On Quitting

Two weeks ago to this day, I quit my job to start my own company. It’s been one of the scariest, strangest, and most exciting things I’ve ever done, so I wanted to write a post to anyone who’s thinking of doing the same. Specifically, I want to help a few of you get a sense of what it’s like to quit and what it’s like to not have a job. That’s one of the things no one has been able to explain to me, so I thought I’d try to shed some light.

To start off: it feels great. There’s absolutely nothing in the world like being able to focus 100% of your time doing what you really want to be doing. If you’re the entrepreneurial type – and I think you have to be really honest with yourself to figure this out, but that’s not the point of this post – then there’s really no alternative.

There are a few reasons I decided to quit. In talking to a lot of friends, advisors, and people who have started their own companies, the one conclusion I’ve come to is that: in life, you generally get rewarded for taking risks. In her article in the New Yorker, Sheryl Sandberg describes a poster on the wall at Facebook that says, “What would you do if you weren’t afraid?” Clearly this doesn’t mean that you shouldn’t ever be afraid - that part’s inevitable - just that you shouldn’t let fear dictate your actions.

The truth of the matter is that there’s absolutely no better time to take a risk like quitting your job. It’s never been easier to raise money and get the support of others. The other thing to realize is that there’s almost no downside. A friend of mine who dropped out of school to start a company sold it less than a year later. No, he didn’t make a huge amount of money, but the experience allowed him to get a VP level job afterwards at another company in his early twenties. And the reason for this is obvious: if you were interviewing someone for a job, who would to stand out more, the kid who started his own company (even if it didn’t succeed) or the kid who worked in an entry-level position for the last few years? (It’s a rhetorical question.)

Finally, and a bit more cynically: if you’re not working for your own vision then you’re working for someone else’s vision.

A few of you might be thinking that all of this is obvious, but that there’s value in working someplace and gaining experience. I think that’s definitely right. When you work somewhere else, and this is especially true for working at a startup, you learn some great lessons that they don’t teach you in school (and most importantly, you get to fuck up on other people’s dime). I’m extremely grateful for the amazing experience I’ve had and the people I’ve met over the past year working at a startup.

But I think it’s important to realize that when it comes to starting your own company, the consequences of waiting probably outweigh the positives. As far as I’m concerned, it looks something like this (click to expand):

Up until a certain point in time, when you’re working at another company you’re meeting great people and developing skills that will help you in starting your own company, but once you reach and pass that optimal time to start your own company, the things you learn at your job stop being as valuable as the things you could learn on your own.

Even worse, you start to get comfortable with the material things that you have. That consistent cash flow becomes more addictive over time because it starts funding things like rent on your nicer apartment, clothes, food and other luxuries you won’t have as an entrepreneur.

Finally, you never know when optimal time to quit is and chances are you won’t get it just right. I think it’s better to quit earlier rather than later, lest you look back and realize you missed your opportunity.

So what’s it actually like to quit? It’s one of the scariest things in the world. As much as you would like to be able to prepare yourself for that moment you walk into your boss’s office and deliver the news, when the moment comes you’ll feel completely and utterly unprepared. So many thoughts will rush into your head trying to stop you: How will I support myself? What will people say? What if I’m not as prepared as I could be? And before you know it you start to think that you should maybe stick around for just another week and do it then. Note that it’s just procrastination and rationalization talking. If you’ve really thought this out in advance then you should be able to recognize that these are not rational thoughts but emotional ones.

Still, when I made the decision that Monday at 4:30pm, my heart was pounding in a way I hadn’t felt before. I decided to stop thinking and IM a few of my friends for support:

ME: I’m about to give my two-weeks notice. Could you give me some words of support?

FRIEND: About time.

FRIEND: Way to take control of your destiny.

That did it for me. I walked into my boss’s office and basically didn’t let myself think ANYTHING. Once I closed the door and got the words out of my mouth, the rest was easy. It actually felt good. After that, a few things happens that I didn’t expect.

First, although I gave my two-weeks notice on Monday, they wanted me out by Tuesday. This happens a lot, especially if you tell your employer what your plans are, so you should expect the possibility. It’s just their way of minimizing the risk of you doing something like grabbing as many proprietary documents as possible (which is illegal, by the way). Sometime it’s done out of spite. Either way, you should expect it.

Second, things get really political really fast. People you’ve been close with for a long time may suddenly start acting strange or be awfully formal. That’s definitely to be expected. Basically once you quit it’s your interests vs. the company’s. And everyone there still works for the company, so very few people will side with you on any issues. I’m still dealing with some of this so I won’t speak to it any further for the time being.

Finally, other people were super supportive. Nearly every one I told congratulated me on my decision, which was something I didn’t expect. Even my parents were proud of me (that may not be the case for you). I happen to have a lot of friends who are also entrepreneurs, but I can imagine that if most of your friends work 9 to 5 jobs, your experience may be different from mine. But for me it felt like all of a sudden in was my birthday. It was a great way to start off unemployment.

So what’s it like not having a normal job? It’s really hard. There’s no one telling you to be in the office by 9am. The cliche is true: you are your own boss. The truth of the matter is that some people are bad bosses. You have to be hard on yourself. Managing your own time and being productive is a whole other topic that I won’t cover now, but if you’re interested, I would check out Paul Graham’s post on the Maker’s Schedule and read Tim Ferriss’s Four Hour Work Week.

One of the most interesting parts is having nowhere to be. That is one thing I suggest you figure out before you quit. Co-working spaces are a great place to start because the community of people is so supportive and they’re fairly cheap. I’m currently working out of the General Assembly, but there are plenty of co-working spaces you could work out of, not to mention incubator programs where you wouldn’t have to pay anything.

That leads me to money, which is probably the biggest concern for most people. A lot of people who start their own companies also do freelance work on the side, which I recommend if it’s an option. I’m doing a bit of consulting at the moment and it definitely helps me get by. Another option is to set up a few passive-income businesses (Four Hour Work Week also has a few great things to say about that too).

That being said, you should figure out ways to limit your expenses as much as possible until you get some sort of consistent income stream. For the time being, I’m subletting my apartment and finding cheaper living options. Cooking your own food also helps a lot with your budget and you obviously won’t be able to go out much (if at all). You may feel like people will think you’re anti-social, but I tend this find this is the opposite of the case. People will respect you much more for making personal sacrifices for something you believe strongly in.

So what’s the plan now? Well, I’ve got a few projects in the works and I will write about them here over the next few weeks.

I want to leave you with a quote from a book I love, Orbiting the Giant Hairball by Gordon MacKenzie: