We’re in the throes of September, so for most of us (in the Northern Hemisphere, at least) that means summer vacation is now a slowly fading memory. I had the good fortune to spend almost the entire month of August on holiday with my family in the Eastern U.S., half in the New York/New Jersey area and half in New England, primarily Maine. A major component of how we’re able to do that is the fact that both my wife and I are self-employed.

Strictly speaking, all we need is an internet connection and we’re able to work from anywhere in the world. We’re also able to work whatever hours we wish rather than have to clock in for a typical 9-to-5 job. That sounds great – and it is! – but while being self-employed means you can take off and vacation for as long as you’d like, it also means that all vacations are essentially “unpaid leave.”

Funny as it might sound, taking a vacation from running a poker business (or any business) can present a number of challenges; I know I certainly faced quite a few! If you follow me on social media and subscribe to Cardplayer Lifestyle’s monthly newsletter, you might be aware that something’s been a bit amiss for a little while, as I’ve dropped subtle hints here and there, but I haven’t really come out and said anything too publicly. Part of the reason for that is that it would seem quite unrealistic and “first world problem-y” of me to complain… after all, I was on vacation! I was having a great time with my and my wife’s extended families. I’m sharing gorgeous pictures…

That all might be true, but pictures – the 1,000 words apiece they might represent notwithstanding – almost never tell the full story. Great as my summer vacation was, there was an underlying roughness to it that up until now I’ve dealt with privately.

Rather than wallow in negativity and self-pity, however, I’ve decided that now is the right time to share some of the challenges I faced in running my poker business over the summer. The reason? I know it will be a blog post I can always turn back to for inspiration when times get tough once again. After all, it’s September and I somehow made it through the gauntlet, right?

Time

For better or worse, I’ve grown accustomed to living with a certain type of guilt over the past two-and-a-half years since becoming self-employed. There’s a constant, persistent feeling I’ve developed of “if I have time available, I should be using it to move my business forward.” Sure, I take breaks, I watch YouTube videos; hell, I sometimes even take a short midday nap! I just can’t seem to do any of that without feeling guilty that “I could’ve been working.” Mentally getting myself out of that place was a huge challenge for me.

By definition, part of being on family vacation means spending extra time with one’s family. I didn’t fly halfway around the world from Israel with my wife and three kids just to keep sitting in front of my laptop and working all day. Indeed, save for one day out of the entire month, my pure work time was limited exclusively to a couple hours each night after the kids fell asleep. In effect, however, I still “worked” here and there throughout the day each day. Nowadays, with our smartphones, we’re never fully disconnected.

Thus, when an urgent email came in that needed to be addressed, I was on it like moss on a Mississippi tree stump. I pre-programmed some social media posts to share the content being published here, but some comments and replies are far better responded to immediately rather than 12 or 24 hours after the fact. Diving into your work world via your smartphone means you’re not “present” to watch your kids playing at the park even though you might physically be sitting right there on the bench. It means your wife might get (rightfully) upset with you for constantly staring at the new notifications as they pop up instead of keeping your eyes on the road from the driver’s seat.

It’s a tough balance to strike. There’s nobody to “take over for me” when I’m away. If I’m not running the business, the wheels don’t keep turning. Nobody wants to visit the Cardplayerlifestyle.com homepage and keep seeing the same articles front and center for weeks (or even days) on end. This is a poker media site and the hungry content beast needs to constantly be fed. Thankfully, my wonderful contributing writers helped fill the void in my “absence.” Chief among them was Geoff Fisk, who traveled to Spain to provide EPT Barcelona coverage for us and pump out great interviews and features from the Catalonian capital. Even so, I still functioned behind the scenes as the site’s editor.

Anyhow, as much as I wanted to allow myself to just STOP, I couldn’t do so completely. But THAT’S OKAY! When all was said and done, this vacation was the most relaxing period of time I’ve had in years. Challenges notwithstanding, that’s what I’d call a success.

Money

Money is a topic that almost all of us always prefer to keep quiet about, myself included. It’s nobody else’s business how much money one makes, and as far as having financial challenges go, it’s tough to admit when you’re having them. There’s strength in vulnerability, though, so before I begin, for those of you wondering how my poker business actually makes money, I spoke about that last year in detail with my good friend Barry Carter on his Poker Media Pro site.

It goes without saying that one ought not to spend beyond one’s means. That’s something I’ve thankfully always been quite good at, even as a kid. You don’t just decide to head off on a month-long vacation without being financially prepared. With that said, in the weeks leading up to our vacation, we took a number of hard, unexpected hits to our cash flow.

For starters, after close to a decade without any hiccups, all of a sudden not one, not two, but three new business partners of mine with whom I had made deals decided to withhold payment for services rendered. Let’s just say that it was unpleasant in multiple ways.

