My First Career Lesson: Know When to Ask a Stupid Question

With summer jobs on the horizon, professionals recall the first jobs that launched their careers. Read more, then write your own #CareerLaunch post.

I was 17, fresh out of high school, feeling completely out of place in a Washington, D.C., newsroom stacked with grizzled editors. It was my first day.

My boss, Reginald Stuart, told me he needed some papers faxed. Seeing as I'd just left the 12th grade about a month before, I'd never had reason to use a fax machine. He handed me the papers and the cover sheet, and continued typing.

"O.K.," I said. "Where's the fax machine, and how do I work it?"

He glanced up briefly. "Ask somebody."

Months earlier I'd won a national competition sponsored by Knight Ridder, a corporation that owned the newspapers including the Detroit Free Press, the Philadelphia Inquirer and the San Jose Mercury News. Along with a much-needed scholarship to help with college costs, I had a guaranteed paid internship every summer, starting with this one. It was a big step up from the summer job I'd had the previous two summers, a day camp counselor for elementary schoolers.

The three other winners that year had internships with their local papers in places like Miami and Lexington, Ky. But KR didn't have a newspaper in the D.C. area, so I would intern at the chain's Washington bureau — the special unit that covered the federal government. Journalists toil for years to earn a slot in a Washington bureau, so starting the greenest of interns there was a little like sending an eager Boy Scout to train with Navy Seals. I was in way over my head.

Ask somebody? I thought. Is he hazing me?

Ask somebody? I thought. Is he hazing me? In retrospect it's clear what was going on. Reggie knew that my internship wasn't going to work — heck, my entire journalism career wasn't going to work — unless I learned to ask questions and fend for myself. The fax machine was just my first exercise in finding an information source, taking notes, and following through. The exercise forced me to meet people in the office, which I found agonizing because they were busy and I was asking really dumb questions. It forced me to get over myself and ask questions of people who were smarter than I was. Perhaps most important, it quickly shook me free of the notion that the working world would hand me step-by-step instructions.

The rest of that summer was equal parts humiliation and exhilaration. Up until that point, I fancied myself a good writer; teachers seldom used the red pen on papers I turned in, especially when I gave them the attention they deserved. Everyone needs editing, of course, but I thought I didn't need much. Wrong.

Reggie assigned me a story about the tax breaks the federal government offered workers to take public transit. I don't remember the details, but there had been a change in the rules. Of course, I did more reading and made more phone calls for that story than I had for anything I'd written for the high school paper. And when I turned in my rough draft? Reggie politely ripped it to shreds. My writing? Bloated. My lead? Trite. Worst of all? The story was boring. After working on the story for a week, I felt like a failure. 

But there were also small moments of triumph. On assignment for Knight Ridder Financial News, I got a temporary Capitol Hill press pass. One of my assignments was to track down Labor Secretary Robert Reich and Treasury Secretary Lloyd Bentsen at committee hearings and call in anything they said about interest rates or the labor market. This required that I carry a reporter's notebook, a micro-cassette recorder, and a pocket full of quarters for the pay phones. I doubt I got many valuable scoops, but I did chase Reich down a hallway at least once, and I called in several tidbits. 

Five years later, I'd finished college and started my journalism career. I'd begun covering local business at the Lexington Herald-Leader, a newspaper where I'd interned twice. I eventually got an offer to join the Wall Street Journal in Washington, D.C. — my home — covering economic indicators and tax law. Working for the Journal had been a specific goal of mine, and the job paid almost twice what I made in Lexington. Then again, my pulse didn't quicken at the mention of economic indicators.

I called up Reggie Stuart. Don't take that job at the Journal, he told me. Interview at a couple of bigger papers in Knight Ridder, like the San Jose Mercury News. It's Silicon Valley's hometown newspaper, and you're really into technology.

He had a point. I interviewed in Silicon Valley, took the job. I still cover tech today.

Above: I interviewed Microsoft CEO Satya Nadella at the company's Redmond, Wash., headquarters in October 2014.

More posts on this topic:

• “Here’s the Scoop: Why My First Job Mattered” — President Barack Obama
• “How Winning This Contest Changed My Life” — Oprah Winfrey
• “My First Job Lasted One Summer — But It Changed the Way I See the World” — Katie Couric, Yahoo Global News Anchor  
• “Dream Big But Be Humble: Lessons That Led Me from the Factory Floor to the Executive Floor” — Ralph de la Vega, Vice Chairman of AT&T, Inc.
• “Before I Became a Stylist, I Sold Shoes at the Mall. Here's What I Learned.” — Rachel Zoe, CEO, Rachel Zoe, Inc.; Editor-in-Chief, The Zoe Report
• “What Designing a Shampoo Bottle Taught Me About Business” — Meg Whitman, CEO at Hewlett Packard Enterprise
• “Just Starting Out: The Life-Shaping Potential of Our First Jobs” — Arianna Huffington, President and Editor-in-Chief at The Huffington Post Media Group
• “What I Lacked in Qualifications I Learned to Make Up with Courage” — Suze Orman, television host and motivational speaker
• “Practice Makes a Career” — Bernard Tyson, Chairman and CEO of Kaiser Permanente
• “What I Gained from Choosing the Rocky Road” — Ban Ki-moon, Secretary-General of the United Nations
• “Summer Jobs Are Your First Shot at the ‘Grown-Up World.’ Soak Up as Much as You Can.” — Adena Friedman, President and COO at Nasdaq
• “Delivering Papers and Working as a Security Guard Taught Me How to Hustle” — Maynard Webb, Chairman, Yahoo!; Former COO, eBay
• “Be Curious. No One Limits Your Career But You.” — Marcus Samuelsson, Chef and Author at Marcus Samuelsson Group
• “Everyone Should Have Access to That First Job” — Valerie Jarrett, Senior Advisor to President Obama
• “Remember Your First Job?” — Tom Perez, Secretary of Labor at U.S. Department of Labor
• “Employers: Young Workers Are Your Diamonds in the Rough” — Maria Contreras-Sweet, Administrator at US Small Business Administration