Poker – The Day I Chose Happiness

Today I would like to share my emotional journey in poker, and discuss “the day I chose happiness.”

The basis of this blog post begins way back in middle school, at a time when I began experiencing insomnia. I had a television set placed in my room, and it was unknowingly messing with my Circadian Rhythm. This negatively affected my school activity, and I went from All As to tanking just about every course besides math and science from about the 6th grade on.

On top of that, I had a gradual “falling out” of sorts with school and just the general educational structure designed to serve the masses. I realized that school just wasn’t for me and that I was becoming extremely bored with the Monday-Friday routine. I would act out, not pay attention and not try during most school activities, and this — combined with my poor sleeping habits — made me dread going to class. This problem only got worse once I left private Catholic grade school and moved on to high school.

To be honest, much of the beginning of my poker career consisted of unlearning certain things I had picked up as a child and adolescent. I began playing various card games for fun and got very competitive in video games (namely Warcraft III) at age 14.

I got into poker during the second semester of my senior year in high school. I really wanted to make money and needed an outlet similar to competitive video gaming that rewarded me for hard work, performance and overcoming challenge.

My Poker Journey Begins

Throughout the early days of my poker career, I assumed I had selected the life of a professional player over a normal job, when in fact I had chosen happiness over being miserable.

I initially deposited $300 online and played poker nonstop while at the same time enjoying a Flow State (i.e. a mental stage of “complete engagement” with a particular task or challenge). The profit-making aspect of poker was actually a positive side effect of the personal validation associated with striving to become the best at something which is very difficult to obtain.

During my high school days, I would wake up and grind poker an hour before school and then play in the evenings while consuming everything poker-related on the TwoPlusTwo Forums.

Throughout my life I have been a person who learns things by “seeing” them in action. This was one of the great advantages of poker and learning the ropes at $.10/$.25 NLHE ring games.

I eventually ran $300 up to $17,000 in my first year and then told my Dad that school wasn’t working out for me and that I wanted to pursue poker. I wasn’t aware of this back then, but playing poker for a living made me happy. It wasn’t that I was being some sort of rebel by not pursing a more “typical” means of supporting myself. It all boiled down to becoming immersed in something that made me smile at the end of my sessions and look forward to coming back the next day.

I’m hopeful that my story will inspire others to communicate their experiences of how they got into poker. Fortunately my parents were more or less on-board with my aspirations to play poker. That $17,000 swelled into $200,000 by 2008 through my online poker cash game play, and I moved my way up to $10/$20 NLHE.

Live Tournament Success

LAPT San Jose 2008

To celebrate my online cash game success I traveled to Costa Rica to visit some friends and entered an event I hadn’t planned on competing in. This was in November 2008, and I wound up winning the $3,700 buy-in LAPT San Jose Main Event for $285,000. The story of how I registered for that tournament is pretty funny, as we were pretty much landlocked in the hotel. I got drunk that night with my friends and signed up on a lark. That effectively doubled my poker bankroll, which was pretty sweet.

I always thought it would be cool to win a tournament, but assumed that would just never happen since I rarely played them — so it was awesome to win the first live event I ever played in. Online cash games continued to be my main source of income, and I studied obsessively to improve and stay on top of the curve. I did quite a bit of personal growing and maturing during this period, but it all revolved around eating and sleeping poker from 2007-2013.

Breaking Out of Your Shell

I have made a lot of money and met a lot of cool people over the duration my poker career, and eventually parlayed my success into becoming a more well-rounded person.

Ryan Fee July 1 2016

There was a certain side of me that accepted poker as a living, but there was still a significant stigma associated with not following through with the school grind — and I initially felt somewhat guilty about this. But in hindsight, I actually feel the opposite now, and believe a structured educational environment can be counterproductive to the needs of an individual who wants to forge his or her own path through life.

There are a lot of people who go through school, then college, then a “normal” job — and spend their adult life seeking out a role that isn’t quite the right fit for their aptitude or skill set. I got really lucky when I found poker and turned pro, in that it’s a role that I feel comfortable in.

Realistically, most people will not enjoy the level of success in this game that I have. However, the point of this Blog Series is to reach out to aspiring poker players — by sharing my experiences with our Twitch Channel subscribers, readers and Lab users. Most serious poker players fall into this category of individuals who couldn’t quite find the right fit with school tasks and moving on from there to a traditional job.

I hear these stories repeatedly from our fans and friends I’ve met over the years. Poker players can often find themselves afflicted with guilt that correlates with not going down a traditional career path. So the moral of the story is… don’t knock yourself for pursuing happiness.

