How one simple “yes” completely changed my career path

When I was just starting my first post-college “Big Girl” job, I was determined to show the sort of dedicated drive and excellence that lands young professionals at the top of their game by age 25. A pretty hefty goal for a creative writing major with little-to-no actual professional experience.

I was 23, had just finished a year-long service fellowship, and had miraculously scored a job in content marketing, which honestly, I was in no way qualified for. The COO of the small tech company saw a storytelling spark in me, and decided I had enough promise to fill a content creation and videography role on their growing team. I fumbled through my first week like I fumbled through my interviews, but somehow, both ended pretty well.

While wandering around trying to look productive my second day on the job, I found myself in the senior partner’s office, and smack dab in the middle of one of the most bizarre, yet fortuitous exchanges of my career.

Like an idiot, I didn’t know who the partner was. I hadn’t done my homework, but that was okay, as part of my task that day was to sit down with important people at the company and ask them about their work. I didn’t realize, however, that work office etiquette often suggests you make an appointment before barging into the owner’s office demanding to know their life story. Whoops.

I found myself sitting across from a happy-looking, reclining, inquisitive man of about 65, wondering who I was (and probably, what I was doing in his office). Unsure of what I was walking into, I began to engage Jack in conversation. We talked about his background in geology, his days playing ski bum at a lodge outside Durango, Colorado, his wife Marilyn (who happened to be the HR Director! I was really striking out that day), their daughter, and his many hobbies. The conversation flowed effortlessly. I explained to Jack how I’d all but talked my way into the job, how I was admittedly anxious, but excited for the work, what my future plans were, what they were paying me, and how grateful I was to be working for his company.

Before I knew it, it was time for Jack’s many errands of the afternoon—and apparently, for me to join him in completing them. I had piles of paperwork to complete, a crash course in website tracking to sit through, and hours of employee on-boarding meetings to endure, but even with air of pressing work hanging over me, I couldn’t bring myself to pass up the opportunity. Learning the office messaging system would apparently have to wait.

I told my supervisor about Jack’s request for my presence and asked nervously if it was ok for me to accompany him. He looked at me with a funny smile and said, “well, if the owner invites you to do something, you better do it.” So off we went.

That afternoon, I accompanied Jack to a haircut at his favorite three-chair, locals-only barbershop (I don’t think he had an appointment, but it didn’t keep him from sliding right into the next open seat), a car wash, and a Cajun seafood lunch with Marilyn–where they shared tales of travel, first-job horror stories, and how to be successful in business. I thanked them profusely for their time, and arrived back to the office a few hours later feeling elated, and like I had some sneaky, success-story secret. From that point on, Jack, Marilyn, and I chatted regularly, about way more than software and client relations.

Months later, when I received a call from my mother that my Papa was in very poor health and wasn’t going to make it, I asked if I could head back home for the weekend to be with family. As I was packing my bag at my apartment, I got a call from Jack, who had gotten wind of the situation, and wanted to offer his condolences. As I thanked him, stuffy-nosed and choked up, he made me an offer I’ll never forget. “Actually,” he said, “I’ve got the plane gassed up, and would love to fly you home real quick so you can say goodbye.”

Real quick. Like offering the use of his personal plane to someone else was the easiest thing he’d do that day.

I stumbled over some, ‘’I couldn’t possibly let you’’ and, ‘’oh, that’s way too kind of you’’ until he brushed off my objections with an, “I promise, it’s nothing, and I’d be happy to do it.” It was in that moment that I began to understand the depth of Jack’s generosity and leadership, and how highly he regarded me as an employee. He picked me up, we drove to the small Texas plane hangar, and made the flight to Tulsa. I arrived at the hospital a few hours later, and was able to be with my grandfather as he passed away.

Looking back, I might have been overly earnest in my supreme happiness, but I think it was that very unassuming appreciation that made Jack take such an interest in me. A desire to work hard, a drive to learn as much as possible, and the ability to build relationships will take you miles in the workplace—whether you’re 22 or 42.

Rather than saying “no” to an opportunity to spend time with my superiors—an afternoon that ultimately resulted in some catch up—saying “yes” to a zany office exchange set a path for me to succeed at that company, and grow my career. When it came time for me to leave the job, Jack offered his full support and blessing, along with a shining recommendation for any future endeavors. I never would have pushed myself into his presence otherwise, but his advice throughout my career has been invaluable, and has cemented in my mind the absolute power in saying “yes” to curious opportunities.

Megan Shepherd is a writer, blogger, Gemini, aspiring lady boss, and foodie with a major case of wanderlust. She won ‘Best Hair’ in high school and refuses to let it go. Read all about her semi-fabulous life at or find her on social @mmmmmmmmegan.