Adventures in Career Change: Part VI—Learning to Expect the Unexpected

“Sometimes we let life guide us, and other times we take life by the horns.” – Brandon Jenner

I’ve had to make a difficult decision recently. It’s one that I’ve felt looming for some time, though the opportunity to deliberate hasn’t made the decision any easier.

Four years ago I didn’t want to spend another day working for someone else. I had been in the workforce for fifteen years, and most of those years I spent in careers and jobs that didn’t suit me. I had grown disillusioned by the greed, self interest, and rampant destructive politics of corporate America. I had worked for more than a few raging assholes, a boss who banged coworkers, a supervisor who fired my peers because they didn’t behave as yes men, an unstable business owner who sometime after I left his company attempted suicide with a gun at the end of a boat ramp, a boss who bragged about beating up boy scouts, and bosses who weren’t satisfied with employees working eighty hour weeks and meeting soul crushing demands. I worked at huge companies that neglected employees who served their customers, at prestigious accounting firms where style was rewarded over substance, and at a small “family” company run by “friends” who never missed a chance to give less than a rat’s ass about my family or about me. I had seen just enough of the working world to realize I no longer wanted any part of it. People—in general—had proven themselves to be astonishingly awful. People I had trusted and considered friends had abandoned me or shunned me. I was intensely jaded and bitterly cynical, and I was exhausted by working with people who fell short of not just their potential as human beings, but fell short of who they appeared to be.

I wanted to work for myself not just because I had worked for some crappy companies. I also worked for several outstanding organizations. But the common denominator for most of my working life is that my bosses and coworkers didn’t understand me. And to be fair to them, I didn’t know enough about myself to help them understand me. I only thought I knew what I liked and what constituted my strengths and weaknesses. Instead, I was trying to force a false narrative down my own throat. I ignored what I really wanted and needed. In retrospect, I can see that I’ve always been an incredibly bad fit in traditional corporate America, and an even worse fit in the traditionally conservative and notoriously black and white world of accounting.

I should have known from a multitude of clues. Most—practically all—my friends throughout life, people I like and those I can relate to, approach life and work in unconventional ways. In college, my friends were fine arts or humanities majors. In fact, I knew virtually no one from the business school in college, I had so little in common with them. In graduate school, my favorite classes were two electives: Ethics and the History of the Roman Empire. In the former, I wrote a paper my professor implored me to publish in a trade journal. The later provided me what I consider my crowning achievement of graduate school—a twenty page essay on the Roman Coliseum. In my chosen career of accounting, the friends I made that stuck have practically all left the profession because they themselves were bad fits.

Though I received my master’s degree in accounting, I originally intended for that to be just a stepping stone on my path to be a tax attorney. I wanted to write legal briefs and I appreciated the abstract nature of law. I had reached out to both the University of Denver and the University of Colorado law schools, and I was preparing to study for the LSAT when the crushing demands of my “stepping stone” career put an end to my ambitions. And while being crushed by those demands, I found accounting to be suffocating and confining. In the words of one of my present colleagues, “Accounting is black and white. There’s always a right answer, and in the end the books should always balance.” To some types, those who receive a degree of comfort from satisfied expectations and who are fulfilled by predictable outcomes, accounting is ideal. But to me the inherent security of accounting’s precise results seems so limiting. I need more ambiguity, more gray area; freedom to find answers that aren’t anticipated or so cut and dry.

With all this in mind, I resolved to work for myself, pursue my passion of writing alone, and let the rats devour each other in their pointless race. I just needed to find a job to buy some time before I left the corporate world forever.

I met a guy in the spring of 2016 who would turn my world upside down. Rick Whipple’s calm and friendly demeanor overshadows his intense lifestyle. He never brags about his accomplishments—hell, he practically never mentions them. Perhaps that’s because he considers them bad habits. Those habits include summiting Denali and several Himalayan peaks, circumnavigating Iceland on a bike, and climbing everything from easy sport routes in Colorado’s foothills to gnarly suicidal Alaskan climbs. He hates the word “boss” as much as I do; like me he considers the word “too authoritarian.” He has claimed the only reason he owns an accounting firm was because he couldn’t work for anyone else. In his words, he’s “unemployable.” And he just happened to be the CEO of an accounting firm that operates like no other accounting firm in the history of human civilization. One that took a chance hiring me in April 2016 to be a part time tax accountant.

