How to express your true self at work

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It is harder to know who you are than it is to be who you are. Everyone says, “The important thing is to be yourself!” I say that when I give them career advice. People like you better when you are being authentic. Gay people do better in their careers when they are out of the closet. Women do better at work if they are feminine at work instead of trying to be like the guys.

But there is very little advice on HOW to be yourself.

1. Don't be boring.

On the way to our board meeting today, it was me, and Ryan Paugh, and Ryan Healy, in a car, running late. Ryan Healy told me not to write about him on the blog anymore, but I think only because I used to write about him like he was my little brother or something. At this point, Ryan Healy is COO of the company, so I think I can write about him because really, how can I undermine him when I'm agreeing to report to him?

So I'm riding in the car with Ryan and Ryan and I finished my needlepoint and I didn't have anything left to occupy my hands during the board meeting. I know that as a board member, and the majority shareholder in the company, I'm supposed to be enthralled at these meetings, but honestly I find them largely very slow and repetitive. (I know I am not the only one who feels this way because another board member went to the bathroom and when he came back and found out that we waited for him, he was disappointed.)

Anyway, I was in the car with them and I was panicking that I didn't have anything to do in the board meeting except listen to the board meeting. Then I said, “I think I'll pop a Xanax.”

And no one said anything. Ryan and Ryan are largely bored with my antics.

But when I'm anxious I'm chatty, and they had already said no to playing the license plate game. So I said, just to make casual conversation, “What do you guys think would go well with Xanax, because I don't think this is working. And pharmaceuticals have been such a disappointment to me.”

Ryan Healy said, “?You sure are a late-bloomer to this. By the time you're going to board meetings you're supposed to be done with this stuff.”

In fact, I am enthralled with mixing pharmaceuticals off-label. I am also enthralled with trying new things, learning what I'm like with new things so I know who I am.

But it gets old. Not knowing who I am. And anyway, it's boring for other people when you don't know who you are. I know that because when I was dating the twenty-five-year-old with the perfect butt and long, thick, curly hair, he had no idea who he was and it got boring, very boring very fast.

(Links about boringness: People do not want to know all of you. Some of you is interesting, some of you is boring. This is why confessional blog posts mostly stink. And it's why you need to omit most of your life from your resume.)

2. Try a range of tools to express who you are.

I like to think that I know myself well enough to present a consistent and insightful portrait of myself. And when Eva, from Songza, emailed me to see if I'd put together a playlist that they could use on their music streaming site, I said sure. (By the way, if you want to get me to do something, make it fun. People ask for posts all the time, but few people ask for playlists.)

So I start doing my playlist and I think: People judge other people by their playlists. (Which is why Ramones t-shirts outsell Ramones albums ten to one.) I want people to think I'm fun and edgy and self-confident.

(Ad for my company: It think about this issue a lot because my company, Brazen Careerist, is basically a tool to let people know who you are by showing your ideas and potential. The tools on the site encourage you to display your best self in a professional, online setting. And every time I pitch my company, I end up telling people that you can't show your true self if the tool you're using is wrong for who you are.)

3. Understand how people perceive what you put out there.

I picked Moby and TruSkool for edge. I picked Beastie Boys and Arrested Development because I read that people who like hip-hop tend to have high self-esteem. And I picked Fergie for fun. I think when people say she's for girls, they mean that she makes guys think of girls dancing while they watch. Then I picked Lilly Allen, Regina Specktor to say that I didn't feel too much like an old-school Gen X-er. I picked Kings of Leon because Lilly and Regina are both girls.

It turns out that I would have done fine just picking out all Miles Davis, which would have probably been my instinct, but I thought it would be boring and pedantic (which is almost redundant but mildly nuanced instead, I think). It would have been just fine because people have positive impressions of people who like jazz.

This is surprising to me because people do not have positive judgments toward blog posts that are like jazz—complicated and difficult. In fact, my editor will probably slash this whole paragraph because it is off topic and difficult to read and jazz is not writing and so what if my brain runs like an Ornette Coleman composition?

