I sipped my second cup of coffee at my desk, dividing my attention between a newspaper article that was supposed to run in the Tribune next week and my boss, Ben, who was in the middle of a very heated argument. I watched as Ben resumed pacing, making sure he wasn’t facing my desk, before my gaze drifted back to the article. My eyes landed on a picture of Ben leaving a hotel with Mrs. Slater, the wife of a city commissioner. At three p.m. On a Tuesday. I cringed at the next picture of the two locked in an embrace that was nowhere near close to professional. Leaning forward, I tried to locate Ben’s hands in the second picture. It was like a skeevy Where’s Waldo?
“Evelyn, my office!”
“Shit,” I hissed. Ben’s voice had startled me, causing me to jump and sending hot coffee onto my hand. I shook off the scalding hot liquid before grabbing my tablet with my non-coffee-burnt hand, then made my way into Ben’s office.
He sat behind his desk with his back to me, staring out the large windows that overlooked downtown Chicago.
“Ben, what’s going on?” I asked tentatively, sliding into a chair.
He swiveled around, let loose a sigh, and scrubbed both hands down his face.
“You’ve seen the new article the Tribune is running next week?”
The original article was supposed to be part of their 40 Under 40 series, in which they featured forty of Chicago’s most influential citizens under the age of forty. Unfortunately, a photographer from the Tribune had spotted Ben with the commissioner’s wife and the story had changed direction.
“I did. It’s… not great.” I offered, unhelpfully.
“Yeah, well the board agrees with you.” He sighed. “They want me gone before the article is released.”
I sat up straight in my chair. “Gone? What does that mean, exactly?”
“They want me to lay low until this whole thing blows over. They’re worried about what this ‘scandal’ will do to our stock prices.” His voice held a note of defeat I didn’t like. This was the same man who had negotiated multi-million-dollar contracts without breaking a sweat. He had been described as cunning and ruthless, both in his professional and personal life. Ben practically grew up following his uncle around the boardroom. I doubted anyone knew this company as well as him.
“So what are you going to do?” I asked, watching as he picked up a pen to twirl between his fingers.
“I’m going to lay low—for now.” He sighed, eyes focused on the pen. “It’s important that the board of directors and our shareholders don’t lose confidence in me.”
“How are you planning to ‘lay low’?” I asked.
“I’m going to Montana,” Ben responded, finally dropping the pen back to his desk and looking at me.
“I’m sorry—did you say Montana?” I wasn’t quite sure I heard him correctly. “Did you mean London?”
“No, I said Montana,” he confirmed, one of his eyebrows winging up.
“Montana,” I repeated. “The state?”
“Yes, Evelyn. The state of Montana. You know, the place where I spent my childhood. Where Pinehaven Ranch has been located for the past hundred years.” He spoke slowly, like I was a very small child who didn’t fully understand English yet.
I did, in fact,I know that Ben’s family owned a ranch in Montana, courtesy of the article. The Danver family had started out as small-time ranchers way back in the mid 1800s. By the time Robert Danver took over the ranch in the early 1900s, he was inheriting one of the largest working ranches in the western United States. He also had the good luck of finding an oil field on their ever-expanding property. While the oil well hadn’t been enough to give them oil-money status, Robert thought it would be wise to invest his money in something other than cattle. He’d traveled to Chicago to meet with a finance guy at Sterling & Sterling and happened to meet Laura Sterling, the daughter of the owner. The two married less than a month later and the Danver-Sterling dynasty was created.
“Wow, Montana. That’s…” I cleared my throat, trying to come up with the right adjective. “A big state.”
He shrugged. “I’m overdue for a visit anyway.”
“Okay, and how long are you planning on visiting?” I asked, glad I’d grabbed my tablet.
“A month?” His statement came out sounding like a question. “And I’d like you to come with me. I have no intention of stepping down from Sterling despite whatever bullshit the Tribune is peddling, so your legal background might be helpful if anything comes up while I’m there. Think of it as a working vacation.”
I fought the urge to point out that the story wasn’t exactly bullshit but the concept of a working vacation was. “You want me to go to Montana for a month?”
“Don’t say I never take you anywhere nice.” Ben said, a trace of his normal confidence resurfacing. “Pinehaven is still a working ranch. We’re in the process of acquiring a piece of land adjacent to the current property. Then there’s federal contracts for grazing on federally-owned land that need to be reviewed, contracts with beef wholesalers—and I’ll make it more than worth your while.”
My mind reeled. This man knew my weaknesses. Contracts and money. Not that I was greedy—I would be perfectly happy as long as I could pay my law school loans and afford a latte every day.
I pulled out my phone to scroll through my calendar. It was wide open. Wide, wide open. Much like I pictured Montana.
“I guess I could make that work,” I said unconvincingly. “But wouldn’t you rather hide in Paris? Or on a warm island with a beach?”
“I’m not hiding. I’m laying low,” Ben grumbled. “I’ll give you until the end of the day to make a decision. And I’ll need you to rearrange my schedule for the next month regardless of what you decide.”
I made my way back to my desk, making a list of things I would need to get done before the end of the day. My email icon dinged and when I saw my name in the subject line of the newest email, I opened it right away. It was from Ben to HR and the board. He was informing them of his travel plans and requesting appropriate compensation for his executive assistant, who would ideally be making the trip with him. My eyes widened almost comically when I saw the amount he was approving for my time.
An executive assistant wasn’t my dream job. In fact, if you had told me a year ago that I would soon be an executive assistant, I would have said you were crazy. I wasn’t a total snob—there was absolutely nothing wrong with being an executive assistant. They were some of the hardest working people here. But I had meticulously planned my career trajectory the minute I received my acceptance letter to law school. In truth, I had been planning for my career practically from childhood. While my sisters wanted to play house, I wanted to play work, so I was often cast as the reluctant husband in exchange for my sisters’ participation as my employees.
Everything had gone perfectly according to my plans. At least for a while. I’d landed a coveted internship my first year of school, made law review my second year and graduated at the top of my class. When I was chosen from a pool of highly-qualified candidates for an associate position in Sterling & Sterling’s legal department, I felt unstoppable. All my carefully made plans were finally coming to fruition. Even the long hours in a tiny cubicle devoid of anything that would inspire happiness didn’t faze me. I faced it all with a sense of contentment, knowing it was just the next step in my plan. Another box to be checked.
It took a year of missed birthdays, holidays, and weddings spent tucked away in my cubicle for me to realize I absolutely hated the life I had so carefully planned. The realization left me feeling totally adrift. I had no contingency plan. I was a planner by nature. I made lists, I planned, I organized. Nothing made me happier than checking items off lists. Planning made me feel like the world could be neatly organized, like everything had its place and was manageable. I had been so completely focused on this one goal that I hadn’t even considered the possibility that I might need a backup plan. Planners did not fail! And this felt like the ultimate failure.
When the opportunity to become an executive assistant to the CEO came my way, I shoved aside my pride and plans, and took the position. It hadn’t been a bad year either. I was making more than I did as a new attorney—which was incredibly depressing—and Ben was a really good boss. I actually got to see my family, and sunshine. I had even added a couple of stamps to my passport. As I looked at the number in that email one more time, just to make sure it was real, I accepted the fact that I was about to add a trip to Montana to my list of new experiences.