrazenCareerist.com.

  22. Thursday Bram
    Thursday Bram says:

    I think this post highlights that really, when you’re asking for career advice, don’t go to someone with an interest in your life. Parents, friends, significant others, etc. all have a close interest in your life and, as a rule, they’ll tell you what they think is best for you.

    Generally, what’s best for you is not the most ambitious path – no rocking the boat or striking out on your own. But what’s best for you will never get you where you want to go.

  23. Maggie
    Maggie says:

    OMG he is hot–maybe now that you’re single you should suggest meeting so you can offer your apologies for the bad career advice in person. Or you can send me to deliver the message.

    My take on seeking/accepting advice from anyone is don’t do it. To me, asking anyone what they think you should do with your life is a waste of time–no matter how close they are to you or how professional or wise they may be. Asking HOW to go about accomplishing what you want to do is another thing–that I think is a good idea.

    Here are the various bits of career advice I’ve received in my lifetime: you should be a writer, you should be a lawyer (which was met with “you’re too stupid to be a lawyer” when I mentioned it to my mom–a confidence building comment if there ever was one), you should be in sales, and, my personal favorite, you should be in Playboy. Now that I’m 40 I don’t think the Playboy one would work out so well, so I guess I can cross that one off the list. Ditto lawyer, since I fully subscribe to Penelope's post about grad school being a waste of time.

    While I’ve received plenty of advice on what I should be doing, I have received exactly none on how I should achieve any of those career goals. Maybe I’ve gone about it the wrong way and need to find a mentor or something, and I know Penelope has blogged about that before. So far my attempts at finding a mentor have resulted in exactly one piece of advice: just write. That’s it.

    BTW, not to sound like a moron, but I 100% believe in the Secret and it definitely has worked for me. The good thing about it is that you’re not asking someone what they think you should do; you decide what it is you want to do and somehow the details figure themselves out. I know it sounds stupid but I swear it’s been true in my life in many, many ways and I’m confident that it will eventually steer me in the direction I’m meant to go career-wise.

  24. tinyhands
    tinyhands says:

    Knowing what you now know, about an advisor’s preconceived notions and having a solid advisor-advisee relationship, how would you reevaluate your advice from the last post, which appears to have been especially poorly received?

    (FWIW, I think it’s perfectly acceptable for an advisor to admit that he or she has given poor advice, especially as a means of self-improvement. I’m not suggesting that you SHOULD admit that, with respect to any particular advice, but that you needn’t beat yourself up over the actor. He seems to have turned out just fine. Some leaders or so-called experts refuse to be flexible and admit that they are human. Examples abound.)

  25. blink
    blink says:

    You can’t judge your advice solely on the fact that he had positive results in his acting. That wasn’t obvious from his “talent” when you spoke to him. He probably has some, but he probably also got lucky or was able to navigate the right connections at the right time somehow. Just as there are many more that tried the same path and failed.

    Does this mean you should tell every aspiring actor/actress that thinks they have talent to quit their job and run off to hollywood because it worked out for this guy? No, you’ve got to stick to your insight and expert advice. Perhaps just adjust it a little as you see fit.

    In reality the odds are against potential actors. And stardom is very tempting form of self-validation for egos. Almost everying aspiring one thinks they are good looking enough and acticulative enough to make it. And they want that validation. Many spend their entire lives on this go-no-where passion. Even if it go’s no-where, is it still worth the life-long experience of trying? There is no right answer there.

    For the more rational minded folks, one set of good advice on the matter I heard once is to give it a go for a set period of time, say 2 years. If after 2 years you’re no better of than the start, then give up and try a second choice of careers. That way you don’t regret it for life, but you don’t doom yourself to failed career perpetually.

  26. Marla
    Marla says:

    You know, I don’t think I’ve ever heard any good and useful career advice – people only talk about their own experiences, biases, preferences and what they want you to do (your mother wants you to be a MD or JD, the MDs and JDs want you out of their way, etc.). Or they talk about what they read in the WSJ that week on career trends, which may have nothing to do with your question or life at all.

