Lessons in self-confidence (from Amanda Blank)

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What I’m listening to right now: Amanda Blank. Here’s a song to play when you’re not at work.

Amanda is a white-girl rapper, darling of the hipsters, and hot-girl candy for the intelligentsia. Right up my alley, right? My favorite line so far is “My rhymes are painful and fresh/My p*ssy’s tastin’ the best.”

Today, Ryan Healy and I were in D.C. for a marathon strategy meeting with a board member. The second half of the meeting was about marketing strategy. The first half of the meeting was about finding a strategy for ending how Ryan and I are at each others’ throats over subjects that having nothing to do with the company.

When the board member left the room for a minute, we had this conversation:

Me: It’s so awkward to be left in here with just you.

Ryan: It’s not awkward. The meeting is going well.

Me: Right. It could be more awkward. Like when it was us not talking in the airport.

Ryan: At least we weren’t sitting together on the plane.

Me: Yeah. I know. I changed my seat so we didn’t sit together.

Ryan: Really? So did I.

Then the board guy came back and I bitched about how a vendor we hired was doing no work, and how a year ago I told Ryan we should fire them and then Ryan told me to shut up and so I did.

Then board guy said some obvious things: Ryan should not tell me to shut up, I’m the CEO, and I should take decisive action faster.

Then we all talked more, and Ryan and I started getting along again. And we all plan the next twelve months of the company, getting excited about the community. This is how it always goes with us.

But the whole time, Amanda Blank is running through my head. Why does she say “My rhymes are painful and fresh?” Why are her rhymes painful? I ask myself this. And then I answer philosophical questions about why LinkedIn appeals more to Gen X than Gen Y. And then I go back to Amanda.

She says, “My p*ssy’s tastin’ the best.”

I have never said that. I am too shy. Even when I was her age, and I was running around in a bikini in Budweiser ads for spending cash, I would not have said that.

And this is why her rhymes are painful. Because they exude so much self-confidence. And every regret I can think of is about self-confidence.

There’s a really interesting study from Harvard, reported in the Atlantic, that I have spent way too much time reading.

The study follows Harvard students for more than 70 years to determine what makes people happy. Here is something: The fact that people are totally pulled together and focused and in Harvard has no bearing on whether they’ll have a happy life.

Here’s another thing: There best indicator of if someone will be happy in the future is if you are 47 and close to your siblings. After I read that, I started calling my brothers more often. Really.

But you don’t have to wait for your mid-forties to find out if you’ll be happy.
Look at how you frame your life now. If you frame things in a positive light, you’ll be happier later in life. The optimists win. Plus, the Harvard study finds that people get better at optimism as they grow older. And I believe that. Maybe when I have a startup at 70, I will trust myself enough to act decisively and avoid all management conflicts.

And then this becomes clear to me: I have spent way too much time in my life worrying that I was doing my life wrong. But now I see that I can change. Right now. Right now I can be someone who assumes I am making good decisions. Because we each have to make decisions. So we may as well assume they are good. There’s not really anything else to do.

Besides, no one was ever penalized for believing in herself, even if her raps were not safe for work.

68 replies
  1. Michelle
    Michelle says:

    Self confidence and faith in my decision making process is something I have recently dealt with. I’m going through a legal battle with my ex over visitation time with my child. This past year she has done some pretty nasty stuff to get back at me and I’ve been letting my fear feed my self doubts. I kept trying to keep her happy to avoid conflict and retaliation. The other day I finally said screw it, I’ve seen her worst and her legal options are limited. I stopped letting my fear tell me I’m a crappy parent because I’m the one that keeps the vegetables on the table. I’m the parent, the CEO of this family and love me or hate me, I’m the one that gets to make the decisions. And yeah, music is a great way to shake off the negative messages I like to give myself.

  2. Liza
    Liza says:

    You and Ryan squabble like siblings.
    You two make a great pair.

    I was a little surprised that you listen to rap. hopefully not with your kids around. Punk is cute, until puberty. :)

  3. Vicky
    Vicky says:

    Thank you Penelope. I believe it’s true that most of my successes in life were due to my self-confidence and not just my knowledge. Also, I’m close to one of my sisters and that has proved to be my rock many times.

