Let me first say this: I was not a fashionable teenager. To be honest, I’m not sure any  teenagers are… The ones I see who are trendy look totally ridiculous. I think your school becomes your own little world, and whatever is cool there, you think is cool everywhere.

Which isn’t actually true.

Any kid who’s been moved from city to city while in middle and high school can tell you that. One brand is hot in one city, and kids in another city have never even heard of it.

But what happens is the one kid who has the balls to wear something new and be confident in it is the one who sets the trends. I’m not talking about the kids who dress purposely ugly (goths spring to mind), ridiculous (Uggs in the summer? Really?), or skimpy (enough said).

I’m talking about that girl who seems to wear whatever she likes, and then everyone wants to wear it too. That girl. Be that girl.

Here’s what I’ve figured out about following trends.

They aren’t you, and you’ll feel uncomfortable and look uncomfortable in them.

When I was in high school, around 10th grade, I finally came around to “normal” clothes after an ill-advised stint in novelty t-shirts and big jeans. I started dressing like all the popular kids. In those days, it was khakis from The Gap and Doc Martens sandals. It wasn’t me, and I still didn’t really fit in. I didn’t figure it out until much, much later in life. I never looked good in them because I never felt good in them.

Not all trends are all that flattering.

(Bubble skirts pop into my mind.) Pick clothes that actually look good on you. I kept trying to pick clothes that looked like what I saw in magazines or catalogs, but they looked horrible on me. My mom would do this thing when she took me shopping, where she would pick up something I didn’t like and say, “Humor me.” Which loosely translated means, “Go try this on or you’re not getting anything.” Then, if it looked good, she would say, “That looks so becoming on you.”

Becoming on you. Not really the words every teenage girl is dying to hear in the dressing room. But she was onto something. There are lots of beautiful clothes out there. Just because you put them on, doesn’t mean you’ll look beautiful in them. It doesn’t mean there’s something wrong with you. It just means that some clothes look good on certain shapes, lengths, and sizes of woman. There are some clothes that just don’t look good on anyone. Period.

Pick stuff you like, whether anyone else likes it or not.

Now, this piece of advice, I sometimes followed and sometimes didn’t as a teenager. Sometimes I followed it to my own detriment (like the Star Wars athletic tee I wouldn’t take off for most of age 15), and sometimes I didn’t follow it, also to my detriment (see above, where I wore clothes because they were trendy).

The times in my life I remember enjoying my style, and consequently felt the most confident, is when I wore what made me feel good. A lot of times it included really, really short hair, which didn’t always thrill my mom and certain types of boys, but I pulled it off because I felt good in it. I actually kind of rocked the short hair.

Cultivate a personal sense of style.

I spent a lot of time trying to look exactly like things I saw in magazines and catalogs, but that stuff passes. What’s hot today isn’t hot tomorrow. And then you wasted money on clothes that aren’t cool anymore. And you just got them like, last month. (I still make this mistake sometimes. That’s why I have 5 embellished t-shirts in my closet that I just got 6 months ago and probably won’t wear ever again.)

You’ll find items that you’ll literally cry over when something irreparable happens to them. I’m not talking about materialism; I mean pieces of clothing that you feel like are a perfect representation of you and your own style, that make you look and feel great. Look for things like that, and hang onto them.

The girls I remember wishing I could look like weren’t following trends or letting what everyone else was wearing dictate their style. Well, they weren’t trendy anyway. There was just something about them… they were comfortable, they owned their look, and most of them probably still do today, over a decade later.

Find your own clothing personality, and live outside of the trends. Ironically, this will make you the trendsetter.

Just a little advice from the me I am now to the me I was then.

This is the first post in a series called Letters to a Teenage Girl. Read the intro here.

I’m getting a little tired of Gen Y bloggers proudly flouting their “workaholism” in post after post of how they love their jobs, don’t see a need for work/life balance anymore and question whether or not their relationships are holding them back.

Of course, I’m guilty of several of these posts myself.

I remember Ryan Paugh from BrazenCareerist once wondering in a post if he was going to feel embarrassed by something he wrote 10 years later (I couldn’t find the link). His conclusion was that he probably would, and I concur. Even just a year later, I look back at some of my own posts and shake my head. I’ve changed my mind about some of those sanctimonious posts I wrote. (Maybe I’ll change my mind about this sanctimonious post, too at some point.)