Of course, I am very fortunate that I found an activity I’m passionate about that also pays the bills… that fact is not lost on me. Yet poker is my vessel for obtaining happiness and enjoying freedom that you simply can’t have working a 9 to 5 traditional job. Poker has become a means to constantly test myself — to learn more about who I am.

Professional Poker and Risk Taking

From my experience, playing poker for a living is actually a far less risky venture than doing something such as attending graduate school, getting an MBA and then going to work on Wall Street. It will take a lot of time and money to go into a related profession. After years of hard work and sacrifice, people can easily arrive at a point where they simply hate their professional life.

I’ve seen this numerous times personally and there are many documented cases of this such as PayPal co-founder, Facebook angel investor and billionaire entrepreneur Peter Thiel.

Image Credit: Getty Images

Image Credit: Getty Images

Thiel’s stint in a prestigious Manhattan law firm shortly after graduating from Stanford Law School in the early 1990s found him desperate to escape a place where “everybody wanted to leave” once they were exposed to its atmosphere. You can read more in this article published by Business Insider (February 2015).

There are certainly people who will absolutely love that type of life, but it’s obvious that the 48-year old German-American had to seek out his own vessel for obtaining happiness and validation. Relative financial success does not automatically guarantee peace of mind. It doesn’t always satiate our needs as human beings to overcome adversity or carve out our own station in life either.

The abstract pursuit of a formidable challenge has been the primary goal throughout my poker journey — not making money. Spending the better part of a decade being miserable during your youth (working or studying insane hours in a controlled environment) is one way to achieve a certain amount of stability… or I could just do whatever I wanted with my life and make the switch back to a traditional career path if chasing happiness didn’t work out.

A decade of nose-to-the-grindstone hardship versus $300 and a shot at The Dream. Selecting poker wasn’t nearly as risky as the other route in my opinion. On top of this poker — even considering the bankroll risks involved — is not an activity that you are necessarily “pegged” to if it doesn’t work out over the course of a lifetime (more on this below).

Share & Compare Experiences

I believe it’s healthy to actively seek out references… situations we can relate to our own personal circumstances and guide us along the way. That could be anything from helping us become a successful poker player to an established investment banker.

As Hollywood film actor Eddie Murphy once said, people are sculptors, “constantly chipping away the unwanted parts of their lives trying to create a masterpiece.” For me achieving success as a poker pro is more closely aligned with how I perceive myself as a person. And the guilt that goes along with bucking the system is something I had to chip away at. Taking an introspective look at our lives can often be beneficial.

For some professional poker players, grinding all-day every day is a natural fit for them to arrive at their own Flow State, which is perfectly fine. However there are others who will get into the online game, have a relative amount of success at it for a few years, then move on — which I also think is great.

A friend of mine (who I’m hopeful will share his story with Upswing readers one day) began his adulthood by completing college. He got a job at Goldman Sachs in the Human Resources department. Despite the prestige, opportunity for growth and institutionalized vibe the goes hand-in-hand with making it into that corporate circle, he was supremely unhappy.

Image Credit: WSJ.com

Image Credit: WSJ.com

So he was interested in poker, took a crack at it and played professionally for a couple of years. He made some money, but eventually realized poker wasn’t for him and found out more about himself in the process. My friend has applied with an HR position with a company that has a for less restrictive office environment, and I think he’d be a really great fit for that job.

For him, poker was extremely helpful in that it gave him time to get out of a circumstance he felt he was “boxed into” and spread his wings in another endeavor. Poker was a winning pursuit for him, and he left the game with a more rounded understanding of himself.

Coming to Terms with Your Own Vision

Albert Einstein

Albert Einstein once said, “Everybody is a genius. But if you judge a fish by its ability to climb a tree, it will live its whole life believing that it is stupid.” Individuals have vastly different mindsets, and methods they experiment with to achieve success. Some may be great poker players but woefully unequipped to make a long-term stab at formal education. Or vice-versa.

Consciously bidding farewell to a toxic environment and discovering your own place to flourish in can be an intimidating experience. Yet even small successes in a profession that is more suited to your strengths can lead to increased self-esteem, confidence and opportunity. I discovered this personally in my journey from micro-stakes online cash to higher limit games.

Branching Out

Starting my own business and becoming an entrepreneur has been one of my goals ever since I remember. Through first-hand experience I’ve learned that having a formal education is a non-factor when it comes to growing a small business — whether that be as a poker pro, business owner or both.

Myself, Doug Polk and Matt Colletta approach Upswing Poker with the aim of doing new, cool, and interesting things for our subscribers and readers. Our day-to-day responsibilities not only allow us to engage with talented individuals within the poker industry, but also grant us the opportunity to constantly explore new methods of communicating with our members and fans.

