How to be more interesting to other people

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For a while, I was a visual artist. Well, sort of. I mean, I made money from it. But as you may know, I am a big advocate of specializing, and I realized that I had a better chance of being outstanding in my field by focusing on writing instead of visual art.

But I did learn some lessons from my visual art mentors, and one really cool thing someone taught me is that the color I choose is most interesting where it intersects with another color. Just knowing the right color to use is not the clever, interesting thing. Rather, interesting is when I am unsure what the two colors will do when they interact. (Here’s a great set of paintings that illustrate this idea.)

The same is true for writing. The interesting part of writing is not the part of the piece where you know exactly where it’s going. The interesting part is when you get to an unplanned moment in a paragraph and you surprise yourself by what you write next. It’s the moment of uncertainty, when you have to look inside yourself to keep going, and pull out something you didn’t know you had before.

When I taught writing at Boston University, it took most of the semester to get students to get to that moment. Most people are scared to get there.

That’s why most people do not appear to be as interesting as they really are.

We each have spots in our lives where two colors are coming together and we’re not sure what will happen. That’s the part we should talk about when we talk about ourselves. If you limit the conversation, discussing only what you are certain about, then there’s no chance to stand on equal footing with your conversation partner. You stand on equal footing when you both reveal your struggles with what you don’t know yet, and the conversation can contribute to the answer.

A while back I wrote about Moira Gunn, and how she is good at interviewing people because she can find what’s interesting about them. She interviews scientists, and she is a pro at finding the quirky, unexpected moment within the topic of their science.

You can do this with any subject. I do it with careers. Every week, for my column in the Boston Globe, I interview someone about their career. The beginning of the conversation is always the part they expect—where they tell me what they know about themselves and their career. There is not room for a real conversation. I just take notes.

And then I don’t use them. Because then I try to ask questions to get to what they don’t know. What are they trying to figure out? And we have a conversation about how people do that. And that is the part I use. Because that is the part that is interesting.

So look, interesting does not come from greatness. Interesting comes from conflict. Tolstoy opens Anna Karenina with the line, “Happy families are all alike; every unhappy family is unhappy in its own way.” This is true of everything—not just families. So talk with people about the issues and problems you’re struggling with. That is how to be interesting. You don’t have to describe your life as if it were all struggle, with all the drama of Russian literature. But find that small moment when two of your own colors collide, and point it out to make interesting conversation.

38 replies
  1. Kosta Kontos
    Kosta Kontos says:

    Pen, I like to think this advice is potentially fruitful to one’s relationships.

    But how do you suggest we go about revealing our struggles (so as to spark interesting conversation) without inviting our listener to assume an advisory role?

    This predicament doesn’t really surface when the other party is just as open about their struggles.

    I think it’s important to select our audience carefully whenever we feel the urge to turn our cards face-up.

    * * * * * * *

    Such an interesting question. It’s true that it is very annoying to having someone turn into an advisor. Of course, as someone who gets paid to give advice, I have thought about this problem a lot — I work hard at making sure I am not the one being an intolerable know-it-all in conversation even though surely, that is my proclivity. And this is why: Because I have found that it’s hard to connect as a friend if I am always the advisor.

    So, in the case you bring up, someone who takes the know-it-all position in a situation like this acutally hurts herself more than you. It’s nost skin off your back if someone says she knows how to run your life. It just means that she will not be making a good connection with you as a friend and you’ll have to find someone else to connect with that way. So the person who always tells people what to do in their life suffers because connections are hard to make. And the person who reveals their weaknesses opens up the opporutnity for connection and probably benefits more than not.


  2. Caitlin
    Caitlin says:

    I am a writer. I make my living from freelance journalism, which includes coverage of the media industry, some serious social reportage, and food and travel writing. I am fairly successful at what I do and in the future I would like to build on that, perhaps going back to a staff job in a senior editorial capacity, or perhaps remaining freelance. I also aspire to write fiction and I am working on that in my spare time.

