Can You Afford to Become Your Own Boss?

That’s where Ashley Feinstein Gerstley comes in. When she left her job in investment banking to move to the corporate side, she wanted to get a better understanding of her personal finances. After doing some research, she realized many personal finances resources are, well, dull.

In 2014, she left her full-time job to run The Fiscal Femme, a platform that demystifies personal finances with online courses, coaching sessions, and engaging content. Below, Ashley shares the money advice aspiring self-starters need to know as they’re becoming their own bosses.

It All Depends on Your Career

How much money do you really need to leave your full-time job? According to Ashley, it all depends on your new venture. “If someone is a full-time writer or accountant and wants to go freelance, they’re more likely to build up [their finances] quicker,” she explains. “If it’s a startup, it might take more time than you expect until you can start to pay yourself.”

So does that mean you’re a-okay to leave your job if you have zero savings? Not necessarily. Revving up your business will take time (more on that later). If you can swing it, try to score a client or two before saying sayonara to your full-time gig.

Do the Numbers

Before Ashley left the corporate world, she had a spreadsheet called “Project Freedom,” which outlined how long her business could thrive based on her current income. In fact, Ashley planned to pursue The Fiscal Femme full-time when it was profitable. If you want to become your own boss — but have yet to take the leap of faith — think about how much you’ll need to stay afloat. What are your monthly expenses? Do you need to invest in a new website, fancy technology, or a manufacturer? Will you need to wine and dine new clients? If you have an understanding of how much money you need to save, you’ll be able to start this new chapter with confidence. (Psst…you can download your own Project Freedom spreadsheet here.)

Have a Back-Up Plan

Just like Rome, your business will not be built in a day. It will take time to build a full roster of clients, so Ashley suggests having a Plan B. But thanks to the current shelter in place order, it feels virtually impossible to score a temp job or land a part-time gig at your favorite bar. Instead, think about how you can use your skillset in this current climate. Dreaming of opening up your own food truck? You can earn some extra cash by creating (and selling) a virtual cookbook. Got laid off from your fitness instructor gig? Train your favorite clients on Zoom for a small fee. Not only can having a back-up plan create income, but it can also lay the groundwork for launching your business.

Get Strategic About Your Savings

It doesn’t matter if you just launched your business or are already a few years in, Ashley says that one of the biggest mistakes self-starters make is not setting money aside. “We don’t realize money isn’t being set aside for taxes, so we assume that the money in our bank accounts is just for us,” she says. “But then, you get a big tax bill and have to set up a payment plan with the IRS.” (Yeah, that doesn’t sound pretty.) Put a little bit of money from each paycheck into a savings account. (I’m a huge fan of apps like Digit and Chime.) By setting aside a few dollars here and there, you won’t have total sticker shock once it’s time to file your taxes.

Prioritize Passion

While being your own boss can be a very exciting, lucrative chapter, it’s by no means an easy feat. There’s a good chance you’ll accept unglamorous projects and lower rates when you’re just starting out. For many, it’ll take a couple years until you’re making the big bucks. Before you leave your cozy, nine-to-five job, ask yourself the million dollar question: Is it worth it? “Passion in entrepreneurship or freelancing is important because it takes a lot of perseverance,” she says. There’s no shame in admitting you don’t want to be your own boss. (This line of work isn’t for everyone, and that’s okay.) However, coming to that realization before you leave your job will save you a lot of time, energy, and money.

A huge thank you to Ashley for sharing her two cents. (Pun intended.) You can support her by signing up for her newsletter, Money Musings, and joining The Fiscal Femme’s Slack community.

Hustler of the Week: Dani Greene

What inspired you to become your own boss and launch Passport Seven?

I was laid off from my [job] in 2010 as a result of the economic recession. I decided to use my free time to travel using my savings. After traveling, I decided to take up a hobby of candle making because I love all things home décor, and candles are my favorite item in the home décor department. My desire to travel and new-found hobby birthed Passport Seven. My hope was to evoke travel in others when they burn Passport Seven candles.

What’s your favorite part about being your own boss? Least favorite part?

My favorite part about being my own boss is doing things on my own terms. For example, I love branding my business; it brings my creative side out. I love seeing people’s reactions to my new packaging, destinations, and images. I also work with an all-female team who help me bring my vision to life. My least favorite part is that, as a small business, I’m responsible for the day-to-day operations. Because I don’t have a large team, I am the secretary, candle maker, social media manager, etc. Taking on so many roles at once can be overwhelming.

You’re also the co-founder of an interior design firm! How do you balance multiple projects at once?

I recently launched an interior design firm, Blue Jane Interiors, with my business partner. I balance multiple projects by prioritizing the most important task first. I also make sure to stay in communication with my clients and set realistic expectations for myself and for them.

Give Dani some love by following Passport Seven, Blue Jane Interiors, and her personal account on Instagram. (You can also satisfy your wanderlust by picking up a Passport Seven candle — Sydney Opera House is my favorite!)

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