Founders, do you ever feel like packing it in when things are going ok?

Yes a lot of time. I run a bootstrapped SAAS of about 15 of us and I think about quitting almost every 2-3 days lol. It is the nature of the beast. This shit is hard. It grinds you down. Oh is it 7 PM ? Guess what, your customer doesn't care. Bam, 6 new support tickets in queue while you wanted to get up and go play with your kids. Ok we can leave them for my support team but wait, 1 is critical and needs attention. oops, I gotta do something. All "employees" are gone for the day. While doing this, I get an angry email from another customer about some crap and why they only want to talk to me, the founder about it. All this when I have 15 people. I can only imagine the plight of solo team founders :).

But then I close my eyes and imagine myself NOT doing this. Oh well, a shitty corporate job where I feel soul less. And right then, I am back to the grind. This is my own shit. I get to decide. I can scale back if I want to. Some days, I can tell the clients to wait 3 hours. Some days, I am just not in the mood and that wouldn't make my boss upset (I have none. Customers can again wait). Just made a new sale. What a feeling. I am back on the high horse. Woohoooo. Rinse and repeat.

It's not just you. I founded a bootstrapped side project/startup that has gone viral during COVID. It's been a wild success, people love the product, but going from solo to now a team of 5 in a period of 2 months and handling a huge amount of users has been stressful. Business-wise, I shouldn't be anything but super happy, and advisors say we've won a lottery, but honestly I miss having less responsibility (e.g. keeping people employed, duty to thousands of customers 24/7) and pressure (don't screw this up!). Don't get me wrong, the ride can be exhilarating and I'm sure I will look back on it one day with pride, but at times I yearn for the days of "just" being a freelance dev who had relatively low stress and tons of time for my wife and kids.

Yeah, it's a lot of responsibility and commitment. Sometimes it would be nice to just be able to spend your month's income on anything, instead of saving every cent for a rainy day. Or just sit on the weekend playing games.

I feel like it's just the next step to growing up, sort of like getting married and having kids. There's plenty of perks to being in another phase, but it's important to remember that plenty of people have sacrificed to get you where you are. Your investors, your staff, your family, customers, government, mentors, and of course, yourself.

It's similar to college - it's tempting to just want to take a blue collar job when you're pulling all nighters and have to deal with student loans.

I guess a good reminder is to talk in an anonymous group with others who wouldn't believe you, lol. Maybe a Fortnite discord group or so, lol.

Yess, especially when again and again my friends are doing something cool like having a party or a weekend out of town and I have to stay working.

It is certainly a grind. Delegate, automate, and take vacations. Also hire someone to replace you ASAP. But not before making sure the business can be run by a dummy.