Don't quit your job yet
In April 2019, I was burned out in my day job and decided to quit to work full-time on my new business and try to get it off the ground.
Back then, I was still serving tables and tending bar in between acting gigs/auditions in Los Angeles.
I had already built v1 of the software that I was going to literally sell door-to-door.
It was called OKDentalPlans, a platform that helps dental offices "productize" their dental services by allowing them sell subscription plans to their patients.
Costco for dental offices basically.
I resigned, and, for 3 months straight, I tirelessly cold-called all the dental offices in the country, plus I went door-to-door to dental offices in the LA area, wearing a suit, carrying a briefcase and an iPad to demo my product to dentists and office managers, trying to sell my product.
Guess what?
With all my hard work, cold-calling like a maniac, and running around town like a headless chicken in a dorky suit and iPad in hand, for 3 months in a row, I signed a grand total of 0 customers.
Yes, I had completely failed, my product had totally flopped, I burned 3 months' worth of living expenses for nothing, and I had to look for another job by August 2019.
I tossed aside OKDentalPlans, and this was when I started looking into another business idea I had on the back-burner: a Twitter automation tool.
But this time instead of quitting, I chipped away at it while holding down a day job and building up my savings.
A 4-hour coding session before my shift, 2 more hours after, and then 10-hour uninterrupted coding marathons on my off days. They added up fast.
And well let's just say that this one went a lot further than OKDentalPlans.
Don't quit before you see a clear growth trajectory
I know a lot of aspiring entrepreneurs dream of quitting their jobs prematurely to go "all-in" and bet the farm on themselves.
I'm not saying it's not good to have self-belief — I think it's admirable.
But unless you have significant cushion (2+ years of runway at the minimum), it's unlikely that you will gain sufficient traction before your money runs out.
Hell, you don't need your money to run out or even close to it.
At some point, seeing your hard-earned savings get depleted just gets really old, and you lose all will and motivation to stay the path.
Sometimes you just can't force traction; everything takes time to compound.
- You need time to create your products.
- You need time to build an audience.
- You need time to figure out your distribution.
- You need time for your monetization strategies to bear fruit.
Financial anxiety = Mental impairment
There's a growing body of research that shows that poverty/financial anxiety lowers your IQ by 1 standard deviation.
So while you may think that you have full-time focus by quitting your job, you actually don't.
The other half of the time you're worrying about running out of money.
And that will severely impact your focus, productivity, and judgment when building your business.
So hang in there, stick it out, and don't focus on the negatives of your day job (of which I bet there are plenty).
Focus on the positives, think like a businessman (i.e. "I have a stable source of revenue that I can use to bootstrap my business") instead of resenting it, keep chipping away at your business, and eventually the pieces all fall into place, the wheels start turning slowly but surely, and your business starts taking off.
That's how winning is done.
If you're reading this, I hope you win — and win bigly — in 2024.
PS I'm currently building Zylvie, a 0%-commission platform to sell your digital products.
You may subscribe to my email newsletter here if this post resonated, I send out weekly 1-min reads about my most salient learning point of the week.
🔥 Roast My Landing Page
Hey good stuff and I agree with the risks and observations but I’m gonna disagree on the interpretation. Sort of a half glass full view vs your half empty.
I just quit my job so maybe I’m gonna bite my tongue in a few months but here’s my views on why you should quit your job
So for those reasons I think it’s still an option to quit your job. All the reasons you gave can be addressed with proper planning and I’m convinced your success today wouldn’t have happened if you didn’t quit your job the first time.
I think it boils down to risk tolerance.
You're right, it worked out for me, I got another job on short notice.
But I don't think it's even necessary to quit one's job just to try to bootstrap one's business.
Ideally the best-case scenario is you're quitting because your business is taking off and requires your full-time attention.
Otherwise it's possible that you're quitting for the wrong reasons (e.g. you hate your day job).
I hope it works out for you of course, it's completely possible that I just have a negative impression of it because it didn't work out for me.
I actually came here to share similar learnings. I quit my job a year ago and have been living off savings, paying developers (part time) on the build and now, 14 months into our journey we are finally seeing traction and have excellent market validation if we can ever finish the product (have built multiple MVPs and learned SO much), right as the money is running out. So your 2 year advice feels about right to me.
