“Robbie, if things don’t work out, you can always go out and get a job again… Your site won’t disappear, you could still work on it at nights and on weekends, like you’ve done until now.”

Those words, from my wife Miriam, were meant to be comforting, but they actually haunt me.

There I was, leaving my job, jumping off the diving board into a world of the unknown, and rather than casting out a safety net, it almost sounded like a sucker punch. If I’d ever have to abandon self-employment and go back to that lifestyle of an employee, I’d be crushed. More than a desire to succeed, a fear of failure has also lit that continuous fire under my ass for the last year… this venture better be successful; it HAD to be!

And here I am, looking back now on the 1-year anniversary of the last time I clocked in to work, and I couldn’t possibly be happier and more grateful. My “trial year” has come to an end and thankfully I’ve not just met, but in fact exceeded the goals I set for myself. There WILL, in fact, be a year #2!

The Highlights

I mentioned “a world of the unknown” and that’s a description that’s pretty apt. As ambitious and hopeful as I was to have a successful year #1 doing poker media work full-time, there’s no way I could’ve expected some of the things that have happened over this past year to happen. Here’s a very partial list of some of the major highlights:

TRAVEL

RECORDS

  • We published almost 200 articles
  • We’re now averaging approximately 10,000 unique monthly visitors to this poker site
  • I generated 10% more income than the one-year target I had set myself

PERSONALITIES

The Ups and Downs

In addition to the above-mentioned highlights, we migrated the Top Pair Home Game Poker Podcast, which I co-host along with Bruce Briggs, to the prestigious PokerNews Podcast Network (story here). I had my first ever public speaking engagement at the Wednesday Poker Discussion Group (WPDG) in Las Vegas and completed my first 1,000 km #charitypoker Running Well challenge. Of course, there have been many other exciting and interesting things that happened as well as phenomenal people in poker who I’ve gotten to meet with and interview over the last year (way too many to list in further detail).

One of the biggest blessings of no longer having to “clock in” for work is the absolute, unbridled freedom you get. There’s no longer a boss to report to or pre-set benchmarks you’ve got to hit. I save three hours each day not having to commute. I have the liberty of saying “yes” to pretty much any potential opportunity that comes my way without worrying about any sort of conflict of interest. I get to spend more time than ever before with my wife and children. I got to take a month-long holiday over the summer, road tripping the U.S. East Coast with my family, all the while being able to keep on working, as all I needed to do so was an Internet connection. I set my own hours and worked whenever we didn’t have activities planned… it was surreal, and fantastic!

rollercoaster

On the flip side, there’s also the unrelenting pressure of self-employment. You constantly have to be a self-starter, come up with ideas, brainstorm, find advertisers and sponsors, pitch ideas to potential partners, etc. There’s no sitting back on your laurels waiting for that guaranteed salary to come in at the end of the month, even if you’ve done a less-than-stellar job. There are no employer-match pension benefits, stock options, year-end bonuses, sick days, paid vacation time, or any of the numerous other perks that come with working for a big company. It’s easy to think that everything is right with the world as money flows freely during summer’s WSOP season, but then February rolls around and you start wondering “where did all the business go?” Like in any industry, there are ups and downs over the course of the poker year, and it takes a lot of (for lack of a better phrase) “intestinal fortitude” to be able to withstand and ride its ebbs and flows.

Moving Forward

In the interests of full disclosure, I’ve made FAR less money over this past year than I would have, had I stayed an employee. Yet, I have precisely zero regrets whatsoever about the decision I made to set out on my own. Perhaps the best part of this adventure is that for the first time in my life there’s no longer any sort of nagging voice in my head to “take time off and have a vacation.” I’m doing what I absolutely love to do and while I’ve worked hard this past year, it sure doesn’t feel like “work” in the traditional sense. It’s almost like I wake up every day and AM on vacation! It took me many years to 1) realize this and 2) be able to get to the stage where I could act on it, but I’m an infinitely happier person chasing my own dreams; it’s the type of happiness that money simply cannot buy.

Of course, bills still have to be paid, I’ve got a family to help support, and it’s not like I’ve retired; LOL! Far from it! The goals that I’ve set myself for year #2 of self-employment are quite a bit higher than those of year #1. Upon crunching the numbers, thankfully I was able to prove over the last year that self-employment in poker media is possible, even for a 36-year-old family man living in Israel. Now I need to prove that a full-time Cardplayer Lifestyle is sustainable.

to infinity and beyond
Image for illustrative purposes only

I don’t know how to adequately describe how encouraging it is to look back at this past year of my (poker) life. My outlook for year #2 is certainly a positive one, I’ve got some big plans, and I’m very confident it will be a great year. Specifically, there’s one thing I’d like to try and start doing differently, namely being proactive rather than reactive on the funding front, so that I can showcase an increased amount of excellent work from my contributors.

Yet, much like in the game of poker itself, there’s no guarantee that #rungood for any length of time will continue. Things could potentially turn sour at any moment, but I’m not in the business of letting any negativity creep into my thoughts; there’s just no reason for that. That quote from my wife, with which I opened this essay, for better or worse, will always hang over my head.

In the meantime, it’s upwards and onwards into year #2. Thanks to all of you, dear readers, for sticking with us, sending words of encouragement, subscribing to our monthly newsletter, liking, sharing, and commenting on our articles on social media, and in general just showing that you care.

Unlike my annual poker blog anniversary posts, I don’t think I’ll be producing something similar to mark this yearly milestone in the future, but at least this one time, it’s an occasion worth marking and celebrating. I feel so fortunate to be in this spot, and it’s something I will never take for granted.

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