Gambling With Your life Thumbnail

Is it time for you to take some risks?

As many of you know, in addition to rambling about how to buy a car, I’m a bit of a poker junkie.  I find it both intellectually stimulating and a mildly profitable hobby.  It’s also a great source of personal finance analogies!

Professional poker players and entrepreneurs have many things in common.  Both take risks to achieve the lifestyle they want to live and succeed financially.  Poker players take a risk on every hand they play, while entrepreneurs take risks by investing their time instead of spending it other places (like a traditional job).

The key to winning at poker and entrepreneurship is not giving up when you lose a bet or an idea doesn’t pan out.   Dan Harrington (my favorite poker strategist) explains a fundamental rule of wagering:

“All successful gambling is based on one simple idea: making good bets at favorable odds…over time, if you kept making the same bet, you would win money.”

A successful poker player will consistently make bets when given the proper odds.   And over the long run they will be profitable.  The same goes for an entrepreneur.  If you take risks and invest time (and occasionally money) on good ideas, over the long run you should succeed, even if there are a few lost wagers along the way.

Three types of risk takers

Extending the poker analogy, entrepreneurs can be divided into three categories based on the amount of risk they are willing to accept:

The Grinder…works some type of side hustle, to supplement her income or to express herself creatively.  She’s not actively looking to quit her day job, but has extra energy and wants to apply herself to something stimulating.  Bloggers are often grinders and can make a decent amount of extra money with a little bit of traffic and luck.

The Semi-Pro…has initiative and wants more freedom (and money) than her day job can provide.  But she’s somewhat cautious and wants to keep her safety net intact while she tests the waters.   She may want to establish a foundation in a new venture and reduce some uncertainty before making the plunge full time.

While the Semi-Pro and Grinder are very similar, the Semi-Pro wants her side hustle to become her full time gig and is taking steps to achieve her dream of becoming…

The Shark…drops everything and learns to swim…QUICKLY.   This lifestyle is not for the faint of heart.  The Shark usually has a ticking clock to make something happen before she runs out of money to pay the bills.  You need to have a lot of gamble in you, but this option can end up with the biggest payback.

What type of entrepreneur are you going to be?

I choose the path of the Shark ten years ago.  I left my 8-7 job without a safety net and an overwhelming drive to run my own life.  I’ve found the freedom to be both invigorating and terrifying at the same time.  And while I’ve yet to make enough money to stop watching the clock, I live comfortably and am happy to know that I still hold a lottery ticket that may someday payoff big.

But while becoming a Shark is exciting, often times the smarter approach is to try your hand at being a Grinder or Semi-Pro first.  If you keep your day job and put in some nights and weekends the risk is minimal.  You only give up a few hours of free time for the potential of a new life.  What are your interests? See if you can turn a hobby into something profitable.  Do you like writing? Maybe blogging is for you.

If you’re not satisfied in your day job, maybe it’s time to consider taking a few risks to lead the life you want to live.  I’m not suggesting you become a Shark, but anyone can run a small grind.  It only requires a little risk and a lot of hard work.  Even if you never achieve an obscene pay day, think about whether you’d be happy just being able to support yourself while being your own boss.  Or see if you can simply generate enough income from your hobby to pay for a night on the town once a month.

Going out on your own can be a path to wealth and living the lifestyle of your choice.  All it takes is a wager on yourself.  I’ll leave you with another favorite quote:

“Entrepreneurship is living a few years of your life like most people won’t, so that you can spend the rest of your life like most people can’t” – Anonymous


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It’s 2015 and the bull market continues. Make a decision to be wealthy by taking control of your finances!