When I sent my song list to Eva I asked her to analyze me. I said, “I bet you read song lists like I read resumes, so can you tell me what you see?”

She said she usually doesn't see such a wide a range of songs on one list.

On a resume, lack of focus is bad. And in a life, doing many different things at once is bad. And in fact, I'm a stickler for focus because I love knowing one thing well, so it's counter-intuitive to me that I would have such an eclectic list. In fact, it's the result of me being scared to just be who I am and accept that I'll be judged for it.

But P.S. Here’s the playlist I made at Songza. And here’s my favorite Miles Davis CD.

49 replies
  1. James
    James says:

    Thank you for the great post!

    I’ve struggled with a question for a few years and the “Gays who are out of the closet at work have stronger careers” comment/article brought it back up in my mind:

    During the workday, I’m an IT Security guy – geeky though charismatic, yet on the weekends I travel the country teaching people how to tie each other up, experiment with open relationships, and generally have better sex lives – pretty much all of it NSFW. How can I express any of this at work?!

    Living on an IT professional’s salary is a lot more comfortable than trying to eek out a living in “the [porn] industry” yet going back to work on a Monday after spending the weekend as a small-time celebrity is quite jarring.

    • Justin
      Justin says:

      Really odd that you should mention that. I was at a bachelor party last weekend and we stopped by a strip club. One Dancer there was the most shockingly honest person I have ever met. She was a dominatrix when she wasn’t stripping. She used to be in the Navy but couldn’t get any of the jobs she wanted, so she left. Did she do cocaine? Yes, of course she did. How did she hurt her wrist? She got drunk and fell down some stairs the night before. She thinks marriage is silly, but is getting engaged because her boyfriend is in the Navy and the benefits for spouses would help her a lot. She acknowledged that the her industry is pretty awful, but it pays well, it’s made her more outgoing, and she finds human sexuality interesting and she tries to think of her jobs as research. I ended up leaving with a really great impression of her and was actually inspired that she completely embraces the life she is living. I know that doesn’t help from a HR standpoint of whether or not you would get fired for telling people what you do, but from a personal standpoint, I think it would make you a hell of a lot more interesting than anyone at your company, and I’d have a lot of respect for you being confident enough to tell people what you do.

  2. Amy
    Amy says:

    Can I just say that’s a hard comment to follow??


    I think the thing people like best about you, and your writing – if not your playlist – is that you just can’t seem to help showing who you are. It’s like we can kind of see this constant tug of war between your totally outside the lines personality…and Ryan and Ryan feeling compelled to pretend they need to reel you back in.

    I love a lot about my day job, as a reporter, but there is some aspect of it — as there is with most jobs, that is fraudulent and that’s the part that repulses me. Which is why I’ve been loving the blog thing, because it’s much closer to my truth.

    As a sidebar…I had just gotten up to go exercise and then I saw your new post. I told myself it would still be there when I was finished. Then I sat back down on the couch and read it. :0)

    Amy Parmenter

  3. Elizabeth
    Elizabeth says:

    I find perceiving how others’ view what I put out there to be a major challenge. It’s probably what drives a lot of people to writing–because when you right you do not have to be spontaneous. You can think about what you say before it ‘goes live.’ I’m definitely one of those people who would benefit from having edit functions on my actual speech and behavior.

    At this point, I’m fairly resigned to having a gap between what I think I’m putting out there and what others see. I have gained a lot from your openness to seek feedback from other people, Penelope. That used to be a major source of anxiety, but your recounts of experiences doing this are some of my ‘life savers’ when I’m freaking out. Thanks for so many great posts!

  4. Jess
    Jess says:

    Every single one of your posts in the last few months have followed the same tired formula. Find some tortured work theory to explain away you acting psycho at work and actually present this justification-for-crazy as legitimate workplace advice.

    It sounds like you would be an absolute nightmare to work with.

