This post is presented by OPEN Forum(R).
If you surveyed the recent success stories in Silicon Valley, and looked at where their founders hailed from, you’d see a common thread emerge:
- Kevin Systrom of Instagram came from the Google Gmail team;
- David Friedberg, who recently sold his startup The Climate Corporation or $1 billion, worked on Google’s corporate development team;
- Bryan Atwood, co-founder of recent $350 million Twitter purchase MoPub was previously a product manager at Google.
It gets to be a little repetitive. But the point is this: All of these very successful entrepreneurs made the decision to leave what is almost unanimously considered to be one of the best, happiest companies to work for in the world in order to strike out on their own.
Not all startup founders have Google on their resumes, but they did come to some flashpoint in their careers where they realized it was time to quit and start their own thing.
How did they do it? The next three questions are meant to be a litmus test for budding founders determining whether to leave the nest.
1. Do you spend most of your time working ‘on’ something or working ‘toward’ it?
If you asked everyone you know, most people have a side project of some sort. And many of them would love to do it full time. Whether they’re blogging about music or building a website to sell fair trade goods online, they actually find themselves looking forward to spending hours on this other project. They can’t wait to leave their day jobs so they can go work even more. Maybe they’re even checking in on this other prospective business during their day job.
Of course, this isn’t enough evidence to make the leap to a startup. But if you find yourself spending more hours thinking about or working toward something rather than actually dedicating your life to working on it — that’s an alarm bell. And it will only get louder until you do something about it. So keep an eye on how you allocate your time.
2. Are you confident in your network’s ability to help you succeed?
Having an idea and the passion to execute is one thing. But you need resources too. This isn’t just about the funding. The most valuable resource a new entrepreneur can have is the right people. Do you have a co-founder with incredible technical skill or business acumen? Do you have mentors from your previous companies or school who would be willing to champion your efforts and make introductions that open new doors?
This is how you eventually end up with the funding and the space and the staff that you need to make your dream a reality. If you’re not confident that you have this supportive network around you, maybe it’s not time to call it quits just yet. The good news there is that your existing career can give you the tools you need to assemble a stronger network. It might afford you the opportunity to go to happy hours and industry events where you can meet more people. It also gives you the chance to impress co-workers and higher-ups that might become critical contacts in the future — even if they’re your peers for now. So, before doing anything rash, assess the caliber of your personal community. Deciding to become an entrepreneur should never truly feel like you’re going out on your own. It takes a village to raise a child — and to found a startup.

Above: It takes a village…
3. Is your product or service developed enough for you to start experimenting?
If you’ve ever been in San Francisco at a bar, or on a bus, or walking through a park, you’ve probably overheard a conversation that goes a lot like this: “You know what would be a great startup? A combination of X startup and Y startup…” or “Z is a huge problem that needs to be solved… someone should found a startup to do that.” It’s in the air wherever you go. But these ephemeral thoughts do not a company make. You need to have something built out, that not only functions and that you can show people, but that’s well-developed enough to start test driving.
Succeeding as an entrepreneur has a lot to do with your ability to suss out what customers or users want, fail fast, break and remake your own product, and do it again. Unless you’re at this stage, you shouldn’t feel comfortable going full time. Because as soon as you do, you’re going to have to start making changes immediately to get people’s attention, recruit more users, string together funding, credibly hire good people, etc. All of this requires proving that you can be nimble and that your service or product has enough to it, and is fully-featured enough to add real value.
These are the vital questions to ask. But one of the best ways to make any decision is to learn from the wisdom and experience of others. Today, it’s easier than ever before to connect with seasoned entrepreneurs and learn how they decided to quit their jobs.

Above: Human connections are your most important resources.
While no one will know the time is right or wrong better than you, surrounding yourself with a virtual community of supporters and experts willing to provide advice and mentorship is a good first step to take. Innovation doesn’t take place in a vacuum. In many cases the building blocks you need to do something truly unique are already there. You just need to find them.
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