Kicking Out the Ladder

Last week at work, while scrolling through our Twitter feed (work in social media and you’ll never work a day in your life!), we happened upon a great thread about the relativity of “career success,” started by writer and Design*Sponge columnist Ashley C. Ford. The conversation produced tons of insightful advice on the subject, but the one adage that stood out was from fellow writer Jill Smith: “It’s important to know you can reinvent yourself. You’re a helicopter, not a train.

If we’ve learned anything over 15 years of interviews, it’s that very few successful people claim to have followed a “straightforward” path to success; more often, we hear words like, “meandering,” “circuitous,” and, “almost like, totally random.” And yet, you’ve probably seen the same neat little track laid out in ladder-form on a million career advice websites:

  1. Take these classes.
  2. Land this job.
  3. Get this promotion.
  4. Then this promotion.
  5. Then this promotion.
  6. Become CEO!


Don’t get us wrong: we’re ALL about taking actionable steps towards your goals, and becoming the CEO of your own company/selling your app/writing the next Great American Novel are all awesome outcomes. But apparently, in a perfect world, you climb to the top of a ladder, hit some sort of happiness plateau, and are expected to chill there for the rest of your life — the end. And while in a perfect world, owning your own company, or publishing your book would fill you with a lifetime’s worth of happiness and contentment, in real life, that’s not usually the case.

More often, you complete one of your goals, and then you get the urge to helicopter — to move laterally, to hover around, explore a little bit, and eventually land upon another interest. And then another. And another. You’re still moving forward, you’re still making progress, but you’re not resigned to one straight path in one straight line — and that’s totally cool. Take it from these four helicopter-y leaders, who ditched the traditional ladder in favor of exploring their interests and passions:

“All I Have To Do Is Redefine Success”

Pam Gaber had definitely reached the top of the the traditional “ladder”: she told us, “I’d worked my whole life to get to where I was: I was the V.P. of sales for a pharmaceutical company, I made over six figures, and I flew first class.” But eventually, she stopped feeling fulfilled by her job, and the constant travel and time away from her family was wearing her down.

When she finally worked up the nerve to quit and instead started devoting her life to her dog and her volunteer work, people initially thought she was “flipping crazy.” But by taking that time off, Pam allowed herself to discover and pursue her next passion: founding Gabriel’s Angels, a program which has provided pet therapy services to abused, neglected and at-risk children in the state of Arizona for the past 15 years, with Pam serving at the helm.

Besides pharmaceutically funded first-class flights, nothing says “I climbed the corporate ladder” quite like having your picture on the cover of a business journal: just ask Lori Pappas, face of the March, 1998 edition of Minnesota Business Magazine. Raised at a time when girls were expected to be mothers or secretaries, and not much else, Lori told herself, “To be successful, all I have to do is redefine success.” After building up and selling a software company at the height of the tech bubble, she’d far surpassed the traditional definition of success. But she quickly realized that retirement hadn’t put a damper on her drive, and once she grew tired of golfing, she began exploring other interests, starting with travel. Upon visiting Ethiopia, she was struck by the incredibly high rates of preventable diseases — she’d found her next landing pad.

In her interview, Pam Gaber had told us, “In every facet of our life, we are shown our mission and our passion…but usually we’re too busy, or too young, or not ready. You have to catch yourself — don’t ignore your journey of self-discovery.” And just as Pam had to quit her job to find the headspace to recognize her mission, in retirement, Lori had found her own sweet spot — she’d built up enough time and earned experience to successfully found the Global Team for Local Initiatives, which has since provided 50,000 Ethiopians with clean, sustainable water sources and has directly improved the health of over 75,000 people.

Living in Beta:

To be clear, being a “helicopter” doesn’t necessarily mean that you have to uproot yourself every some-odd years, fly around until you find a brand new calling, and set yourself back down in a completely different career. (That sounds totally daunting and kind of insane!) It can also mean periodically reevaluating which parts of your career are making you happy and unhappy, then starting new projects or new side jobs to keep you engaged. It’s a process that our book calls “living in beta,” because you’re constantly developing and testing new iterations of yourself.

One of the best examples of this is director Thomas Kail — when we talked to him in 2008, he was running a small theater company with his friends and working on a rap-based show called Freestyle Love Supreme. At the time, if you had tried to build a straight track from what he’d studied in college — American history — to what he was puring as a career, nothing would’ve lined up. But since then, he’s directed plays about NBA player Magic Johnson, NFL coach Vince Lombardi, and most famously, a guy named Alexander Hamilton — hopping from subject to subject to form a complex (and historically rich!) career path.

He told us that the key to building a complete career was by throwing yourself at each of your interests, but never resigning yourself to one thing:

“Finding confirmation that you’re going in the right direction has to be something that you’re constantly assessing.”

Similarly, Larry Brilliant, former director of, told us that the thing that has woven his life together has been his interest in anatomy and physiology; he has worked extensively in both medicine and in computer science, but what keeps him happy in both fields is understanding how a system runs, and figuring out how he can improve it. That interest seems incredibly specific, but he’s followed it across the world, from touring with the Grateful Dead as their band doctor, to leading the team of doctors and researchers that eradicated smallpox in India, to running Google’s massive nonprofit arm.

Always a bit of a counter-culturalist, Brilliant never let the idea of a straight path, or a “ladder to success” keep him from pursuing an opportunity that grabbed him in the moment. Instead, he followed his interests with the belief that “the multiplicity of experiences that you have will make you unique for exactly something that you should — and want to — do.”

Ditching the Plans:

Part of the reason that the “ladder to success” mentality still dominates the career advice sphere is because as awesome as it sounds to just “helicopter” from plan to plan, as humans, we naturally want something safe and neat and pretty. We want our IKEA directions to make sense, and then when one of those stupid little screws inevitably go missing, we freak out…and that’s just our bedside table — when we think about that on a LIFE scale, it becomes full-on panic-attack material. So think about an in-between situation: say, a night out. When your day or night works out according to plan, you usually have a solidly good time. But at the risk of sounding like an ad for cheap beer, when you go with the flow and let your plans evolve, that’s when you stumble upon a cool new restaurant or hole in the wall, or make a new group of friends.

Look, planning out a career path is going to be daunting, no matter what. But if you build in some wiggle room and let yourself pursue different interests, rather than sticking to this boring old “ladder” myth, the long-term payoff will be infinitely better.

Interviews of the above leaders — and hundreds more — can be found in our Interview Archive, at A version of this article can be found on the Roadtrip Nation blog.