Confidence boosters that work for me

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I woke up today with crust all over my left eye: Pinkeye. And on the way to the bathroom I stepped on edible gold-leaf dust for decorating cupcakes. And apparently sometime in the night the cat ate my son’s map of Wisconsin. And threw it up.

At times like this, I wish there was a morning-after type anti-depressant that you could take as sort of an immediate pick me up. I remembered my agent once told me that Advil works that way, once in a while. So I popped a couple.

They did not work. I put antibiotics in my eye and tossed on an old sweatshirt and jeans that are so big they fit like sweat pants. And I headed out the door to go work.

Then I turned around, and went back in the house.

I think people do startups for a variety of reasons. Sometimes we are not even sure what the reasons are until after we get started.

I moved to Wisconsin from New York City a year ago. It was a traumatic move, where we had to leave almost everything we own behind. And there was big culture shock in Madison when we got here.

The way I dealt with the trauma was blogging every day (therapeutic structure to a crazy life) in my pajamas (a nod to the fact that I was working alone and in fundamental disarray).

For the most part, when I had to show up to meet someone somewhere, I would pull things together a bit. Although when Ben Casnocha met me in Madison for breakfast his first comment was, “You don’t look like your photo.” And when I met Rebecca Thorman, she blogged about my ratty shoes.

So it was clear that I wasn’t holding things together that well. And when I convinced Ryan and Ryan to move to Madison to start a new business with me, I decided I had to go back to dressing up for work. Not suit and skirt or anything like that. But not pajamas. Not ratty sneakers.

And something happened – immediately I felt differently because I was back to getting dressed to go to work, because there were people I had to see every day. This moment converged nicely with the blossoming of my speaking career, which is one of the most lucrative career moves I’ve ever made, so I spent a lot of time at Bloomingdales, buying Joe’s Jeans and DKNY tops, to replace the expensive jeans and black tops that I bought six years ago, which was the last time I had to get dressed to go to work.

Then I started wearing makeup. Not a lot, but enough so that I could mark the difference between cleaning up cat puke and writing a blog post. And I felt a little more organized, a little more focused.

So today, I walked out of my house in ratty clothes and no makeup and I turned around. Because now I know that one way to feel better – maybe the most noninvasive anti-depressant of all – is to get dressed up to do work. The best days of work are those when I have the self-confidence to attack the hardest things on my to-do list with the most vigor. And one way to bolster self-confidence is to dress like someone who is self-confident.

48 replies
  1. GreatManagement
    GreatManagement says:

    Beautiful, beautiful story and one I can exactly relate to – when it comes to clothes and confidence.

    I think it’s amazing what clothes can do to the confidence, and they don’t have to be expensive or designer labels. As long as they fit well, are ‘your’ colours and are clean, they will give you an instant boost. I do believe it is worth investing in getting some help. Here in the UK, I have a great friend who is an image consultant and she’s fantastic. I go shopping twice a year with her ($300 a time) and for me, it is well worth it. She knows what works for me and it gives me that extra spring in my step!


  2. Prashant Jejurikar
    Prashant Jejurikar says:

    Spot on! I’d add one more thing in addition to dress: stand up straight, pull in your stomach, plant your feet firmly on the ground and take a look in the mirror.

    It has never failed to work for me.

  3. Joe Grossberg
    Joe Grossberg says:

    “At times like this, I wish there was a morning-after type anti-depressant that you could take as sort of an immediate pick me up.”

    There is; it’s just that the nanny-state government thinks it knows what’s best for you.

    In any case, yoga, meditation and deep breathing are all great — healthy, completely safe, free, no equipment needed, can be done anywhere, take little time and actually work.

    Also, why don’t you treat yourself to a massage. I had one a few weeks back, for pain in my shoulder from too much computer time, and by the time I left, I felt like I had just taken a vacation.

  4. theo
    theo says:

    You make a great point here. I would expand it a little. What’s going on here is not — to me — about dressing up to make you feel more confident. It’s about making yourself feel confident, strong, focused, and driven.