  4. Dan
    Dan says:

    Like most women, you lack focus. That is why most women aren’t CEO’s, they simply can’t focus on one task like men can, their mind’s wonder too much.

      • Dan
        Dan says:


        This is very true, I am an idiot who also happens to be a CPA and was in contention for one of the type five highest test scores in WI when I took it. However, intelligence is in the eye of the beholder.

        That doesn’t mean the statement isn’t true, women do lack focus, and by the way, my wife and infant daughter are quite happy to have me in their lives, FYI.

  5. Forrester
    Forrester says:

    “Their mind’s wonder too much” . . . I love it. Rarely do you get idiocy, a grammatical mistake, and a misspelling crammed together simultaneously in a mere five word-sentence.

  6. Jessie
    Jessie says:

    Just remember there’s rarely a decision that can’t be un-done (whether directly or indirectly) so just go with your gut, trust in it and if the decision turns out to be shit… eh, so what… you can start thinking of ways to correct it tomorrow.

    Life is too short to always worry if you’ve done the right thing.

  7. www.GenerationXpert.com
    www.GenerationXpert.com says:

    I think I know why you let Ryan make the decision regarding the vendor. Gen Xers have a unique style of brainstorming. I noticed this when I had to brainstorm with Boomers and was like WTF? when they were tearing down each others ideas right from the start. Xers try to gauge who cares more and the person who thinks they care less backs down. Not on everything. Just on things that could go either way.

    When Ryan told you to shut up, your instincts may have told you he had a stronger opinion on the subject.

    • KateNonymous
      KateNonymous says:

      It’s always surprising to me how often my boss and I have to tell our Boomer co-workers that there are two stages to brainstorming: throwing everything out there, and then determining what does or doesn’t work. All too often, they just want to slam any idea that isn’t their own.

  8. Alex @ Happiness in this World
    Alex @ Happiness in this World says:

    Seems to me the happiest people are the strongest. How else can you enjoy life if you don’t have the strength to overcome all the obstacles it throws at you? Strength and genuine self-confidence are what provide the path to true optimism. Optimism based on anything besides a reservoir of inner strength is merely wishful thinking. Effective optimism must be grounded in action you take yourself to make things better.

  9. Monica
    Monica says:

    I wish I could be close to my brothers, but one of them tried to get me fired and the other has called my mother every name in the book because she gave up custody of us when we were young. Good thing I’m an optimist- I live by the expression, “It’s never too late to have a happy childhood.”

  10. Curmudgeon
    Curmudgeon says:

    Okay, here’s the deal. You can’t avoid management conflicts. You can prepare, have your position down cold, and resolve most of them successfully. By successfully, I mean making sure everyone gets what they need (though not necessarily what they want) out of it.

    The downside? That takes energy, energy that many of us would rather put to more productive uses. But here’s the rub – when you accept a management role, you accept that baggage.

    Self-confidence helps here, but you don’t need to believe that your private parts taste the best to have enough to carry the day (disclosure: I’m pretty sure mine don’t). But you do need the energy to prepare and the fortitude to believe that you can resolve those conflicts.

  11. Jen
    Jen says:

    The whole happiness thing is tough. I read somewhere the that the more self-aware people are and the more honestly they view the world, the less happy they were. Or something depressing like that. I started reading a lot about happiness in general (What Happy People Know is a great one) A blog you might like is Gretchen Rubin’s Happiness Project. She seems to have a different style than you do, but in this case, the same goal. I really like her – thought you might like her too. I don’t agree with ALL of her ideas or ALL of her suggestions. But good stuff.

    http://www.happiness-project.com/ – in case you’re interested.

  12. jrandom42
    jrandom42 says:

    “Here’s another thing: There best indicator of if someone will be happy in the future is if you are 47 and close to your siblings.”