Next up, I plain and simple struck out on every single potential business opportunity I had tried to drum up during the World Series of Poker. Having spent two-thirds of the WSOP in Las Vegas, I used the opportunity to try and network, build relationships, and set the stage for some potential collaborations with a number of individuals and companies in the poker industry. To boot, I unfortunately even lost my gig as the host of the Red Chip Poker Podcast (listen here for details).

Naturally, one can’t expect every pitch to connect for a home run, but this summer represented the first time that not a single initiative of mine ended up materializing. It’s nobody’s fault, of course, nor am I bitter about having gone down swinging. There are a number of reasons why a business deal might not work out or why a business relationship needs to end: perhaps there’s no marketing budget available, maybe my platforms and services aren’t the right fit for certain potential partners, or it’s possible that an organization wishes to redirect its resources to other ventures that might yield higher profits. Regardless, it’s a bitter pill to swallow.

As for the trifecta, I’ve got to give thanks to the good old Internal Revenue Service. Without going into too much detail, apparently we underestimated the amount of money I was “supposed to have earned” last year, and I “made too much, without having paid them enough” so the good folks from Washington, DC sent me a pretty startling notice to that effect just as I was about to embark on my family holiday.

Yippee.

When a perfect (shit)storm like that hits you, no matter how financially prepared you are, you’ll be adversely affected. To have it hit and be affecting you while you’re ostensibly supposed to be having a blast and vacationing with your family is surreal to say the least. What can you do? Not much else other than hunker down and wait for the storm to pass, while preparing to rebound and get back to normal.

Oh, and when your social media feeds are constantly being bombarded by news of poker players notching ever-higher scores in 5-, 6-, and even 7-figure buy-in events, you can’t help but shudder.

If they only knew what the “real world” was like, right?!***

Oomph

I mentioned earlier that my work time during the month of August was almost exclusively limited to a couple hours at the end of each day. That’s not to say that I actually worked each night for a couple hours. As a matter of fact, more often than not, I didn’t. For the first time in what had felt like ages, I allowed myself to do some binge-watching of movies and TV series.

Quite frankly, by the time the kids finally dozed off most days, I was completely drained. Notwithstanding the fact that I work better at night, generally speaking, each day’s activities sapped me of my energy. If your standard workday is spent indoors, in air conditioning, in front of a screen, being outdoors in the sunshine and quite actively moving about expends a LOT more from your batteries.

And of course, I had all of those aforementioned financial issues worrying me either at the back or at the forefront of my mind, depending on the time of day…

More often than not, I found both my physical and mental reserves fully tapped and I simply didn’t have the oomph needed to begin working late at night. Plus, I kept telling myself “Robbie, screw it, you ARE on vacation! You ARE allowed to relax and have some downtime for yourself! Your poker business and all that work you need to get to will still be there for you when you’re ready to get back on the horse.” Nine out of 10 times that last argument won out.

I relaxed.

I let go.

I binge watched.

It was fun.

I barely got any work done.

AND THAT’S OKAY!

Conclusion

Part of the reason I wrote this post is that it feels like way too long since I’ve been able to sit and truly write. For well over a month, I’ve had a number of thoughts brewing in my head that I just haven’t had the time or energy to sit and compose. This is a good first step, and boy does it feel good to finally fully express my thoughts and feelings once again.

I mentioned “having made it through the gauntlet.” It’s not as though all of the challenges I listed suddenly dissipated into thin air when September arrived. It’s just that I’m back home in my regular routine now and doing my utmost to get back to business as usual. Having a “work hard, play hard” motto means that you do eventually get to play hard, but once play is over you’ve got to get back to working hard.

The other reason I felt that penning this piece was a good idea is that I imagine the thoughts and feelings I expressed might resonate with many people, pros and recreational players alike, as well as other small business owners beyond the poker realm. I often feel like a lone wolf, running my poker business on my own and not really having “office mates” to share my sentiments with. It would seem that the same is true for a poker player, whose business is by definition attempting to make money to support oneself via playing the game.

In a column I published at the end of July, a number of well-known poker pros shared how they’d be spending their time in the aftermath of the World Series of Poker. Just as the point of compiling an article like that was to give helpful ideas to you all, I hope that by sharing my own experiences I’ll have helped you in some way.

Finally, I encourage you to also find ways to express yourself about the challenges you’ve faced in similar circumstances, rather than keep things bottled in. I don’t know how “successful” this article will be in terms of Web traffic, but I certainly feel a lot better now than I’ve felt in quite a while.

***Disclaimer: I imagine that sentence in particular might trigger lots of emotions among the professional poker player community of high rollers. Of course I mean no disrespect towards you, your lifestyles, or your achievements. You’ve all worked your tails off to get to the stage you’re at, playing for those nosebleed stakes, and I respect that. All I ask is that you acknowledge the validity of that statement juxtaposed with my feelings in the context they were given above.

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