    For a lot of people, clothing and makeup are good ways to do this. I would remind everyone to manage these things in their own way. For me, a shirt & tie does not make feel confident. It makes me feel self-conscious. Dressing in clothing that makes me feel un-natural is more likely to make me feel out of place, like a bad actor in a role he hasn’t studied well. For me, the trick is grooming myself impeccably and dressing in something that feels natural, that feels like it’s an expression of who I am.

    That means loose, comfortable pants and shirt. It means silk, cotton, or satin. It means a sarong and sandals, or wrap-pants. It means brushing my hair until it gets that perfect shine and the big curls near the ends.

    For some people it means a three-piece suit. For others it may mean jeans and a polo shirt. For another it might mean A&F. Don’t let the worlds idea of ‘dressing for work’ infect your self image or make you uncomfortable. We do our best work when we are in situations that make us feel confident. Build a situation that makes YOU feel confident, not one that you think is ‘appropriate.’

    * * * * *
    Thanks for adding the to the idea, Theo. I think really, the bottom line of all this is that if you’re not feeling self-confident, try doing new things that are relatively small and easy to do in order to shake things up a bit. The best way to change a bad situation is to make a change yourself. I am grateful for how easy it is to change clothes and how big an impact it has. But there are tons of other things like this people can do. I wonder though what are other things people have found to do…


  5. Queercents
    Queercents says:

    My best friend, a Southern woman from Atlanta, always said her mother's suggested remedy for a day like this was: "Go put on some lipstick and you'll feel better."

    Hopefully, the Advil will kick in too.

  6. PunditMom
    PunditMom says:

    Funny you should talk about this, but I’ve been doing this recently, as well. Nothing fancy — black pants instead of jeans and little tinted moisturizer. Aside from the personal impact, I have to say people have noticed and I’ve thought, “Wow, how bad did I really look before?”

  7. nyczoo
    nyczoo says:

    Kitty puke. As any cat owner/survivor of early morning feline surprise can attest to, there is no two-word combination in the English language that at its mere mention can immediately conjure a reaction from all five senses. :)

  8. Norcross
    Norcross says:

    I started wearing pressed pants, shirt, and a tie, even though it was above the “business casual” requirement (whatever that means). Not only do I feel better, I don’t feel intimidated by senior management. I guess it’s that “dress for the job you want, not the one you have” idea.

  9. Melanie
    Melanie says:

    I feel best when I’m wearing something professional but still trendy at the same time. I always put my best outfit on when I have a presentation or a meeting with a manager. Somehow it just gives me that extra boost and makes me feel like I have more power. Nice post Penelope.

  10. lizriz
    lizriz says:

    I totally agree about getting dressed for work.

    Have you tried St. John’s Wort? I take St. John’s Wort and B6 for my PMS, but I’ve noticed that it improves my mood right when I take it, too.

    * * * * * *

    Thanks for the recommendation. The right-away part is so appealing to me. I will have to google this….


  11. Alison
    Alison says:

    It is important to get dressed for work. I like to look smart when I need to feel smart.

    I also think it’s important to dress for home too. It’s a different kind of dress code. Kids, dogs, cats – all messy things. But I respect myself for the work I do at home and I need to feel smart there too. So I make sure the jeans fit, and the sweatshirt hasn’t been chewed by the dog (been there, done that). Even a little bit of makeup so I don’t scare myself passing mirrors. Mainly about respect for myself, and the people around me.

  12. Kim J.
    Kim J. says:

    I’ve also noticed that color makes a difference, too.

    Even back in college, when I had a big presentation or even a test after an all-nighter, if I wore a particular red top that complimented my hair/eye coloring, it made me feel better and more confident. Stronger.

    Same thing at work now. If I know I have to go to a particularly tough meeting or something, I make sure to wear something from my closet that compliments my coloring and gives me a confidence boost. (And I always wear my pointy-toe kick-butt black high heels, too!)

  13. Dale
    Dale says:


    You hit the nail on the head with this one. My wife has been saying it for years, and one added bonus is the positive difference in the way people interact with you. Being complimented always helps.

    One thing that works for me is to have time to relax and eat a proper unrushed meal and perhaps a small success before a major meeting or undertaking. Success breeds confidence, so don’t let too much time pass between those successes – even the little ones.