    After seeing my siblings literally hound my mother to death, and then proceed to plunder her estate, chase off all of Mom’s friends, do their best to institutionalize my father and take over all his finances, then spend Mom and Dad’s money like there’s no tomorrow, there’s no way in hell I’ll ever be close to my siblings. We won’t discuss the frequent attempts at using the grandchildren to blackmail money from me.

    I’m happy being far away and totally noncommunicative with them and it suits me just fine.

    • KateNonymous
      KateNonymous says:

      Unfortunately, I can think of all too many people who are happier with siblings (or other family members) as constant presences in their lives. I can believe that this statistic may be true, but it doesn’t necessarily work for everyone.

      • KateNonymous
        KateNonymous says:

        It’s unfortunate that these people don’t have siblings with whom they can have better relationships.

        I suppose it’s also unfortunate for anyone who has a bad relationship with siblings, sees that statistic, and concludes that their own happiness is doomed. That kind of conclusion is drawn all too often.

      • KateNonymous
        KateNonymous says:

        Hmm…my comment seems to have vanished (or perhaps shown up somewhere unexpected). So:

        It’s unfortunate that these people don’t have siblings with whom they can have better relationships.

        Also, it’s unfortunate if people who have bad relationships with siblings see this statistic and think it means that their own happiness is doomed. People draw that kind of conclusion all too often.

      • KateNonymous
        KateNonymous says:

        Ah hah! I just caught the typo. My original comment should have said that I know too many people who are happier WITHOUT, etc. No wonder you asked what I meant!

  13. Mike Duffy
    Mike Duffy says:

    No matter how timely or well-informed the decision, no one gets every decision right. The real skill is to recognize and recover from bad decisions as quickly as possible.

    It helps if you can avoid decisions where the consequence of a bad decision is immediately fatal.

  14. William Bruce
    William Bruce says:

    Regarding the substance of this post, here are some bones of contention…

    “The fact that people are totally pulled together and focused […] has no bearing on whether they’ll have a happy life.”

    This is something intuitively reasonable, to the point of having been obvious to persons throughout history, while at the same time being impossible to actually determine as a “fact.”

    “Here’s another thing: There [The ?] best indicator of if someone will be happy in the future is if you are 47 and close to your siblings.”

    Again, we are looking at merely an “indicator,” which cannot establish that which you assert (and possibly presuppose). All this really does is give emotional resonance to already held beliefs based in intuition.

    “But you don’t have to wait for your mid-forties to find out if you’ll be happy.”

    Actually, you do. Statistical entities like means and medians do not determine the course of your life. Nor can one wiggle out of this with some sort of Spinozist distinction between relative and absolute freedom.

    “If you frame things in a positive light, you’ll be happier later in life.”

    Again, this seems intuitively and philosophically tenable, but such considerations make a hash of your primarily empirical criterion.

    “The optimists win.”

    I was not aware that life was a game with a single metric for evaluation. Your rhetoric is unsettling.

    “Plus, the Harvard study finds that people get better at optimism as they grow older.”

    I do not doubt it (for psychological and philosophical reasons), but you do not directly address the intriguing or relevant question: Why? My own suspicions lean toward an answer incompatible with your earlier assertions.

    “Besides, no one was ever penalized for believing in herself…”

    That assertion is patently false. I take it that you are unfamiliar with the idea of “hubris”?

    “Right now I can be someone who assumes I am making good decisions. Because we each have to make decisions. So we may as well assume they are good.”

    Wrong answer to the “hubris” question.

    “There’s not really anything else to do.”

    Simply a wrong answer.

    “And every regret I can think of is about self-confidence.”

    This statement casts a disconcerting shadow on your entire bit of commentary here. Concepts like “selection bias” and “Texas sharpshooter fallacy” immediately spring to mind. But that is something for you to confirm or disconfirm, and explore further.

    To sum up:

    “And this is why her rhymes are painful. Because they exude so much self-confidence.”

