As a midlife entrepreneur in the midst of starting a business and trying to exit the corporate world I find myself dealing with the conflict of whether or not to hedge my bet and keep the day job as long as possible or go all in and hope the net will catch me when I jump.  For each entrepreneur that has achieved success one way there is another that preaches getting started with the opposite method.  What I have come to see is that every family and business is different.  Circumstances dictate what is possible and your unique set of skills makes a tremendous amount of difference.  Lets take a closer look at the defining factors that determine the steps you should take on the journey from burned out employee to globetrotting Mogul.

      • One of the first and most important factors in this equation is….  How Much Do You Have To Lose? And how much are you willing to lose?  The entrepreneurial journey is a mess of broken dreams and burned out failed businesses, many of which were just about to succeed or not allowed to fail fast enough.  The result is failure, frustration and disappointment, which has hopefully translated into valuable lessons, wisdom and insight.  The point being, that the less you have to lose or if you are just careless and not really worried about losing then you will be more likely to succeed.  If you are a family man and father of 10 with kids in college and a single income, you have a lot to lose and a high level of responsibility.  The truth is that as a husband and father it is your responsibility to provide for your family.

Some choose to not heed this responsibility and instead carelessly and selfishly barrel     down the path of financial ruin.

What is most difficult about this particular situation is that there is a certain level of motivation and do or die associated with the jump.  The theory that hedging your bet will lead to taking the path of least resistance and remaining in an unhappy but stable situation is also common.

This choice ultimately comes down to you and your family’s level of risk tolerance.  What is certain about either approach is that once you have made your decision you must commit to doing the work.  Both approaches require a tremendous initial super human push that can quickly burn you out and leave you questioning your choice.  It is in these dark hours that you will find out if you really have what it takes, many do not.

      • How Bad is Your Current Situation?  Some jobs suck worse than others and some jobs not only suck but are dangerous, counterproductive or destructive.  If you have a good job that you are just tired of that allows you some opportunity to work on your entrepreneurial venture you may want to take a hard look in the mirror and ask yourself if you can commit to making a single all in push that will really get your business off the ground.  This may take months and it may mean that you give up your weekends, sleep, or both but it can also mean that you can retain financial responsibility during your transition.
      • Do You Have a Marketable Skill?  Something that you can that you can do on the side that will allow you get started but still generate income.  You may still be trading hours for dollars but you will be charting the course, setting the price and dictating the terms.  Marketable skills abound and you very well may overlook many things that you could do to earn a side income.  For the purposes of starting a micro-business I am limiting these ideas to things that can be done by yourself with a laptop from virtually anywhere.  This list is by all means not all inclusive and is really just meant to get the idea juice flowing.
        • Tech Skills!!!! – Web design, coding, graphics design, social media expert, etc.  If you are lucky enough to have one or some of these skills your transition can be much more simple than some.  These skills are all in high demand and can pay reasonably well.
        • Write….  This one is so overlooked!!!  As a society we have engaged in information production overdrive, we have produced more content in the last 2 years than in the rest of history combined.  Writers are in high demand.  You can write for SEO companies, content marketing companies, technical manuals, transcription services, or ghost write books, opportunities abound.  Some of these gigs are not wildly high paying but they may be able to hold you over until you get your business on its feet.
        • Consult – To be honest I really don’t know anything about this particular business but I do know that there are numerous people out there that are making a fortune consulting and you can work for yourself.  If you have knowledge of this industry you hopefully know better than I how to market these skills and services.
        • Hire on with a company that will let you work virtually.  You may need to take a pay cut or change your expectation but there are numerous companies that act as agencies for virtual assistants.  There are also numerous entrepreneurial ventures out there that are looking for virtual workers to do a wide variety of different task.  Working at a company such as this can teach you the ropes of the startup world and give you some valuable ammunition for getting your own business off the ground.
        • How Much Savings Do You Have – Having a runway that will allow you to get started can be hugely important.  If you want to take the plunge and give it all you’ve got but can’t make the bills next month you may be setting yourself up for failure.  Base-lining your expenses and focusing exclusively on your business can be incredibly powerful but you have to keep the wolves away.
        • Do You Have the Support of Your Spouse? If you don’t have this you don’t have much.  I tried for years to start a business without really letting my wife know what I was up to.  Bad idea, this is immediate grounds for business failure or divorce.  Without family support you will certainly have to make some drastic efforts while continuing to pay the bills.  This most likely means that you will also have to generate a level of income fairly close to your current level of income before you can expect to leave you current job.  If you are in this situation I wish you luck and hope you do not build resentment against your family.  You have a tough road ahead.
        • What State is Your Business In?  If you have been working on a business for years but just need that last push to get it profitable you are in wildly different situation from someone who is just learning how to install a WordPress site.  Often businesses are primed and ready to go they just need to be pushed off of the cliff in order to spread their wings.  If this is you, evaluate your business based on all of the other criteria and make the tough decision.  I suggest watching Shark Tank and thinking about how the sharks would rate your business.  Do you have a product, do you have sales, do you have skin in the game, do you have a track record, do you have a patent, do you have distribution, have you done your research, built procedures, measurable metrics, or a team?  If you can’t answer these questions or can’t say yes to the majority of them then you need to get busy.  All of these aspects take time and are crucial for success.  In addition the most looming question and most important piece of the equation is, do you have a product?  It seems almost silly to ask this but in the world of affiliate marketing, AdSense sales and free products it is worth asking.  Without a product and clear sales path you don’t have a business, without a business you don’t even have a chance to generate income.  Business is about getting your minimum viable product into the hands of consumers and working the details out later.

The choice is yours and your future depends on it.  Working a job you hate really isn’t an option and we live in a time when it is not only ridiculous to keep working this job but not required.  Anyone can start a business it just takes putting in the hours, building and marketing something that people want.  Learn how this is done, put the steps into practice and you can build the future that you desire for your family at any stage in the game.