Perpetually Uncool: Financial Lessons from a Complete Weirdo

Growing up I was a pretty special kid. By special I mean awkward, annoying, and desperately uncool. At the time I felt like my uniqueness held me back from everything great. I didn’t make friends easily and the friends I did have were the other members of the weird people brigade.

Being cool was the ultimate self-actualization of the 11 year old and I so badly wanted to be part of the club. Slowly but surely, I traded my outgoing and loud ways for a quiet, cool sensibility. I did activities I didn’t even like because the cool kids did them. I had my mom buy me the stylish clothes and the newest technology. Unfortunately I spent the better part of my teenage years trying to cover up who I really was with a nice shiny veneer of cool.

The Self-Acceptance Search

To me being cool felt like a status I was always on the cusp of achieving but never could. I don’t know if I ever succeeded in being cool but I do know that a lot of money got spent needlessly. I see now that if I wouldn’t have been so worried about what others thought, I could’ve spent all that energy finding self-acceptance.

The funny thing is, the more I searched for acceptance in others the less I accepted myself. I guess the idea was that only if others liked and accepted me would I be worthy of self-acceptance. If I could just get the approval of my peers I would give myself permission to be worthy of love and belonging.

I think we spend a lot of our lives hustling for social acceptance. We do it at the expense of many wonderful things like our natural personality, our self-confidence, and worst of all our bank accounts. I didn’t realize it at the time but I was embarking on a lifelong journey of me not being enough within myself, and always needing outside sources to make me feel better.

Denying Uniqueness

I realize now that the uniqueness I spent years running from was what made me great. As a kid I felt like it made me stick out when all I wanted to do was fit in and be the same. Other kids bullied me because I was different but I see now that they were probably intimidated.

In adulthood the search for social acceptability happens in such imperceptible ways. We don’t care so much about being cool anymore but we tend to mold our lives around acceptability. You might not decide to buy a used car or shop at the thrift store because those things are embarrassing. It’s easy to take on these attitudes without realizing it, one after another. One day you find yourself sort of backed into a corner of other people’s opinions.

In adulthood I’ve spend plenty of time thinking about how I can be the same; I want the nice car or the beautiful house. I’m seeing more and more that that thinking is not so different as wanting to be cool. It’s still a grab for status through outside things and that will never lead to anything fulfilling.

The Cost of Cool

The other day I was walking down main street in Santa Monica and I couldn’t help but notice the amount of coolness around me. All the 20 and 30-something girls were wearing high heels and jeans shuffling into the coffee shop I was posted up in. Seeing style and fashion used to be a huge draw for me. Somehow people who look all dolled up just seem happy. Then I thought about myself, in my $1 thrift store jeans with my 7 year old “so outdated” laptop, drinking a $2 coffee instead of a $5 latte. I was so very uncool and yet, I felt perfectly ok.

Wanting to be somewhere else in our lives is the main source of fear and unhappiness. When we want to be cool or fashionable or just plain rich, we are giving away the most powerful aspect of ourselves and that is our innate okness.

Think about yourself as a five-year-old. Did you care what you wore or what hair cut you had? No. You were pretty happy with any old thing. At five years old what gave you happiness? For me it was playing tag on the playground and getting to go to Disneyland. Sure, I’d get excited about toys but I don’t have any specific memories about my toys. I can tell you who we went with to Hurricane Harbor when I was 9 but I can’t tell you what I got for Christmas in any given year. As kids we know innately to seek experiences and becoming a grown up somehow undoes that.

Keeping Up With the Joneses

The aspect of “being cool” we are most familiar with as adults is wanting what the neighbors have. Maybe we don’t consciously think about it but our brain is very good at making sure we’re taken care of and one of the ways it does that is to compare. Comparison helps us make sure that we have enough and that we’re not being treated unfairly by others but it has another side. When we compare ourselves to our peers it robs us of feeling ok. In fact, it creates a new obstacle between us and achieving our goals.

I find that the times I do the best work are when my mind is quiet. A mind that is busy with the compare/contrast game is not at peace and cannot do good work. When you run a comparison and you are found to be less than, as you invariably always are, you will create a resentment that’ll keep you from that thing you want.

I think we’re all guilty of the feeling that other people have nice things and we deserve to have nice things too. When I get into that toxic way of thinking I remind myself that I’d much rather live a life full of lasting friendships and love where money was never something to worry about, rather than a life of scarcity where nice things were a substitute for the things that really matter and money is always in short supply.

This is the defining characteristic of the mythical Joneses: they have lots of stuff but little money. They drive nice cars and put a huge addition on their house, but they’d have trouble paying for an unexpected car expense or a sudden medical bill. They live like most of society does, looking for new things to buy while they service $15,000-$20,000 worth of consumer debt.

Trust me, you do not want to be like them. You should pity them.

Be As Uncool As Possible

After 10 or so years of chasing cool I have thrown in the towel. Today I embrace my inner uncoolness and flaunt my hand-me-downs. When I roll my bike out of the garage or take out my old duct taped backpack I’m proud of it because I know in a way these things represent my freedom. I have freedom from needing to be socially acceptable through status items and I’m no longer embarrassed when I don’t have the latest and greatest thing.

