A Grammy Winner, A Circus Master, And An Apple Veteran On Career Reinvention

I grew up in Cupertino, California, before Apple ever existed. Later, I spent 12 years leading the company’s music and entertainment business. My office at the time sat right where I’d picked apricots as a kid.

Leaving Apple to set out on a new career path wasn’t easy. But as a Silicon Valley native, I found the entrepreneurial spirit I needed to reinvent myself was pretty close at hand. And I’ve been fortunate over the years to have made friends with creative, inspiring people endowed with a similar spirit—many whose careers have taken even more unexpected twists and turns than mine has. Here’s what my experience after leaving Apple has taught me, plus a few things I’ve learned from them.

Learning To See The Signs

I’ve always been passionate about music—it’s driven my career goals from the very start. But in 1998, with Apple in a period of serious financial trouble and the launch of iTunes was still another three years away, digital music just wasn’t the company’s top priority.

It was tough, especially after more than a decade at the company, to come to grips with that reality once it had become apparent. But other factors—from management politics to constant reorganization—helped me decide to take a different course. One thing I’d enjoyed in my time at Apple was that it satisfied my passion for the intersection of technology and music, so I took my expertise and launched my own business to focus on those changes—setting up shop just a mile down the road from Apple headquarters.

Once I’d made that decision, I faced a fresh series of challenges—obstacles that anybody setting out to reshape their careers needs to confront. And along the way, I’ve looked to friends and colleagues who’ve done the same for inspiration.

1. Always Return To Your Strengths

As my friend Stewart Copeland knows, the greatest impact you can make—no matter what you do or where you do it—comes from knowing and utilizing your strengths and talents. Best known as cofounder and drummer of The Police and recently named Rolling Stone’s 10th greatest drummer of all time, Copeland is a gifted performer and composer who’s long found ways to channel his abilities into a wide range of projects.

Born in the U.S. but having grown up in Lebanon, Copeland wove the region’s musical style into his own, through trial and error, feedback from local musicians, and tons of practice—three crucial elements for anyone looking to pull off a career move.

Throughout all that experimentation and learning, though, Copeland’s core strengths remained constant. You can see (or rather, hear) that throughout his various musical endeavors. In addition to The Police, Copeland also launched a successful second act composing scores for films, TV, video games, operas, ballets, and symphony orchestras.

How? To be sure, Copeland made powerful connections while topping Billboard charts and winning Grammys, but if he hadn’t formed strong creative partnerships along the way, he might not have gotten as far—and each of those relationships proved a way to channel his talents, to push them further through collaboration. In other words, he didn’t need to become a musician he wasn’t. Instead, Copeland built a network that allowed him to find new outlets to express the talented musician he already was—to test his limits and grow, staying open to feedback from other artists, directors, and producers who opened doors for him.

To launch a successful second career, identify your key strengths through external feedback and internal reflection. Where have others reinforced your talents? Where do you feel you’ve excelled? Don’t worry about how you’ll make your venture happen; focus on the what and the why—your strengths and the interests that drive you to keep deepening them.

2. Use Your Passions To Set A New Course

My friend Michael Marlin (or just Marlin) is a master of reinvention—so much so that it’s difficult to sum up in a single sentence what he does. Passionate about so many activities, Marlin is unwilling to give any up. He’s run away to the circus to become a world-class juggler. He’s tried his hand at toy design. He’s created a light show called LUMA, written books, developed TV shows, and even starred in a Christmas movie.

Not everyone is as natural a Renaissance man or woman as Marlin is, but his keen sense for what animates him is worth paying attention to. Many career coaches counsel against following your passion, calling it a less-than-strategic piece of worn-out advice. But that’s more likely to be true if you’re unwilling to let your passions evolve and multiply.

Before you can integrate your personal and professional passions, you first need to identify and prioritize them: Which ones excite you most right now, regardless of what energized you at the time you launched into your previous role? What resources will you need to put your current passions into play? What’s your time frame? Consider your finances, too: Which of your passions can generate revenue, and how quickly? If you need outside investors, how can you attract them?

Answer these questions and establish a market need, then use your passion to differentiate yourself from competitors—and then, as Marlin has done time and again, just go for it.

3. Build On Prior Successes, Don’t Leave Them Behind

I put myself through college by working at Guitar Player and Keyboard magazines and as a talent producer, which led EMI Music to hire me as a young A&R exec and Apple to recruit me to run its music and entertainment group.

The knowledge and networks I built in each of those roles led me to where I am today as a founder and CEO of my own company. And, as Copeland has also found, it’s been the strong connections I’ve made while doing what excites me that’s helped carry myself forward on my own steam.

Jerry Seinfeld and I once chatted before a corporate event I’d booked him for. Knowing my deep connection to Apple, he wondered whether I could help introduce him to Steve Jobs. I was happy to oblige. My strong relationships add value to two major players in one go—but it benefited me, too, as the person responsible for that introduction.

With every win, build your network out. Use it to offer things to other people. Over time, you’ll be better able to leverage the resources and connections you’ve amassed. By creating new opportunities for others, you’re basically putting a down payment on future opportunities for yourself.

4. Never Stop Asking, “What If?”

I’ve found that successful second-career builders are typically curious, creative people who are continually questioning what’s possible. After working with companies like Apple, Yahoo, and Paramount, my friend and colleague Randy Haykin asked himself, “What if I could get more involved behind the scenes of this ecosystem?” He went on to become a partner in a VC firm, an angel investor, and a professor at the University of California, Berkeley.

Haykin’s subsequent work as a philanthropist led him to pursue yet another dream of his: He created a nonprofit, The Gratitude Network, to help millions worldwide through social-impact ventures. He launched his own winery, Entrepreneur Wines.

Sure, Haykin’s experience, successes, and powerful network helped propel him into each of these new ventures. But it was also his curiosity and capacious sense of what might be possible that helped him pull each of these new moves off. To do that, you sometimes need to zoom out, quiet your mind, and adopt a beginner’s mind-set. Accept that you don’t have all the answers; instead, ask questions. What don’t you know that you’d like to find out? What’s one possibility you’d love to explore?

Launching a second career can be difficult, but I’ve found it’s also one of the most meaningful and satisfying ways to change your life. If you feel weighed down, bored, or uninterested at work, don’t just put up with it—you can always choose again.

Kelli Richards is the CEO of The All Access Group. She facilitates strategic business opportunities in digital distribution among innovative technology companies, talent and media companies, and brands. She is also the author of a best-selling e-book The Magic and Moxie of Apple: An Insider’s View.