I get asked this question a lot, as I left my job 2 years ago to work full-time on our startup Renly.co. And it's a tough question to answer because it's a unique and personal choice for anyone that attempts to do it. There are many factors to consider before taking this plunge into entrepreneurship.
For example, if you have a family to maintain then quitting your job to work from a basement for 2 years probably isn't going to boast well of them. However, if you're single, don't own many possessions and are kind of tired of sitting behind a desk all day making someone else wealthy, then maybe it's right up your alley.
Having a strong financial start is important
If you were highly wealthy, then working on a startup is a moot point and you should go enjoy life. Unless you really enjoy startups. Otherwise, you should have enough in savings for a good 6 month to 1-year runway living frugally. To be fair, you are taking part in a startup, so you will be very busy most of the time.
You probably won't feel like spending your weekends in dive bars with 200$ bills at the end of the night, because you'll be busy with server issues and refactoring code and such. Frugality will mean different things to different people. For me, it essentially meant no more random Amazon orders of things that I didn't ever use, no more concerts, and it also meant no more daily food deliveries for lunch, which add up. And it eventually meant having to leave my apartment and staying with friends and family.
And it will literally mean doing whatever it takes each day to get a few more extra hours of work in. Each day is as important as the last because the work that you do will determine both, how much you will spend that day and how much your company will grow. You either spend your time burning through your runway or you spend it working essentially.
The honeymoon phase
In the beginning, this new found freedom is amazing though. You own your company (kind of) and you're starting your entrepreneurial journey finally after so long. You're working from coffee shops, or from your favorite cafe's, or at home on a rainy day, and it's pretty nice. As it should be. You're starting to see this new possibility in the world where you don't have to be tied down to anything really. Except for the startup. You have to be somewhat tied down to the startup.
You might be starting to get users at this stage which is also equally exciting. So in the beginning, things are great. Or at least they seem great. You still don't have a fully viable business model more than likely, and you probably wouldn't be able to afford a server with a high traffic load. So you're in a comfortable place, but you're also on borrowed time as far as your finances go.
Enjoy this time is my only advice. Order the fancy coffee drink and hear your favorite music and work. Work like there is no tomorrow. Delete and start over if you have to. But both enjoy it and work. You need to break the mental walls of living this different life. You need to make it "ok", essentially, to be able to do this. It sounds simple,
but after years and years of corporate work, believe it, it won't be.
Hesitation and fear are normal
Change is difficult. If every single moment of your life was different, you would feel exhausted by the end. Alive. But exhausted. Which is why we settle for comfort and familiarity many a time. Which is why people go to work for most of their lives and take 1-2 vacations per year. Familiarity. But there is nothing familiar about a startup. You have one goal and that's it. You want to build your product as best as you can, get it to market and in clients hands as soon as possible, and to exit at some point to do whatever it is that you wish to do. But all of this takes time and a massive amount of effort.
Most people around you probably won't get it. They have to go to work every day, so why shouldn't you. Psychologically, this can play a role also in how well you do with your startup, at least for first-time founders. Being surrounded by people like this will inevitably sneak in some hesitation and fear. Not yours, but theirs. You probably weren't thinking anything related to fear. Your mind is on your product and that's it, as it should be. But your aunt that's visiting wants to know how that fancy job is doing. And you have to tell her that you work from the coffee shop in your pajamas all day long and make a negative income.
Fear and hesitation are good. It just means that you're doing things that are out of your comfort zone. And if you truly wish to be a successful business person in your life, then you will have to pretty much destroy this comfort zone. The Jeff Bezos of the world don't live with fear and hesitation. But the good thing is once you continue doing what you're doing, this fear and hesitation get drowned out. You can think of like when you were first learning how to drive a car. It was a terrifying experience. But now, you don't think twice about the act. But you needed to go through the fear to realize that it isn't so bad on the other end.
Don't look back
So, do you want your startup to succeed or don't you? This is the mistake that many people make, and you can't blame them of course, as people need to eat and such. But hitting that edge where you're starting to question if you should get back to a "normal" day to day job is good. It means that you've done an insane amount of work already. It means that you're getting tired and you've tested a thousand ideas and your runway is fast approaching, so you'd better work smarter, not faster.
The human mind is this fantastic problem-solving machine that we use. If you give it a problem or a stressor, it will do its best to overcome it. Just like when you first play any video game. You're relatively slow at first and losing alot. But soon after, once your brain has made the right neural pathways, you're #1 on the leaderboard and you can't figure out why.
Having come this far just to go back to the old ways, the ways that drove you to this way is insanity. And that's also a big lesson in this startup game. If you're going to do something, plan on going all the way. It's the only way that you'll get to learn the entire process. A month after your self-doubt, when you're just fine, still alive and eating, you'll realize that you really do tend to exaggerate things.
The end of the runway
If you're crazy enough to take part in a startup, then at some point you're going to come to a crossroads. And you'll know what that is. You have to know because it will be a huge moment in your life. A moment where everything gets weird and you're going to wonder how you get yourself into this situation. And that moment is when you can no longer financially continue with your usual day to day operations in your life.
That extra shot in the morning in your coffee? Say goodbye. That "Gluten Free" cupcake that picks you up on a rainy day. Afraid not. You're an adult and you have a phone bill fast approaching.
Every great entrepreneur has his this wall. Elon Musk has talked many a time about sleeping in his office and eating off the dollar menu for years in order to successfully get his first product to market. As have many of us. Now we know what he was talking about. More than likely at this stage in your startup, you will pretty much be an entirely different person. Other people's opinions will have zero effect on you. You will have solved a thousand and one problems and you're company will have hit good traction with dozens of meetings lined up. But your financial runway is up. So what to do?
Congratulations. You're now one of the very few people that managed to get to this point in the careers. You already know what to do, so I won't type it here. But I will wish you luck in your endeavor. When you get to the end of a runway, there's still a whole other world in front of you. It doesn't just vanish. But just take a look back at how far you traveled and think about where you'll be if you decide to start the long walk back, or the unknown march forward.