    On the other hand, business models are changing and the long-term job prospects for journalism are not healthy. Journalists even now don’t usually make a lot of money and in the future it is likely there will be even fewer journalistic jobs and they will be paid even less than they are now. I am very interested in the rise of new media and that’s why I have started blogs in some of my areas of specialty ( and The idea is that not only am I leveraging my existing knowledge into something that *might* make money (if anyone ever clicked on the ads or I found a better way to monetise it, that is!) and marketing myself as an expert in my field, but I am also educating myself about online publishing. I have been an online writer in the past but being a publisher is different again.

    I love being a writer, but I also want to afford a house and a family and a nice lifestyle and to be able to support people I love and causes I care about. So my dilemma – the intersection of two colours – is whether I stay on the editorial track, or whether I cross over to a publishing/business track. I know a bit about what to expect because of my years writing about the media industry. Most publishers rise up through the ranks of the sales team but some publishers come from editorial backgrounds – maybe that should be me?

    The main way that journalists change to a more lucrative career is to switch to PR. I already know that this is not for me. I haven’t tried it but I have friends who do or have done it and I’ve been on the other side for many years. It just doesn’t interest me.

    I love writing and journalism and undoubtedly I would miss it. There is part of me that says I should not give up now when I am starting to get the kind of work and professional success I want. Yet on the other hand it’s not giving up and it’s still working within an industry I love, at a time of enormous change. There is no doubt that the job stability and pay would be better and I would be both building on existing skills and learning new ones at a rapid rate. There is also no reason, aside from time, why I could not continue with freelance writing and fiction in my spare time.

    So my dilemma is – is this what I want to do? And how would I go about doing it? If it’s not what I want to do, then how will I afford the life I want?

  3. Andrea C>> Become a consultant blog
    Andrea C>> Become a consultant blog says:

    Caitline, I studied journalism in college, then switched to English. I started freelance writing when I was still in college. However, like you, I realized the financial constraints. So I prepared myself for a career in marketing communications, specifically in the high tech sector. After a while, I went out on my own as a freelance marcom specialist and writer. When I realized that marketing paid more than marketing communications, I learned how to do that and went back to work for a software company as a marketing manager. Then I worked as a marketing consultant — on my own. I got an MBA, so that I had even more skills and credibility. I’m still a marketing consultant, but now I have some people working for me. But I could also go back to a nice corporate job in marketing or business strategy, likely at the director level. I still do some freelance writing, though. I don’t have the opportunity to be an investigative reporter or foreign correspondent, but I get to use all my writing skills.

  4. Kelvin
    Kelvin says:

    Interesting advice Penelope, but wouldn’t talking to your interviewee about your OWN issues and struggles during an interview sort of turn the whole thing around? It wouldn’t really be an interview anymore but simply a conversation, which the interviewee may want to put “off the record,” since you are just swapping tales.

    And doesn’t talking about your own struggles run the risk of losing the train of thought, and even the purpose of the interview? It might even turn off the interviewee…

    I mean, those are just my thoughts about your ideas right now. My two cents. ^_^ Nevertheless, very interesting post.

    * * * * * * *
    Right, Kelvin. I think this would be too much in an interview situation. But in an interview, the point is not so much to be interesting as likable. A slight difference, but material here, yes?

    Though, I want to make the point that when the democratic candidates were asked, recently, what their weaknesses are, Hillary lost out by giving an answer that was not really a weakness, and Barack referred back to the moment (where he did give a real weakness) many times. So you really do have to be prepared to show something of your weaknesses in an interview, but not all of it.


  5. Maureen Sharib
    Maureen Sharib says:

    Tolstoy's original manuscript, in its original pre-edited form, read, "All happy families are alike; they have dinner together and the children do the dishes; each unhappy family is unhappy in its own way; it could be anything: drunkenness, sassy back-talk, refusal to clean up one's room, tantrums, nose-picking, adultery, don't ask."