  27. Spike
    Spike says:

    One look at Rob Buckley and you can see that talent isn't the only thing he's got going for him –

    Oh my, yes. (!)

    I’m glad he persevered!

  28. Christien
    Christien says:

    Did he look like that in college? Because my thought is that your bad advice wasn’t don’t become an actor. Your bad advice was the advice you didn’t give him to dump Vegas girl and take a look at Ms. Trunk. Haha.

  29. Kare Anderson
    Kare Anderson says:

    The way Ben leads those “juntos” exemplifies the advice you offered here. Have not seen Chris facilitate one. Re your last graph, commenter Jon Snitz might benefit from it

  30. Carol
    Carol says:

    Penelope, how does this work with your “Don’t do what you love” post? Have you changed your mind on that one?

    I always thought that post was flawed – “I love sex but I don’t want to be a prostitue” – because you can love more than one thing. I love cooking but I don’t want to be a chef. I regularly hate computers but I absolutley love my job (IT technical consultant).

    Maybe the best advice is “do what you love, but be realistic. If it’s a highly competetive field then have a backup plan”.

  31. Peter Wootton
    Peter Wootton says:

    I’m sorry but in all intentions of positive criticism, I’m smart but this post has made little impact on me. If anything it has left me a little bemused. I have really enjoyed your other posts- especially the one on self promotion. There you hit the nail on the head. I am not fazed however and I will be adding you to my favourites lists. There is nothing more refreshing than reading what I consider to be unbiased intelligent literature. Thank you.

  32. Dale
    Dale says:

    Most of the time we ask advice of people we feel comfortable with, as opposed to those who care for us or those who are subject matter experts. Now this is a perscription for disaster. Most people do not know you or care for you as a parent or sibling does, so they will not give your questions as much thought as a close (albeit subject matter inept) relative will.

    Even worse, don’t expect deep thought or expertise from coworkers or casual acquaintances! They neither know nor care;)

    Choose advisors wisely and perhaps give your advisor the opportunity to think about your question overnight so as to add gravity to the situation. It works for me.

  33. Cathy Goodwin
    Cathy Goodwin says:

    I’ve struggled with this issue, both giving advice as a career consultant and getting advice when I wanted to change careers.

    I would say agree with the comment to beware of unsolicited advice. Ignore anything you haven’t asked for.

    Secondly, I distinguish between information and advice. When you want to learn about a new field, get information from people who have been there. But don’t let them give you advice.

    Most people are clueless about how they reached their own successes (although they’ll never admit it). Better to ask, “What’s a typical day” type questions instead of, “What would you advise…”

    Third, as other readers pointed out, you have to distinguish between a good/bad decision and a good/bad outcome.

    Finally, if you hire someone for career consulting or coaching, ask directly, “How do you work?”

    Some coaches believe they should encourage your dream, no matter what. Others believe they should give information and/or opinions. Some believe in the Law of Attraction. And so on.

  34. Ken
    Ken says:

    Your article applies to so many people in my life, it’s really astonishing. People who haven’t dated in a decade, drowning in debt, bicker with their family, are exasperated with their jobs and generally unseasoned in the ways of the world seem to be the most opinionated and eager to give advice. My phrase lately has been a very direct, “You don’t know what you’re talking about.” Try it.

  35. Daniel
    Daniel says:

    One question:
    1-If, after some deliberation, I feel my parents are in a poor position to give me advice, what do you think a parent-child relationship should look like? The parent I’m closest to has a mental disability, whose outlook on a lot of things seem narrow and unlikely to change, especially at that age.
    I’m asking because it’s a stark contrast from the way I’m used to interacting with them as a child, coming to them with problems and seeing what they think, et cetera.

    I believe there is something to learn from everyone, but am discovering this is true more if you pay attention to what they do, how they act, and how they justify those actions (so, not the ‘logical conversations -> direct advice’ impression the phrase implies).
    Right now I’m taking the time I spend with them as ways to practice patience and listening skills. Any thoughts on this?

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