There are a lot of people in these comments that I think are totally missing the point. I’m sort of like you in that I want to work toward a semi-retirement. I don’t desire to stop working all together, I just want to be able to pick and choose what I work on, preferably while also building my own businesses. I plan on having a mix of assets before I can officially transition to this lifestyle though. For instance, my employer offers a decent 401k match, so I contribute enough to get the full match, but this is money that I am not considering accessible for my semi-retirement strategy. Hence I could end up with $50k in this 401k by the time I semi-retire but I won’t be factoring that into the equation.

I’m still not 100% sure what my number will be, but I do live less frugally than you. In my head, it’s probably 5x my annual income needs, or about $400-500k. In liquifiable assets (cash, savings accounts, brokerage accounts, crypto, etc). The way I see it, I could reasonably expect that I’ll still earn $50k or more on average per year, even with being very picky about work, with some years earning $150k or more, and maybe some earning nothing or almost nothing. So $400k could probably last a good 10, maybe 15 years when you factor in the income I’m still bringing in. I think that’s more than enough time to end up starting a successful business that carries me through the rest of life.

Also, I may go for it earlier if I have more reliable monthly income from non-job sources that can supplement the total income I need to live. So like every $1000/month of stable income would potentially reduce the total retirement number by $100k.