Turning what you love to do into a second income stream

Well, no: not THAT what you love to do!

My late friend Jerri, about whose shopping hobby you read recently, had an incredible eye for clothing. She owned racks and racks of really cute clothing, much of it designer-label and most of it purchased on sale. She absolutely loved to shop, and she was very good at it.

Right now I have on a beautiful silk shirt that her daughter gave me. It’s a couple of sizes too large—Jerri was a bit portly in her old age—but worn over a coordinating shirt, it works to create an awesome, arty-looking tunic. The effect is really nifty.

If I had known that Jerri could do this—find amazingly cute clothing in stores where I never shop at prices I never manage to extract from retailers—I would cheerfully have paid her to help me shop.

I’m no good at shopping. When I go into a clothing store, what I see is a jillion square feet of look-alike clothing that
a. doesn’t fit me;
b. by and large is ugly;
c. looks like it was designed for or by a teenaged hooker; and
d. is hugely overpriced.
It’s a real struggle to force myself to paw through rack after rack after endless rack of this stuff searching for something that fits, that looks OK on me, and that I can afford. To me, shopping isn’t fun; it’s a pain in the tuchus.

Jerri’s shape was even less like a 17-year-old babe’s than mine is, and she managed to find a boutique’s worth of clothing that looked good on her. Two or three sizes smaller, and it all would have looked good on me, too. She had a real skill. IMHO, it was a salable skill.

I know I’m far from the only woman who views shopping for clothes as an unpleasant chore—several of my friends have expressed the same sentiment, including one with a real flair for style. It seems to me that Jerri could have made herself a nice sidestream income by hiring out as…what? A shopping coach! She could have indulged her joy in shopping by selling her time as a shopping consultant to women who don’t enjoy searching for that one thing that works among the acres of chaff. Because she had a wonderful and funny personality, she could make a shopping trudge into a fun outing. I’ll bet she could have found enough women who would have paid her to help them buy clothing to supplement her Walmart salary pretty handsomely.

On the other hand…

Some years ago a friend of mine was left penniless during a divorce. Literally, for two or three weeks she ate nothing but zucchini out of a backyard garden, while she used the few dollars she had to feed her two small children. She let the dog run loose to forage out of the neighbors’ garbage cans. She took a miserable job waiting tables, an occupation for which she was decidedly not suited—this was in the days when coffeeshop owners felt free to order their waitresses to wear skimpy costumes and bone-crushing shoes (sex sells hamburgers, too), and so you can imagine what the job was like.

This friend had studied photography on the college level for several years and had quite a gift for it. She had an acquaintance who owned a major portrait studio in the city. I asked her why she didn’t try to get a job there or at least see if this person could help her get in with some other studio.

She said she didn’t want to spoil something that she loved to do by having to make a living at it. Since she didn’t last long at waitressing, apparently she felt strongly enough about this that she was willing to go hungry rather than turn a pleasurable pursuit to profit.

What say you? Given that it’s a good idea to establish more than one stream of income, is turning a hobby into an income-generating occupation out of bounds? Would you convert your favorite pastime into paying work?[polldaddy poll=1169792]