I’ll never understand why Rick hired me, honestly. Perhaps he saw something in me similar to himself. I’m a misfit. I’m socially awkward. I often see issues far differently from my peers and I come up with hairbrained ideas that clash with the conventional sensibilities of virtually everyone else. In a nutshell: when others zig, I zag. I just do not fit in well with a typical organization, where conformity is key. Still, accountants are accountants, and accounting jobs require a certain skillset and frame of mind, no matter the firm one works for. It didn’t take long for Rick to notice I didn’t like my job, and he sensed that I was just biding my time until I found something else. He should have fired me. He should have let me write books and be the misfit I wanted to be. Instead, he did something accountants never do: the thing least expected. The guy put me in charge of the day to day operations of the whole damn firm. A year after I got this part time (and “temporary”) tax accounting job, artfully planning my exit from the workforce, I woke up and suddenly found myself with the title of “Firm Administrator,” the public accounting lexicon for Chief Operations Officer.

I’ll admit to having no clue what I was doing in my new position. I arrived at the office every day completely winging it, figuring out things as I went along. I had no job description, no clearly understandable role, and a team of employees who were looking to me to lead them. I fumbled through my first year so aimlessly that I ended up thriving. My job contained so many paradoxes that it made sense to me. Drawing on all those years of public accounting experience that I thought was wasted, I reorganized and reimagined the administrative and operating functions of the firm. Whether by choice or by chance, I turned over almost my entire team—replacing those who left with handpicked successors hired not for their skillset but for their personality and demeaner. Through that effort, we redefined their roles. We rewrote, revamped, or entirely scrapped bad processes. As a department, we studied the “1% Better” concept to strengthen principles of constant improvement, and we read the book “The Fred Factor” to redefine what customer service means.

WhippleWood isn’t a great place just because Rick understands his people, puts them in the right roles, and then gets out of their way to let them do their job. It’s also a place that truly respects its employees’ time and personal lives. Doctor’s appointments, my son’s physical therapy appointments, meetings at church—I have the freedom as a professional to balance whatever commitments I have outside of work.

Through all of this I’ve realized that I need the firm just as much if not more than the firm needs me. I need the challenge of coming to work every day and trying to figure out just what the hell it is I’m supposed to be doing. I need to face these daily situations of not knowing how to handle a given problem, but knowing we will find a way. These spaces of uncertainty, this occupational Wild West, is where I thrive.

So the decision that I’ve made, the one that took me so long to deliberate, is that I’m making the commitment to be full time as of January 1, 2020. With any luck, in the years ahead I’ll never really figure out this job. I hope I will continue to not know how to handle every problem, and instead ask questions and relentlessly probe for answers until a solution presents itself. I hope every day is ever so slightly different than the one before so I never know what to expect.

Of course, this doesn’t mean I will stop writing. The factor most impactful to my decision was the effect it would have on my unquenchable thirst to write. For this change in my day job to happen, I had to promise to myself that I would find ways for it to enhance my availability and passion for writing. Too often in the past couple of years, I’ve crammed nearly a week’s worth of work into four days, then spent Friday detoxing, recovering from it rather than writing. I will need to do a better job integrating writing into my weekly routine, and utilizing my evenings—which are typically my most creative and productive times—for writing. I’m also beginning to write more material just for myself. Writing is my outlet, my escape, my means to make sense of life and my place in this world, but in the past few years it has grown stale as I focused on how I could commercialize it. I need to be OK with the possibility that half or more of what I write will never see the light of day, and just let the creative juices (and words on the page) flow.

I am still focused on the research for my book about the plane crash here in Colorado that killed the 1970 Wichita State football team. I have two short stories that are in the final stages of editing—and I hope to be shopping them around for publishing this year. I have many more in various stages of writing. I’m tinkering with the concepts for at least two novels. I have a dozen blogs or more that I just need to put finishing touches to. And now every night I’m writing something that you, dear reader, will never see. It’s work that’s just for me, because that’s the place where my mind goes to play, where it has fun and never has to worry about being judged. It’s a place where ratings and reviews are of no concern. It’s the place where coal is polished into diamonds.

“It’s tough to make predictions,” Yogi Berra once said, “especially about the future.” The irony never escapes me that I’m a CPA who fought so hard to leave public accounting, only to fall back into it with a position that doesn’t really have all that much to do with actual accounting. And I have a boss who hates the word boss; who thinks outside the box just enough to realize how he could utilize my skills and my personality to benefit us both.

I never could have predicted at any point in the past that this would be my present. And I can’t predict what I’ll be doing five or ten years from now. That is more than enough ambiguity to drive an accountant bonkers—and just enough to give me peace. I do know that I will never work for someone ever again besides myself or Rick Whipple. Rick and his firm restored my faith in people, and most importantly myself. So I owe it to him and to myself to say when I leave WhippleWood CPAs, no matter the circumstances—whether it’s their choice or mine, whether it’s tomorrow or ten years from now—I am considering myself retired. I have seen enough in the business world to know my present situation is the best it will ever be—short of sitting in my pajamas writing best selling books from my living room. And maybe someday that’s where I’ll be, writing in my pajamas while sipping from a coffee mug inscribed on one side with a WhippleWood CPAs logo, and on the other with the words “Happy Retirement.”