On Dodging the Nine-to-Five Life Indefinitely

Becky just wrote about the comforts of the nine-to-five life post-college, so I thought I’d weigh in from the perspective of someone who’s entirely avoided that life for almost 16 post-college years.

Yep, 16 years. I graduated from college in 1997, and decided to push straight on to grad school since (a) I didn’t want to go to work doing what I’d studied in college, which was being a preschool teacher; (b) my college roommate was also going to grad school in Boston, and I could live with him; (c) having grown up playing video games, I didn’t want to quit the academic game until I’d defeated the final boss.

My first graduate program led to a research assistantship, which led to a second graduate program, which occupied me right up until the year of my ten-year college reunion, when I successfully defended my dissertation and was presented by Princess Toadstool—or rather, by my advisor Jason Kaufman—with a doctoral hood. I’d gone to grad school more to go to grad school than to achieve any long-term career goals, so rather than take a seven-year tenure-track job in God-knows-where, I moved back home to St. Paul, Minnesota.

So there I was: in my early 30s, unemployed, single, and living with my parents in my old bedroom, glow-in-the-dark stars still intact on the ceiling. I took some writing jobs and ultimately landed a part-time position at a nonprofit news publication, later supplementing that with freelance writing jobs and college teaching gigs.

I’m now 37, living in Minneapolis, and working at two jobs plus occasionally writing freelance pieces and helping to run a blog (this one) that recently graduated from being a “personal project” to being an officially registered limited-liability corporation operating at a loss of $20 per month.

I have no 401k. I buy my own individual health insurance plan, with a $5,000 deductible. Since I only started paying my student loans in 2007 after letting interest accrue on them for a decade, I’m still almost $50,000 in debt. I live in a studio apartment. I drive a ten-year-old Ford Taurus that sometimes makes a weird clanking sound when I hit the brakes.

Will I ever work in a real office? Will I ever have a job with benefits? Will I ever be completely out of debt? If not, not, and not, is that a problem? I honestly don’t know. Becky’s been lucky to find a good nine-to-five job that she loves, but I’ve never had one of those, so it’s hard to know what it would be like. Having benefits would be nice, making more money would be nice, enjoying the day-to-day camaraderie of an office would be nice, and it would be nice to have it be someone else’s problem when my computer doesn’t work…but then, it would be hard to give up the perks of being a free agent.

When I want to take a break in the middle of the day and write a blog post, I can. No one’s looking over my shoulder. On most days, I work from home, so I can sleep until 9:00, open my laptop, and be at work at the same time as some other people who had to get up at 7:00. I can listen to whatever music I want to, all day long. If I feel like it I can take a day off, often without asking anyone or giving any notice, and make the time up over the weekend. I can plan trips without counting vacation days. My boss seriously says things like, “I’d love to have you at that meeting tomorrow, unless you have something more fun to do.”

Best of all, I can wake up every morning and actually look forward to my day at work. I don’t mind working at night or on weekends, because my jobs usually don’t even feel like work. My online journalism job often feels like an only slightly more structured version of the kind of putzing around online that a lot of people choose to spend all their leisure hours doing. My college teaching job involves reading and talking about media and society, and reading my students’ posts on Tumblr. Because both jobs are with nonprofits, I’m working to advance worthy missions—social equity, education, media access—instead of creating value for shareholders.

So nine-to-fives have undeniable benefits, while a looser (no, that’s not a typo) job situation has its own perks. Whichever path you take, here’s my advice:

1. Do what you love.

2. Work with people you respect, and who respect you.

3. Keep challenging yourself.

4. Whatever you do, never work at a job where you’re not allowed to swear on Twitter.

- Jay Gabler