Lately I’ve grown interested in 30-day challenges. I see bloggers and vloggers talking about skills they’ve learned or goals they’ve accomplished over the course of a month. Some of what they pull off is pretty amazing.

I’ve watched people learn how to spin a pen over their thumb, lose 8% body fat, and learn to solve a Rubik’s Cube in seconds—all over the course of 30 days.
It occurred to me that gamblers might enjoy some 30-day challenges, too.

Here’s a list of 10 goals you can try to achieve as a gambler over the next 30 days. Not all of them will require 30 days, though, and at least one of them will take longer than that.

Nonetheless, these gambling challenges are certain to spice up your gambling hobby:

1- Win a Poker Freeroll Tournament

Many poker cardrooms, both online and off, have freeroll tournaments. These are tournaments with n entry fee, but they still offer cash prizes.
So here’s the thing about gambling:

It’s all about expected value.

That’s just a fancy way of looking at how much you risk versus how much you stand to win. It also accounts for the likelihood of winning or losing. Since there’s no entry fee for a freeroll, the expected value is always positive—as long as there are cash prizes.

Most freerolls have a lot of entrants, though, so you face a lot of competition for the cash prizes.

A few years ago I read about a challenge that Chris “Jesus” Ferguson engaged in. His goal was to win a freeroll, then use that money and careful bankroll management to build $1000 from nothing. The point was to prove that poker is a game of skill and that an expert could get from point A to point B via skillful play and careful bankroll management.

Starting with a freeroll is one way to do the same thing in your own life.

Becoming a winning poker player is a worthwhile goal to achieve.

2- Win $1000 Playing Slot Machines or Get a Royal Flush Playing Video Poker

Slot machines are a negative expectation proposition. If you play long enough, you’ll go broke.

But also, if you play long enough, you’ll almost certainly win a jackpot sometime.

My suggestion to set a goal of winning $1000 playing slot machines is a suggestion to play until you have a winning session where you win $1000.

Most flat top slot machines—games where the top prize is fixed, rather than progressive—pay off 1000 for 1 for their top prize.

The probability of winning that top prize is, of course, much lower than it would be if the game were a break-even proposition. The casino has to make money, after all.

$1 slot machines are probably the best games to play to try to achieve this goal. And your goal isn’t to have a net win of $1000. It’s just to play until you hit a jackpot.

Once you’ve done so, I think you should quit playing slot machines forever. You’ve won a jackpot. Now move on to gambling games with better odds.

An even better challenge is to try to hit a royal flush on a video poker game. That’s the top prize on every video poker game I know of, and the odds of winning are better than they are with slot machines. Video poker does require a certain amount of skill, too—so go buy a book about how to find the best pay tables and play with the best strategy.

A royal flush comes up, on average, once out of every 40,000 hands. At 600 hands per hour, you should be able to hit a royal flush within 67 hours.
You’re not guaranteed that, though. You might hit your royal early in the cycle, or you might hit it late in the cycle. You could hit a royal flush on the first hand you play.

Be sure to insert your slots club card when trying to achieve this challenge.

You should get all the “free stuff” from the casino that you’re entitled to.

3- Double Your Money at the Roulette Tables

The easiest way to double your money at the roulette table is to make a single large bet on one of the following:

  • Red or black
  • Odd or even
  • High or low

In fact, the bet doesn’t have to be for a large dollar amount. You can do it for the table minimum if you want to.

The trick is to make one bet and walk away, win or lose.

This is one of the easiest and fastest challenges on the list.

On an American roulette wheel, your probability of winning one of these even-money bets is 47.37%. You have 18 ways to win and 20 ways to lose, or 18 out of 38 possible combinations that win.

On a European roulette wheel, the probability of winning is better. You only have 19 ways to lose an 37 total possible combinations. The probability of winning this bet is 18/37, or 48.6%.

The probability of doubling your money at the roulette table goes up as you make fewer bets, and it goes down as you make more bets. That’s because roulette is a negative expectation game.

The more bets you make, the likelier you are to get results similar to the mathematically expected results.

If the probability of winning a single $500 bet at the roulette wheel is 47.37%, the probability of winning one $250 bet after another $250 bet is much lower. That’s because you have more possible outcomes:

  • You could win both bets.
  • You could lose both bets.
  • You could win the first bet but lose the 2nd bet.
  • You could win the 2nd bet but lose the 1st bet.

Only one of those 4 outcomes results in doubling your money.