There’s nothing like a good round of cancer scares to put things in perspective. As I’ve been forced to relax and let my “workaholism” tendencies fade into the background, I’ve figured out a few things. One is that the stress in my life came from the label I gave myself as a “workaholic.” I have found that I’m not actually working on less projects now, but that my mind has released the “have-to, have-to, have-to” thoughts that kept my mind racing even when I wasn’t working on something.

I’ve also watched my boyfriend run his distribution business over the past few months. He travels 3 hours away to tend his business weekly, aside from his local branch. He has a business in the sense that he’s not freelancing or consulting or designing websites – he has an office manager, employees with health insurance, customers who demand his time, and expenses that would make me cringe. He experiences a kind of daily stress and time demands that we Gen Y I-run-my-personal-brand types can’t imagine. I don’t care how many nights you slept in your office waiting for your start-up site to go live.

So here’s the deal. You’re not a workaholic. And you’re no different from the young-go-getters of the 1980s. (Please watch “Working Girl.” I mean, those people were always on and always “working.” We’re not the first people to discover taking our jobs seriously.)

We’re simply at the work-hard-to-get-ahead life stage. Like I said, we’re not the first. We’re supposed to be working hard right now because later, we’re going to want to take a break. I know, I know. You luuuuuuhhv your job. Great. For now. Later you will find that you luuuuuuuhhv being home to cook dinner for your kids. The other thing is that “getting ahead” looks different today than it did 20 years ago. Our parents worked late hours, took extra projects on, and went to night school to get higher degrees and certifications. We still do all that stuff, just now we’re also tending to our blogs, websites, overall web presence, personal brands, etc.

We don’t have a “life” to balance yet.
We’re in our twenties. We don’t have kids yet (for the most part), and we might have girlfriends or boyfriends, but not the kind of relationships that require time, energy and work to maintain because they simply haven’t become that important or demanding yet. We’re not trying to figure out how to make our 10-year-old marriage last because we see the love of earlier years fading. We don’t have children pulling us away from our “me” time. Jesus, you’ve still got time for the gym. Ask a working mom if she’s got time for that… if she does it’s at 5 a.m. while everyone else is still sleeping. That is what work/life balance is – not trying to schedule time in for a trip to the bar with friends.

We regard our life activities like they are work.
We blog because we love it, and yes, it gets us ahead in our careers, but that’s not why we keep at it. Blogging, networking, going to social media conferences and volunteering for organizations isn’t your job. We do it because in our day and age it is the new softball team. I spoke on a panel at an economic summit this week and I tried to stretch my mind to figure out how this will advance my career. My boyfriend pointed out that I did it because I think its fun. Oh yeah. That’s my LIFE, not my WORK.

We haven’t suffered the consequences of workaholism yet.
You probably haven’t even been burnt out yet, let alone laid off from your first job at a start-up, driven to real addiction, been divorced or suffered stress-related health problems. When you get there, remind me again of how much you OMG luv luv luv your job. Because I want to know if it was worth it. (The only one I haven’t done is divorce. And no, the 80-hour work weeks from the start-up that went under were not worth it. I’d happily give back the crow’s feet those earned me.)

We’re still seeking definition and identity with labels.
I wrote two weeks ago about my struggle to let go of my self-image as a go-getter, a woman on the make, etc. Elysa Rice seconded my “who am I if not a…” idea. We’ve been students forever, and now we’re joining the workforce and struggling with this notion that we need a label. We don’t. It’s a personal revolution in thought that occurs when you realize that you just are and that being a “workaholic” or a rising star or a go-getter is just a label that you try to live up to.

We like to inflate our own self-importance.
I’m really talking to myself as much to anyone else here. I think we inherently have some kind of egoistic tick that makes us trump up our own value. Gen Y doesn’t do this anymore than any other generation… we just have a syndicated platform by which to do it, in my opinion. When I declared myself a workaholic with no respect for this work/life balance nonsense, I was always rushing around in a state of self-importance trying to do everything I “needed” to do. My reality was that when I backed off, nobody suffered as a result of my loss in super-productivity, in fact no one really noticed.

