Why: Beyond the Poker Table
My poker and business career, investments, and coaching... What do these all have in common?
They are some of the ways in which I've learned the lessons I'm going to share with you today.
Last week, I wrote to you about the critical importance of "Why" on the poker table. Today, we step away from the table and take our "Why" with us. Let's dive in.
Risk Non-Management
This will surprise many of you who don't know me well, but I've been financially irresponsible for the majority of my career.
Due to a levelheadedness that likely won't surprise you, along with a little luck at times, I've managed to survive and thrive in spite of my risk-management skills – not because of them.
This started in poker, where my dream from the beginning was to compete at the highest stakes and on the biggest stages. I would grind away, building my bankroll at $5/$10 NL, then take $50k shots at $50/$100 NL, often losing half of my bankroll in the process before eagerly grinding my way back up so I could do it again.
Once I finally did reach the highest stakes, that pattern didn't really change.
I was usually under-rolled for the stakes I played. I'd sometimes have to drop down a few buy-in levels for a period of time to make sure I didn't go broke.
Then, eventually (as the online games did have a maximum buy-in level) my bankroll grew large enough that I no longer had the option to be in over my head.
Why?
Why did I consistently put myself at risk the way I did?
At the time, I thought it was for three reasons:
1. It was exciting.
2. It motivated me to work harder.
3. I wanted to maximize my EV.
During the second decade of my career, I figured out a better approach and better “Why”.
Risky Business
Eleven years ago, I co-founded Run It Once Training. I loved teaching poker, and I felt we could do it better than everyone else. My co-founder and I made the product that we wanted as players.
It was an instant success.
For the first five years, I was still a full-time poker player. So, I had poker-playing income and cash flow from the business. I was in a good spot.
But I didn't "cash in" on it and live the easy life. I wanted more.
We reinvested all of our profits into the creation of other businesses. I'll save the full story for another time, perhaps, but the end result was this: In the past eleven years, despite running a profitable training business the entire time, it hasn't contributed to my income.
If I had to guess, I'm just now approaching being roughly even after several of the reinvestments didn't pan out the way we'd hoped.
At times, I was actually risking far more than I'd planned to. There were times when, despite a successful two-decade poker career and a great business, it looked like I could end up in pretty rough financial shape.
The Realization
A few years ago, through my work with coaches – most of all, Elliot Roe – I took a good hard look at my Whys.
I thought about my values and priorities. I thought about some rough financial goals.
I realized that if I'd kept things simple, just running a nice cashflowing business while continuing to play poker, I'd have already reached the levels I wanted to achieve.
I was making investments that I deemed +EV, which, on average, should work out for me, but EV isn’t the whole story.
This is where my true realization came. I’d been playing poker and business exactly the way I had since I was 19 years old. No thought of the practical use of money or the diminishing returns of net worth as it increases – just this compulsion to aim higher.
I was taking all of these shots to create multiple $50m+ businesses (as a majority owner).
Why did I want that? What would I use the money for?
I'd never thought about it.
I was just chasing EV. And, unfortunately, I was constantly putting pressure on myself to do much more than I’d ever managed to get done. I always felt behind.
After some proper goal-setting over the following years, I settled on financial targets that would allow me to be “set” and take a step back from my 60+ hour work weeks (now down in the 50s, by the way!). I envisioned the life I wanted to live in ten years, and I looked forward to hitting my goals and taking the edge off of my constant need to push for more and more success.
And I began treating risk a bit differently. I no longer wanted to bet a great life for the chance of a massive score. Once I sat and thought about the future I actually wanted, and what was needed to get me there, I couldn’t unsee it. The way I made decisions was forever changed.
Your “Why”
Just like you do at the poker table, you’re making decisions every single day for a reason. And, just like at the poker table, the more of those decisions you make without thinking, the further off track you can get.
The solution, in my opinion, is curiosity and awareness – bringing awareness to what you are thinking and feeling at your decision points, and curiously asking yourself why you want to make the decision you do.
Even more importantly, bringing curiosity and awareness to what you truly want in life, long-term, can help your future decisions become more purposeful and aligned with your goals.
You don’t need hundreds of hours of coaching like I’ve had to focus on your own Whys.
You simply need to ask yourself some questions and take the time to answer.
Consider these eight categories:
Finances (Income, Net Worth, Debt Reduction)
Career (Job, Achievements)
Relationships (Family, Friends, Romantic)
Personal (Knowledge, Projects)
Contribution (Service, Community, Legacy)
Wellbeing (Physical)
Wellbeing (Mental, Emotional, Spiritual)
Fun (Hobbies, Travel, Relaxation)
(There are several versions of an exercise like this with varying numbers of categories. I like these ones!)
Which of these are most important to you and your happiness? List your top four in order.
Ideally, what would these important areas of your life look like in ten years?
How can you focus your time and energy differently to help you get there?
What Did You Learn?
If you truly take a good look, you may notice several parts of your life – the things you spend your time and energy on – that don’t align with what you really want. Perhaps you view your physical health as hugely important, but you’ve not been where you want for years now.
Maybe your mental health is at the top of the list, as you notice its ripple effects onto every other area of your life.
Or perhaps your career isn’t nearly as important as your relationships to you, but you’ve consistently neglected those relationships for your career.
The first time I did an exercise like this was with Elliot Roe, and it was eye-opening for me. I’ve done several variations of it since, and I teach my own version of it as a small part of the intro to Beyond The Game.
What’s interesting about exercises like this one that prompt self-reflection is that they tend to impact you differently over time. Your priorities may shift. You may find that you’ve overcorrected since the last time you audited your life.
You might not get much out of it on one occasion, and it might change everything for you on another. Either way, it’s a freeroll. You either notice that your life needs realignment, or can take a moment to congratulate yourself for all you’ve been doing.
These types of prompts help because they force the awareness and curiosity that can serve us so well. They bring a little bit of clarity to the destination we’d like to reach.
Do You Have a Destination?
A GPS works great if you tell it where you want to go, but ask it to take you north, and you won’t be impressed.
Most of them these days, if you tell it you’re looking for a farm in a certain area up north, will present you with a list of options.
Not bad.
You could start driving north towards a cluster of them and make the decision later. For now, just pick one in the group and let the GPS point you in that direction.
But, if you’re like me, you’ve spent most of your life without even that level of clarity about the destination.
You know you want to go north – more success, better relationships, better health – but that’s about as far as you’ve thought it through.
You’re so busy and preoccupied that you often drive around aimlessly. You get distracted, caught up in the day-to-day grind and the barrage of unexpected issues to deal with that is adulthood.
Before you know it, you’ve driven somewhere you never really wanted to be.
If you’d just plug the destination into your GPS, you’d start making true progress – progress in the direction you want.
Sure, there will be roadblocks. There will be detours. You might need to make emergency stops far out of your way. You may make a slight change to your destination as you go.
But you won’t be aimless.
Every time you come to a crossroads and have a decision to make, you’ll glance at your map and know which turn to take.
And one day before you know it, in the midst of all the chaos, you might look up and realize your destination is in sight.
PS - When you're ready to take your poker game to the next level, here are some ways I can help...
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