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Onwards & Upwards

 
 
 

Onwards & Upwards

I'm not sure exactly when it happened, probably somewhere in the frenzy of moving back to New York, but I completely dropped my morning writing habit.

To be fair, it wasn’t incredibly consistent to begin with.

So, in an attempt to kickstart the habit again, I organized my scattered thoughts on what happened last year.

It was a ride, to say the least.


The Proof

At the start of 2019, I left my first job in venture to start a blog. If I read that sentence a few years back I'd give myself a stern talking to.

Borderline certifiable.

I still don't know what to call this thing and I'm definitely not sure what it might become. But, I can say with certainty, this blog gave me everything.

More importantly, it keeps me sane.

Through The Proof, I talked to people I've looked up to for a long, long time.

In a weird twist of events, a lot of those same people became close friends and mentors. I followed these friendships and curiosities around San Francisco, to Los Angeles, and finally landed in New York.

Much love to those that lent me a couch along the way.

For a semblance of structure here, I tried to distill my learnings from this past year into two buckets. Learnings may not even be the right word here.

Reflections is closer to the truth.


Take Off the Mask

Every day, you put on a mask.

It covers up your insecurities and perceived flaws.

It protects you, or at least that’s what you tell yourself.

If you take it off in public, over coffee, the person sitting across from you will notice. More importantly, they'll remember you for the rest of their day.

To paraphrase Italo Calvino, the people who move through the street are all strangers. At each encounter, they imagine a thousand things about one another.

But, no one greets each other. Eyes lock for a second, then dart away.

Never stopping.

When you take off your mask, and along with it the walls that you erect to protect yourself from the world, it gives others the permission to take off their own.

Do so by speaking freely about intimate and vulnerable moments, both in times of failure and success.

The more public the better.


Ask for Help

A cold DM got me my first job. Thought I was lucky.

Hundreds of cold emails landed the first dozen interviews on here.

Might be a fluke.

Another cold DM landed me my second job. Definitely a pattern emerging.

Good things tend to happen when you ask for what you want.

The less friction you introduce in the ask and the more value you provide up front, the greater the chance of a response.

Maybe that person hops on a call with you.

Maybe that call strikes up a friendship or leads to a job down the line.

Might just change your life. It did for me.


Onwards

My first mentor out of college was Ryan Bethencourt — a brilliant investor, entrepreneur, and friend.

To say I owe him a lot is an understatement.

When I think back to what he taught me, I'm reminded of his email sign-off.

“Onwards & Upwards.”

I didn't think much of it at the time, but as I experience more highs and more lows, that line started to resonate more deeply with me.

When I'm more stressed than I'd like to admit, I'm reminded of Ryan's sign-off.

One foot in front of the other. Onwards.