And the more bets you make, the harder it gets to double your money at roulette.

This is a fun challenge, but don’t bet money you can’t afford to lose on it.

4- Have a 1-Hour Winning Session Using the Martingale System

Most roulette players have a passing familiarity with the Martingale System. It’s just a betting system where you double your bet sizes after a loss. You recoup your previous losses and show a small profit after a successful series of double-ups.

Here’s an example of how it works:

You’re playing roulette at a table with a minimum bet of $5, and you bet $5 on red. You lose. Now you bet $10 on red. You lose again. Now you bet $20 on red and win.
You lost $15 on the first 2 spins, but now you’ve won $20, which means you got the money you lost back. And you have a $5 profit besides.

In the long run, the Martingale System doesn’t work. The logic behind it ignores the fact that having long losing streaks is more common than most people think. Also, if you’re doubling a number repeatedly, it becomes very large much faster than you think.

If you double a $5 bet repeatedly 8 times in a row, you’re having to risk $640. Most roulette games with a $5 minimum have a $500 maximum bet. The system doesn’t work because you can’t make the next bet in the scheme.

But in the short run, you can see small winning sessions with the Martingale System. In fact, if you stick with short gambling sessions, you’re likelier to win a small profit with the Martingale than you are to lose.

You might win 4 times out of 5, but on that 5th game—the one where you lose—you’ll usually lose enough money to make up for the 4 winning sessions.
That doesn’t mean you shouldn’t try it.

5- Win $100 Playing Scratch-Off Lottery Tickets

I’m not a proponent of the lottery at all. I know that some of my readers enjoy playing lottery games, though. In fact, in some locations, it’s the only gambling game in town.

I know one thing about the lottery, though. The scratch-off tickets are the best in a batch of lousy games.

The payback percentage for most lottery tickets is 50% or lower. You might be able to see a payback percentage of 60% or 65% playing scratch-off tickets, though.
That’s a lousy payback percentage compared to slot machines or video poker games. But it’s better than the other lottery games.

One of the tricks to making this work is to play scratch-off tickets that aren’t associated with some kind of trademark. Since the lottery corporations have to pay for trademark usage, the payback percentage on such games is lower.

Another trick for winning at scratch-off lottery tickets is to pay attention to how new or old the game is and whether the big prizes have been won by someone else or not.

You see, with a scratch-off game, the company prints X number of cards with Y number of winners on them. If half of those cards have been sold, and no one has won the big prize yet, the expected value of those tickets is almost double.

Finally, the payback percentage for scratch-off tickets is higher when you buy the higher-priced tickets. If you stick with the $1 tickets, you’ll see the lowest odds of any scratch-off game.

But if you buy the $10 or $25 tickets, you’ll see a better return. It will still be a negative return in the long run, but it will still be better than you’ll see playing the $1 games.

As with the slot machine challenge, I suggest playing until you in a lottery jackpot then never play again. You can find better gambling games with better odds.

6- Count a Deck of Cards as a Blackjack Card Counter

Counting cards isn’t just for idiot savants. Heck, even Ben Affleck can do it. You don’t have to memorize an entire deck of cards, either.

Card counting uses a heuristic system to estimate the percentage of high cards to low cards left in the deck. Aces and 10s are considered high cards in blackjack.

The goal is to place bigger bets when you have more 10s and aces left to be dealt, because you’re more likely to get a blackjack and the corresponding 3 to 2 payout.

The simplest card counting strategy that most beginners use is the hi-lo count. It’s a single level, balanced count. You just add 1 every time you see a low card (2, 3, 4, 5, or 6) and subtract 1 every time you see a high card (10, J, Q, K, or ace). Since you have the same number of +1 cards as you have -1 cards, if you count through a 52-card deck, you’ll wind up with a total of 0 when you finish.

Does this sound easy?

It’s harder than you think.

The first time I tried to count through a single deck of cards at my kitchen table, I came up with -3.

The second time, I got +2.

I didn’t get an accurate count (a total of 0) until my 5th try.

Counting cards takes more focus and skill than you might initially think.

Being able to count through a single deck at your kitchen table is a good starting point, though.

7- Have a Winning Sports Betting Season

To win at sports betting, you need to have a 53% or higher winning percentage to compensate for the amount of the vig. Winning 53% of the time against the spread is harder than you might think. After all, the handicappers are good at what they do—so they set the lines in such a way that they expect a 50% probability of winning.