    I have this plastered on my refrigerator, above my eye level, for the express benefit of my grown children who are taller than I am.

    As I read your post I was reminded of pundits who minimize an artist's work. If you have ever tried to "copy" what appears to be a "simple" work of art by a great artist, you very quickly come to glimpse (and then stand in awe) the original artist's genius. It's surprising when you first make this discovery and eye-opening.

    There was a blog post a day or so ago by Donato Diorio, founder of Broadlook. The blog is called, I, Donato and in this particular post Donato was bemoaning the lack of creativity in our culture; asking why we were all so obsessed with copying content from each other.

    He makes a good point. However, I believe this "copying" brings some of us to this same new place of recognition; vitalizing new understandings and heralding new concepts we build upon to go to different places in our own developments.

    Thanks for this piece, Penelope. I thought it was wonderful.

    * * * * * *
    Hey, Maureen. I love that you came up with the content of the original manuscript. Thanks.
    Also, this is a great moment to learn about editing. Editors almost always say “be more specific” but in this case, leaving out specifics is stronger opening.


  6. Shefaly
    Shefaly says:


    Interesting post. I do think that those not of a “talk-therapeutic” bent of mind may find this approach a bit odd.

    You say: “So the person who always tells people what to do in their life suffers because connections are hard to make. And the person who reveals their weaknesses opens up the opporutnity for connection and probably benefits more than not.”

    You make it sound like friends cannot be advisers, and advisers cannot be friends. In fact, to find a friend, who gives advice untainted by blind emotion and only with your best interest at the core, is a rare find, a rare friend. The same goes for the most trusted and best paid advisers. The trick is in demonstrating that balance, and doing so consistently (latter if you do it for money, like I do and you do).

    Connections needn’t always be made at an emotive level; some of the greatest, most powerful and most profound connections I have with people are at an intellectual level. Rarely does our emotion come into it, yet some of these verisame people are also my friends for nearly 2 decades. That sort too is a rare connection, and one, that cannot be appreciated unless experienced in all its splendour.

  7. Caitlin
    Caitlin says:

    Andrea, it was interesting to hear of your career path. It’s always interesting to me as a journalist to hear how people have leveraged journalistic skills (writing, interviewing, research etc) in other careers. It sounds like you made those decisions early on in your career. One of the challenges I face is that I am 10 years into my career and I don’t want to start again at the bottom. I don’t think marketing is for me, though media buying is interesting, but ultimately I think still want to work on the publishing side, whether as a writer, editor or publisher.

    Kelvin, an interview is not a conversation because that implies something more casual and two-sided. I know Penelope used that word but I don’t think she meant it literally – I interpreted it to mean that the topic of discussion or the subject of the interview shifted. The interviewer might have input in order to ensure the interviewee feels at ease, but they would still be in control and the interviewee would still be doing most of the talking. Penelope didn’t say that she would spend the interview talking to the interviewee about her *own* problems; she said that she would be asking probing questions to get them to be opening up about theirs.

  8. Tiffany Monhollon
    Tiffany Monhollon says:

    I think it’s really interesting how this post touches on something that we’re seeing in the digital world – the rise of value placed on transparency and authenticity. When I studied journalism, one of the hardest things to learn to do was to take myself out my my reporting. Now, as a blogger, one of the hardest things to do is to learn how exactly to put myself back in it.

    But there’s a value in that – in how it helps you form more real relationships – relationships that can really impact your life. I think of the recent example of the Frozen Pea Fund – – that sprang up out of Twitter. And how that’s changing lives, and inspiring people. All because a woman was just open and honest about her struggle – and in such an open forum. It made her struggle real, and people responded with support and compassion.

    Because it takes a certain amount of courage to be open and transparent enough to show the world when your colors collide, as you put it. But people respect that and connect to you. I think your writing is a great example of this, and I thank you for it.