  5. Mark W.
    Mark W. says:

    “In fact, it's the result of me being scared to just be who I am and accept that I'll be judged for it.” (in reference to the eclectic playlist list) is the sentence that stood out for me in this post. It’s the dilemma of item #3 (Understand how people perceive what you put out there). A person can either craft a result to look good, fit in, or whatever OR express their true self. The price is a “heavy” one to pay when it’s necessary to worry about how you’ll be judged by other people. I/we are judged – period. Judged by action or inaction, focus or non-focus, sensitivity or insensitivity, and the list goes on. As long as we’re being judged, we should do it on our own terms and be our true selves.

  6. Kelly O
    Kelly O says:

    I find it interesting that your third point is “understand how people perceive what you put out there” when your first point mentions a need for attention to the point of mixing pharmaceuticals before a board meeting.

    Honestly I’ve never been in a meeting at any level where doing needlepoint would be an acceptable way to keep your hands busy, if you have a need to keep your hands busy. Yes, I think we all get bored, especially at a higher-level meeting, but that’s when you normally see people “taking notes” – which might mean actually taking notes, or doodling, or making a grocery list, or whatever.

    Trying to medicate yourself in order to deal with something is just not healthy. I know you blog with intent to shock – it just takes a couple of posts to realize that – but I sincerely hope you’re exaggerating your behavior for the sake of comments or web site hits. I honestly debated whether to comment, because I don’t want to feed the beast, but I’m just hoping against hope that this is all an over-the-top exaggeration for site traffic.

  7. Jens Fiederer
    Jens Fiederer says:

    “A human being should be able to change a diaper, plan an invasion, butcher a hog, conn a ship, design a building, write a sonnet, balance accounts, build a wall, set a bone, comfort the dying, take orders, give orders, cooperate, act alone, solve equations, analyze a new problem, pitch manure, program a computer, cook a tasty meal, fight efficiently, die gallantly. Specialization is for insects.”

    -Robert A. Heinlein

      • Jens Fiederer
        Jens Fiederer says:

        Good point, I think there is some room for both.

        Perhaps it is even a good thing that we have a few insects to really excel in their narrow fields.

        I’d rather pay a mechanic to repair my car with money I earned computer programming than waste my time doing it myself – but I think it is still a good thing I’ve done some of my own work (replacing oil filters and headlights, once even replacing a fuel tank (which I do NOT recommend)) and have some grasp of the basics – gives me an edge in selecting an honest mechanic.

        I’d say I’m about 75% specialist (computer programming) and 25% eclectic (mechanics, electronics, dancing, piloting, scuba diving, singing, linguistics, skiing, woodworking, ….. you can get a lot of flavor as a dilettante)

  8. Perle Champion
    Perle Champion says:

    Are you sure that wasn’t speed instead of Xanax? This post seemed a little rushed and scattered. I, too, hope the Xanax was for emphasis and not a reality in your purse. I can't imagine picking a playlist to impress anyone

    I've worked in corporate America, and survival is easy if occasionally stressful. I always considered it a game of sorts. As with any sport, there is a uniform, boundaries, and rules that some consider a hindrance. If that were true, we would not have superstars, those people who excel in the game leaving the neggie nellies in the dust still making excuses for their inability to shine.

    I will forever be grateful to team sports of my youth, because the equipped me for every part of a working life. I think more men function in that arena better than women, because more of them played on a team of some sort.

    Through it all, I've remained myself, and the only opinion of me that matters to me is my own. As long as I can look myself in the eye with a clear conscience, I'm fine with that.
    Miguel Ruiz's 4 Agreements have always been how I strive to live my life.
    1. Be impeccable with your word. Speak with integrity. Say only what you mean –
    2. Don't take anything personally. Nothing others do is because of you. What others say and do is a projection of their own reality –
    3. Don't make assumptions. Find the courage to express what you really want –
    4. Always do your best. Your best is going to change from moment to moment; –

  9. Jess @OpenlyBalanced
    Jess @OpenlyBalanced says:

    If knowing who you are is not a prerequisite to being yourself, what is the added value in knowing who you are? Is there some disadvantage to just going through life being yourself and not worrying about “knowing who you are?”

