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The time is now, that voice inside your head says: Go for it, go out on your own, you can do it!

But is it really the right time to take your hard-earned skill set and become your own boss? After all, gut instincts are one thing but the reality is that, at the end of the day, there are bills to pay.

There is no perfect time to strike out on your own, but there are ways to consider whether or not today (or soon) is at least well-timed in terms of succeeding.

Here are three questions to ask yourself before making the leap from employee to entrepreneur.

1. Is This an Impulsive Decision? 

First, know that going out on your own is something you truly want to do, and not a knee-jerk reaction to a bad day. Decisions that are solely emotionally based often turn out to be poor decisions.

Frustration, anxiety, anger -- all part and parcel of a bad day at work -- are emotions that can blur the logic that needs to be part of any big decision. Not that there shouldn’t be some emotion. But, make sure they are emotions that are propelling you toward the new project, and not just out the door of your current job.

After all, the new venture deserves to start on a positive note.

2. Am I Ready to Accept The Risks?

Once you decide that this is a business you really want to start, you have to ask if you're ready to accept the risks. 

As mentioned earlier, there is no steady paycheck when you’re first starting out. That’s significant to most people on both the personal and professional front. 

In addition to investing financially, the newly-starting-up will also face investing significant amounts of time and energy. In 2013, hundreds of small business owners responded to a survey by The Alternative Board (TAB.) The resulting article reported that almost half of those surveyed worked 50+ hours a week.

That’s due, in part, to the fact that small business owners are doing more than making the widget they invented, or meeting deadlines for clients. In addition to doing the work of the business, they are also working to keep the business thriving. In the beginning, particularly, everything from accounting to creating advertising plans falls on the shoulders of the owner. 

That's where one more risk comes into play: learning to trust a partner or employee. At some point the business will need more than one person can offer, and at that point you’ll have to risk trusting part of this fledgling, fragile passion project to another person in order to have it thrive.

3. Do I Have a Plan?

Now that you’ve assessed your reasons and accepted that the immediate future will have multiple risks, it’s important to turn thought into action by codifying a plan-of-action. 

Why? Because without a plan your business is very likely to fail within the first five years (as about 50 percent do) rather than survive and grow. 

The plan should address the practical parts of the business, such as where you’ll work and how you’ll pay bills. It should also address some of the “how” and “why” of the new adventure. 

Do you have a unique value proposition that you can communicate in a direct, compelling way? Do you know your market? Have you actually done a deep dive to prove that your perceived market exists? Once you’ve done that, it’s important to determine your proposed revenue streams.

It’s exciting to think about starting your own company, to contemplate going out on your own, setting your own goals and schedule, and bringing your unique ideas to life. With a little self-reflection, plus the reality-check about risk-taking and an actual plan in hand, it very well might be time to hang up your own sign.

About the Author(s)

Sonny Kalsi GreenOak Real Estate

Sonny Kalsi is a Founder and Partner of GreenOak, based in New York. Sonny has oversight responsibility for GreenOak’s US business and is a member of the firm’s investment committees globally.

Founder and Partner, GreenOak Real Estate
Questions to Ask Before Starting Your Own Business