The organizing principle behind this grouping, appropriate economic units, is relatively simple: if the activities are located in the same geographic area; if the activities have similarities in the types of business; or if the activities are somehow interdependent, for instance, if they have the same customers, employees or use a single set of books for accounting.
The way many people reach Blockbuster Financial Independence with income of $250,000 – $300,000 is through a combination of investment income and passion project cash flow. Since FI allows you to do whatever you want, here’s your chance to follow the cliché, “follow your passions and the money will follow” without worry that there will be no money. My passion so happens to be this site.
Hang in there, Adam. I’m in the similar boat as you. I’m 51, looking to retire @55 when my son goes to college (his tuition is already saved in separate 529 account). @4% withdraw rate, we have enough assets to generate passive incomes of $250K+, and our annual living expense is <$100K. Neither me or wife have pension or medical coverage, but we do have 401K and some prior HSA savings.
The topic you choose must have enough depth that you can create a lot of content for it. This is important for building an authoritative site, for search engine optimization, and most importantly, for the end user. If you don't have enough content about a topic, you're not going to be taken very seriously as an authority on the topic and it's unlikely you can convince someone to make a purchase from you. 
I am not the poster boy suckup or the golden boy on the team. Those guys work on the new stuff and they attend meetings all day to show how busy they are. They do the dog and pony shows to mgmt. I make 172K a year and I only work 10-20 hours a week from home. When there are problems or after hours or late weekend work then it can be stressful. Being on 24×7 online support sucks but that is part of the job. I am the ONLY one that knows my systems so if they want to get rid of me than so be it. I just want to gracefully try my best to make it to 55 and just retire.
The key to acheiving FI is just living below your means. When I was a 9-5’er, I would spend $10 on coffee and $20 on lunch and $30 on dinner. I was miserable. Living on the cheap now has made me much happier and has given me more time to do what I love (surf, in my case). Everyone has a choice and if you choose to live below your means and save you will save. That’s a fact!
I guess I’m in the Blockbuster Category, but living in the Midwest I’d have a hard time figuring out how to spend $300k/year even though the math says it is not a problem. I think the reality is most people who are super savers are going to get to Blockbuster eventually assuming they don’t inflate their lifestyle along the way. There is a lot of truth to more money not bringing you more happiness…I spend less in “retirement” than I did while working and I’m exponentially happier. I checked my taxable account for the first time this year and it in the first 11 days it is up more than I’ll spend this year, interesting times indeed.
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