    True, being around those with intractable self-confidence can be painful. That has certainly been my experience. Of course, that is anything but what you actually meant…

    • Will at Virtualjobcoach
      Will at Virtualjobcoach says:

      Don’t you realize that P has deviated from ‘career stuff’ to random thoughts about life and how she lives. Her stories tend to be interesting (in her ‘oversharing way’) and well written but maddening to those who expect anything that resembles practical career advice. She definitely has her audience, but my fear is that this demographic may be too narrow to drive a return that her investors are looking for.

      Of course, I could be totally wrong and she actually IS the voice of Gen Y, I cannot say for certain as I am not a member of that group.

      Her stories are funny though!

      • econobiker
        econobiker says:

        “Don’t you realize that P has deviated from ‘career stuff’ to random thoughts about life and how she lives.”

        And this noted before the miscarriage blog posting plus added publicity on that…

  15. Cesar In LA
    Cesar In LA says:

    I love me my Penelope Trunk…

    You know I copied/pasted today’s article to three friends and that was the subject of my email. Thanks Big P, to live from self-esteem, go for life and stay in dedicated consistent action towards that aim. That is the goal for my life. Thank you for giving me food for thought and a smirk today.

  16. Timothy Wright
    Timothy Wright says:


    You wrote: And every regret I can think of is about self-confidence.

    I have many regrets and many situations come to my mind where self confidence plays a part, I would wonder if you ever experience shame. I do.

    When I think of the many selfish acts that I have done in my life, they were just that, selfish, me wanting what I want and using, people, situations to get what I want at the expense of valuing another person for who they are instead of seeing them as a vending machine.

    I give them what they want, and they give me what I want.

    After wards, we are both less than who we hoped we would become.


  17. John Feier
    John Feier says:

    Besides having deep philosophical reservations about “confidence” as a concept, I’m so glad you even assume that women should even BE confident. In the world of gender role expectations, men are confident and women are passive. It makes me feel slightly upset when women strive for confidence in their careers, but not in their social concerns. Men have to be confident in BOTH arenas. I don’t think that’s right and I pursue it ferociously every chance I get.

    If you’re still wondering what kind of problems I could possibly have with confidence as a concept, then please read the following letter I sent to a CPA here in town yesterday:


    I was raised in Staunton, Indiana, a small town about 14 miles east of Terre Haute. It took me a long time to figure out what I wanted to do with my life. I was 34 when I finally decided to pursue accounting as a career at the added recommendation of an academic advisor. Up until then, I had been in and out of restaurants, performing mostly dishwashing jobs. My family’s life and my life has been one continuous struggle to get out of poverty and to dare to believe in the American Dream. I have no children and have never married (not even a girlfriend).

    Accounting appeals to me as a career because of the analytical and intellectual faculties required of accountants. I’m thrilled when I’m able to apply the innate detective-like skills I possess. I also enjoy gathering additional information from clients in order to clarify specific transactions. Some of my weaknesses include public speaking and being confident in social interactions. I feel that the weakness in confidence and social interactions is due to a desire to keep all conclusions about anything or anyone until I’m absolutely convinced that such conclusions are, in fact, warranted. This comes across as a lack of confidence to some, especially male employers who cannot understand why I’m so hesitant and prospective girlfriends, who are looking for a “confident” man (which I think is a very stereotypical expectation).

    I want a position in accounting that will challenge me to make tighter some of the loose ends in my personality, since that seems to be what the world wants from me. I just wish that the world was a little bit more tolerant of the true essence of reality, which seems to be of a messier, ambiguous and qualitative nature, not neat, clear and quantitative.

    Thanks for taking the time to read this!


  18. John Feier
    John Feier says:

    So you see…”confidence” is an entirely CULTURAL construct, not one born out of necessity. To an Aquarius, like myself, all things cultural should be intensely scrutinized and dissected with cold-ass logic and any woman who needs “confidence” in a man has some insecurities she needs to deal with. Call it culturally-reinforced all you want, but it’s still a problem and problems need to be solved.

  19. Téa
    Téa says:

    I am grateful for this post P.
    I’m an exec assistant. Thurs I lost my self confiendce BIG TIME. I worked my heart out, hoping to please my boss, In the end, I got barked at and sent home feeling like a looser.

