#Question: As an entrepreneur, at what point can you say yes, I feel successful?

It makes me laugh, I always have to spell check entrepreneur.

Here's the song that goes with the post ...

Anywho, am on a kick as of late in studying words. I even looked up the word for the study of words and it's called etymology. It started with the word "creativity" and coming to the general conclusion that despite its name, creativity has more to do with applying perspective than literally creating something. (click here to read the post)

What about "success," I thought, and the concept of being "successful."

I then got this email ...

Am I successful, I thought?

I've recently been on television, and recently been in the news because of hard work on my lit agent's part - but does that make me successful? It doesn't feel any different than the day before. (Although hearing from literally every single guy you have dated was weird.)

Is it going to change when I cash the check, I wondered?

No, I thought back to myself. I am going to throw an awesome party thanking everyone from TNTML, buy Buster a bow tie collar, and myself a new pair of shoes just so I could literally say mama bought a new pair of shoes. Everything else will go into savings.

I was in the car last week with my best friend and asked her what she thought "success" was? How do you know if you've ever achieved it, I asked? It seems like a very personal thing.

What do you mean?

Think about it, for some people, getting out of bed is a success story. For some people being able to see, walk, or eat without assistance would be success.

We are bombarded daily with lifestyle marketing telling us how we should live, and how happy we'll be once we get to X place - but it doesn't exist. You're always going to want more, and more and more. It's life in the key of Varuca Salt circa Charlie and the Chocolate Factory:

Now now now ... not now but right now. It's gluttonous, and frankly kinda gross. 

My whole life I wanted to be "successful." Looking back it seems "impressive" to whatever degree (no pun intended) to finish high school at the age of 16, when in fact it was the SINGLE most difficult decision of my life.

Back in the early 2000s, (and especially at the very, very competitive Hall High School) your road map to success was outlined for you. Do well in high school, have x amount of AP classes, x amount of extracurricular activities, know (or be from) a legacy family at an ivy league school, have kick ass recommendations - and you're in! After college, you'll get an entry level job at some firm that you know the head of because of whatever fraternity or sorority you participated in, and after a handful of years you'll get married, pop out 2.5 kids and get a golden retriever. After the kids are at a certain age you might get your masters or whatever advanced degree required for you to move up in your career - and UPPPPPP the corporate ladder you go.

I not only didn't want any of that (as I learned more studying abroad than I did in classrooms), but I viscerally knew I didn't need it.

I'd like to talk to you about your future, said my guidance counselor.

I'm moving to NYC, I said.

I am going to work for a year (which would have been my senior year), and then move to NYC after I have saved enough money. I don't need to go to college.

Everyone needs to go to college, she replied back, and you should be fortunate that you're in a position where you're even ABLE to go to college.

My parents made me take the SATs but not only did I barely study (flash cards, FTW!), but I didn't even bring a calculator. I vividly remember everyone in the class seeming super stressed (understandable), and there I was not only cool as a cucumber but brazenly walked up to the instructor asking if they had any extra calculators.

You didn't bring a calculator? she admonished.

Nope. Am not going to need it.

I was an asshole for sure, I'll admit it - but I KNEW anything I did in life I could have a fall back working in tech in some capacity. I had been building in the space since I was 8, and even if it wasn't the best it seemed more likely than not that I was able to accomplish some sort of proof of concept and move onto whatever the next step was. Even at that age, I was never afraid to try something new - in fact, I loved it.

<tangent> That's SUCH a common misconception, btw. Failure isn't actually "failing" by whatever definition your ego wants to place around it. Failure (IMHO) is not trying. Even if something doesn't go exactly as you planned you at least TRIED and took away new skills that will SURELY translate to your next project. I throw so much fucking shit up against the wall EVERY.SINGLE.DAY. You get "lucky" because you're doing. No one sees the 100 other projects that didn't work out, but there you are confidently and quietly acquiring new skills. </tangent>

Classmates weren't supportive either. I got to a point where I started lying to people just to get them to shut the fuck up.

You need college to be successful, said one classmate.

What would I got to college for? Both careers I wanted to pursue (since social wasn't even invented yet) didn't require college. It's not only a waste of a handful of REALLY good years, but a waste of money.

Cannot stress this enough - still TO.THIS.DAY. that was the single most difficult decision I have ever made.

(Even more difficult than deciding to give up everything I owned and live in a car bartering social media to live.)

I was 17 with an apartment in Union Square, and an hour after my family left I sat on my cute little twin sized bed and cried wondering what I had gotten myself into.

I only knew ONE person in this city (Michael Schur, who at the time was a writer for SNL). Even then, that was a bit of a stretch as I only knew him from my high school when he came into speak to our drama class.

It wasn't an easy decision, but I stuck by my gut and stuck by my convictions.

Was I PETRIFIED of not being "successful?" ABSO-FREAKING-LUTELY, but I also knew that it was time to bet on myself.

Don't just post shit like this in social - GET OUT THERE AND LIVE IT!! IT WORKS!

Don't just post shit like this in social - GET OUT THERE AND LIVE IT!! IT WORKS!

Being SCARED SHITLESS didn't stop me, nor should it ever stop you.

14 years later I am not only proud of that decision, but after watching my episode of West Texas Investors Club, my parents laughed saying that thank GOD we didn't send you to college. You didn't need it.

Thanks for listening,  I said with a smile. I can't imagine how hard that must have been for you.

So, after all this analysis, do I feel successful?


I am proud that I can get out of bed and not need to put on 100 lbs of makeup to feel pretty. That confidence makes me feel successful.

I love that every day I get to help people understand tech in a very simple capacity. Being of service makes me feel successful.

I get jazzed to wake up every day knowing that I am exactly where I need to be doing exactly what I love. That passion makes me feel successful.

I have amazing friends, and family, whom I adore and would do anything for. That really makes me feel successful.

The rest is all just people like me trying to sell you shit that you prolly don't need.

That is all.