Should you quit your full-time job?

If you're serious about starting a side project in the future, look at moving to a company who support side projects and who may in future allow you to transition into a part-time role if it succeeds.

Both Jonathan and I supported EmailOctopus in the early stages through changing our work patterns. I quit my full-time role and joined another startup on a 6-month long contract working 2 days a week, allowing me to spend the other 3 on EmailOctopus. Jonathan dialled his hours down at his full-time role, allowing him to spend 2 days.

Everyone has different commitments and stresses, but for us it was important we could continue to live a good life and not just ramen profitability. We also wanted to avoid diving into savings.

I quit my job and I think it's a mistake.

I had no plan. I just had a stupid idea (which I didn't even work on after quitting). And my company had a good work life balance, enough for me to pursue my side project but I still wasn't really doing a side project.

I was a data-scientist but I wanted to build things which had a look and feel to it (a.k.a web/mobile). I was just learning all the time and wasn't even launching, primarily due to motivation. I wasn't in the right environment to make any projects. I didn't build any projects but I wanted to yet couldn't, I'm a serial procrastinator. I clearly didn't want to do the job. I know I could build something good if I could just find the right motivation.

I had good savings. Lots of runway. So, I quit.

This was 1 yr back now. I still am a procrastinator. I build but don't launch. All I have launched is a personal website with a single about page. I have 4 unlaunched half-baked projects. I have 4 first-drafts of blog posts in Notion. But what I learnt is, myself. I knew YC is not for everyone. I discovered Twitter creator community and IndieHacker Community. I understand what my strengths and weaknesses, so much so, my confidence increased.

What are my options ?

1. Quitting and joining a job. Back to where I started.
2. Keep trying till I make it.

I choose 2. Since the upside of not quiting is too good. I can be my best self and it seems too good of an ROI to not invest in. (see below) *

So I quit and I think it's the best decision I've taken, even if I fail tomorrow.

• I still have runway. So kind of enjoying life.

Understand your monthly financial needs

I discovered the power of having a personal monthly budget and actually understanding where I spent my money.

My Story
I was recently house shopping, and was anxious about looking at houses outside my budget. I was shopping in a very competitive market with other high-income individuals bidding on the same houses as me. When I couldn't find any houses that worked for my family, I decided I needed to do some financial homework.

I actually sat down and did the math of all my bills vs my income. I realized that I could afford a more expensive house, and keep my mortgage payments the same as before. Note: I went from a 15 to 30 year term, so the cost to borrow the money has increased, but I'm ok with that because I prioritized keeping my monthly payments the same. That's how I view debt, I will pay more to borrow if it help me accomplish a goal.

Conclusion
My point is, if you understand you financial needs, it's much easier to make difficult life changing decisions such as "should I quit my job?".

The book 4 Hour Work Week talks about a concept of dreamlining. (it's been a while since I read the book, so I may be a bit inaccurate) but dreamlining is all about figuring out how much income do you really need to accomplish your goals.

Do some homework, and maybe you'll figure out that you can still live comfortably working part time. This assumes your current employer will let you work part time. I switched from W2 to 1099 and was able to stay with the same employer part time.

I think it's a lot easier to just starve and focus on your side project, if that's an option. I think many if not most people who've made it out of working for a living have done it that way. When I started, that's what I did, and it was hard, but it worked. If you're only responsible for yourself, I think going back and forth between focusing on your own projects, and then working for a while to get your savings back, is probably the easiest and most effective way to do it. Expect for it to take a couple iterations before you're finished, most folks hit some snags along the way and have to go back to working a couple times before they're finished.

That said, I have responsibilities now and I gotta do the next thing the hard way, nights and weekends. I don't know if I'd have the drive, and most importantly, the belief in myself, if I hadn't already climbed that mountain by going all-in in my younger years.

Depends on each person! But my 2 cents:

Quit if you can (frugally) survive 6 months with your side project giving you no turn-over. I.e save a lot & assume the worst case revenue scenario.

I quit my job in October to go all in on ContentUK (main job said no to part-time). This is after working on my side gig alongside a high pressure job for months.

Savings + living with parents meant i'd be okay if i earned £0 for 6 months if i quit.

My business is growing slower than i'd like but 0 regrets! May need to do some contract work/part-time job to supplement growth but it's not unexpected and a situation i've planned for.

I'm working on my side project, and it will be a side project, until the income it makes is on par with my current, full-time job, salary. And not the first month it is on par either, I figure once it's been on that level for half a year at least. And even then I will only quit if I have enough savings to survive a whole year with no income. I'm getting too old to take risks and am quite liking comfort in life.

I'd say wait until you really have to. I quit my job a year ago to focus on my side business, but I think it was too soon. I was also probably partially motivated by boredom at my current job. So I went back about 4-5 months later. Even though I was making money from it, but not really enough to just keep messing around in NYC. Things somehow just did not work out the way I was expecting them, mostly I did not see the growth that I was projecting and it really started messing with me. I think to go full time on a project you need a really solid plan on how to get where you want. Otherwise it just feels like you're wasting lots of time and could potentially be leaving tons of money on the table (e.g. your job). I wrote briefly about my past two years https://vilkeliskis.com/blog/saas-bootstrap-journey.html

Great post @jic!!

At one point in my career I left work to go full time on a side-hustle and got badly burnt. I was young and dumb, posted it on LinkedIn, told friends.

It was so embarrassing crawling back into work and I didn't want to go back to the same career. It took me a while to rebuild confidence and navigate the change into Product Management.

Another thing is, people need to consider the risks they can take. A lot of my friends grew up helping their parents pay some of their mortgage.

I love your point about getting recurring revenue and hiring someone so you can start working on the business and not in the business. Love the edits shared by the community.

The other thing I would add is whilst you are working it doesn't have to be wasted time. Get paid to learn. It's the best thing you can do as you'll need incredible talent at every level.

Why not work in a place where you can get product/sales/marketing experience and build contacts whilst doing it?

Thanks again for this post!

My long term goal is to build a "real" passive income so that I theoretically never have to work again. By "real" passive income I mean investing in stocks, real estate, etc. I invest all the money that is left at the end of the month.

So ideally I have a full time job + side business to have even more money for my investments. I would only quit my full time job if I could expand my side business to generate more income than my full time job + side business combined.

As a general advice I would say: You have to know what you want in life. Based on that you make your decisions.

I worked full-time and then part-time until I replaced my income, before quitting my day job.

It was a privilege not everyone has. Very thankful to the team I worked with for being 1000% more understanding and supportive than they had to be.

My situation is slightly different. My full-time job ends in April (fixed-term contract). I could look now for a different contract or focus on human-matter.com. I decided to focus on my project, support us through freelance work (anyone wanting to improve team health?), and move to a cheaper country. I also started saving two years ago.