The NY Times recently ran a piece on an increasingly common practice: college graduates taking internships in lieu of proper jobs. In For Interns, All Work and No Payoff, Alex Williams explores the pros and cons of essentially working for free, especially among college graduates with oodles of debt.

Breanne Thomas is interning for a tech company in New York. Karsten Moran for The New York Times

The article was of particular interest to me, as I too am an ex-intern with no shortage of thoughts on the matter. In my twenties, I interned several times–once when I was 20 for three months as an undergrad and again at 23 for three weeks during my first winter at grad school. In each case, I lacked relevant experience for what I thought I wanted to do upon graduation. I figured that the juice was worth the squeeze. I took a paid internship at the age of 24 for the now-defunct Data General.

Why not hedge your bets and start your own shop?

The idea of working for free post-graduation never occurred to me. I didn’t spend a tremendous amount of time and money on my education to volunteer my time and skills. I am not passing judgment here; I am not better than those who have made this choice.

Simon Says: Find a Middle Ground

If you want to give away your time, go right ahead. No one is stopping you. It’s not hard to understand the motivation of even highly skilled and educated folks to get their feet in the door. That goes triple for highly desirable companies and industries like sports entertainment, Hollywood, etc. Many if not most organizations will gladly accept the toils of those who want to work for free. But before doing so, ask yourself a few key questions:

• Is that sacrifice likely to result in your desired reward?
• What happens if your best-case scenario doesn’t unfold?
• Can you afford to be wrong?

Instead of working as a full-time intern, why not hedge your bets? How about two or three days of interning while you start your own shop? These days, it’s not terribly difficult or expensive to set up your own company. In The New Small, I explain how the cost of powerful technologies have dropped by orders of magnitude. The benefits here do not accrue exclusively to existing small businesses. For well under $2,000, anyone can incorporate, register and build a functioning website, purchase a customized logo, and the like. Putting all of your eggs in one basket is extremely risky, especially when it’s an unpaid basket. Several irons in the fire may very well increase the likelihood of a desired outcome, whether that’s working for a particular company, in a particular industry, or something else. While unlikely, if your own venture takes off, would you even need a “real” job?