In my view, there are three strata of businesses that a person can start:
1. Small business - Bakery, barber shop, golf store
2. Lifestyle startup - Unique product, smallish market, little chance of liquidity event
3. Venture - Startups with the potential for massive, fast growth
Every time I think about starting #1, I dismiss it immediately. I see it as merely the illusion of freedom.
A girl from my hometown opened a Pure Barre. Sure, she doesn't have a "boss", per se, but she's still working like a dog to send most of her money to the .1% -- the rent she pays in the shopping center, the utility bills, the franchise fees, the Gatorade she sells from the fridge, the fridge itself, etc... and probably makes There are exceptions, but generally I think the same thing is true of restaurants, bars, computer repair shops and franchisees of all stripes.
Having experienced #2, first-hand, I can tell you that it's much harder to do than it sounds. I think the universe wants growth or death in all things. Hanging out -- safely -- in equilibrium between them is a rare feat.
If you aim at a market that's a bit too large, you're going to get crushed by the big boys. In fact, there are myriad examples of large corporations butting into small markets first discovered by startups because, heck, why not? The big corporation has the resources to inject itself into the small market on the off chance that there's actually something there. It's like buying insurance.
If you aim at a market that's too small, then you don't make any money and you're on your own to pull it off because no (worthwhile) investor should want to get into a small market with MAYBE a $5m buyout years down the road. Ditto good co-founders and employees. If you're able to get investors and rock-star help, you're probably in "venture" territory, not "lifestyle".
What happens with a lifestyle biz is you end up turning a small profit and living on the edge, fearing that something doesn't go horribly wrong. One lawsuit... one legislative change... you, the lifeblood of the company, have a medical emergency... and it all goes poof.
Worst of all, you're stuck. Because it's a middling market, it's difficult to find anybody who could run it in your stead (they're at Google, etc), so it's always and forever on you.
Again, there are many exceptions. Like the guy who runs The Chive or the guy who runs Fark. It's possible, just harder than it sounds. If you're going to take all the risk and invest your time, why would you knowingly aim small like that?
No, for my money, #3, swinging for the fences, is the only way to go. Anything short of that is setting yourself up for years of anxiety and frustration with little chance of making real money. I'd rather put my money on red or black and see how it turns out quickly.