It's very frustrating, and I've resisted the urge to put the build on hold to raise capital (can't easily do both at the same time) - so now I'm looking for a job that is low stress, hopefully part-time just to stay afloat so we can close that first enterprise customer. We have paying "users" but no actual enterprise sales (for a B2B product).
So if any of you are looking for some cybersecurity expertise, hit me up. But in meantime, I'll be job hunting for 2024 and keeping the startup dream alive! Just a tiny bit slower. For now.
Good luck!
Not a lot of people are willing to do what you do.
Hope it pays off very soon.
About Zylvie, do you think to expand to other countries?
What do you mean?
It's global already.
Hi Jay, the platform could be config in spanish? Thanks
Not yet, but we're already working on localization!
Thanks, I was thinking something simpler than localization, but the ability to choose the language showed in the frontend store.
Do you have a promocode to I give try?
Worthy sharing, thanks.
Still struggle ing!
If you have to work, try to find some relaxing job, just keep a living!
It's almost impossible to do 2 jobs good at the beginning. If you wanna do both, make sure you can accept a bad result at one :(
Unfortunately there's no such thing as a relaxing job these days.
Everything is stressful, including minimum-wage jobs.
What I can say is take a part-time job instead of a full-time one, so you at least can limit the stress to fewer hours.
I actually did quite my job. But have enough funds for a year. I believe figure it out. Thanks for sharing.
How did it work out?
Yesterday was my last day at office so starting today. I know it's a risky move. But I'm very optimistic about it. I'll figure something out. I wish I knew about IH a couple years ago. Anyway stay connected I'll be sharing my journey as I make any progress or not.
An helpful sharing, I'm about to quit my job to launch my business so this really resonate to me. Thanks!
This resonates for sure!! I just started my new venture after being laid off, and while I'm 1000% happy with where I'm at and our prospects for success...I would rather launch a company while still working my day job.
Thanks for the reminder and glad you've gotten to a good spot with Zylvie.
Hey Jay, hats off to your grind with OKDentalPlans and the shift to your Twitter tool. Balancing a day job while bootstrapping a dream is no small feat.
Your story's a solid reminder: "don't rush to quit the day job. Stability can fuel the hustle."
Keep rocking it with Zylvie, and best of luck for big wins in 2024 🙌
Thanks, Zeki.
I find that most people who rush to quit their day jobs actually hate their day jobs.
Perhaps the correct move in that scenario would be to look for another day job, not go all-in in a nascent business idea.
Lesson learned. Now, how I do I get my day job back in this hiring environment haha
I think this is overall good advice for a lot of people. There’s definitely a sweet spot where quitting the day job makes sense. It’s just like taking in funding in a way. For funding you ask yourself “will $x for x% equity help me multiply my business in a way that I couldn’t do otherwise?”
Similarly for quitting the day job one should ask themselves “would x more hours a day for $x less monthly income help me achieve a better outcome?”
Sometimes people are tired and frustrated with their day jobs and may be feeling that the grass is greener working on their idea. This is a fair feeling to have, but as you mention it’s important to have the data in your favor as well.
If you're quitting for the right reasons, it will be quite obvious -- you can feel it.
The traction is there, people are signing up in droves, influencers are singing praises about your product, you have an ever-growing list of to-dos/feature requests to work on, and revenue is slowly but surely creeping up.
If these things aren't there yet, it's most likely premature to quit, meaning you could have achieved the same outcome without quitting at that point.
Thank you for sharing your experiences and wisdom.
If it doesn't work out, you can always come back to the corporate world. Just make sure you keep the door open! :)
You're right, but hopefully it doesn't come down to that.
Worthy sharing. Thank you.
Awesome article! I've been contemplating quitting my day job to work full time on just building a product that might never have any potential. I'll probably keep chugging along on my off hours and wait for some sort of growth trajectory.
Just to build?
Definitely not.
If it's already built and you've soft-launched, it can be a worthy gamble provided you already have a clear distribution strategy mapped out.
