What do blackjack tables, first dates, and entrepreneurial ventures all have in common?

They all require you to decide how far you are willing to go before you start to achieve the best personal outcome.

Or, another way to look at it is that they all require you to know what you really want before you get in the card/dating/business game.

We’ve all had that experience of playing one hand too many… or rounding one too many bases. Our basic human nature has the ability to overcome our premeditated analysis and allow situational momentum to carry us well beyond our rational comfort zone.  The thought process goes like this:

“Well, I know that I said that I would stop at this point, but at the time, I didn’t realize it would be going this well, so I should just go with it or I might miss out.”

When it comes to cards and dates, situational momentum can make you go home empty-handed – or have to endure the walk of shame.  But when it comes to entrepreneurial ventures, it can cause you to overshoot the mark of success and land in miserable territory. 

This fact was illustrated so clearly for me this last month when I ran into two friends at a business conference.  Both women run their own businesses, yet both are in dramatically different places: one had chosen to keep her business a Job Business and one had allowed her business to grow into a Bona-Fide Business (as Carol would say).

Katie, a management consultant, had originally wanted an alternative to her corporate HR role, so that she could earn more and be more available for her family.  Initially, she had worked out of her house and felt like she was fulfilling her goal.  But to keep up with demand, she eventually hired an assistant. And then a content writer. And then a website developer.  And then an account manager.  Before she knew it, she had a Bona-Fide Business… and she kind of hated it.

She had to rent a small office to house her staff, and as the CEO, had to be in the office most days to manage the team, work on sales, and interface with clients.  When the recession hit, her stress level peaked: not only did she have to struggle to keep her own head above water, but she also felt the weight of responsibility for the livelihood of five people.  Now, orders continue to come in, meaning she is contemplating hiring even more people to deliver and be in the field.  “How can I say no,” she said to me over coffee, “this is success, right?”

Not according to Joan.  Like Katie, Joan left her position at a biotech giant to start doing product design work on her own because she wanted more flexibility and money.  When more business than she could personally handle started to come in, Joan opted to subcontract with a few trusted freelancers to reduce the burden on her and maintain her independent role.  “If business is good, I can give them more work, and if it is slow or I decide to go to Cambria for a month, I can go without any worry.” Joan told me between conference sessions.  “I don’t want to be a CEO; I want to be exactly what I am.”

The moral of the story is that a key factor in entrepreneurial success is knowing what you want and having the awareness and good sense to override situational momentum when it calls you to move beyond how far you really want to go.  No one wants to go home broke.  Or wakeup next to a swamp creature.  Or realize that they are unhappy and unfulfilled in a venture they’ve worked hard to build for themselves.

So, as you move through your day today, I encourage you to seriously think about what you really want and how far you want to take your business.  There is no right answer and your personal results may vary, but there is a wrong answer and that is “I don’t know.”

So, what do you think?  Where do you want your business to go?  Are you creating a job for yourself or looking to be the next big thing?  I’d love to hear your thoughts.