Edited by Jen McFarland Flint; illustrations by Ross MacDonald

Here’s the humbling truth: no matter how high your career soars, how many awards you win or companies you sell or differences you make in this world, everyone has to start somewhere. And in those first forays into gainful employment, it’s almost an unavoidable fact that blunders will be made. We might wish we could forget them and focus instead on the more successful stages of work life, but the lessons that we take from those earliest failures have a way of sticking with us for good, often playing a fundamental role in shaping the leaders, entrepreneurs, and innovators that we become later in life, paying dividends that far exceed any minimum-wage salary.

Here, alumni share stories about their entry-level errors, as well as the personal and professional takeaways from those early experiences.

As a teenager I worked at Kwinters, the hot-dog stand in my local mall, where I learned how to cook five varieties of hot dogs, managed cash, cleaned the oily fryers and greasy hot-dog containers, and earned minimum wage. It was a great initial lesson in how, sometimes, you have to roll up your sleeves and do the dirty work. I also learned that spending an hour talking to your girlfriend on the company phone when the boss is trying to call in is a quick way to get seriously reprimanded.

Kwinters customers had two options: a ready-made steamed dog or a barbecued option that took longer to deliver but, in my opinion, was much tastier. On my lunch and dinner breaks, I would make myself a free barbecued dog (perk of the job), but I could not seem to convince the customers to wait the extra few minutes for a more delicious outcome. That was my first introduction to the concept of giving the customer what they want.

As an aside, I ended up marrying my aforementioned girlfriend, so while I don’t endorse slacking off on any job, in this particular case the reprimand was worth it.

—Brian Ginsler (MBA 2003)

"My First Job" - HBS alumni reflections (video)

Leading from the Frontlines

In 1991, I was working in a furniture business when a fire started in the factory’s ventilation system. The fire alarms were loud, and every instinct I had learned in school told me to leave the building, but the president of the company grabbed my arm and told me to follow him. We raced toward the factory floor to make sure that the rest of the employees were safely leaving the building and that the fire was contained. I learned that real leadership means running toward the fire and being concerned about the safety of others before your own.

—John Fees (MBA 1999)

Dream Teen

I was a sales assistant in the confectionary department at a Woolworth store back when they had manual cash registers. Candy bars used to sell really quickly, and the department needed constant restocking. During lunch, hundreds of customers would come in to buy snacks, and the lines grew long, so I needed to punch in data quickly, do refunds, watch for shoplifters, and keep smiling to maintain customer service. I was 16 and it was a real stretch, but I became quite good at juggling it all and was made a department supervisor. By age 17, I was managing coworkers in their 40s and 50s. I learned a lot about the value of hands-on work versus more conceptual exercises, managing employees with very different ability levels and life situations, and being responsible for the business and others. Some of this has stayed with me throughout my career. Even now, I manage by getting involved with employees at all levels in my organization.

—Moz Thomas (MBA 2003)

I was a server for the catering service on my college campus. Working at the banquets hosted by the university president was my favorite because sometimes it meant seeing famous people. One time Stephen Covey (MBA 1957), author of The 7 Habits of Highly Effective People, was visiting. As I served him, I managed to spill soup on his suit. I thought my life was about to end. Fortunately he was very kind about it and didn’t make a big deal. I learned that responding calmly when other people mess up goes a long way in fostering a good work environment.

—Liz Calder (MBA 2022)

Due to an Error in Editing…

In 1992, I was a subeditor and occasional reporter at the Times of India. We did very little work on computers. Most editing was done on sheets of paper that were later typeset by other colleagues. There was no Google or any other point of last resort, except for a battered dictionary. Late one night, I decided that the chairman of Air India and Indian Airlines was “Russi Modi,” rather than “Mody,” as Parsis would spell it. The next day, when I entered the office, proof of my stupidity was hanging on a clip outside the editor’s office, marked in red ink. I also got a “note”—thus far the only one of its kind in my 30 years of work. The lesson? The first mistake might pass, but never the next one. I made it a point to never misspell a name again, even in my phone address book.

—Rohit Bansal (AMP 177, 2009)

Waiting for Waves

My first job upon graduation was to help Taiwan build a presence in the semiconductor business. Taiwan’s government had set up an economic planning group led by Morris Chang, formerly of Texas Instruments, who conceived of and started what is now Taiwan Semiconductor Manufacturing Company (TSMC). As a consultant to the project, I was issued badge number #A001 and tasked with figuring out which markets would be best to enter and at what size to build the first manufacturing line and facility.

What was my mistake? While I was willing to take a bet with the start of my career, I was unable or unwilling to put my own capital into the project. The company went on to be the world’s top chip manufacturer and among the 10 most valuable companies in the world in 2021, approaching $800 billion in market value. A mere 0.2 percent of TSMC at that valuation would be more than a cool billion. I learned that big markets mean big companies, and if the teams are solid and continue to execute, a lot of value can be built over the long term. Over time, I have learned to concentrate my time and capital into a very few companies in new, potentially massive markets, looking for projects whose shares I’ll never want to sell, ever.

While there is a lot to be said for being lucky rather than being smart, I’ve learned that being smart means putting yourself in the path of luck at the right time. Investing and life are a lot like surfing that way: One mostly needs to hang out, be in tune with the environment, paddle gently every once in a while to be in front of the right waves, and conserve energy—until it’s time. The key is to know when to paddle hard to set things in motion. Conversely, life is also about knowing when not to waste time, energy, capital, or opportunity cost when no amount of paddling will help because there is no wave. If one expends energy efficiently, lives life authentically, and eliminates noise to focus on the signal when it matters, things tend to work out well. And it leaves a ton of time to be on the water, kitesurfing.

