Should I Stay or Should I Go?

The calendar has ticked over to 2021, a new administration has taken the helm, compensation figures are in and bonuses have been given. For those who have tinkered with the idea of starting their own business, this month brings about the inevitable question: is this the year? Before you storm into a Zoom ready to tell off your boss, here's what our founders have to say about when they chose to make the leap.

Trading in a stable job and income for an entirely unstable situation as an entrepreneur is (almost) never an easy decision. It’s not about being risk-averse—it’s about making an informed, prepared decision. Bill Gates didn’t just drop out of college to follow this crazy computer dream. He had already logged thousands of hours in the computer lab (at an expensive private school) and had parents who could financially support him during the experiment (which most people do not have). Successful entrepreneurs don’t just leap. Before you do, you might want to give these questions some thought. 

Is it love or hate? In other words, are you considering a move because you are passionate about your new business idea or because you hate your current job. Now it’s possible for these two to coexist, in which case, amazing! But if it’s more the latter than the former, consider your options. Can you imagine a job that you would love to do? Maybe that job exists and you should devote your time to finding it.

Am I valued? This reason is the one I hear most often when I am listening to women share the origin stories for their businesses. You have all risen up the ranks, gotten the big titles, been offered a good salary (although not as high as your peers), and have been told you have a seat at the table. But maybe it doesn’t really feel that way. You don’t control the management of the company, you don’t get to choose who you work with, and you just never quite feel like you belong. If you are getting a lot of lip service, but just aren’t really buying it, it may be a good time to get out.

Do I like the people I work with? This usually goes hand-in-hand with the value question because it’s hard to like people who don’t value you. Are you excited to see your team? Do you enjoy the discussions, feel like your voice is heard and that you are surrounded by voices that you really value? Or do you cringe each time you open your inbox for fear that you are going to get another sh*tty email from that one partner or that one client who just doesn’t know how to be a professional? If liking who you work with sounds like a pipe dream, talk to some of your friends who do like their colleagues. It is an entirely different world for them and that world is available to you.

Now, assuming that after answering the first three questions you are thinking that 2021 is the year to make a change, the next question is: what kind of change? Is it my own company or a much better position at someone else’s company? One is objectively no better than the other, but will be better for you right now.

Have I laid the groundwork? Regardless of all the romanticized portrayals of entrepreneurs in the media, an idea is not enough. Not a single entrepreneur I’ve worked with left her job with nothing more than a hope and a dream. You have to work at it. You pull double-duty for months or even years, working full-time while also piecing together the infrastructure for your new venture. I could not have launched All Places if I hadn’t spent the preceding three years committed to building and supporting my professional community. It was that community that stepped up when we launched to not only become our clients, but to make unbelievable introductions for us, and to give us frank feedback along the way. And they are still there for me on a daily basis, propping me up when I dive into that pool of entrepreneurial self-doubt that was filled during my law firm years. If you’re still not convinced, listen to just about any episode of How I Built This. All these huge businesses we think came out of nowhere—they didn’t. Zoom was founded ten years ago. Ten years.

Can I do this financially? Let’s be frank, this is what it really comes down to. Being your own boss sounds liberating and sexy, but it also means you have one person to count on to pay your salary: you. For most businesses, there is a significant lag between when you start the company and when money begins to roll in, and much longer before you can pay yourself a living wage. This situation is even more extreme for asset managers, who often won’t be in a position to match their previous salary for upwards of 5-7 years (we’re doing a separate post on the financial timeline for starting our own asset management shop—stay tuned!). This is a big part of laying the groundwork. Map out how long it will take for money to come in and make sure you have enough socked away to supplement your income during that time. Being an entrepreneur is stressful enough without spending every month terrified about making ends meet (that time will come soon enough, no need to rush it!).

What does your gut say? I am a shameless fan of Scandal. Yes, it has it’s problems (Why does Olivia always need to be saved by some guy? Does everyone really need to talk so fast? How does she keep all those white coats so clean?). But I am fully onboard with one Pope-ism: trust your gut. Our bodies are often much smarter than our minds. So as you sit there envisioning the next year try out all three scenarios: staying in your current role, finding a new job, and then founding your own company. What does your gut tell you? If you’re like Oliva Pope, your gut is never wrong.

--Jessie Gabriel