  14. Kathy S
    Kathy S says:

    Very true stuff. I completely agree. Unfortunately it’s not always possible to “look your best” but I try to be “perfect” at least one day a week.

    The 2 main things you need are blush and mascara. And, if you want to tone down your lipstick, put a smudge of foundation on your lips, works wonders and looks 100% natural.

    Someone once told me that the neatness of your room represents how you feel. So, try to pick up after yourself and leave little mess behind. Open the curtains and windows and get lots of light.

  15. Dale
    Dale says:

    Also, I must mention the S** word. Nothing boosts your confidence more than a recent rendezvous. It doesn’t hurt to face a challenge feeling like Conan the Barbarian or the King of the prideland:)

    * * * * * *

    Yes. So true. It’s amazing that I did not mention this myself, right?


  16. Derek
    Derek says:

    I remember making a New Year Resolution one year to stop dressing like a slob. It felt great and was one of the few that I’ve stuck to.

    As a side note, good luck keeping up with the habit while in Madison. I lived there for four years (East Side) and the shopping is not that great. You’ll find yourself driving to Chicago for anything beyond a Badgers sweatshirt.

  17. Brian
    Brian says:

    My job responsibilities have changed somewhat in the last couple of months, requiring me to wear a tie more frequently. I agree that dressing a little better has improved my outlook on work — and, therefore, life.

  18. Gladstone
    Gladstone says:


    1) Dressing up instills sense of purpose, that there is a reason you got out of bed.

    2) Accomplishing something speaks for itself.

    Result: Too busy accomplishing and appreciating accomplishments to get down in the dumps.

  19. Lane
    Lane says:

    Seriously, I keep thinking that I have to somehow arrange to meet you. I live in Milwaukee, so Mad-town is only a bit away (and heck, I could meet Thorman while I’m at it.)

    Are you doing anything public in Madison any time soon? Anything with both you and Thorman (I like to make as much as I can efficient as possible.)

  20. Pat Patterson
    Pat Patterson says:

    Yup – I always work better those mornings when I shower and get dressed first, instead of sitting down at the laptop in my bathrobe when the kids leave for school at 8am ‘just to check email’ and suddenly realizing it’s lunchtime, 4 hours later.

    Come and talk to us in San Jose sometime soon!

  21. SuperUser
    SuperUser says:

    You link to a prior post about how one of your business partner “Ryans” had groin rash a couple weeks back, and now you have pink eye.

    Does it itch?

  22. David B. Bohl
    David B. Bohl says:


    There’s an old adage in 12-step recovery groups that says: “Suit up and show up.” This is how folks in recovery begin to “become citizens of the world” that they rejected and were rejected by.

    I can make the choice to suit up and show up each and every day. I do so by getting up at the same time each day, meditating, dressing for work, and often times running out (I work in a home office) for my morning coffee.

    Thanks for sharing and the reminder.


  23. Kathryn
    Kathryn says:

    Heh, “thinking that you look Good” is everyone’s best kept secret in the fight against casual depression.

    As far as cat vomit goes: get the cheapie Bissel Spotlifter. Infinitely easier and faster than manual carpet cleaning. Also try out Nature’s Miracle if you haven’t already discovered the product.

  24. cindy*staged4more
    cindy*staged4more says:

    Shockingly something seemingly so simple can make such a difference! ;) On days where I stay in my PJs my productivity is pretty low because all I think about is napping and being lazy… Now I force myself to dress up even just sitting at home office doing admin work. Better yet, I force myself to go to local cafes so I can not turn on my TV. The house is full of distractions!


  25. Olivier
    Olivier says:

    For me, dressing up can have the opposite effect. I work from home now and whenever I dress up too much I am in this I-will-go-out-in-a-few-minutes mood and I can’t concentrate. Very annoying. I found that what works for me is wearing freshly cleaned clothes; never fails to put me in a good mood. That and washing my face in the middle of the day (I have oily skin).