  10. William Bruce
    William Bruce says:

    “And in a life, doing many different things at once is bad.”

    Since I differ adamantly, I am compelled to request some explication. The linked post addresses only expertise; a host of considerations must fill the breach.

    As stated, the claim seems indefensible — or indefensibly vague.

  11. Liza
    Liza says:

    I think I warped back into middle school with this post…

    ‘know who you are’…. ‘be yourself’….

    The title of this post is a lie: ‘How to express your true self at work’

    your answer: Take Zanax and mix it with whatever you have on hand…

    …great advice (sarcasm). I understand you might be a little off the deep end, but I’m pretty certain your advice no longer applies to the workplace, and it should not be applied to the workplace. Unless you suggest I come to work drugged up because I just can’t take the boredom of waiting for something to do…

  12. groovecat
    groovecat says:

    they aren’t bored w/ your antics. they just don’t want to bite the hand that feeds. somehow, they are making money off you. doing drugs in front of your employees is less than professional. bad career advice. notice i’m writing in short direct sentences. so that those of less intellect can understand. and no need for formal grammar rules. as well.

    you are nuts.

    and doing needle-point during a board meeting shows your commitment. to the over-all. health. of the company.

    in case you’re wondering, i read your blog because it’s like watching a train-wreck in slow motion.

    meh. but based upon results you have me beat.



  13. Margaret Goerig
    Margaret Goerig says:

    I was driving all day and at one point, I thought, “I hope there’s a new P. Trunk post when I get there,” but I didn’t think there would be, because you are not posting so much these days. And wouldn’t you know it? There was a new post waiting. So, it may not have been my favorite post in the world but who cares? It’s just nice to see you out here again. All that business about trying to be this and trying to be that is so exhausting. Just be in the moment and you’ll be authentic. It’s when you’re genuinely interacting with people that things get amazing.

  14. Margaret Goerig
    Margaret Goerig says:

    I was driving all day and at one point, I thought, “I hope there’s a new P. Trunk post when I get there,” but I didn’t think there would be, because you are not posting so much these days. And wouldn’t you know it? There was a new post waiting. It’s just nice to see you out here again. All that business about trying to be this and trying to be that is so exhausting. Just be in the moment and you’ll be authentic. It’s when you’re genuinely interacting with people that things get amazing.

  15. dmg
    dmg says:


    I have read your blog for the past 3 years and your recent string of posts have been extraordinary for me. Your blog makes me feel “normal”. Your blog makes me feel strength and hope- not that life will ever get any easier- but that there are people in this world strong enough to keep on going.

    For the first time in my life I feel like I can be myself at my job (I’m 26 and at my 4th job since age 20). A major factor in this is that my boss is “normal”. He is normal in the sense that… hey, sometimes he’s late. Sometimes he’s NOT right and is okay with admitting it, sometimes he just wants to go home and do anything but be at work… and ::gasp:: says it!

    This flabbergasts me because in every previous job I have had, I’ve always felt a great amount of pressure to always be happy- always be productive- always be willing to ‘go the distance’.

    The fact that my boss is a 2 x cancer survivor and that his wife is a cancer survivor and has just again been diagnosed with cancer has GREATLY influenced the fact that for him LIFE IS SHORT and its not all about work!

    When you add to the fact that I work in an industry where I know a person who dies almost every week (assisted living communities), it has made me realize that the only thing you lose by not being yourself at your job…. is yourself.

  16. Irving Podolsky
    Irving Podolsky says:

    Hi again, P.

    Your recent letter to the world got me thinking, as always. The title suggested success in the work place, but the undercurrent pulled me into the world of “I STILL FEEL LOST, EVEN IN MY OWN CREATION.”

    I could be completely wrong about that. And if I am, I apologize. But if this is the case, and even if it isn’t, I’d like to add a few twigs to your fire.

