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When to Make the Jump to Small Business Ownership

- Thursday, February 28, 2019

You've been thinking about it.  Dreaming about saying goodbye to your thoughtless boss or excessively burdensome system. Dreaming about putting your skill set to work for yourself! How do you know if you'll be able to successfully make the leap from employee to small business owner? Here are a few things you might want to think about and check-off in the affirmative. You might find it interesting that small business insurance is not on this list.  We'll close with the explanation why.

You are REALLY ready to be your own boss:

Transitioning from being employed to being your own boss means losing (for good and bad) established structure and expectations. There is some degree of comfort with known structure even though you find that structure increasingly hard to accept. Be honest about your own work ethic, organizational skills, and discipline level. How self-motivated are you? Your going to work harder as your own boss, have no doubt about it.  

You have savings:

Make sure you have at least six months' savings (the more, the better) before you say goodbye to a consistent income. Give some serious thought to how you will pay the bills if your new venture isn't successful right away or at all.

You can go back:


Are you in good standing with your current and former employers?  If yes, great.  Do not burn bridges on your way out.  Depending on the type of work you do, it may or may not be easy for you to find employment or pick up a job on short notice. But if getting back into your previous job or line of work would be relatively simple, it may not be that risky to pursue your great idea for a while, just to see what happens.

You're ready to sacrifice:

In the beginning, starting your own business might mean adjusting your lifestyle, working more than full time, or doing tasks you really don't enjoy until you're able to hire an employee. If all of that still sounds better than your day job, then you might be ready to pull the plug.

You can't keep up with demand:

A high demand for your service or product may be a strong indicator of your potential success. If your "side" project is slowly taking over your life, that's a good sign.

You have support:

If your spouse, friends and family are saying "go for it," take note. It doesn't necessarily mean that you're bound for success, but, at the very least, it means there's potential. Plus, having a support system means there will be somebody to pick you up and help get you back on your feet if things don't go as planned.

You're not the only breadwinner:

Having a spouse or family member who can help support you while you're pursuing your new venture might minimize the financial risk and make your decision a little easier. But don't take this kind of generosity for granted: have an honest conversation about what's reasonable, and stick to your end of the bargain.

You can't take it any longer:

This is one indicator that could at least partially trump all the rest. If you don't have absolutely everything in place to make quitting your day job a sure bet, but your intuition is telling you "it's time," you might want to pay attention. We're not suggesting that you make a careless decision, but if you're completely miserable at your "real" job, maybe it's time to really find out whether you can make your dream a reality.

All of us here at TriState Business Insurance (serving VA, MD, and DC) are your biggest fans.  You'll need to have progressed reasonably far in business plan development in order for us to serve you best.  When it comes time to insure you and your business, the details of your business model and your personal circumstances matter.  Any insurance agent worth his or her salt will spend significant time with you to understand the details.  It is only then that the agent can act on your behalf to secure the very best value for your small business insurance.  Don't let anyone under-insure OR over-insure you. 

Contact us!