Leaving something steady and stable to go all in is hard. To me, it has come down to that nagging feeling that I'll always wonder what if. No big corporate job has left me with that same feeling or pull.

First of all, this is not an easy decision for anyone. In my case there are 2 things which helped me jump the bandwagon: - Financial security for at least an year (for me and my family) - Amazing friends turned co-founders to start something with So glad that I took that plunge back then. We have had hard times as well, but worth it.

It is a luxury to quit a job to pursue a side hustle because not everyone has the opportunity to do so. I began my side hustle while working a full-time job and successfully managed both until I could quit my job and pursue my side hustle full-time.

oooh this is tough. I did not go back to work after my startup got rolling. just need to be in a good spot financially, a trade to lean on if it doesn't work so can get back into the workforce quick.

Ideally, the hustle forces you to quit. So maybe the hustle starts blowing up, or you realize a bigger opportunity awaits, etc. My story: I was a lawyer. My company Sleek got accepted into YC on a Monday night. I quit Tuesday. It happens quick

This is my 3rd startup and I see patterns now... 1. Having a significant other who can support the family while the income is low. 2. Having a right partner who can do things that I can't 3. Having the idea somewhat validated

I've done that almost ten years ago. I'm originally from Brazil and had just received a promotion offer for my employee in Ireland, where I lived at the time, but I was already in conversation with two friends to start our company. I though a lot, but in the end I left and moved back to Brazil to live in my friend's house. He had a spare room and it became my home and our office. I had some saving for a year living with bare expenses (nearly 10% of my previous expenses). To be honest it was a lot easier than I expected. I didn't miss my previous lifestyle and was really excited creating our first product. Don't get me wrong, as the time pass and you don't get new income you start to get nervous, look at other options and so on. Our first product flopped completely and we were looking for consulting gigs to extend our time when we met some entrepreneurs in an event that loved our product and asked to invest on us. From there we still spend another year and half to get back to my previous income and the rest is history. It's a completely different experience than being employed. I wouldn't change it for anything but I think it depends on your moment in life, your economic conditions and how many people depend on you. Today for example even after I've had a good exit (not life changing) and with a lot more saving I'm holding up on leaving my current position (CTO on an EdTech) to go full time on my personal projects. I'm pretty confident I'm going to do it again. But I'm starting as a side project to see if it works.

Im in this position now where I have several side projects that I think could be interesting avenues to pursue but I just don't have the time or the ability to take a year off of work to go all in. I have some side hustles that make good money, but it just takes so much to replace the insurance and other benefits that a corporate job offers. So for me it would have to be a year of complete financial security for my family at minimum, probably even 2 years.

I was so focused and passionate about doing my own thing that it was easy for me to take the call. And since running my own startup was my passion I was able to sustain myself on a low monthly budget for a long time. Besides this, I also had support and backup from my parents who believed in my dream.

First things first, to be clear, my previous, "I-went-to-school-for-this" office job was practicing law, first criminal defense and then immigration defense. My side hustle, at first at least, was betting on sports. Basically, immigration defense became a total kafkaesque joke when the government stopped following their own rules that they themselves made and interpreted. I had a lot of scattered skills but outside of writing a decent legal brief the only thing I had some serious dedication to was watching sports, especially baseball, and that included watching west coast games while living in New York and Boston for years, averaging out to 150 in the regular season. Also, almost my entire family lives in Nevada, as did the entire family of my partner, a sheer coincidence but it made the "where to next" question a lot easier. I got back to my mom's 3 days before spring training with 2 grand in the bank and a bunch of suits and 2 computers and that was pretty much it. 5 weeks later I had made 18% ROI just from spring training and enough to move out to a place that cost the same as my place in New York but did not share a wall with a subway station or have a slight grade to the floor that resulted in the slow shift of furniture. And this was before I had set up any models or use any analytics - it's no longer relevant today but when only the AL had the DH, bookies always over-valued their impact on offense when generally by the 5th inning no starters were left on the field anyway. This would be obvious to anyone who actually obsessively watched spring training games, but turns out, the bookies weren't, and gradually I found that the bookmakers really were only good at setting the spread and with the help of analytics, it's essentially passive income - and it would be entirely passive if only casinos opened up their APIs. About 5 years have passed and in conjunction with a long but generally ironic association with crypto until suddenly everyone FOMOed I'm in a position to actually give money to the public interest firms I was sending resumes to only a few years ago. Also, it turns out that math and statistics, at least as applied, is not as daunting as high school made it out to be, and without the terrible pedagogy I was able to teach myself a lot of programming and analytics mostly by looking at other people's Github. Sadly, I lost a lot of faith in all of the institutions I worked with, even though always in an adversarial capacity I used to think that I could at least make a difference and now I'll settle for leaving the world with a little dignity left. Also, because I had zero formal training in anything not related to the humanities or law since the 11th grade, I'm never fully convinced that I'm not actually totally crap at what I do now and the results are all random luck. I had imposter syndrome before as well, who knew it never goes away whether you have all the qualifications or none of the qualifications. I'm also not entirely convinced that the world didn't end when David Bowie passed and all that we experience is just what happens when the space-time continuum breaks. so tl;dr: it took the casinos becoming more trustworthy than the government to jump ship, and it took an unhealthy obsession with baseball to enable the whole thing. or blame david bowie.

