My Chief Operating Officer (former – she’s moved on to greener pastures) called a meeting last year and during the meeting our Chief Executive Officer asked my coworkers and I about what we saw for our market in the coming year. Specifically he asked, “What keeps you up at night?” I remember the question because I remember both my response and my thoughts about the question itself.

First, I thought that this was a weird question because it is the rare employee that brings their work home with them. Then I immediately thought that this might have been the CEO’s way of asking us about ourselves so he could ascertain what we were like outside of the office. I figured that this was too awkward of a question for him to ask in a personal sense so it must be directly related to the job. I remember my response, given in a typical brash, young, over-confident tone, “Nothing keeps me up at night. Once the day is over I drive the hour back home and either teach at the college, do work for my website company, spend time with friends, or enjoy some down time.”

Dope.

Here we are a year later and I find myself bringing more work home with me, engaging my company in their proposed plan to get us Blackberries (which I supported from the beginning) so that we can be connected on the road, and looking at a calendar that is overstuffed with events. I also find myself not pleased with the potential for upward mobility in my current position and coming to the realization that working for my current company will not help me achieve any of my financial goals in a respectable time frame. Finally, I find myself in a job market where it would be unwise to up and leave one’s current employment to look for a better deal; especially when you really enjoy the job that you currently perform (and I do enjoy my job and the work that I do). In some respects, it’s a paradoxical time to be someone young in their career.

To get back to the point, though, the question was an odd one. What really DOES keep you up at night? What things weigh on your mind so much that you actually miss sleep to ponder the issues? I thought about these questions and came up with an answer or two…

The biggest thing that keeps me up at night is my student loan debt. And frankly, if that’s the biggest thing that keeps me up at night, then I’m in good shape! It’s the sheer size of the loans that keeps me awake. At the end of last year I owed a little more than $110,000; by the end of this year I should owe a little bit more or a little bit less than $105,000. I’m making significant progress, but I need to make much more progress and much quicker progress if I’m ever going to be in a position to be financially free. Related to the student loan debt is my ability to secure a mortgage when I finally buy a house in a few years. My credit rating is through the roof (somewhere between a 750 and an 800), but who knows how long the tightening credit markets will impact the housing industry?

That’s really about it in terms of what keeps me up at night. Sometimes I wish I had more of an ability to slowdown and relax or travel, but I work in the time to do an adequate amount of that stuff. One thing that I am well aware of is that you can’t live above your means and there is nothing more financially disturbing than when people live a credit card lifestyle. You know, the people who need to borrower from one source of capital to pay another source of capital or those who use money from non-permanent sources to pay semi-permanent expenses (constantly asking parents for money to the rent or for groceries, for example). But those people generally get what they have coming to them – you can’t live through a market fluctuation like we’re currently seeing and not expect that you need to personally change your financial habits.

What keeps me up at night? Student loan debt. But I’m working my plan to pay it down and I’m making good progress… I’m hoping that I can kick the repayments into high gear in the next few months!