To answer your question:
Since you are self employed you can put whatever you want on your resume --ie you can call yourself the VP of Development, dish washer, or whatever. In fact, I have a friend that called himself VP of Business Development for his company in the early days.
So I don't think it will hurt much from a political perspective. You just need to be able to tilt the narrative to your favor if things go wrong.
ie: "I left XYZ company because I wanted to try to solve this very important problem. I starred the company, got investors, hired a team, delivered product to customers, and we ran into some market difficulties so shut it down and am now looking for a job"
The one thing that will change, however, is you. When you pass through the looking glass & start your own company, you will fundamentally change. You will develop skills in many area and you will know what it feels like to work on something that you really love that is really difficult. This is what makes it the hard to work a job after a project. Because you know what that feels like and you will want to feel it again. So you will be VERY picky.
Also, there is the power law to consider. If you start a co, the skills you acquire will compound over time. Quickly they will become the biggest asset you have and you will realize that.
My #1 advice for you is to stop thinking about what will happen in a downside and look at what will happen in an upside. The more you think about how a new venture can screw you, the more likely it will.
If you want to chat more DM me on twitter @jsfour
Very true. I might add, your approach to solving client problems will likely grow more sophisticated. Mid-tier corporate managers and HR flunkies might not get you, but true decision-makers will.
While you're ramping-up your contract business, here's a good read on consulting> http://www.summitconsulting.com/store/ultimate-consultant-in...
A lot depends on your specific situation. How accomplished and in demand are you right now? Do you have a network of people who would hire you in a heartbeat or at least enthusiastically recommend you and actively help you find a job? If you are in demand (i.e., frequently turning down overtures from recruiters) and/or you're very confident that if you lost your job tomorrow that you could find another equally good job in a matter of a couple weeks or less, then going out on your own for awhile probably won't have any negative impact.
On the other hand, if the above does not describe your current career situation, then I'd think hard about it. There are many recruiters and hiring managers who look at self-employment as barely better than unemployment. That's outrageously stupid, but it's reality. I personally know half a dozen people who experienced significant setbacks to their careers after leaving their jobs to try self-employment or work on their own startups. (But, again, a lot depends on how hireable you are currently, where you live, etc.)
I view entrepreneurial experience as a positive that tends to correlate with intrinsic motivation, follow-through, and analytical risk-taking.
Obviously YMMV, and a lot depends on how you execute. If you have a crappy idea and throw years of your life away with no demonstrable progress, obviously it's not going to be easy to tell a story about. But a failure reasonably well done will be a good learning experience -- and obviously even a modest success has lots of upside.
The biggest real issue is opportunity cost, factoring in not just income but the potential to be part of something epically successful and all the experiences, halo effects, and relationships that come from that.
The tech industry illustrates this regularly with company cultures that embrace diverse career backgrounds.
Of course i think your field will probably determine how much my statement applies. For my field in software, independent contracting is a common feature in ones work history especially for the younger generations. I would look at your peers in your industry and domain for clues.
Bwahahahhahaha.... Wait, sorry. Ok, has working for clients hurt my future employability?
Who cares? I wouldn't take a job now if they offered to pay me!