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 an MVP and have some awesome co-founders. But is it worth pursuing the opportunity full time—or should it just be a side gig? When I was 32, I started my company, Havenly, with my sister Emily. We wanted to change the way people decorated their homes, and allow ordinary people to have access to the resources of an interior designer. It was exciting and felt like a big opportunity lay ahead of us, but to be honest, it wasn’t easy to decide to leave our jobs to work on Havenly full-time. I was working in a VP and GM role overseeing a division of a large internet company, and was nervous about the risk associated with early-stage startups. I kept thinking that if we failed, I’d be out a few hundred thousand dollars—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.
I can’t say this often enough: Entrepreneurship is hard. For all the buzz and press that successful startups like Glossier or Classpass get, “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—whether that’s in customer acquisition, funding, or news coverage. 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 Havenly, and the idea of building a new consumer company, out of my head. Emily and 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 we were working on other things during the day, I ate and slept and breathed online interior design—so much so that it was a relief to finally make the company my full-time job.
We might as well start with the hard truth: Very few companies are able to immediately raise multi-million-dollar funding rounds that allow founders to take huge salaries. Plus, even if you do have the funding, salaries vary tremendously between founders building young companies. 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 the company. 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 years worth of living expenses saved and liquid. 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 when multiple investors have turned you down for your next round of financing, your website crashes, and your competitor gets a big press hit… all in the same day.
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.
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 employees and future investors—will take you seriously when you ask them for their time and capital. 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.
The thing is, there’s no perfect time.
Starting a company 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 a company 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 an IPO. 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.
Five years ago, when my sister and I were 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 my favorite people—and while we’ve still got a long way to go before we achieve all of our (admittedly large) ambitions, I never look back with doubt on my decision leave my corporate job to start Havenly.
Words: Lee Mayer
Photos: Morgan Levy / Courtesy
Lee Mayer is the CEO and Co-Founder of Havenly, an online interior design and e-commerce platform making beautiful home design accessible for everyone, on any budget.