Priceless reactions to my big career change

Published by Ryan Healy on September 24th, 2007 in Career Development, Entrepreneurship, Work/Life | 13 Comments

Last weekend at the bar, my friend and I went to the upper room and got some drinks. We spoke with a couple of girls who told us it was a private party, but nobody else was there.

"It doesn't seem like much of a party to me," I joked.

One of the girls replied: "Well you can leave if you want. We didn't invite you."

…I deserved that response.

I apologized, and bought her a drink. She wanted nothing to do with me after my snide remark, but then she asked what I did for a living. I told her about our plan to start Brazen Careerist.

The next thing I knew, she was telling me her life story. She even tried to sell me on why she would make a perfect accountant for our new business.

I'm constantly amazed at the range of reactions I get when I explain my next career move. Then again, there are always a few familiar responses.

Are you hiring?

Hands down this is the most common response I get and it almost always comes from other Gen-Yers. I am amazed at how many people seriously ask me this question.

The conclusion I have drawn from this is that millennials all want to try something fun and interesting, but most of us either don't know where to begin or are too scared to risk everything on a startup. This should say a lot to employers.

First off, small startups should have no problem recruiting young people. If you have a somewhat established small business that can pay employees without giving up equity, the market is incredible. Secondly, if you are a large corporation, figure out how to operate more like a startup. See Google for instructions.

You need to do it while you're young.

The most common response I get from Gen-Xers is, "Go for it. You have to do it while you're young or you never will."

I love this response because it completely reaffirms my thoughts that the time to get ahead is in your twenties – before a spouse, before kids and before a mortgage. Most folks who tell me this are completely happy with their lives, but they seem to admire that I'm giving it a shot. I often repeat this response to myself when I'm lying in bed wondering, "What the hell am I doing with my life?"

What on earth could make you move to Wisconsin?

This is a tough one. I have always lived on the coast. I was born in the Bay Area, went to grammar school in Seattle, High School in Connecticut, College in Pennsylvania and spent the past year in Washington D.C.

There are two things that could make me want to move to Wisconsin. One would be the girl of my dreams (of course, I would try to convince her to move to my area first). The second would be a chance to finally start a company. Who knows if I will like Madison or not, but I'm not making the decision based on the city, I'm making the decision based on my career.

If this explanation isn't sufficient, I usually tell people about my trip cross country when I moved from Seattle to Connecticut. I was 12 years old. Of all the places we stopped on the 11-day journey, I liked Madison the best. I told my mom that I wanted to move there one day. Maybe it's fate. Then again, I was 12.

Finally, if it's a guy, and they still aren't satisfied, I just tell them Madison has tons of beautiful college girls. They wish me the best of luck!

How can you afford to support yourself?

This is a great question, and one that I often ask myself. Truthfully, I'm not totally sure. We have raised some angel money, so I can draw a salary, and I do have some savings. But beyond that, there are no guarantees.

In a strange way, this excites me. I have never experienced life without a steady, guaranteed stream of income.

The health insurance thing is my biggest worry. Even with a small salary, I don't think it's realistic to draw enough for full coverage. I'll get a catastrophic plan at some point. But I guess there will be no more visits to the doctor for my annual sinus infection. I'm definitely rolling the dice, but it's worth the risk.