  9. Recruiting Animal
    Recruiting Animal says:

    When someone goes into a job interview without having articulated his daily job functions in his own mind he usually has to do the thinking on the spot. That means a lot of silence and looking at the ceiling while he does his homework there and then. That’s not interesting.

    Things get interesting when he has thought things through in advance and therefore has the a ready grab bag of ideas which he can use to consider something related but new.

    My point: that you can’t be interesting until you have, in fact, mastered the stuff you claim is uninteresting.

    Sparks may fly when you go beyond it, true, but the way you have worded it implies that there is no value in dwelling on the commonplace. But there is.

    Chances are that you can’t be a great musician until you’ve mastered the scales. And the same is true here.

    The same is true on the readers’ side. If they don’t know the basics, they’re bound to be interesting whereas they don’t have the background to understand anything more.

  10. Brian Johnson
    Brian Johnson says:

    Love the background on the use of color. Tonal music follows similar rules. A major chord by itself has a certain organized quality to it, but if it’s positioned as the resolution to sounds that create tension and unease, especially dissonance, most agree that it sounds much more pleasing and powerful than in isolation. For a great example of this unfolding, listen to the 4th movement of Respighi’s “Pines of Rome.”

    I always enjoy seeing rules in nature that cross over various disciplines.

  11. John Feier
    John Feier says:

    When I first went to college, fresh out of high school, I was wanting to major in journalism. I wanted to make a living giving my opinion about political and social matters. But that was 1984 and now we got PLENTY of editorialists…they’re called bloggers. :)

    Once I get my accounting career going, I can write in the night time on my favorite blogs and keep the day job. I enjoy giving my opinion on political and social matters and I really don’t care if I get paid for it or not.

    Good article, Penelope.

    I too encounter “uncertainty.” Sometimes it’s a stroke of genius…other times, it’s an illogical and confusing heap of letters strung precariously together, pretending to be a structured thought.

  12. etavitom
    etavitom says:

    This is a very interesting and helpful post. Thank you! I am an “actrepreneur” and would welcome the chance to be interviewed by you. :) All the best, Brad

  13. Mary S
    Mary S says:

    Very interesting post. Also, very timely for me as I was bemoaning my feeling of “blandness” (for lack of a better word at the moment). I’m currently struggling with figuring out my next 5-year plan and I have a difficult time sharing that with people, because I’m worried that I’ll be seen as having nothing to contribute to a conversation.

    Your post is helping me to reframe my current thinking. My husband and I both thank you for your perspective.

  14. Milena
    Milena says:

    Reading this post made me think of my recent attempts to become more interesting. You tell us we can do it with any subject and talking about what we are uncertain of is the most interesting part of ourselves. I agree.

    With my father’s recent death I was catapulted into uncertainty and felt compelled to begin a blog to discover and catalog his fascinating life. I’ve become wrapped up in revealing the things about him that made him tick, made people love him, want to be around him and made me want to be like him. Talk about a Russian novel, his life was a Russian novel. I recently told my husband how uninteresting we are in comparison to a man like my father. A mix of old world european and modern mentalities, he was just at home at the Mac store as he was in a Bosnian village, with wealthy Indian and Jewish doctors or foreigners without a high school education. He is my ultimate example of how to be interesting to others. He was mostly quiet, but if you struck a chord of intest – he could talk for hours, weaving tales with history, politics, philosophy, poetry. He was at ease blending lines, cultures, disciplines.

    In the wake of sorrow I’m also forced to observe where I stand in life and in the back of my mind find I’m comparing myself to him. Where I fall short, where I surpass. I want to be more interesting, adventurous, follow in his footsteps. I guess I’m more interesting because my dad died. It would be a shame if I stayed the same.

  15. LP
    LP says:

    Recruitng Animal makes the right point: great thinkers ask interesting questions, but the intersting-ness of thier questions is based on their expert knowledge on some subject. Mediocre thinkers and non-experts ask boring questions, because they all ask the same questions. But to get at why someone’s question/issue/struggle is interesting, background on their expertise is pretty important.