—Bill Tai (MBA 1987)

I worked as an investment banking intern at JPMorgan as a junior in college. My manager invited me to an open-bar event in the final week of my internship, after confirming that I had turned 21. She hoped I would get a glimpse of the company outside the workplace. Unfortunately I barely had the opportunity. With limited experience with alcohol, I spent most of the evening in the restroom and was sent home early.

Waking up the following morning was one of the worst experiences of my life. I arrived at the office with notes of apology in hand, fearing that I had jeopardized everything I had accomplished. But before I could utter a word, my manager cut me off with a smile and quipped, “Work hard, play hard. I get it.” Moreover, instead of approaching me with their usual solemn demeanors, my colleagues were suddenly more jovial, alternately teasing me and sympathizing with me about my embarrassing plight. It occurred to me that a barrier had fallen, one that I had not even realized existed.

I had thought work was about being an island and performing well, and I had been so focused on proving that I had the intellectual merit and tenacity to succeed, I had neglected to get to know my colleagues on a personal level. Alcohol-related mistakes are tricky, with consequences that can be serious from both a health and a career perspective, but that experience showed me how important relationships are in a career. My colleagues had come to my help when I needed it, and they made sure I got home safely.

—Jessica Chen Riolfi (MBA 2013)

In All Honesty

My first job was in the college promotions department at Warner Bros. Records. I called the college radio stations to make sure they’d received the records I’d sent. When they asked for my opinion about them, I told them I thought the records were really bad. I learned that promotions was not my thing. I wanted to make great records, not promote bad ones, so I kept going until I got the opportunity to do the thing I came to New York City to do: make iconic rap records.

—Drew Dixon (MBA 2004)

Hard Work and Lucky Landings

My first job as an MBA was in a consulting unit within the actuarial department of Aetna Insurance Company. I had interviewed for two positions in the company. The woman who got the other job worked for a superstar who burned out, and all his protégés eventually were eliminated. In my case, hard work and political support positioned me for opportunities that allowed me to succeed. My boss, Steve Matheson (MBA 1974), eventually became president of CIGNA Healthplan. He was my mentor and remained a good friend until his death three years ago.

That first placement set the tone for the rest of my career, and I stayed in insurance for 25 years. I became an officer of the company in record time and was appointed a vice president within 15 years. Insurance was a clean industry, with gentlemen leaders. I liked the values. I lucked into a company firmly committed to developing human resources and affirmative action. I got jobs that gave me diverse tasks, global travel, and independence. It was a great ride! The lesson I learned is that your work ethic and luck both count, since you can’t always know how to pick a winning horse when you’re green.

—Marki Ware (MBA 1975)

The Company You Keep

I was hired as a manager of business development for a private upstream-energy company in Houston. Within months, I discovered that principals were using raised funds for personal benefit. I resigned, even though the energy industry was in an economic downturn and jobs were hard to find. A private investor had told me that a good reputation is slow to earn and fast to lose. That advice and my decision to resign were formative to my management and leadership philosophy throughout my career. For example, in the 1990s I was a vice president for a major Enron subsidiary. After I initiated the sale of the subsidiary, Enron wanted me to stay on. At the same time, Rich Kinder, to whom I reported indirectly through my boss (and I greatly respected), decided to leave and was infamously replaced. I chose to leave Enron instead.

—Bob Herlin (MBA 1982)

I worked at a self-service car wash named Magic Bubbles in Baton Rouge, Louisiana, in the mid-1990s. I was paid a flat rate of $10 to hose down the dirt and debris in eight car wash bays with a high-pressure spray gun. It was an especially dirty job when the Jeeps and pickups came in after “mudding,” or driving off-road in mud. Unfortunately for me, mudding was a popular pastime where I grew up. I got paid based on completion, not time, and at first it took me at least two hours to do it all, if not more. I was close to quitting after the first few weeks, but eventually I choreographed the process to eliminate any wasted time and got to a point where it took me less than an hour. I stayed for three years.

—Scott Benson (MBA 2008)

Purchase Power

Waking up at 5 a.m. to deliver papers by bike in all of Boston’s seasons: That was memorable. But being able to buy my first pack of baseball cards on my own, as a result: That was unforgettable!

—Dan Rosen (MBA 2006)

Sugar Rush

My first job was selling boxes of chocolate candy in Boise, Idaho. My folks had offered to buy me a bike and required that I pay my part, which was about $40. My dad’s friend, Gene, was a regional salesperson for a company that was wholesaling boxes of chocolate. I earned $32 by knocking on doors in our neighborhood, but when I excitedly showed Gene how much I’d earned and the empty candy cartons in my Radio Flyer, he kindly explained that his company had paid to make the goods I’d sold and that he must be repaid from my $32 sales revenues. Disappointed though I was, I acknowledged that it did make sense and thus had my first lesson about COGS (cost of goods sold). It took me a few more months to earn enough for the bike. After that, whatever I desired beyond basics, I had to earn myself—including HBS, during which time I started a retail store to support my family and pay tuition beyond what one could borrow.

—Ryan Englund (MBA 1982)

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