My favorite Whitney Houston song is How Will I Know. I had the cassette in college and listened to it often. I mention it because someone asked me, “How will I know when it’s time to go to a major market?”
They then rephrased the question like this, “Is it better to be freelancing and looking for opportunities while living in my desired market, or should I stay where I am and tough it out while pursuing other opportunities?“
I lean towards moving to the market where you want to be because most employers prefer to hire regionally. My first job was in McPherson, Kansas but I always wanted to work at XTRA Sports 690 in my hometown of San Diego. I sent nearly 10 cassettes to the program director Howard Friedman. I never heard back.
After three years in Kansas I felt like I’d learned all I was going to there. I moved back to San Diego figuring I needed to live there if I wanted to work there. Howard hired me less than three months later. He wasn’t going to hire somebody from Kansas, especially when new hires usually entered as part-timers.
My career flourished after I arrived.
When you feel there is no more room for growth…
That is when it’s time to move to a major market.
Ultimately, go where the opportunities are. If you’re a play-by-play guy and you’re currently getting play-by-play opportunities in the small market, maybe stay longer. The best way to get better is through reps.
If you feel like the flower that’s outgrown the small pot, the only way you’re going to improve is by moving to a bigger market. Just understand that it is probably only going to be part time at first and you will likely have to find additional work to help pay the bills.