Jenny Galluzzo, a former journalist and serial entrepreneur, co-founded The Second Shift to provide meaningful work for highly skilled women who want the flexibility of a freelance life, and to help create gender diversity in the workplace. We’re honored to have Jenny and her co-founder, Gina Hadley, speaking at The Great Jane, the weekend retreat for aspiring mamas looking to connect with like-minded women and inspire their next chapter, both professionally and creatively. You can get a taste of what we have in store with Jenny’s article below on starting your business, but there will be so much more offered during the weekend retreat. To join us for this mind-blowingly inspiring and relaxing weekend please book your tickets here as space is limited.

Pitfalls to Avoid When Starting Your Business


I have lived through the start of three different companies; one failed, one was a hit, and one I am currently hard at work building. Below are some of the lessons I have learned along the way and things to keep in mind if you are thinking of changing your career path, starting a passion project business, or freelancing.

Be realistic.

Much like childbirth, starting a business is far more glamorous and exciting, in retrospect. When you are first starting out, there is the thrill of seeing your idea get off the ground, but then the reality of the actual work sets in. Here’s the thing about starting your own business– it is really hard. It takes a lot of work, time, and often money to succeed, and while you put all of this into the business immediately, the business doesn’t tend to pay you back very quickly. That’s the unvarnished truth; however, the flipside is the joy, fulfillment, and continued ambition that comes from seeing the business you birthed grow and thrive.

Before starting any endeavor, make sure you know the numbers.

Sit down and do the math and figure out how much it will cost to get up and running. You shouldn’t count on getting funded, so make sure that you can afford to keep the business afloat until you are making money. Some of the best advice we got when we started The Second Shift was to think about money as if it was before venture capital funds and angel investors existed. We are very conservative about what we spend our funds on because most of it came from our own bank accounts and from people willing to trust us with their hard-earned money.

Be honest.

Before you decide to leave a lucrative career to freelance or start your dream catering company, think through a few very important things:

How much money do you really need to be making and how quickly do you think you can earn that?

It takes a while to get a freelance/consulting career off the ground. If you depend on your income to live, you should start networking and taking projects before you quit your day job.

How much time is this going to take from your life and are you willing to give that time up?

 If you left your full time job to spend time with your children, or care for an ailing parent, how much are you willing to cut into that time to pursue your new business? Think it through and plan a job or a business around that.

Be prepared.

Make a game plan!

Create a list of things that you need to know or set up ahead of time. Are you better off creating a personal LLC or being paid as an individual (check out our blog on The Second Shift for lots of tax and legal help for independent contractors)? What time of day are you needed the most and do you have help and childcare to open up your free time? Do you have a separate office with a printer, scanner, and a strong WiFi connection, or do you need to find flexible workspace? Take it from me– there is nothing worse than being in a business meeting and realizing your child was never picked up from school. The more organized and prepped you are, the more you can relax and dive into work mode.

Stay positive!

Err on the side of realism.

While not trying to sounds like a downer, you may find out, when you do a deep financial analysis of the company you want to start, that the idea is not a business that will ever make money, or you can’t afford to quit your current job.

Don’t be bummed. You can use that knowledge to work around it!

Instead of starting off with a whole big vision, break it down to a feasible nugget, start that, and grow from there. Try finding a partner to share the cost and work load with. Work together at night and on weekends to get things going while you keep earning money at your full-time job.

Don’t quit.

The best advice I can give is don’t quit.

Even if you take on work here and there, it is harder and harder to get back to work the longer you have taken off. Tread water! And if you believe in yourself and your ideas don’t let anything I say, or anyone else says, stop you! Along the way you will have a lot of moments of self-doubt, but if you love what you do and it gives you joy, then you know you are on the right path.

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