When the sportsbook forces you to risk $110 to win $100, you have to be really good at picking winners to compensate. If you lose $110 half the time and win $100 half the time, it doesn’t take long to realize that you’re going to lose money in the long run.

Look at the math:

If you win 53 out of 100 bets, you’d have $5300 in winnings. Then if you lost 47 bets of $110 each, you’d have $5170. That’s $130 in winnings over 100 bets, which isn’t much.

But it’s also a minor miracle.

To succeed at this challenge, I suggest you start by specializing in a single sport. Most people like to bet on professional football. That’s the easiest sport to make straight bets on with a point spread.

But if you hate football, you could also specialize in baseball, basketball, or hockey.

If you’re going to succeed in this challenge, it’s a great idea to read Sharp Sports Betting by Sanford Wong, too.

8- Host a Home Poker Game

Every gentleman should know how to host a home poker game. It wouldn’t hurt a woman to know how to host one, either.
But it’s a requirement for men and just an option for women.

If you’re going to host a home poker game, you need a set of clay poker chips. Don’t use cash at the table, and don’t buy cheap plastic chips. No one enjoys that.
You can find the chips you need on Amazon, and they’re not that expensive.

You should also have at least 2 decks of cards, although 4 is better. I like to buy expensive plastic cards like Kem cards. They’re almost impossible to destroy, but they cost significantly more than Bicycles or Bees. Don’t go cheaper than Bicycles or Bees, though. Those cards aren’t fun to play with either.

Since you’re hosting, you should probably also act as the banker. When the players buy their chips, you hold the cash. When they’re ready to cash out, you buy the chips back from them.

Be sure to invest in some change, too. I played at a home poker game recently where everyone bought in with $20 bills. At the end of the night, I had $67, so the host had to give me $80 with the understanding that I owe him $13. Save yourself the hassle and have some smaller bills there to make change with.

You should invite at least 8 people. You can’t realistically play poker with fewer than 4 players, and some people will RSVP and not show up anyway.

You should also decide on the house rules. In my home poker games, I require everyone to announce their bets aloud to avoid confusion. We also play dealer’s choice, which is great, because most of the responsibility for adjudicating the bets falls on the dealer.

I know that in some home poker games, check raising is frowned upon, but I allow it in my games. It’s a standard poker maneuver, even if it does piss some people off.

I also ask everyone to contribute $10 to the house, but I provide drinks and food. I stock the fridge with beer and soda pop. I serve hot food, but it’s always something people can help themselves to out of the crockpot. Meatball subs are popular, but I’ve also had a lot of people enjoy barbecue sandwiches.

If you enjoy hosting a home poker game, you should try making it a weekly event.

9- Learn a New Poker Variation

Let’s say you’re a break-even or even a winning Texas holdem player, but you never play any other poker players. It might be worth your while to spend a month learning how to play Omaha 8 or better.

When I say “learn a new poker variation,” I don’t just mean learning the basic game rules. Anyone can learn that in moments. I mean learn how to play well enough that you can break even or win at the game.

This gives you more options to find juicier games in the cardroom. With more games to choose from, you have the option of leaving the Texas holdem tables for the Omaha tables if the action there seems juicier, and vice versa.

If you only play one game well, you’re stuck there.

It’s never been easier to learn new poker variations, either. You can find a strategy book about any variation of poker you can think of. In fact, if you don’t know how to play Texas holdem well, you can find dozens of excellent books. Anything from Two Plus Two is worth reading.

You can also practice other poker variations on the internet for free or for real money, too. In fact, since you can play for much smaller stakes online, it’s often a good idea to learn a new poker variation at a web-based poker room.

10- Read a Book about a Specific Advantage Gambling Strategy

Advantage gambling strategies are tactics you can use when gambling that give you a mathematical edge. With most gambling activities, the edge is with the house, the sportsbook, or the cardroom. Overcoming that mathematical edge in the long run is no small feat.

This is well-trodden ground, though. Card counting in blackjack has been covered in detail in multiple excellent books. You can find volumes about playing poker better than your opponents, too. You’ll have trouble finding good books about betting on sports, but spending a month studying Sharp Sports Betting isn’t a bad way to spend a month.


If you’ve enjoyed watching YouTube videos of people completing 30-day challenges, maybe it’s time you took on a gambling challenge of your own. I bet a lot of people would love to read your blog post or watch the video you make about your results.

What ideas do you have about gambling challenges you could undertake?

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