Dealing with a string of business Failures? Is there a time to get a job and drop the dream?

Similar to Usman Sheikh's answer, I'd say if you've had a "string" of business failures the #1 thing you need to settle in your mind is: why? You said, "for one reason or another", but is there any underlying theme to it? Could it ALL have been terrible luck, or is there something you are doing (or not doing) that is the root problem? My guess is you are a significant component in this.

That you see possibilities in every vacant building strikes me as problematic, because many locations are awful, many businesses are under-performing, etc. You can't just be gutsy and think you will succeed--there has to be market research, really careful execution, and usually a lot of sweat..and yes, some luck.

I'd say consider a steady-income job--it need not be 9-5, of course--for now and after you are settled into that some months work on a small and very low-risk sideline business that requires nearly zero starting capital from you. Even if it is making a handicraft at home and selling it on Sundays at a flea market (or the Internet Age equivalent), just something to show you that you can make a small profit and sustain it over the course of a year. Ramp up from there. And good luck.

You mentioned that you started several businesses in the past that didn't end very well. A useful exercise would probably be taking some time out and documenting all the past ventures that you have created or have been a part of. What you want to be looking for is patterns; what worked, when were you the happiest and mistakes that may have been common to a few ventures. It should actually make for a very interesting document that you could potentially blog about and get feedback from the community as well.

In the end I do not think that suppressing the entrepreneurial flame is the answer. Rather it is taking some time out to fully understanding where you are in life, what your priorities are, what your short term and long goals need to be. Based on this you could probably draw a more defined pathway of how you want to get to where you want to be.

Best of luck on which ever path you may choose to pursue.

First things first. That means your family.

This is the worst job market in our lifetimes. This is why it will mean even more to your wife when you land a "regular" gig. Great people are being hired for decent jobs, and you can be one if it is important enough for you.

None of this means you can't be an entrepreneur. As mentioned by others, the modern job market (even in better times) means that we are all effectively independent contractors anyway, so even with a "regular job," you are essentially running your own business.

So on one hand, none of us are actully working "for the man" anymore, but that is not really the point, is it?

As recommended above, keep your entrepreneurial dreams going by developing your ideas on the side as a part-time effort. You don't have to sacrifice your financial well-being to be an entrepreneur. It is harder to launch something part-time, but it can be done. This time, let the business "earn its way" into a full-time gig.

Let your wife know how important this is to you, but first let her know how important she and your daughter are. First things first.

Don't give up you must have learned so much about starting a business running a business and what does not work as a business use that information when you start the next business don't waste that experience by getting a 9-5 job.

On the other hand your wife is pushing you to carry part of the financial burden the options that I can think of are

I just wrote out the details of my failures here: http://answers.onstartups.com/questions/571/which-is-more-important-the-right-people-or-the-right-idea/595#595

...but i'm still trying! I'm currently working a 9-5 (more like 6am-8pm) but can't shake the urge to do something from scratch myself. In fact, the longer I work for big business, the more I learn about big business and why it ends up the way it does (On a side note, a great book to read about big corporate's is 'Billion Dollar Lessons' by Paul Carroll and Chnuka Mui).

I don't however have a wife or kids so I am sure that makes the decision a little harder. If I think back to Maslow's hierarchy of needs, physiological and safety needs are the 2 most fundamental things to satisfy for a human being. Maybe by taking a 9-5 you can appease your wife, and potentially yourself and ensure these basic needs are met. Then, to ensure your happiness, talk to your wife about some blocks of time that you can allocate each week to working on your ideas. Whilst it might take a bit longer, you'll get the best of both worlds and hopefully get one off the ground!

I've had to wrestle with this same question and I came to this conclusion. I am an entrepreneur - so giving up is simply not in my DNA. Try it and you'll see!

Make the wife happy by trying hard for a new full time job. In this market it's nearly impossible to get one anyway, but don't just do it half-a**ed! Try really hard. If you succeed, then it gets the family breathing room for a while. Then again all full-time jobs are really temporary since you could be fired or laid off for any reason.

On the entrepreneur side, this advice: Those empty buildings are expenses for you and income for the owners!!! Even in the best location, you still need to spend $ on rent and inventory before the 1st customer! Try to start from your apartment in a corner near the bed. It makes for a better story when you finally do succeed! Beside, at the start you need to keep expenses low, while making some money from your venture.

On the "too many voices in my head" question, this: Stop and think. What idea/industry have you always wanted to be involved with - that WILL be the last thing you ever do. If it takes 50 years, at least you will be happy you tried it. Let's hope it takes only 5 months to succeed, but you get the idea. It could be a long, winding road.

If you're like me, those other ideas will always come, but since they're not your main idea it should be easier to ignore. They go away after a while as new ones come along. And heck, you might gain friends and notoriety from giving them away to others looking to start new businesses...

Good luck (to both of us :)

You don't have to give up on the dream, but there are many good reasons for taking a steady job for a while.

1. To repair your personal finances after the last business failed.
2. To build up enough cash (capital) to start you next venture.
3. To develop contacts in the industry or sector you want to work in.
4. To learn the ins and outs of the business from inside another firm in that space.

There are great tactical reasons for taking an "ordinary" job for a while. Contrary to popular myth, most business owners started out as employees working in the same or a similar area.

its never time to give up, the moment you give up you turn in your "entrepreneur" hat. You never were one if you give up. You won't give up because you're an entrepreneur. You might get a job, but you won't enjoy it. You'll probably spend your days thinking what a better job you could do than your boss. And you probably would.

Starting a business is hard man. If it was easy everyone would be doing it.

Your next venture might be the one, or the one after it. How will you know if you don't keep trying?

Don't give up. I'm sure your daughter wants that pony. If anything, having a wife and kid will make you less likely to fail as it'll hurt even more if you do. Don't give up.

You can get free counselling at your local SCORE office. Seasoned, successful retired business executives will meet with you and review your business plan, offering sound advice on any questions you may have, or referring them to some one who can answer. The Internet has changed many things, so I don't rely on them too much for Internet help.

Is there some middle ground?

One option that a lot of folks in similar situations do is consulting and contract work. I have no idea what industry you're in, but quite a few lend themself to this.

Alternatively, is there another business owner you could partner with... perhaps not on an official (i.e. legal) level, but certainly not at an employee level. A friend of mine (with no experience in the field) joined a small insurance agency a few years ago on a commission-only structure, and has since built a book of business and is considering his own practice.

It sounds like the key thing is getting spousal support... but that's clearly something I'm not an expert at.