    For me, part of self confidence is determining “does this situation allow me to live within MY values and behaviors”. I value a non-hostile/agressive environment, and I do fear standing up to supervisors who are “big wigs”.

    Yes, I can change… and I can also develop for myself a work environment that does fit into my values.

  20. Jim
    Jim says:

    At least you have your ego in check, Penelope. And it’s good that you and Ryan can vent, insult each other and then move on with the biz. He’s a cool dude.

  21. Grace
    Grace says:

    No one was ever penalized for believing in herself? Really? Confidence does attract some people, but it also threatens. It’s funny – I was once at a conference with a group of men. I was funny, confident, and strong. One of the guys told me I was great to work with and…that I must be a lesbian.

    • Jennifer Ellis
      Jennifer Ellis says:

      Are you suggesting that the assumption you are a lesbian is somehow a penalty? That seems a little offensive.

  22. Jay Koch
    Jay Koch says:

    Here’s the secret: Everyone one of us has difficulties in one way or another. We look at a someone who seems successful, even the confident ones, there are issues and problems in their lives.

    Here’s another secret: Whenever encounter difficulties, we can choose to focus on them. Or we can choose to be grateful for the good things we do have, like your brothers. Some people fret about past mistakes made, but don’t give themselves credit for all of the good things they do.

    I applaud you for your moment of clarity. Forget the things you think you did wrong, and make a habit of acknowledging the things you do right. I am sure there a many more things you do right than wrong.

    Do the same for Ryan, too.


  23. Isha
    Isha says:

    Thanks Pene, I will forever be indebted to you, through out my practicing career. This is a cool article, some business decisions are difficult to make though, and you shouldnt have to run a one man show, even if you are the CEO. Ryan made a bad call, but neither of you could have known that at the time. Atleast Ryan and you are back on talking terms. Stay awesome. :)

  24. Mark W.
    Mark W. says:

    What I’m listening to right now – Whitney Houston’s ‘Greatest Love of All’. It exudes self-confidence in my opinion and the message is clear. These lines really stick out for me –
    “I decided long ago never to walk in anyone’s shadow
    If I fail, if I succeed, at least I lived as I believed.
    No matter what they take from me they can’t take away my dignity”.
    I see you as having self-confidence even though you describe a lapse here in this post and you don’t have a category for it on this blog. My biggest regrets are a result of procrastination/inaction for whatever reason which you describe here so you should make some room for me and the rest of us that suffer from the same malady. I view this type of regret as a lesson from which I have learned and can move forward … another lesson to draw from to make a better decision in the future every day as I get older. My assumption about my decisions is not necessarily whether they are good or bad but rather they are getting better and improving as I get older. I think it’s called experience and as a result I am more self-confident and optimistic as I get older.
    This post prompted me to do an Internet search on self-confidence. I found and read a very good post by Leo Babauta at Zenhabits ( http://zenhabits.net/2007/12/25-killer-actions-to-boost-your-self-confidence/ ). The 25 actions he briefly describes to boost self-confidence remind of posts you have already written here on this blog. He says in this post – “It (self-confidence) is not genetic, and you do not have to be reliant on others to increase your self-confidence.” While it is true that we don’t have to be reliant on others to increase self-confidence, I think it’s important to have a support network to occasionally draw from and bolster our self-confidence. So my answer to your most recent poll question – “What’s your number one priority right now?” would be ‘Improving family or other personal relationships’ with an important addition of adding new personal relationships.

  25. dr aletta
    dr aletta says:

    “My rhymes are painful and fresh” could be comparing her the rhymes with a wound. Self-inflicted or otherwise? Maybe they are like lancing boil, a metaphor I use often in psychotherapy to explain the pain of facing our fears and the healing that comes from getting on the other side of what scares us.

    • Will at Virtualjobcoach
      Will at Virtualjobcoach says:

      Of course the obvious answer is that fresh = fresh (a common word in the rap world that can be equated with the word ‘cool’ in common English) and ‘painful’ is pure bravado that is used to project power to others who may ‘disrespect’ her. So the line basically translates to “don’t screw with me, I am the best” which would be inline with the norms of the ‘rap community’. Which would be the simple interpretation but I am not the intelligentsia so could be totally wrong :^)

  26. Matt Secor
    Matt Secor says:

    “Plus, the Harvard study finds that people get better at optimism as they grow older.”

