I haven't left my day job, but I've definitely struggled with the same thoughts about whether I was "flaking out" by not leaving a stable but non-challenging job.
First, you should never feel guilty about providing for your family. We glorify start-ups in silicon valley because of survivorship bias and it's silly given the realities of a person's family responsibilities. So let's get that out of the way.
Second, if you think about leaving all at once it can seem daunting. Instead, you should prepare yourself over the next years to manage the risks of starting your own business. This means understanding your family finances, saving money, setting a timeline for your business, and setting a time to call it quits and go back to a salary job to reorganize.
Make a plan, communicate with your family about your goals, and then prepare yourself to execute that plan. Good luck!
You know, I faced something similar when I felt I have finally found "success". It was a difficult time to get motivated not only because of the lack of any more challenges, but also because I felt I had lost a worthwhile goal to pursue.
In any case, it seems that you're financially successful, love what you do, and right now may be looking for the new challenge.
I would definitely recommend you take some time to think about what are new challenges you'd like to tackle. Brainstorm and don't let reason hold you back from making big and daring goals. Then review your resources and see what you need to work on to start on another path.
Hope this helps. Obviously a lot of other great recommendations in this thread, so I definitely recommend you start writing down your thoughts and how you're thinking through things. It'll help you keep track of your progress.
I feel like the quality of sites aren't too great on flippa. Additionally, it generally takes quite a bit of time to manage and upkeep a business. What you're looking for is a passive income generator and stocks/REITs are probably going to be the most accessible form.
Don't think of the stock market as being limited to buying Company A vs. B. You have access to other asset classes (bonds/commodities/emerging markets) through mutual funds and ETFs.
Building wealth is a long-term thing. Understanding what you're buying and knowing what your goals are will be key to building your assets so you gain access to the more interesting investment options (rental properties, hedge funds, etc).
Note, I said more 'interesting', not necessarily better.
I echo this statement. Don't forget to specifically identify experiences from your start-up that are applicable to the job you're applying for (sales, project management, coding, etc).
First, you should never feel guilty about providing for your family. We glorify start-ups in silicon valley because of survivorship bias and it's silly given the realities of a person's family responsibilities. So let's get that out of the way.
Second, if you think about leaving all at once it can seem daunting. Instead, you should prepare yourself over the next years to manage the risks of starting your own business. This means understanding your family finances, saving money, setting a timeline for your business, and setting a time to call it quits and go back to a salary job to reorganize.
Make a plan, communicate with your family about your goals, and then prepare yourself to execute that plan. Good luck!