4 Questions To Ask Before You Ditch Your Day Job (For Your Side Hustle)

This is your life we’re talking about—so how do you *know*

So, you have a billion-dollar idea. Maybe you’ve even already launched your side business and you have some clients. But is it worth pursuing the opportunity full time—or should it just be a side gig? I started my first company, Virtual COO Solutions as a side hustle.  I wanted to take all of the skills and knowledge I had gained from my 20 years in corporate and be able to offer those services to businesses locally and virtually.

It was exciting and felt like a big opportunity lay ahead of me, but to be honest, it wasn’t easy to decide to leave my job to work on Virtual COO Solutions full-time. I was working as a Financial Controller, was making a good salary and had great benefits, and was nervous about the risk associated with early-stage startups. I kept thinking that if we failed, I’d be out a lot of time and money—and that I might not be able to pick up where I had left off, career-wise.

Following this path isn’t for everyone, and there’s no hard-and-fast rule to help you decide if it’s time to leave your job, but there are a few things I learned from my own experience that feel universal. Ahead, a few key signs that may mean you’re ready to dump your corporate life and take that big leap.

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Q: Is it all you can think about?

I can’t say this often enough: Entrepreneurship is hard. For all the buzz and press that successful online entrepreneurs post on social media, “overnight” successes are rare. And there’s an incredibly unsexy side to building a company from scratch. Most often, when you start something, you don’t see instant, jaw-dropping results. You work a lot of late nights and weekends, and most importantly, devote all of your mental energy and commitment to your idea—only to face doubt and tough questions about your vision and strategy.

So, how do you know that you’re ready for all of that? For me, I really couldn’t get the idea for Virtual COO Solutions, and the idea of building a new company, out of my head. I would spend hours thinking about what it should look and feel like, talking to other people about it, and trying to figure out who else was in the market. I felt like even though I was working on other things during the day, I ate and slept and breathe my online business—so much so that it was a relief to finally make the business my full-time job.

Q: Are you prepared for some belt-tightening?

We might as well start with the hard truth: You may not have consistent income to start. From a company budget perspective, your salary will be competing with a lot of the other cash outlays you’ll need to make to grow the business. So, make sure you’re ready to crash on sofas, take cheap flights with layovers, and skip the expensive group dinners on Fridays, in your early days.

This has a lot of implications on your life, and it’s tough to know the impact it will have on your financial situation until you’re in the middle of launching an online business. So, make sure you have enough money in your savings account to pay your bills for at least a few months—I had a few months worth of living expenses save. Also, line up people in your life who will support you emotionally (and in a bind, maybe even financially) when things get stressful and difficult. You’ll thank yourself for developing the right support systems.

Q: Are you aching for a change?

Maybe you just realized that if you go to one more pointless meeting in a fluorescent-lit conference room you will scream. Or maybe you are hitting a wall where you know you work really hard, but it’s nearly impossible to see the material impact you have on the company you work for. Or maybe you’ve just been in the same job for ten years, and need a new challenge. None of these are surefire signs, but all of them could be good indicators that it’s time to consider your next move—and maybe that move should be a bit less corporate and more entrepreneurial?

I’ve found that there are meaningful key moments in my career where it has made sense to go back to that idea that I couldn’t get out of my head and assess whether it made sense to think about a real change. For most people in traditional careers, these moments come about at natural decision points in your current job—after promotions or bonuses, or even at the end of the year. Use those moments as opportunities for self-reflection.

Q: Do you have enough industry experience?

Sometimes, it’s important to contemplate making the leap to entrepreneurship when you’ve accumulated some credibility as a working professional. This doesn’t mean you have to put in a certain number of years just to check a box, but I highly recommend building up your resume to ensure that the people you will need as you start your venture—including clients—will take you seriously. Of course, if you do have a golden resume, you probably have a solid paycheck coming your way to accompany it. This can be a double edged sword, since that means it’s likely also more tempting for you to stay put. But maybe it’s time to take a little break to pursue the dream you’ve been nurturing—and can’t stop thinking about? After all, if you’re really qualified, you can always come back to your corporate job, in the event that the detour into entrepreneurship doesn’t work out. (But we surely don’t want that to happen!!)

The thing is, there’s no perfect time.

Starting an online business is a little bit like having a child—there’s no perfect time to do it. You’re never going to have a point in your life where you have all the experience, no other interesting opportunities, and few obligations (both financial and personal) that would theoretically make leaving a high-paying job easy. Signing up for years of hard work and low pay, for no assured success is something that will always be a tough decision, regardless of your personal circumstances. But ultimately, there will be times that are a little easier than others: When you’re itching for a change anyway or you’ve been obsessing over an idea for months, it’s a good sign that you may seriously want to think about making the leap. That’s right: After all of that, it comes back down to your instincts and how badly you really want it.

Which seems fitting, because one of the hardest things about starting an online business is that there are no promises. Unlike the relatively defined path you move down in a corporate job, starting a new venture is a winding, unpaved road—and it doesn’t always lead to 7 figure success. That being said, if and when you’re ready, the experience of building something from nothing can be the adventure of a lifetime—you’ll learn things that you would need ten times as long to learn in a more traditional job, and you’ll get the opportunity to really build something of value along the way.

Two years ago, when I was contemplating making the leap into full-time entrepreneurship I never dreamed that I’d be here today, growing a brand and business with some of amazing people—and while I’ve still got a long way to go before I achieve all of my (admittedly large) ambitions, I never look back with doubt on my decision leave my corporate job to start Virtual COO Solutions and Two Week Notice Society.

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