I have my mind refreshed after reading from this perspective. For me, it has always been a constant struggle between managing full-time work and juggling side-hustle. But then again, I can't agree anymore that cash burn rate without a job is far worse because it can lead to anxiety.
I guess the best thing is to play on your strength and seek help for the things that might take you more time. You showed perseverance and that's what matters.
I wish you the best of luck for 2024!
Both choices are hard.
9-5 jobs are designed precisely to suck your soul and make you completely exhausted so you don't moonlight or start a side hustle.
This is why I've always believed that a happy middle ground is to work a part-time job while bootstrapping on the side.
There's no reason why one can't bootstrap a business alongside a low-pressure part-time job.
Refreshing to see contents like this in indiehackers where everyone over here shares oly the positive side
Unfortunately sob stories don't get traction often, because very few people are interested to learn how to fail (though it's important to learn, otherwise it's a form of survivorship bias).
Your journey is a living example of perseverance and the priceless lessons discovered through adversity.
I wouldn't have it any other way!
(as long as I eventually succeed in the end lol)
This is a really nice article.
Glad you enjoyed it.
I mean it was really anxiety provoking and I'm sorry you went through this, but it's a well-written article, for what it's worth.
Just sharing my side of the story.
Everything is over-positive here, I'm just bringing it back to earth by sharing the not-so-rosy side of entrepreneurship.
The situation when building a product as a side project is really a catch 22 situation.
The advice you provided of having 2+ years in cushion/runway before devoting full time to your product is the dream scenario for everyone, but hardly real for most. While you are piling up your 2+ year runway, things are happening on the market, there are major shifts and without testing your idea and launching it ASAP you might be actually sabotaging yourself.
I agree that everything takes time, but I don't agree with the general advice of playing it safe, the entrepreneurship arena requires taking risks. If you are not willing to make some bold moves, maybe be real with yourself.
You failed with the OKDentalPlans, so what? I bet you learned tons out of that experience. Pick yourself up, dust yourself up and move on, but move bravely again and don't be affraid to fail again. For me it is more scary not to try versus to fail.
My 2c on the topic would be:
Don't get stuck with your 9-to-5 or aim for 2+ years runway or look for formula that fits all, everyone has individual scenarios, capabilities, networks and support systems. Just listen to your gut and make risky, but smart moves when you feel it is the right time.
Well you're right.
"2 years cushion" and "don't quit before clear traction" are just arbitrary guidelines, if you have a different plan (and risk appetite), definitely go for it.
I just wanted to provide a realistic scenario as to what might happen if one quits prematurely.
Traction is hard to get, no matter who you are and what you do.
Sometimes it takes more than sheer courage to succeed in entrepreneurship.
Agreed, it is a very tough game and that's why I mentioned that there is no real formula out there.
Tnx for sharing your realistic scenario, most def we need more of these kind of posts because this is much bigger reality for founders than the successful ones we all read.
Great post, just wanted to clarify that people shouldn't take "2 years" or "before traction" as concepts written in stone. Cheers!
I completely resonate with every word you've written. The struggle between the heart and the head, especially when stuck in a job you feel is uninspiring or unfulfilling, is absolutely torturous. I felt t a similar way back in 2018 and dreamt of quitting my job every single day, but hung in there for an additional 6 months so I could leave with a fat bonus.
And then they made me work out my 3 months notice after resigning.
And had to turn up to a 2-day conference a week before my last day.
It was brutal. But that extra time (and cash) helped me set things up for success and without them, I doubt I'd be doing my own thing now - I probably would have had to admit defeat and head back to the grind of gainfully employed.
Navigating through this phantom zone between a day job and your dream job is challenging. During this period, I came across a fantastic book that offered plenty of insight and practical advice (and talked me off a ledge sometimes).
The book is titled 'Quitter' and it’s authored by Jon Acuff. It’s widely available on Amazon (https://amzn.to/3S3ongn) and if you have a Spotify premium subscription, you can also listen to the audiobook for free (https://open.spotify.com/show/2Fk38CxQCEBr56cnnpQ4Hg?si=96df4392e74942ab). I found it incredibly useful and I'm sure it could help others going through a similar phase.
Thanks for
Your experience. It’s really interesting!
This is a great read. Thank you for sharing your experience.