What I do care about is function; how do my clothes, my technology, and my vehicles function. In the same vein I ask, how does my life function? So far, it functions better and better when I embrace myself. I’m a very quirky, smart, and sometimes eccentric money saver and today I love that.

So here’s the deal: I want to be as uncool as possible. I want to embrace whatever it is inside that makes me me. I want to have fun with the people in my life who build me up and make me feel good about who I am. Along the way I’m saving a boatload of money and redefining for myself what it means to live richly on less.

I don’t have time to hustle for belonging anymore, I’m too busy being awesome.

Readers: tell me about your own unique awesomeness.


  1. “Unfortunately I spent the better part of my teenage years trying to cover up who I really was with a nice shiny veneer of cool.”
    Yup. I tried that too and it didn’t work. Adulthood is so much better, though. I get to be who I am and I’m okay with it. Other people might not like it or might not make the same choices, but who cares? And these days most people are way too busy to care about anyone else’s designer jeans (or lack thereof) for long, so the bullying stayed on the playground.
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    • Elsie says:

      It’s interesting to hear how similar everyone’s experiences have been. I think everyone feels like they don’t fit in at some point. I’m with you that adulthood gets better, the social pressures haven’t been as intense.

  2. Linda says:

    Ah but, you have failed because this is what makes you cool!!! Seriously, it is amazing how when you grow up, you’d think all those gross comparisons would be gone. But they’re not – they’re just different. Free are the people who don’t bother with it. It is a colossal waste of energy.

    • Elsie says:

      I think comparisons never truly go away. We’re always trying to make sure we’re keeping up somehow. I’m glad I’ve gotten some perspective. When I hear those comparison voices I can usually point out the faulty logic before I get into a pity party. Sometimes, though, they still trip me up. Thank for the comment linda

  3. Elsie says:

    Thanks for the share Brian. So many people relate to feeling out of place I think. I try to embrace my weirdness as much as possible these days. Who would want to be like everyone else. I love being unique.

  4. Luann Brown says:

    Dearest Member of the “Uncool Club,”
    I smiled as I read all of this, while silently nodding my head, ending by yelling out, “YES!” and “WAY TO GO, ELSIE!”
    It seems as if every blog you write, I honestly think, “This is the best piece of writing I’ve read from Elsie.” And, again, I feel that. (You are a really good writer!)
    The journey you have taken is an often hidden journey of many…EXCEPT for the ending. Most people haven’t come to their rightful place of awesomeness and acceptance. They haven’t recognized that wonder and grace in living richly while spending little.
    I’m genuinely proud of you and excited as I see your life unfold. You are not only awesome. You are helping others discover their own awesomeness! Isn’t that just awesome?

  5. Love this post! I think almost everyone goes through this at some point — trying to fit a mold that doesn’t work. Some figure out that it’s not working and reject it; others keep trying to make it work for decades.

    I couldn’t help but think about your Portland trip in light of the last paragraph. The culture there totally embraces the “we’re uncool and different” vibe, though it’s funny how even that mindset develops its own distinct look, set of prescribed activities and hobbies, and possessions of anti-cool “coolness.”
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    • Elsie says:

      Ha! The dream of the 90s is alive in Portland. Who knew. I’m going to soak up as much uncool and different as I can there. I think there is something to that non-conformist attitude. By non-conforming you still categorize yourself in a way.

      Hopefully PF bloggers will make frugality cool. Tiny houses are doing some of the work for us, now we need to get the country on track with early retirement!

  6. ZJ Thorne says:

    My uncool is that I’m really interested in other people. Not in a manipulative way. In a way where I want to help connect good people to the things they want. I pay really good attention and remember tiny details (except names, I’m horrible with those) and will remember these for decades. I’ve used this to help set people up with jobs and relationships. I want good people to be happy and I use my power of perception to help link them up. I get nothing but the joy of seeing happiness out of it. It throws some folks off. I’m just uncool like that.

  7. Elsie says:

    I love that. I think people are weirded out by people who want to help often. We’re such an individualistic society people don’t like to need or ask for help. Really cool ZJ

  8. NZ Muse says:

    HAHAHA I love this so much! In my 20s I have embraced my lack of style, my laziness (glasses > contacts FTW), distaste for booze and extreme introversion.
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  9. Hey Elsie,

    You’re right, chasing the cool was pointless in school and it is pointless in adult life! I also think that success, or at least it’s common definition (get a good job, make a lot of money, wear expensive brands, buy that huge house…) is pretty pointless if it comes at the expense of your time and your freedom. If by not keeping up with the Joneses we’re uncool, then uncool is definitely the way to go…you could even say that uncool is the new cool?

    • Elsie says:

      Yes thats a great point. Time is wasted on status and climbing the corporate ladder rather than a singular focus on your time and freedom. I think people slowly give away their freedom, one step at a time. They accept that working all their life is mandatory. They think buying a house and having expensive things is just what people do. I love hearing when people break out of those norms to find what really makes them happy.

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