    That really surprises. I guess I might have to read that article from the Atlantic. Or more likely skim it. That’s one long article!

  27. Helen
    Helen says:

    I am strong, intelligent, independent, friendly, and have a good working relationship with my boss. However, these things seem to bring out the worst behavior in my co-workers. Over the last 2 years especially, I realize I have let their reactions(spoken and unspoken)chip away at my confidence (and I am a strong person). Your post gave me the little boost I needed to try and keep my confidence secure and continue to evolve as a whole person.

  28. neve
    neve says:

    Happiness is simple. Either you seek it, or you spend it.
    Confidence however, is more complicated- you have to hide most of it, spend some of it, and save for all of it.

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

    I’m not aware of Amanda Blank or her pussy, but I’m certainly aware of the role confidence plays in everyday life.

    I define confidence – real confidence – as being able to choose your behaviour with implicit trust in that behaviour.

    That fits in exactly with what you say about thinking your decisions are good ones. It’s being able to trust yourself to make decisions and take steps in your life, no matter what happens as a result of that behaviour.

    That’s the thing, even if your decision proves to be not so good or if it ends up being downright bad, you can trust yourself to make another decision and take another step.

    Trust yourself implicitly to get involved your life, and everything tastes sweet :P

  30. Rae Opengart
    Rae Opengart says:

    I don’t understand “doing life wrong”. The only way one can live “wrong” is to be dead.

    I have never thought of myself as being very confident but after reading your post and the comments that have been made, I may have to re-think it. Do we all define and identify confidence the same way? Probably not, not exactly.

    For what it’s worth, these are the precepts to which I try to adhere:

    Never compare yourself to others; it is apples and oranges. Compare yourself to yourself but only if you find comparisons necessary.

    Stop taking everything personally. 999 times out of 1000 whatever “wrong” you think you’ve suffered has nothing to do with you. The rude clerk, the car that cut you off – you have no idea what may be happening in another person’s life but you can be fairly certain it has nothing to do with you.

    Mistakes are only bad if you don’t learn anything from them. You can’t learn from mistakes if you can’t admit to making them.

    No one is happy all the time; why would anyone want or expect to be? As a society, we are too quick to demand happiness. Perhaps if people recognized that depression is a sign that life changes need to be made instead of just masking it with anti-depressants, we wouldn’t have gotten into a frenzy of debt-financed consumerism that fueled the housing bubble that led to the current economic problems that are a good reason to be really depressed!

  31. Kate
    Kate says:

    I keep getting into trouble in relationships because I am used to being the bitch/poor decision maker/emotionally unavailable one/whatever. Then I go along with whatever the other person is assuming about me and the relationship because I am the one who always makes mistakes, I MUST be wrong, and they must have it all figured out.

    I realised the other day that I am allowed to be right. It was a depressingly simple concept for such an enlightening feeling.

  32. Resveratrol
    Resveratrol says:

    Just because shes taking the classes doesn’t mean she wants to join a strip club Leave her alone ! im sure shes just talking about keeping it in the bedroom and giving her fella a thrill……good for you love, i hope you have lots of fun….im going to burlesque classes with my mate next week should be a giggle : )
    People who slate you for doing something different are just jealous anyway x……miserable sods !

  33. Jonha
    Jonha says:

    “If you frame things in a positive light, you’ll be happier later in life. The optimists win.” There’s nothing more important in this life but our perspective in things.

  34. Arlene Marie Daniels
    Arlene Marie Daniels says:

    I really love your writing style…and how you think. You were able to connect the rapper with the relevant life learning about confidence. Brilliantly done! :)

    Confidence really is important in order to succeed. But what happens if depression, anxiety and fears get the best of you? Here’s a great book that you guys might be interested to read. http://www.depressionatwork.com

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