Winning the Side Business Lottery

I like playing the lottery.  I admit it.  My mother will see me buy a ticket and say in her whiny Fran Drescher voice “Oh Michael, you have grandma’s gambling gene”.  She’s right.  

I’m intelligent.  I know that the lottery is a complete waste of money.  The odds of winning are less than ‘slim to none’.  I do it because, well honestly, I have lost hope in true independence.  I’m paying for a daydream.  When their is talk of a headcount reduction that causes the churning in my gut to start or when an obscene complete luxury comes out that I want but can never afford.  Maybe I get depressed when I think about how long it’s going to be to pay off the mortgage or I want to give up because I have kids that will probably be around until the mortgage is paid for.  The lottery is a way to put a balm on life, it’s the placebo for our existence. A $2 mega-millions ticket is a great way to distract myself on a really bad day, and who knows, maybe I’ll win a smallish prize like $500 and can take my wife away for a weekend that includes a B&B and a nice dinner.   

Like Most professionals I enjoy working.  I love having an expertise in something, what I identify as my speciality, and accomplishing tasks related to it.  Even if I could stop work entirely I wouldn’t and there are very few people I know who would stop and just fish or travel for the rest of their lives.  So why not take these skills I’ve learned and start a business?  Why not do it – whatever it is –  for myself and do it full time.  It can be done, sort of.. I know a few people who were successful, some very successful.  But there is huge risk involved.  I have learned that successful entrepreneurial independence is a combination of unique elements including a certain type of personality and personal luck, and more luck, and even more luck.  Part of that luck can be a spouse that’s supportive of your endeavors and and has a stable and well paying position.   Mostly it’s right place right time.   

If you don’t have that luck then you need one heck of a runway.  We live in an age where healthcare is so expensive it’s laughable to think about paying out of pocket for it.  Where housing comes with the aforementioned mortgage that pretty much starts at a 30 year commitment and never seems to end.   Insurance, Housing, groceries, daycare etc.. they all require regular monthly payments.  Unless you are very well funded for a few years, your not going to be able to jump in feet first.  So what do we do?  

The answer is that we buy the lottery ticket of life, the side business.  There are life traps to be sure in this, especially if we pick the wrong one.  You can usually tell the wrong one because it’s seductive.  The best ones tend to be personal services, like cleaning, wood working, odd jobs, engine repair, or maybe be a wedding DJ etc. These aren’t exactly the types of jobs that lead to economic independence let alone prosperity.  There are simply only so many hours in the day and our services are being sold by the hour, even if we are getting $100/hr we still have to sleep.  These are like a $1 scratch ticket with a small grand prize of $5,000. Even if you won the prize you’d get very little money, certainly not enough for financial independence.  We can attempt to do something related to intellectual property.  You could create music or a video game, or maybe do things like i’m doing, writing a blog or a book.  Unfortunately as anyone who has coded an app for iOS or Android will tell you, the negative of the information age is discoverability.  If you don’t win the lottery of being featured in the store then you are doomed to obscurity.  Your best case scenario is similar to buying a bunch of mega-millions tickets.  You’ll most likely win a few bucks but there is a very slim chance you’ll win the big prize, yet you occasionally see, and sometimes even meet someone who did win, maybe not the full jackpot, but one of the ones that is big enough actually has an impact on your life.  For example, I personally know two people who have won a million or more.  

So like many other professionals I like to play the lotteries, both the side-business and traditional.  I’ll buy my mega-millions tickets and i’ll continue to write this blog and eventually, one day finish the book and get it up on Amazon. – Some days I wonder what will take longer, paying off the mortgage or finishing the book.  The book won’t be a best seller, heck I joke if I sell one copy to my mother i’ll feel like i’m doing good.  But you never know, maybe i’ll get featured in an eBook store somewhere and earn a few hundred bucks.  If that’s the case I hope my wife’s bags are packed because i’ll take her to a really nice B&B.  I’ll just have to write the second book really quick to pay for the baby sitter.