  26. Jeannie
    Jeannie says:

    Interesting comment about how much better you feel after getting dressed. One of my favorites sites is This site originally stareted out using 15 minute time periods to clean your house. It has evolved into much more. The 15 minute principle applies to everything you do in life and really works for a home business. The premise starts with getting dressed to your shoes first things in the morning. Even though I work outside the home I have used this principle on the weekends. I no longer go downstairs in my pajamas. It is amazing how much more I get accomplished on the weekends when I am ready to go.

  27. Jennifer
    Jennifer says:

    Penelope, one thing you should know is that pink eye, or conjunctivitis, is horribly contagious – you might want to lock yourself away from people you care about for the next day or so!

  28. Peter V.
    Peter V. says:

    Penelope, I have to ask the question of why in the first place you were working, albeit at home, in clothes you probably wouldn’t wash the car in? Was it a reaction to the fact that you were at home, and no one could see you, so you consciously or otherwise decided to get as grubby as you could?

    I’ve worked primarily at home for almost two years now, and while I don’t usually put on the quality of clothes I would going into an office, nor do I look like a slob. I’ve always thought that you moved your life forward by exhibiting a certain amount of personal discipline, and that includes looking and acting like someone you would want to be with. Oh yes, and I shave every morning, even though on most days no one would care. I do it for myself.

  29. kristi
    kristi says:

    I wore a military uniform to work for years, and when I changed over to a completely civilian life, I wanted to wear clothes that were comfortable. I had the freedom to choose my style of dress at work, so I wore very casual clothes that were comfortable and if I’m being truthful, also frumpy.
    On a recent conference trip, I brought my hubby and kids along and after the event, we drove down to the beach where we honeymooned.
    I got some sun on my fish-belly-white skin and found a store that had stylish, affordable work clothes I liked, and which fit me. I bought a week’s worth of new outfits and came home with a new attitude.
    The change in how everyone responds to me, from my husband, kids, and friends to my co-workers and supervisors, has been nothing short of thrilling.
    I get compliments, smiles and words of praise every single day now. I felt so good about myself, I finally had the confidence to change my hairstyle. After 7 years of long and straight, I’m now short, layered and wavy. And the compliments just keep coming in…
    I’ve also decided to keep my “sun-kissed” look by using tinted moisturizer every day, which has led to my hubby suddenly start kissing me when we pass in the hall at night!
    My confidence is at an all-time high right now, and my motivation has increased so that I’m taking vitamins again and getting more veggies each day.
    (I even brought some fresh fruit for lunch today.)
    So, even though clothes, hair, and appearance can seem like shallow things to concentrate on, my experience has been that by taking those steps to improve, the results are exponential.

  30. Agnes in NY
    Agnes in NY says:

    I definitely agree that our presence plays a big role in how we feel about ourselves. Each year, typically around Christmas, I begin to clean out my closet and bag the clothes I’m ready to share by donating them. Then I do my best to upgrade my wardrobe by changing my style somewhat each year. I agree that it’s not the name but the quality and fit of the clothing that reflects best on us. But here is something else that I find to be another confidence builder for ME… My home. There is something about me walking into a room with freshly painted (or at least clean, up-to-date) walls, un-chipped furnishings, unstained upholstry, curtains that don’t look like outcasts in your living area and wires that are coming out of your wall as if they are out of control on their own! I try to change things around and replace old with news every few years. Budget allowing of course. This is the year that I don’t like how I look when I go to work (at a job that I enjoy very much) and I don’t particularly like the first couple of rooms I see when I walk into my home after a long day of commuting and working! I keep seeing this image of a new coffee table in my living room, adding a chaise or a chair to it, finally replacing two lamps that have fallen and cracked less than a year after purchasing them!, adding some pillows to my couch, finally purchasing a rug for my dining room and last but not least… Throwing my current desk off the terrace and replacing it to match the rest of the espresso stained wood in the room! The image I project is this exuberant feeling of energy and brightness to add to my “appearance” before and after my work day.

