It Took Me 4 Years to Build a Regular Poker Game – And Why That’s Okay

The second time my roommates and I hosted a poker game in Los Angeles, four people showed up to the apartment.

Three of them — including myself — lived there.

The fourth, he was interning (like us), was car-less, and lived in a hotel in downtown Los Angeles. Armed with a bag of Doritos and pretzel thins, he took a 45-minute bus ride to arrive at our doorstop… to find that everyone else flaked.

An hour later and the Doritos eaten, we gave him a ride back to his hotel.

How hard was starting a small poker game?

How different could it be from the home games I put on in Albany?

Back then, it was simple: I’d coerce a friend to open up their house.

I’d call a few people.


By senior year, with most our futures seemingly cast like a fistful of bones on the floor, we stopped doing actual school work and just had standing games, a few times a week.

Yet here, we couldn’t even get an occasional game off the ground.

By the time I made my round of text messages to the interns who I made coffee, printed scripts, and basically ate crow next to… I’d find out they moved back to, like, Raleigh, North Carolina, to work for accounting companies and car dealerships.

So I’d wish them luck, and cross them off the guest list.

Keep Building

Throwing events isn’t a  strong suit of mine (add it to the list).

It never was. It’s a residual fear of an uncool teenager who skipped school dances and watched BOY MEETS WORLD with his family on Friday nights rather than steal nips of booze before going to Sneaky Pete’s, the underage-age club in downtown Albany.

So the failure of that second game left a bad taste. Over the next four years, my roommates and I would try again every few months, never with much success, to start a regular game.

Still, I kept building my list of people to invite. Literally, one by one — if I met someone at drinks or an event, I’d ask if they wanted an invite.

I’d add them, sometimes months apart from one to the next.

Some who said, “yes, please put on the invite list I’d love to play” to this day, have never even emailed back, which is okay.

I’ve built that list to over 20 people… and the last few games, we’re finally seeing good, consistent turnouts. Nearly four years after that disastrous second game.

Building anything is a process, and it takes time.

In this age of “life hacks” and outsourcing to virtual assistants, we see the success of our peers: people who send out one email and can launch a successful event, or are on a dazzling career track, or make a disgusting amount of money…

And we think, “Why’s it so easy for them?”

“What am I doing wrong?”

“What’s their secret?”

I don’t think we pay proper homage to the process of building, or to the quality of patience.

Building isn’t always elegant. It’s not always a process to “hack.” It happens in fits and starts. It can easily flounder for years, and just as easily, take off with a volition of its own.

What are you building?

The ONE Thing My Friend Taught Me… That Changed My Career, Relationships, and Happiness

I keep a mental list of things I’m awful at:


Making the bed

Writing long lists

Only one thing really held me back, in my career, personal life, and relationships, though.

In college, when I saw how my friend used this one strategy, it was like a strong punch of sobriety after a night of too many cheap vodka shots.

It’s effect in this year alone: I earned more money (almost a $10,000 yearly increase), created my first Hollywood tracking board, and developed a more valuable network of colleagues.

I’ll get to all that. First, though – back to the awful:

One Thing That Held Back My Career, Personal Life and Relationships

I was always awful at asking people for help or advice.

I thought everything was up to me to “figure it out.”

And that asking for help was a sign of weakness.

Plus, I had this screwed up interpretation when others asked for help. I always translated their words, “Can you help me with this?” into “Can you do this for me?” Which wasn’t fair to anyone.

There were so many arenas in which I should have asked for help, but never did:

Soccer – I never learned to strike properly, or attack with confidence. And I never asked for help.

Digital electronics – (Yeah, I was engineering geek in high school…) Rather than damage why reputation as a smart dude by asking for help, I focused on scoring well on exams over grasping the fundamentals (voltage, current, and resistance) that I never understood.

Editing – This was a recent development, in which I learned more, in editing for 4 hours sitting next to a relative expert, than 14 hours editing alone in a dark room.

What was the Game Changer?

Enter: my friend Joshua, who showed me it was okay to ask for help.

He’d struggle through a problem, and if he hit a block, he’d ask for guidance – from a bunch of people.

This idea blew me away: here I was refusing to ask one expert for help, and Josh would ask like 5 people!

It didn’t matter if it was help with editing a paper, navigating a juncture in his career, or relationships.

He always sought the big picture. And he knew how to do it openly and honestly. He’d say, “I’m asking a bunch of people for help. I really respect your opinion, what do you think about this situation…?”

What I noticed was this:

When he put it that way, when I saw that he worked to solve the problem himself first, my “barrier” about asking for help didn’t come crashing down.

I was more than happy to help. It made me feel good. It was a win-win.

Then, Josh would take action (note: not always following my advice. Probably for the better — but that’s not the point). He did something. And I liked being a part of his action, even if indirectly.

That’s when it clicked for me. 

It was a small, but significant tweak.