I’m definitely not the oldest of my blogging compadres, but sometimes I feel like my life experiences have aged me a little. I guess there’s a part of me that wants to save my fellow twenty-somethings some of the pain I went through learning things the hard way. But then again, I didn’t listen to the people who tried to warn me. I figured I was different. I was unique. I wasn’t.

But hey, maybe I’m wrong. What do you think – are we really workaholics?

My life has been an interesting series of transitions, always changing and moving in new directions. Social media seems to mimic our lives, and my life in the virtual world has transformed right alongside my not-so-virtual life (the two are increasingly interwoven… I’m not sure I could separate one from the other anymore).

When I started WorkLoveLife in February 2008, I had no idea it would take me where I am today. What nobody tells you when you start a blog is that you will become a junkie. First, you’ll start devouring other people’s blogs in your genre. Then you start commenting on their blogs, and then you figure out that when you do that you get more readers. Oh that’s neat, you think. I wonder what else I can do to get more readers…

It spiraled out from there. As I grew WorkLoveLife, I began to run across concepts that I was already working with in my day job in marketing. And I was intrigued. Here I had been MySpacing, Facebooking (um, anyone else remember being on Friendster? I was there), Flickring, tagging and tweeting, and mixed up in all this craziness was marketing.

I wrote a few posts that really had nothing to do with Work, Love or Life, but had everything to do brand image, marketing, and social media tools. And they were some of my favorite posts to write. And scrolling through my feeds every day, I would star dozens of articles daily that I wanted to blog about… but they just didn’t seem to fit what I was doing with WorkLoveLife.

One night, not long after my day job had a serious sputter, I sat on the phone with Penelope Trunk, trying to figure out my next move when she spits out the most preposterous idea. “You should be doing social media, Holly,” she says matter-of-factly, as if she’s been reading my tea leaves. “You do it all already. Just start a blog and round out your resume with some bullets by offering to do some social media campaigns for local businesses and friends.”

I considered this and found it hard to swallow that I could offer my thoughts to others on this subject. Then I started looking around my community and saw a major hole. Nobody, and I mean nobody, had any clue when it came to social media. I met with the community in San Antonio, and god love ‘em, they encouraged me. “Holly is social media in Corpus Christi,” Luis Sandoval told someone as he introduced me. And the truth of it hit me. If nobody filled the hole, the snake oil salesmen would show up soon, and I couldn’t have that happen – not to my community, not to social media.

That was about a month ago. Voila, blog. Hello, social media marketing portfolio. And you know, I even ended up falling for the guy who was running the political action group I offered to do a Facebook promotion for.

I love social media.

My new blog is HollyHoffman.com. It’s in it’s infancy, so keep checking back for updates – first up, RSS so you don’t need to keep checking up. And WorkLoveLife isn’t going anywhere. Just doubling up the blogging efforts!

I’d like to start out by saying that I hope this doesn’t affect my readership. I think the world of my readers, and I understand that we are all entitled to our own personal political beliefs. This is simply my opinion. Feel free to agree and disagree, but please do not resort to angry name-calling. Keep it civil and intelligent.

If people are the greatest resource a nation has, then a primary goal of government is to inspire those people to do what is necessary to make that nation great. This is simply an exercise in the marketing of ideas on the grandest scale. While McCain might be a maverick who can help to clean up Washington, Obama is the candidate who has nailed the ability to communicate and inspire people to do more. Inspiring confidence and communicating with people may mean more than any bill either candidate can get signed into law.

– From “Marketing and the Economy; Why America Needs Obama and Coca-Cola” by Joe Marchese, MediaPost

This post may be too late for some, and I actually considered not posting it. I’m not very eloquent about my political beliefs – my expertise is in marketing. Then my mom told me she was still undecided. So this one is for you, Mom.

I’ve been in marketing for about a year and a half now. I’m no Guy Kawasaki, but I’ve really taken to the field. I’m fascinated by what motivates people to make a purchase, choose a certain product or brand, and how pyschographics plays into that. So, when Ad Age named Barack Obama Marketer of the Year, I wasn’t surprised. The man is a marketing genius. I actually think this is why people compare him to JFK. It’s not so much the youth thing – it’s the agent of change thing.

Whether or not you agree with the issues, I think you should vote for Obama.