    What I’m finding out in my line of work, which is a service in the film business, is that generally, managers hire others who can relate to their own point-of-view; who can understand them, who can help build their confidence, and who can be relied upon for loyalty. And this “must-have” list pretty much covers friendships, romances and marriages as well. EVERYONE is looking for understanding and support. Especially bosses. So if somehow we all could stop seeking love, validation, and acceptance, and instead, GAVE it, everywhere, without judgment, I believe we’d find ourselves surrounded by others who wanted us in their lives.

    But who’s secure enough to do that? Not me. Well, on occasion…

    So my added comment is this: in the workplace, (or at home) I think being yourself will take care of itself if you allow your boss (or your spouse) to be himself or herself. Again, we’ve targeted unconditional love. I know it exists, but I’m not a parent, so personally I know it not. Maybe you do.


  17. D
    D says:

    Funny that you refer to it as your “favorite Miles Davis CD.” It was originally an LP, and who buys CDs these days? Perhaps next time you can submit a mix tape instead? :)

    It’s my favorite as well.

  18. Miss SJ Albany
    Miss SJ Albany says:

    1. you used one of my favorite words, pedantic.
    2. are your readers really this tight-assed?? it’s xanax people. it’s not like she snorted coke off a hooker’s ass mid-board meeting.
    3. i think the needle-point thing is a creative solution.
    4. cool playlist.

  19. Steve Errey - The Confidence Guy
    Steve Errey - The Confidence Guy says:

    Hey P

    Couldn’t not add a couple of thoughts to this one. You know what, a lot of people think they don’t know what confidence is and end up second-guessing themselves and making up a bunch of rules that they need to operate by, but which just create more stuff for them to second-guess which ends up making them feel more disconnected from their natural confidence.

    Everyone has natural confidence, and it’s not about following some set of rules based on “shoulds” and “oughts”.

    I actually think you have a pretty good idea of who you are, but it’s all too easy to forget. I think you have self-esteem and self-confidence.

    Confidence is just being able to trust you choices, and if there’s one thing I know about you it’s that – as tough as it is sometimes – you don’t shy away from the tough decision.

  20. GenerationXpert
    GenerationXpert says:

    I think I’m really good at being myself at work. Yesterday at the end of a conferece call, our president said “you all are doing a great job” and then said all our names. It was kind of corny. So I said, “You’re doing a good job, too, Bill.” Everyone laughed. It lightened up a kind of awkward moment. I used to try to be “corporate” GenerationXpert, but it was too draining. Plus I think when people do that, it’s annoying. My best friend does this, and she’s a successful person, but I keep telling her she’d be even more successful if people around her professionally knew about her wicked sense of humor.

  21. Maggie McGary
    Maggie McGary says:

    Brazen Careerist should have a contest where the prize is a trip to Wisconsin to spend the day with you guys at your office because it sounds a lot more interesting than other work places. Or a reality TV show–much more interesting than cupcake bakeries or housewives.

  22. Odessa
    Odessa says:

    Call me when you actually have real clients and orders to fulfill. Until then, you’re working for yourself, writing a couple of blog posts a week. Brazen Careerist isn’t exactly Facebook or Google. You can express yourself anyway you want, because the stakes are so low.

  23. Loribell
    Loribell says:

    Penelope, I thought you might get a kick out of this post from another career/life blogger (cite at end):

    Sometimes things come full circle. Silly things.

    I started my career with Carnation Company. In a marketing management training program. Carnation owned a lot of brands in pet care, baking and other categories. But the brand was best known for Instant Breakfast, Coffee-Mate Creamer and Condensed Milk. And the old tag-line for Carnation milk was "Made from Contented Cows".

    Happy cows.

    So you can imagine that I paid attention on a recent Southwest flight when an article appeared with the following headline:

    Cows with names produce 68 more gallons of milk.

    And as a loyal marketer, I had to read on. It turns out that a few scientists (with nothing better to do) determined that the relationships between the cow and the farmer mattered. That a spike in milk production resulted from those cows with a name. Instead of "Hey Cow", I guess. The scientists believe that personal attention improves cows' comfort level while lessening their fear of human contact.

