Ask HN: Do you regret leaving corporate for entrepreneurship?

How does your full time job's contract deal with side businesses? I'm always wary of starting one because my company requires a lot of paperwork and approval and running it by legal, HR, Joe Shmoe, etc. to do something on the side

Not a chance. If someone wants to hire me, they do not own my work outside of business hours. It's the new serfdom.

I've never had no sales but have had some products that were low volume. They have always been a useful learning experience, either from a technology or business perspective.

I don't regret. I left my day job in late 2016 and started to do this startup thing. I'm still very happy.

I've seen people who left day job to start companies and became very unhappy very quickly (within 6 months). The key thing is to have the right motivation and to manage expectation.

If the primary reason to start your own company is to look good in front of your other fancy friends, then you'd better not do that in the first place. Doing startup is roller coaster. You won't look good in front of others all the time. Actually, for a long period of time (many months ~ many years), you may look pretty bad, in terms of product metrics, income, company reputation...

Some of my friends asked me whether they should start a company, I typically suggest them to answer these questions first:

* Have you made over $10k on your own? Not from your day job salary. Not from public stock market. Making money needs practice. You start a company to make money. You'd better have some experience of making money first.

* What's your longest project? Have you worked on anything for multiple years? Grit & patience need practice. Building a successful company takes multiple years, even decades. Be prepared.

* When was the last time you were insulted by others? If you grew up in a very comfortable environment (rich family, great schools -- because your parents went to those great schools too, great companies, ...), probably you already get used to compliment for your entire life. Now you are going to face very very diverse set of people who don't know your family background or don't recognize your family name, if you start a company. If you are the kind of people that are easy to be upset, you'd better stay in the friendly corporate.

* What happened when you broke up with your ex or your friends? People relationship is complex. You'll experience a lot of bad people relationship if you start your own company -- breaking up with cofounders, firing employees, fighting evil investors, fighting con man, fighting bad reporters, dealing with malicious users, dealing with competitors (sometimes in person)... All kinds of drama. You'd better practice this kind of things before starting your own company.

I started my first business while I was in college, and kept it going on the side while working the real job. After a year at the real job, I decided to leave and focus on the business.

What happened to your company from college-- did you shut it down? Sell it? Did it die on its own?

I don't think anyone can tell you whether it's the right time for you. Neither decision is permanent, though: If you do leave and it doesn't go well, it shouldn't be hard to go back to your old job or find a new one. "I took a year off, started a business, learned a lot, failed, and now I want a job" should go over well with most employers. If you don't leave, you can spend the next year learning more from your employer while tinkering with your idea on the side -- and then leave next year.

As you age, you'll tend to accumulate obligations. Marriage, kids, mortgage, elderly parents/relatives that need care, medical problems of your own -- things like this will make it harder and more risky to quit your job later in life. So if you're going to do it, your 20s are a great time.