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I give you a lot of credit for making the jump. This is exactly what I did, and it was exactly a year ago that I quit my well paying day job to jump in with both feet. Our start was similar to yours too, we had an idea that got some funding from an incubator. We had some prototype and our idea wasn’t really proven at all. I found HN, read Founders at Work and every one of PG’s essays too. I felt exactly what you’re feeling now. Ride that high as long as you possibly can. You’re going to have an amazing journey no matter where this experience takes you in the end, and I can promise that you won’t regret anything.

With that said, please think about if this is really the right time to make the jump. As you know, an idea is worthless, it’s about execution. Testing can take forever to find the right direction to go in. When I was making the jump I always told myself that we’d figure something out before our runway ran short. We had so much time to do it, how could we not? Well, we ran out of time and could never find that key feature to make us profitable. I did a million things completely wrong and so will you, but you don’t need to quit your job to make those mistakes and learn from them. I always try to encourage people who want to make a similar jump to make the really dumb mistakes when you can pay your bills with a 9-5, not when those mistakes can cause you not to eat for a night. I personally think it’s a bad idea for anyone to quit a job just to waste time building and testing an idea. I feel it’s best to make the jump when you find something that’s working and use all the new free time you get from quitting the 9-5 to sell/test/improve that. When you find that revenue driving feature or idea you can easily improve on what you have, but If you have nothing you can be stuck trying to find it forever.

I wish you the best of luck, and I'm looking forward to reading more updates as the company grows. Your team sounds like it has a lot more experience going in than mine did, so I'm sure you will figure something out soon.

If you're interested where I am now, I’m actually writing this from my desk at the same 9-5 I quit a year ago. That’s right, I’m back working at the same place I left (I guess they liked :) ). I don’t regret a thing, but in hindsight I do wish I waited until the vision I was going on was a little more clear and mature. I'm 100% sure I'm going to give it another shot in the future, and I'll get a lot further than I did this time thanks to everything I've learned.



Thanks for the detailed advice Jordan. It's good to know that we're not completely crazy in doing this (just partially). I'm also glad to see that even if the first time didn't work out, you learned an incredible amount and are going to give it another shot. Best of luck!

For our situation specifically, we discussed a bunch of non-terminal options with our employer. This included staying at the job with new incentives, consulting, and prolonging our departure. We also have been given the speech of "call me when you guys need a job again" by them as well.

However, in the end, we think that forcing ourselves, by leaving behind the comforts of a 9-5, is the best way to learn, fail at some things, and hopefully succeed in the end.




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