How Much is Enough?

I had lunch the other day with a friend. He has a has a reasonably high paying job in consulting which he sort of enjoys but would rather be an artist. So the question he posed was “How much is enough?” – meaning how much money does he need to become an artist. We spent the rest of the lunch talking about different options for approaching this.

Here’s a recap of what we have come up with so far:

1. Don’t wait, just start trying to sell some art right now on the side while going full steam with his work. We concluded this was hard given the demands of his job, which involves a fair bit of travel and dinners with clients. So this makes it difficult for him to carve out time consistently to work on art. We agreed though that with a high degree of will power this might still be possible. There are some examples of people having succeeded this way, notably singer John Legend who was at BCG while also launching his music career.

2. Dial back work a lot but keep some income going. This will require him going freelance and losing health benefits. Definitely felt more doable than option #1 but also somewhat riskier. Two conditions seemed important here. First, making sure his expenses were low enough / his income high enough to not require digging into savings (see next option for that). Second, having fairly reliable repeat clients so that there isn’t a lot of uncertainty about his income or a lot of time spent finding clients. I have a musician friend (not a breakout artist) who has been doing this for two decades now consistently putting out new music.

3. Save up enough for a time period of just art. We tossed around having at least two, but better three or more years of “runway.” Enough time for him to really give art a try, and then still some more time for him to restart a consulting job should the art thing not pan out. Definitely more risky than option #2 financially, but it would allow him to focus 100% on art. That might have the highest likelihood of succeeding at art, although as my friend pointed out: “I doubt that I could handle the stress of seeing my savings decline every month.” Fair point. The attractiveness of this option also depends a lot on how confident he is in the ability to restart consulting after a multi-year break. He wasn’t sure about that.

4. Earn enough to be able to generate sufficient passive income. We talked about buying a place that’s so big that he can live in it but also generate rental income to cover the costs of a mortgage, taxes, maintenance and living. This actually seemed doable in due time given his savings and income level but with one important caveat. He loves New York City and, well, real estate here is ridiculously expensive making this challenging. We talked about moving somewhere cheaper, which he’s not super thrilled about (understandably). We are still working through the numbers on this though.

Sorry if you were looking for precise numbers based on the title of the post. We didn’t get that far (yet). In writing this up though, I came up with a combination idea: #4 + #2 (could also do #4 + #3 potentially). Basically buy real estate somewhere outside of New York City, have that generate passive income and be a place he could live should everything fall apart, but pursue art here in the city.

If you know of someone who has successfully made such a transition or have made it yourself, it would be great to hear in the comments how they/you approached it.