This was the game changer:

We like to help people when they acknowledge the help, and take action.

Even when it’s not their advice you’re acting on.

It seems so simple but this idea blew me away.

There are so many things in the past year alone, that I couldn’t have done without asking for help.

A Few of My Game Changers – And My Exact Words

Negotiating salary – I armed myself for two successful salary negotiations by asking my colleagues a simple question and a follow-up: “How much do you make? I’m asking people so I understand the market rate.”

Creating a Hollywood tracking board in my niche – Learning literary contracts and deal points in a vacuum is difficult, but my grasp of concepts more than doubled after I selected a few people in similar roles and asked: “Would you be interested in sitting down once a month  and studying these deal points together?”

Networking – If I felt like I provided value, and genuinely connected with someone at drinks or an event, I’d ask: “Is there anyone else you think it’d be helpful that I talk to?”

Asking For Help is An Art and Science

Meaning, these exact words alone may not produce the same results. There’s a lot going on beneath the surface, months and years of providing value to others first.

You can’t be wearing a sign across your back, “Please Help Me!”

I still don’t ask for help enough. The difference, however is: I’m not limited by the ask.

Instead, I’m limited two things:

The time I know it takes to give back and provide value in return, and… 

The scalability of my own system that prods me to give, give, give to others, first.

Asking for help, in conjunction with these two points, has been a game changer for my career and life.

What’s been your game changer? What systems or outlooks have you implemented that helped you make leaps you didn’t think possible?


I don’t mean it when I say I’m only here for the open bar.

Because the food is nice, too.

But the nicest part, the secret sauce of weddings, is for all the days leading up to it, you know how special it is. Most days, we go through the motions but nothing changes.

The morning of a wedding, though, a couple wakes up in their bed knowing they’ll never experience today again. That for better or worse, nothing is the same.

If you’re a guest, the day still feels a little rote: laying out the same suit, coordinating your tie, slipping into the right shoes. It’s the way you’ve done a dozen times before. Do it enough times, and nothing –the family drama, Chinese wedding games, or the chicken dance – may come as a surprise.

But for two specific people, this time it’s their family drama, their terrible dancing, and they wanted you to be a part of it.

I write this on a flight to San Francisco by the fluorescent purple glow of the Virgin American cabin. I’m en route to a wedding after missing one in New York last week. What’s the point of all the work to live on the west coast if I can’t make it back east for those days that matter? I wish writing this meant, “Yes, I know these days are special, and I’ll make every single one.” Unfortunately, life (as it tends to) gets in the way. I’ll miss more vows, cake cutting, and even open bars.

It’s important to acknowledge the decision. So 10 years from now, when I wonder how I missed out on so much of other people’s lives, I won’t wonder how life got away from me. I’ll know I made my choices.

Low Point

No one expects to wake one morning and say aloud, “Yup, this is it: today’s the lowest point in my life.” You don’t anticipate rolling out of bed and thinking, “I don’t have a fucking clue why I’m even getting out of bed today.”

You sort of just arrive. While you’re pouring your Fruit Loops, or dumbly clicking your mouse. Or head to your unpaid internship, where you watch Youtube videos for eight hours straight in an urban cave shared by two dozen other 20-somethings, an activity gently dubbed as “business development.”

A few weeks shy of my 26th birthday and inside that cave was where I sat, unsatisfied with my work, unsatisfied with my writing. I didn’t know what I was still doing in Los Angeles. Later that day, I trudged back to my car in the rain, and I found a lovely note from the county’s parking enforcement, asking to please remit $63 to their offices.

If a child kicked my shins and a dog pissed on my shoes, I wouldn’t have been surprised. All I wanted was to bury my head in the sand. I wanted to stew in my misery and “figure my shit out,” whatever that means. It’s the approach I took for the first 25 years of my life: bottle it in, tell myself not to be a pussy, and get back to work – except it’s taken me 26 years to realize how self-destructive and insidious self-this behavior was. Doesn’t matter how hard you shovel, you can’t dig your way out of a hole.

Instead I called a friend. And she stayed on the line until I spilt everything I: how incredibly shitty I felt about myself, and what I hadn’t accomplished in two years, that maybe it wasn’t worth it and I should move back to New York. I told her I didn’t know what I was doing with my work, that I hated being poor and stopped feeling good about writing a long time ago.

Nothing was resolved. She didn’t offer any takeaway or sagely advice. But that wasn’t the point. She was there to listen when I needed to say something.

Part of me knew that the job would get better. That if watching Youtube videos and buying up channels was a skill I wanted to excel at, I could get there. I just didn’t know if this particular dip was one I wanted to conquer. No matter how good I got at it, would I be happy signing Youtube talent?

I quit the next day. I decided this wasn’t where I wanted to be in terms of my career, my writing, or my finances. I couldn’t unravel which tangents brought me down this path, so my only choice was to start retracing my steps, trying to remember when my trail was last good again.