Obama is the candidate that has been able to inspire large chunks of the population to believe that things can change for the better. Whenever I’ve had conversations with my acquaintances and friends about why I am voting for Obama, I cite consumer confidence.

Either way, I think the markets will see an upswing after Nov. 2. Any change in leadership is a positive one, in my opinion. But I think we will see a greater upswing in national confidence if Obama is elected. For one thing, other great nations would like to see Obama as president. If he were elected, I think you would see faith restored in the international markets.

If McCain is elected, a large portion of the population will be left dejected and with a total loss of faith in their nation. This election is more to us than any other election. For someone my age, the belief that I can, along with my fellow Americans, create lasting and vital change hinges on the outcome of this election. Obama has been able to inspire a historically apathetic voting demographic to become involved in politics, to show up at the polls (I’ll be voting for the first time since 2000), and to take an earnest interest in the future of their nation.

McCain simply doesn’t connect with people on that level. If McCain is elected, my belief in America as a great nation that can lead the world into an era of positive change will be shattered. I will know that my nation has failed the vision test, that I live in a country blinded by fear-mongering, hatred and impotence. Change will be slow, not swift. We will have elected a corporation where we needed a start-up. It will be titanic effort instead of nimble agility, which is what we see with brands that “act small” versus the colossus of slow-to-change industries.

It takes more than wielding power to get a law passed. Like Joe Marchese said earlier this month in an article on MediaPost, the American brand has taken a beating recently. Which message would we like to send our nation and to other nations – one where we’re too blinded by fear of change and backward-looking issues to make the leap of faith, or one that stands for change, belief and hope?

I for one, regardless of the issues, because let’s face it – it’s less about abortion, the economy, and oil than it is about the kind of nation we’d like to have, would like to put our nation’s best face forward. I don’t think that’s what McCain will be about. I want a strong person in power who is ready to lead this nation into the 21st century. It’s not about the issues – it’s about the message.

What message do you want to send?

I’ve been cursed my whole life with being both right- and left-brained. Not a lot of people can go from designing a new website to working with raw demographic data tables for an unrelated project. I loved logic and trig while being a total art kid in high school. In college, I double-majored in philosophy and art, though I have to admit I could see no use for aesthetic theory – I couldn’t handle philosophy of art.

Thus far, it’s been really useful in my career. When I worked at a non-profit start-up straight out of college, I needed to wear a lot of hats. I recruited, I mentored, I edited news articles, I did research, I designed web pages, I coded, and I took bids on jobs. I had to be able to turn my attention from page design one moment to researching interviewees the next. As a marketing research analyst in a small department, part of the job description was that the candidate should be able to turn on a dime, and I do, from logo design to demographics mapping.

However, I’ve recently realized that my wonderful little gift is also my curse. There are a lot of things I’m good at. I’m not being an egoist; I’m really pretty good at all sorts of stuff. I like trying new things, and enthusiasm will take you far. I’ve been a DJ at a radio station and a nightclub, artist, barista, magazine editor, proofreader, new media director, special events coordinator, bartender, research analyst, blogger, IT consultant. At some point, I was even a pre-med major. I’ve rock-climbed, knitted, done ethnic cooking, trained for marathons, played softball, volleyball and soccer, been a vegetarian, and done some motivational speaking.

The problem? I’m all over the place.

When recently thinking about my career, I realized that I had no specialty. I’ve always had to twist my résumé credentials to fit the requirements (philosophy degree = critical thinking skills + analytical skills + thesis research = market researcher!). Don’t get me a wrong – I’m a great hire. However, I’d really like to be great at something.

I’d like to be great at something.

Not just good. Not okay. Not just ‘oh, yeah, I did that, too.’

I look at the people I admire, and they are either the giants of their fields or they’ve got a particular niche cornered. I’d like to really have my head wrapped around something, not just have a surface understanding or street knowledge about it. I’m tired of being OK at a lot of things.

I’m ready to be great at something. And not just to be Great, but to put the work into it to really understand it, to be an authority on it. When I was a philosophy major, I dreamed of being the Heidegger scholar studied enough to get a glimpse of his unpublished, untranslated papers tucked away in a small German library. As a new media director, I dreamed of taking our little start-up site nationwide, even global.

