Should I take the leap?

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By Claire Wasserman, Founder of Ladies Get Paid


When I was about 8 years old, my grandfather said to me, “If you love what you do, you’ll never work a day in your life.” I remember that like it was yesterday. I also remember watching my parents sit around the dinner table, excitedly talking about what had gone on that day at work since they too, loved what they did.

It wasn’t a doubt in my mind that when I graduated, I wouldn’t have to trade what I loved for making a big paycheck. I could - and would - find something that I loved that also made money.

I now recognize that this is a privileged way of going through the world. The desire - even the expectation - that we should be happy in what we do, is not the reality for most people. A job is a job and a paycheck is all that matters.


As I traveled the country last year, hosting events for thousands of women to talk about work and self-worth, many of them had not been raised the way I was but had developed the itch to do something more. Something meaningful. Some had found what they loved to do but didn’t know how to monetize it, while others were still searching for something to feel passionate about.


Pretty early on in my career, I recognized that I was constantly connecting people and through that, had amassed a large network. I never considered it a job - or even a skill set - until a friend of mine told me it was. (We tend to be too close to ourselves so getting periodic gut checks by people who know us gives us both the perspective and the kick in the butt we need to get going.)


It was upon that realization that I discovered the Art Directors Club, a nonprofit that connected people in visual communications, and I applied to become the marketing manager and head of fundraising. It was thrilling that I could take something that came to me naturally - being a connector - and get paid for it.


From there, I moved on to Working Not Working, a curated network of creative professionals, orchestrating events and content to help people connect with each other and prospective employers. Instead of picking one industry to be part of, I had a birds eye view of many. I was particularly curious about company culture, discovering that it was not so much the job that made people stay or leave, but rather the environment. Did it feel inclusive? Were there opportunities for growth?


Perhaps the lighthouse in our career should not be what we’re passionate about but rather, what we’re curious about.


That realization, coupled with the fact that I was driven to help women succeed, was the spark I needed to start Ladies Get Paid. I began hosting events for women to come together to share workplace war stories. As more began attending, the question then became: can I make money from this? Could this be my full-time job?


Soon after I discovered what the business model would be, I quit my job. This was no longer a side project when I made a game plan for how I could make money and the benchmarks for success. I also created a timeline so I could track my progress and know when it was time to call it quits.


I was able to leave my job because I had no debt, children, or health problems. I didn’t have older parents I needed to take care of, and I was splitting my rent with my then-husband. I also had a number of people who wanted to hire me as a consultant so I could guarantee some side income. I quit because I could. If not now, I asked myself, when?


Figuring out when your side hustle can become your main hustle, is a personal question. It requires you to explore your values with money, dig deep into your finances, assess the amount of risk you’re willing to take (i.e. what makes you more anxious: staying at your job or losing financial stability?), and determine a game plan for not only how, but how long, it’ll take for you to make enough money to live without extreme anxiety.


When you take that leap, do it with your eyes wide open, a lifejacket nearby, and remember: you don’t have to go it alone, and you shouldn’t. There are platforms built specifically to help women with great ideas assess the demand for what they are passionate or curious about before investing in supply (and by supply, I mean wasting years of your life or investing your own money into an idea that isn’t going to work).


Through crowdfunding, you can actually go out there and raise some cash for your business idea. iFundWomen was a great platform for LGP to step up and raise some capital when we were in need of cash following last year’s lawsuits. We turned to our community of Ladies Get Paid members and our larger audience of like-minded feminists, asking them to contribute to our campaign, all in hopes that they would see the value in what we were doing.  Turns out, they did. Whether you are raising money to start, grow or save your business, it’s never too early to monetize and legitimize what you love to do.


One thing to remember: if you go for it, and it doesn’t end up working, it is not a failure. By doing something self-motivated and risky, you’re probably going to learn more about yourself than anything else you do in your life. Imagine it as going to business school (and it probably costs less!)


If you decide to go back to work, don’t look at this time of entrepreneurism as a waste. It shows a character of courage and a belief in yourself. What are you waiting for?   


Join iFundWomen & Ladies Get Paid on October 9th for a Facebook Live discussing how to monetize your side hustle. Pro-tip: RSVP and post any questions you’d like answered during the live stream in the event.