    And my guess is that you can't call a cow by name without eventually adding an upbeat inflection to it. And, over-time, turning it into a nickname. Bessie becomes "Bessie-Girl" or "Sweet Bessie". And the farmer is probably smiling.

    How can you not?

    Here's where it comes full circle. As I constantly am looking for ways to bring you successful ways to become better at career networking.

    So for a lot of people career networking is really hard. Very uncomfortable. And a place of little safety. Since, to do it right, you have to put yourself out there in a big way.

    Similar to my rant about the need to personalize those generic Linkedin invitations, so it is true for in-person career networking.

  24. Celine
    Celine says:

    Really?? Needlework and drugged out? Sure you weren’t on a bad trip instead of heading to a board meeting? Why do they even invite you? You’re certainly the life of the meetings. This is probably the worst post I’ve seen you do in a while and I’ve seen some bad ones. Stop giving career advice. Anyone taking it will be unemployed for life.

    But in case anyone (you) is wondering why I post it’s because it’s like watching a subway accident when you’re on the platform: I can’t turn away. I have friends who have chronic illnesses but none use it as an excuse to be a screwed up, drugged up failure. Try getting some help, you need it.

    • Brad
      Brad says:

      Has this blog ever been about career advice? To quote Hannibal Lecter: “No, that is incidental.” An angle for past paychecks from Yahoo and the Boston Globe. This blog is really about the uniquely screwed-up life of Penelope Trunk. Now that she’s gone conventional by getting remarried (sort of, not legally) and moving to the farm in Podunk Wisconsin, her life just isn’t very interesting (which she values over happiness.) She’s not lost, she’s freakin’ bored.

  25. Jon
    Jon says:

    Hmm….this is a funny post because one of the first things you say is to be yourself, yet your examples under each bullet point allude to not being yourself but, rather, make yourself look interesting or cool depending on who your audience is….

    • MPL
      MPL says:

      Agreed, Jon! How can you build a playlist not based on songs that you actually dig but on what “coolness” other people might associate with the songs? That has nothing to do with actually being yourself. At all.

  26. Sarah James Y.
    Sarah James Y. says:

    I will forever be grateful to team sports of my youth, because the equipped me for every part of a working life. I think more men function in that arena better than women, because more of them played on a team of some sort.

  27. delia
    delia says:

    “Women do better at work if they are feminine at work instead of trying to be like the guys.”

    that assumes that who women “really are” is feminine. i think it fits better with your point about being what people expect/realizing how you are perceived than a point about being who you are and knowing yourself. For many women, and i think sometimes this includes you, who they really are isn’t a “sex kitten” or all that feminine.

  28. Annabel Candy, Get In the Hot Spot
    Annabel Candy, Get In the Hot Spot says:

    I can understand this. Meetings kill me. One time I went to a staff meeting in Zimbabwe with the other teachers at the school where I worked. There were 10 of us in a dark cupboard.

    The meeting was about how one of the other teachers (let’s call her S) was being a pain because she complained about her husband (R) hanging around with a local prostitute. Eventually she ran off crying where upon I followed her. I thought that was a normal reaction in those circumstances but it turned out I made a big cultural faux pas (one of many no doubt!) and should have sided with the husband.

    There were a lot of problems in the school and the cultural gulf was massive. Sometimes I took mogodon but these things don’t help. Music and dancing is better.

  29. lynne whiteside
    lynne whiteside says:

    You certainly opened a can of worms…I completely agree about finding out ‘how to be yourself’. I just stopped working after 35 years, and yes there is a transition to be made. It’ll all work out, Life beats the alternative.

  30. uget1shot
    uget1shot says:

    “it's the result of me being scared to just be who I am and accept that I'll be judged for it”………………………………………………………………………………………………………………………………………………………………………………………………….. Ironic that you have said that, on so many levels…………but so honest…

  31. JZA
    JZA says:

    I’d love to tell people who I am, but I happen to love being a cannabis connoisseur, which is unfortunately still frowned upon by the law in most states.

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