Now, I dream other dreams… dreams of a research analyst (believe it or not), dreams of a blogger, dreams of an entrepreneur. There are so many things I could do though; how do I choose? How do you know which one you have the potential to be great at?

This is part one in a two-part series.

I’m not happy with my personal style lately. It’s sort of been ongoing since I got sober and lost some weight… and you know, stopped spending all my money on booze. I’ve told myself that part of the problem is that I don’t have a lot of money to spend on new clothes, but I think there’s a little more to it than that. I would say the real problem is that I don’t give it much thought until I’m actually in a store, ready to buy some item that I need. Seeing as I give almost everything in my life too much thought, I thought that was a little ironic.

Whether we like it or not, we’re judged at a moment’s glance by our outward image. And as much as the BF hems and haws about appearances not mattering, he plays by the rules and wears a suit to the office every day, even Fridays. In our careers, in dating, we’re judged first by our appearance and our clothing does a lot of the talking. (I wasn’t sure if I was attracted to Date #4 when we met – he was wearing a suit and I always say that it blocked any read I was trying to get from him.)

I’ve been watching the preliminary back-to-school ads roll in, and it amazes me how much time and thought middle and high school kids put into their clothing choices. Their clothes (in their minds) say so much about them – what group they belong to, what kind of music they listen to, what their socioeconomic status is, how in tune they are with trends, which causes they support (if any). Why this is, is an entirely different subject that I don’t wish to touch on here. What it did, though, was prompt me to look at my style choices and think about what they said about me.

That’s when I realized that my style choices weren’t really so much choices as they were lazy acquiesces. I live in a town with few clothing options, but I’m not sure I would be much better off anywhere else.

I love:
Blazers
3/4-sleeve jackets
Cardigans
Dark jeans
Vintage-y blouses
‘40s inspired dresses, shoes, hair… well, anything really
Splashes of bright color
Scarves
Preppy-style flats
Colorful, vintage heels
Long dresses

How much of this do I own? Er… none. I do have a few cardigans, but they’re pretty much a necessity in my 60-degree office. Oh, and I own about 7 pairs of dark jeans, but all in the same style and cut from the same store. Even I know that’s wrong.

Looking at this list, I can see that this is actually how I used to dress in high school. My mom hated taking me shopping – I never saw anything I liked unless we were at a Goodwill. Luckily, times have changed and Anthropologie picked up what I was throwing down. Anyhow, I did think that it said something about me. Like today’s teenagers, I was keenly aware of the message I was trying to send. I was eclectic, creative, a little hip, a little bohemian, a non-conformist, an intellectual.

How many of us can say we put that much thought into our wardrobe post-high school or college? I grab whatever Express is offering that month in the way of office-appropriate attire within my budget and that’s about it. Wouldn’t it be nice to have a personal style again?

It’s not just about sending an arbitrary message about who I think I am. After all, if you’re worthwhile and think I’m worthwhile, we’ll get to know each other and you’ll figure out who I am. When my outer self matches my inner self, who it is that I am, I’m a lot happier. Plain and simple, if I actually enjoy the clothes I’m wearing, then I’m a lot happier overall. I also feel a lot more at home in social situations. I feel more comfortable projecting who I am when I’m not tugging on uncomfortable clothes that don’t fit right. And, of course, I wouldn’t mind standing out from the crowd a little.

In an age when personal branding seems to be all the rage, why are we sticking ourselves in the same suits and brands as everyone else? Why aren’t we spending more time thinking about how our “look” corresponds to our personal brand, our goals, and where we want to go?

Some questions to ask yourself about your personal style:
• How would I like people to see me? Use descriptive adjectives: polished, bohemian, put-together, artsy, sleek, glamorous, etc.
• How would I describe myself in a few words? Are you a corporate go-getter, an intellectual, a tech geek, a trendsetter, outdoorsy, creative?
• What styles do I identify with? What words describe them? Do those words describe me?
• What are some items I really like? Do I currently have them in my collection?
• How do my clothing choices affect me on a daily basis? Am I happier when I wear certain colors? Certain styles?

Me, personally, I’m going to start holding out for items that fit with my now clearly defined personal style. Now, if you’ll excuse me, I’m going to rethink those 7 pairs of jeans…

All images from Anthropologie.com.