“Not all those who wander are lost.” — J.R.R. Tolkien

Brazen CareeristHere are my final thoughts on the Brazen Careerist by Penelope Trunk. This post is actually a continuation of Lesson #3: Thirty is the New Twenty and it’s about Professional Wandering. She writes, “What about the people who pull their life together in a tight little package by age twenty-four? They’re the exception to the rule, according to Wayne Osgood, professor of sociology at Pennsylvania State University. He labels these people ‘fast starters’ and explains that they are only about 12 percent of the population… The other 88 percent of us have to trudge through our twenties formulating a new career plan.”

“The good news is that this is what most people are doing in their twenties: wandering. Taking trips to Thailand, changing jobs every year, volunteering for unpaid work while living at their parents’ house, and starting businesses that fail. All these options are, surprisingly, right on track for making a good decision about what to do with yourself in adult life.”

My career in technology didn’t start until I was thirty. I haven’t written much about my twenties so I thought I would give the decade a whirl and outline 7 defining moments here… I could be the poster child for wandering.

1. I graduated from the University of Toledo in 1987 at the age of twenty with a bachelor’s degree in Business Administration. I completed both high school and college in three years… not because I was some brainiac but because I didn’t like school. My mom was adamant that I get a degree… so I did it as quickly as possible.

2. The year after graduation, I backpacked through Europe and landed at Tauernhof, a Bible school in the Austrian Alps. After a few months, I realized that capitalism was more interesting to me than evangelism and headed home to get a job.

3. I got into sales and sold advertising space for a group of specialty publications. I think one magazine was called Baseball Today. Needless to say, I lasted about 2 minutes. I quit on a whim… announcing to the world that I wanted to start my own business. I could do this because I still lived with my parents.

4. At 22, I talked my sister (she was a CPA with a stable job and good credit) into co-signing a $12,000 business loan and with it I launched a line of greeting cards called The Graduate Works. I was young and naà ¯ve and there were so many things wrong with what I was trying to do, but I distributed enough of them through card shops in college towns that I did it for two years. When the repeat orders weren’t coming in, I could sense my parents getting antsy… I was the last kid left at home and they wanted an empty nest.

5. So at 24 I struck a deal: stay another year rent free, get a real job, and pay off the loan. The real job was in the printing papers industry working with graphic designers and advertising agencies. The story starts to get a bit monotonous, but hang on… the paper part sets the stage for my second stint at self-employment.

6. From here, I moved to Ann Arbor, then Chicago, then Cincinnati and finally Connecticut. The paper people liked me and every six to nine months I received a promotion and relocation package. At 27, I found myself working in the marketing department at Strathmore Papers in Western Mass for a female boss equally disgruntled with corporate America. We’d go to lunch and dream up business ideas. She left first and I followed after she wrote a check for $20,000 to fund a specialty product for the rubber stamping / craft industry. The product was called The Paper Salad and I spent the next two years flying around the country on weekends hawking it at craft & rubber stamping conventions. Doesn’t that sound glamorous?

7. At 29, I followed my business partner to Atlanta. She got her career back on track and I continued to push paper salads. During both entrepreneurial attempts, I supplemented my income by working a host of service jobs… typically these consisted of waiting tables, but the last three were: working the night shift at Kinko’s, cleaning a neighbor’s house for $80 a week and catering during the 1997 holiday season.

I was thirty years old and in the midst of my quarterlife crisis… something had to give. The story picks up here and ultimately it was Partner #2 that brought me to California during the dotcom boom… within 2 years I had a new career in the software business.

Fast forward to present day, I just turned forty and I can’t say I’ve figured everything out with “work” but I found an industry where I’ve been rewarded with good income, stability and the chance to see the world. Sure, do I still fantasize about owning my own business? Absolutely! But the lessons learned in my twenties allowed me to be happier in my thirties (collecting a paycheck).

I own a nice home and invest in rental properties (something a good job helps afford). Between this and my writings / efforts with Queercents… well, I intend to have a lot going on in my forties. One friend always jokes that I’ve settled for the “good life” and in a way I have, but what’s wrong with that? I have a meaningful life with Jeanine and we’ve worked hard to get our finances working for us these last several years. I don’t think my thirties would have been as “prosperous” had I not experience what I did in my twenties.

I wandered! At least that’s what Trunk would call it. Wandering made me the person I am today. Curt Rosengren at The Occupational Adventure calls it tacking. Living in Newport, I know enough sailboat lesbians to understand the concept: tacking is a “course of action meant to minimize opposition to the attainment of a goal.”

Rosengren writes, “There’s this myth that the path to our passions should be clear and direct. The reality is, it takes constant tacking. We take action, it carries us forward, and then at some point we realize we need to adjust our direction. Sometimes it’s only slight. Sometimes it’s big. The beauty of the sailing analogy is that as long as we have the goal in sight, it’s still taking us in that direction. We don’t have to have it exactly right.”

Time and experience is what allows us to get it “exactly right.” So wander away, my young careerists! You’ve got your thirties to buckle down and make up for any lost time. I’m proof it can be done.

If you missed my other thoughts about Brazen Careerist, catch each installment here:

Lesson 1: It’s not about money
Lesson 2: Professional Development
Lesson 3: Thirty is the new twenty
Lesson 4: Manage your personal life

And just as an aside… I’m interviewing Penelope Trunk for the straight BlogHer version of Ten Money Questions later this week. Be sure and check it out. She’s got some fine thoughts about our careers and money.