Ryan Fee May 2016

Because of this, I feel more fulfilled and “content” in my role as a poker player, personality and business owner now than I ever have — with the possible exception of what I felt immediately after taking down that fateful live event in 2008. There is something exhilarating about meeting each day with the goal of providing the most helpful service possible to poker players who are making their own way in the game, and in life — and the positive feedback we’ve received from our users makes taking on new challenges within our business fun.

I could turn my focus to poker tournaments, travel around the world and routinely compete for high stakes in that setting. But choosing mostly online cash games and having the time to concentrate on our users’ needs is more fulfilling. It’s a no-brainer in my case.

Learn to Trust Yourself

Following what you feel is right requires that you trust yourself. You will make mistakes along the way and may eventually have a change of heart… but you should always strive to engage in activities that make you happy. This could be foregoing school for an adventure, changing majors in a formal education atmosphere, or even changing jobs/career paths when you’re miserable.

But there should never be any doubt. Assuming you live in a free country where you can basically pursue whatever dream you want, why would you ever want to go into an endeavor where you’re unsure? Some of you who read this blog may not have a lot of money to scrap together to pursue poker or anything else you please, but if that’s what you want to do, then just do it!

Image Credit: Nike.com

Image Credit: Nike.com

There is a lot of risk in spending your 20s and perhaps even your 30s going through the school, debt and labor grind, then finding yourself locked into a profession you don’t like.

Many of you might enter poker with a long-term vision of making money and achieving a certain level of comfort, but even with this game — sometimes the traditional path to success won’t coincide with a person’s strengths. I see this sometimes in impressionable individuals who are in the midst of developing as a young adult. I wouldn’t advise treating poker as an “end-all, be-all” means to reaching your life’s goals. Rather, you should treat poker as a vessel to discover more about yourself as a person, and use that information to guide you along your way.

If you decide to play poker seriously, ask yourself how comfortable you are with that amount of responsibility, with the schedule, and with the freedom that goes along with it. You may find out after time that you actually appreciate a structured environment more… but you’ll never know until you trust yourself enough to choose to be happy. And if taking a crack at poker doesn’t work out, perhaps there are other pursuits you can turn your attention to that make a better fit — like becoming an entrepreneur for instance.

Surround Yourself with the Right Influences

Image Credit: Friends (NBC) 1994-2004

Image Credit: Friends (NBC) 1994-2004

Choosing your friends and acquaintances is vitally important both in and out of poker. If you’re in a friendship or business relationship with someone and you’re not getting the right vibe from that person, seek out other influences who are more in-line with your vision.

Supply & Demand – The Traditional Career Path

I would like to end by pointing out that the whole educational system mass-produces talent that is tailor-made to enter a corporate workforce. As poker players, we continuously learn about people who have gone the traditional career route and found themselves looking for a job (or accepting a position they’re highly overqualified for). There is not a great demand for certain skill sets because of the overwhelming supply that already exists.

However, there is not a great deal of supply when it comes to individuals who branch out into their own projects and learn from first-hand experience. Carving out an meaning for yourself through this method involves a skill set that many won’t be exposed to in a school or corporate-based setting. Time and again, there are instances where a talented person will spend 12 years going to grade school, move on to college, then enter a workforce that basically tells the individual he or she isn’t qualified to do a damn thing.

So getting into poker can be a great way to expand your skill set — to make it more useful to a larger opportunity pool. Just from my perspective as an Upswing Poker co-owner, I would much rather hire someone who comes in with unique knowledge that can be productive to achieving our goals than a person who is relying on education alone. It’s a choice between someone who knows what’s up and another individual who looks good on paper.


The main point of this blog is to encourage our readers to actively choose happiness. I’d be thrilled to hear your stories and any related experiences from people you have met in poker or in a profession.

Image Credit: Latin American Poker Tour - 2008

Image Credit: Latin American Poker Tour – 2008

You can get in touch with me through the following platforms.

Twitter: @fees88
Email: ryan at upswingpoker dot com (sorry, trying to avoid spam)

Feel free to send me an email with your story or you can also leave your thoughts in the Comments section below.

Best of luck at the tables!

(If you’re interested in improving your poker game, check out the Upswing Lab! Doug Polk and Ryan Fee collaborated on this A to Z training course and the great reviews keep rolling in! Check out our Upswing Lab testimonials page here)

Home > Poker – The Day I Chose Happiness
Home > Poker – The Day I Chose Happiness
About the Author
Ryan Fee

Ryan Fee

I'm a professional poker player and one of the pros here on UpswingPoker.com.

I'm a WSOP Bracelet winner, LAPT (Latin American Poker Tour) tournament winner and a multi-million dollar winner of live & online tournaments.

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