  31. Sifi M
    Sifi M says:

    Another fun set of comments for a pre-Thanksgiving slow day…
    A word on jeans. Isn’t it amazing how they continue to morph? Twenty years ago I never wore them to the office, even on casual Friday. Now I am in them several days a week. I even wear them to internal meetings. The key is to take some time and find some good fitting ones that are current in terms of style. If you can reasonably afford it, SPEND the money. Think of it this way: You would spend the money on a suit that you may only wear a few dozen times a year, if that. If you buy those amazing jeans you will be rocking them 50+ days a year for two years. (For good deals, find your brand and style and search the web.)

  32. Earl
    Earl says:

    I always feel better, too, when I dress a notch better than what’s expected or required – and cleaning out my briefcase and giving it a quick buff (it’s an aluminum Zero that I got for my birthday several years ago) and putting it by the door before I go to bed gets me rolling with a lot of positive momentum, too.

    Remember that quote from Seinfeld about people who wear sweatpants outside the house except for working out? Jerry said they’ve given up. Joke or not, it was true for me, and returned me to my classic(?) prepped-out khakis and button downs. It works for me!

  33. m
    m says:

    I totally agree. I think in the world of personal finance attention to clothing is at times (often?) dismissed as being frivolous and a waste of money.

    Frugality and dressing well and caring about one’s appearance seem at odds with one another in some people’s minds. I, however, couldn’t disagree more.

    I remember even in fifth grade, analyzing a short story in English class, and when the teacher wanted to know why the woman cleaned up the little boy and his appearance after he’d tried to steal from her, we students realized that it was because looking good, neat, and taking pride in your appearance sets the stage for feeling good about yourself–as well as for being viewed in a positive way by others.

    Sure, the priciest items of clothing aren’t required for a neat, respectiable appearance, but spending money on high quality, attractive clothes does not have to be a waste of money, and in many ways is actually an investment in yourself. As paying attention to your appearance reflects that you take pride in how you present yourself and treat yourself.

    It also allows you to dress the part you are playing. PJs are for lounging, more dressy clothes are for more serious efforts.

    Confidence and motivation are not found in clothing, obviously, but taking the time to care about how you present and treat yourself does help to spark the confidence and motivation you already have inside.

    It also sends the message to others that you care about details and care how you treat yourself. Because if you don’t care about how you take care of yourself and present yourself, how can others feel confident that you will care about how you take care of them and present them to the world?

    There are so many reasons why appearance does matter (not your natural looks per se that you can’t do anything about, but your “look,” which you are in control of); the ones you, I, and other commenters mentioned are only some of them.

    Great post!

  34. B.Auton
    B.Auton says:

    A few members of my team bemoaned the fact our company wasn’t strict enough with dress codes and I floated the ideas of a “no jeans” rule. It went down well and some team members encouraged me to go stricter. The next day I took in ties and asked all the men on the office to wear one. Most did and by the end of the week, they all did. I also insisted that they should be worn properly with the top button on the shirt fastened and was amazed at how little complaints I got from the men. In fact, most seemed glad to have such rules and it seemed to increase self confidence in people and the feedback from theother departments was that it had spruced up the whole image AND atmosphere AND attitude of the office. A definite success.

  35. jrandom42
    jrandom42 says:

    B. Auton, just some thoughts on ‘dressing up’.

    It all depends on your audience. Sounds like you work with a group that is involved in operations or marketing or some such. Imposing anything like this on a technology group or IT department is a recipe for disaster.

    One company I worked for imposed a code for suits for meeting external customers, and long sleeve shirts, ties, pressed slacks and shined shoes for all other employees. Within a week, the CTO, the CIO, the entire software engineering team, the database management team, the network engineering team, and the desktop support team quit, leaving only the helpdesk. Each and everyone who quit was working for another company with a much less restrictive dress code within 2 weeks. Several years later, the company is still in business, but it’s only a shadow of it’s former market leading self.

    It’s an article of faith that just about every serious IT person has quit at least one job over dress codes. Often, it’s seen as an attempt to dictate productivity and exert control over a process that really doesn’t lend itself to authoritative methods of management. It’s also seen as a sign that the company has lost control of its market and is attempting to exert control over what it can. Not a good message to send to employees.

    Finally, let’s face it. The “suits” have always been regarded with suspicion by us IT folk, and for very good reasons. Can you say “PHB”?

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