Back in 2011 when I made the jump, here's how I thought about the security piece: + Built up a side hustle while working FT (this was before I was married or had kids, would be nearly impossible now) + Was at a tipping point where I realized I couldn't grow my side hustle anymore without leaving my FT job + Got an "anchor client" that would pay me a good chunk each month. I could take this if I quit my FT job + When I did quit, I combined that anchor client plus the other clients I'd managed on weekends and weeknights... and it was less than what I was making FT. However, without my FT job, I now had the time and energy to close the gap, and I ended up doing that pretty quickly, within several months It's not easy; rooting for you!

It took a bit of realizing my workplace was extremely toxic (harder than I thought to realize. It was like stockholm syndrome took over ha). I had a client in the pipeline that stated very clearly intentions of needing future work and I had formed a great relation with. Had also freelanced on the side before during my FT position so I had other clients that I could reach out to with the great news that I'm now FT freelance! My decision was more based on getting out of the toxic workplace and less about making it as a freelancer. I still applied to FT positions after I quit, landed one and got laid off about 2 months later, but still continued my freelance motion design. I'm very privileged in that I have parents that would've supported me had things took a hard left turn and I was very fiscally responsible with my money so I had a cushion of some money (around 5k) and I also had very very very cheap rent ($500 a mo). All this is to say that I was in a very lucky spot if you ask most people. I knew I had made the correct decision once I started needing to deny projects realizing I wouldn't have been able to take on any projects of the scale I face now with a full time position, and once I starting making 4x more a month than I used to in half the amount of work. There's much more that happened in my journey to FT freelancer, lots of blessings in disguise but in all, being sure you have ducks lined up before jumping ship and being fiscally responsible is what helped me. I always used to think I had to back myself in a corner in order to give something my all, meaning quit my FT job even if I had nothing else going for me...and I realize now how childish that would've been.

Thanks for sharing @david_tedaldi1! This one is one hell of a topic! In my case I never felt like doing it all alone, in my case it's been finding the right people to work with!

Quitting your job to focus full time on a side hustle is not a good idea. Was laid off several time in 70's due to a lot of different things. Oil embargo, then companies moving operations overseas. Kept on working at a regular job. Started different side hustles. Learned first hand so to speak about business. Multi-level marketing was not successful by people I knew. Who were personally involved. Decided early own to get serious about how to start a business. Started a Sub Chapter S Corporation. After speaking to a Certified Public Accountant. Verified knowledge received from CPA. With business oriented attorney. Who helped setup a Sub Chapter S Corporation. Started different side hustles. All were run under one business, company, as a Sub Chapter-S Corporation.

Make enough money from the side hustle to pay “life support”. Then build from there. It’s hard to have two jobs but the sooner you get to MFP (Minimum Financial Position) the sooner you can quit.

You're spot on with those two factors, David. A certain level of financial security is necessary to give you the confidence to make the leap. But that project has to be the right one because you're going to spend a lot of time focused on making it work. It has to become the security for the next phase of your life, to get you to your next goal. That's been my experience, anyway. Best of luck!

That’s for posting this discussion - going to have a good read through all the replies

Great share! Thanks David. Also, a lot of confidence in the core team and the vision

5k month clean