  16. LP
    LP says:

    Also, people who are asking interesting questions in their life, work, etc. (what PT calls ‘problems’) don’t usually care much whether other people find them interesting. So the last paragraph of this piece, about how to ‘make interesting conversation’ is probably misplaced — people who are primarily concerned with making interesting conversation are probably not asking interesting questions in the first place.

  17. Dale
    Dale says:

    Hi Penny,

    There are only four ways I know of to be interesting:

    a. Be genuinely interested in others – as you said in an article a few years ago. Fake doesn’t fool anyone for very long and is definitely not interesting;

    b. Be quirky, in a positive way, e.g. Have a unique past-time, be ultra good at something, or have a different but interesting life (A female blogger, pro athlete, mother of special needs child, with marital issues, who ticks off people because she says what she thinks is interesting and quirky);

    c. Be controversial. Not the same as quirky above, since it does not have to be in a positive way.

    d. The fourth way is to be attractive physically(but this wears off over time if you aren’t applying a, b or c :)

    Just my take on things.

    P.S. Have you got that reality show in the bag yet? It’s just a matter of time.

  18. Matt Bingham
    Matt Bingham says:

    In my opinion, if you do interesting things you are percieved as being more interesting. Things that people wouldn’t expect. Everytime I bring up that I played rugby people always engage. It strikes into other conversations. This just comes down to Penelope’s number one rule for working individuals; Interesting work that serves a purpose. If you follow that you will always have something interesting to say!

  19. Dale
    Dale says:


    Here in the States, you definitely would be considered quirky.
    Rugby definitely isn’t football, although the skill set required is similar. Now, if you combined good looks, a genuine interest in others, and some personal controversy along with that quirky past-time, then you’d go beyond the domestic, garden variety interesting scale, you’d be story book material!

    Just my two cents worth:)

  20. Leslie Forman
    Leslie Forman says:

    I’ve been reading your columns for a while and I think this one is my all-time favorite. I think it’s a really useful and empowering way to think about transitions as a way to connect with people. I personally just returned to the US after working in China for a year and a half, and I have a degree in Latin American Studies. At this point I am blending these colors together on my own palette, envisioning all sorts of possible patterns.

  21. David Theus
    David Theus says:


    I like this one, it’s honest. I sometimes find myself in my own work trying to sound so much like an expert and that all things are going so great, that I forget sometimes, they’re not. It’s that time when we come to reality for a moment and say, I’m hurting, or I’m not sure what the future holds that is true.

    I don’t have all of the answers, and because of that I hope my readers will see the truth in my walk. I call it a walk not to sound spiritual so much, but to let my readers know, it’s about walking into the next phase of our lives because sometimes there might be pot holes around the next turn we can’t see.

    I’m rededicating my work to being real, the good, bad, and the ugly. I’m sure I’m not the only one.

    Love your stuff,


  22. Emi
    Emi says:

    I wish I was more interesting. I don’t have real life friends so I need lots of internet friends. But first I have to look cool on the web.

  23. Adrena Clark
    Adrena Clark says:

    I love listening to your advice and giving advice to but please right now i need major advice and quick. You see i’m in university and i’m writing a essay about what ever i want and it needs to be intresting. All my frinds are almost finished when i still have no idea. Can you help?

  24. Randy Zeitman
    Randy Zeitman says:

    “But I did learn some lessons from my visual art mentors, and one really cool thing someone taught me is that the color I choose is most interesting where it intersects with another color.”

    (And the most interesting thing to me about those paintings is how they interact with the white background they’re placed on. There’s no way to just use one color… it’s always applied on another color…even if you paint on glass. Can anyone create visual art without a border or background? Every image of infinity has a finite boundary, right?

  25. seth t
    seth t 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 Heinlein

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