SUCCESS asked 24 leaders from many walks of life to look back on their revelations—especially when they reached 30, 40, 50, 60 and even beyond—and pass along the lessons they’ve learned. Their insights from achievements and setbacks provide takeaways that can guide you in making a difficult decision or avoiding a major misstep.
Season 3 winner on Fox’s MasterChef and author of Recipes from My Home Kitchen
The world doesn’t stop for our mishaps, and we must move on with fortitude.…I was in college and doing well. I had a summer internship and a good group of friends. But shortly after [that] birthday, I experienced my first symptoms, and years later I would be correctly diagnosed with neuromyelitis optica [an autoimmune disease that causes blindness].
I didn’t dread turning 30; I embraced it. I finally felt like the hardships of my 20s—figuring out my vocation, learning which friends were true and which were fair-weather—were dissipating. I was becoming more and more comfortable in my own skin.
Country singer and judge/coach on The Voice
I know that’s hard to believe. I rushed through my 20s working to establish my career and was pretty damn sure I had all the answers. Now in my 30s, I’ve learned to slow down a bit and take in the moments and listen. I make better decisions in my 30s.
President and CEO, Converse
I went through a number of jobs early in my career, working at Edelman public relations, Wilson Sporting Goods and Nike. In the late 1990s, Nike was growing like a weed…. It was easy to confuse the company’s growth with your own capabilities. I was very ambitious and confident about what I could deliver. In 1999 I got an opportunity at the sportswear company Nautica in New York for the vice president title I’d been pursuing. At the age of 32, I jumped at the chance to set the world on fire in this new position. But it was the wrong job for me and an awful experience. I wasn’t a good fit with their culture.
I realized that getting the job you’re not ready for can be just the worst experience. That was a great lesson: A relentless climb up the corporate ladder, going after titles rather than a job in which you can contribute and learn, can really get you into trouble. I won’t make that mistake again….
A funny story from my time at Wilson: I was in charge of the volleyball program there when we got a request for two dozen Wilson balls from a Hollywood production house. To me it was just another assignment to get off my desk, but the ball became one of the stars of the 2000 movie Cast Away with Tom Hanks, and it turned out to be one of the greatest product placements ever.
Singer and producer
President and CEO, The Humane Society of the United States
As I head toward my 50th birthday [in 2015], I am reminded that success and accomplishment require focus and concentration. With so many portals to access information, it is so easy to be distracted and to forage for information endlessly—accumulating fleeting information, consuming a great deal of time and spinning your wheels. Tangible accomplishment takes discipline. Identify major goals in your life, concentrate on them and work to achieve them. Those are the elements of your life that you’ll remember and that will last.
Director, Global Citizenship and Policy, Abbott Laboratories
When I turned 30, there was a noticeable shift. I had this aching feeling that all of the passion and zeal I had in my 20s to change the world needed something more.
I finally realized I had to define my purpose in life and then pursue that purpose with intentionality.
It’s my purpose that sets me apart, not my passion. The world is a complex place, with many moving parts and characters.… True change in any society, by any player, is made at a systemic, sustainable level.
As I rooted my purpose in this belief—affecting my job, my relationship and my interaction with our global society—I learned that we all have a role to play, and if we each do our part, with passion, purpose and intention, then we’ve done well.
CEO and founder of Overstock.com
In 2002 we went public, which put our company out there in the mix with hedge funds, analysts and brokers. And it soon became clear to me that there was serious criminality on Wall Street. I was quite conflicted about what to do for two years while I gathered information on what was going on.
Finally, I talked to my yoga teacher, and he said, “Usually the right thing is to be loving and gentle, but very occasionally there’s a student who is a bully, hurting other people, and you have to wake them up with a hard slap.” It was a decisive moment…. I decided that night to pull the trigger on my campaign [telling everyone I could about what I uncovered]. And for three years I was widely vilified—until the events of 2008 proved I was right.
I’d do it again, because that’s the way I’m wired: I’m a bit of an Irish hothead, and when I see an old lady getting mugged in an alley, I can’t just walk past.
President and CEO of Volkswagen Group of America
At 50, I realized that experience is everything…. I was grateful for the experiences I’d had, because they helped me to really understand the market and be a leader…
I've learned [you must] concentrate 200 percent on the job you have rather than the one you want to get…
I also learned to balance life and home, because I had a cerebral hemorrhage in 2002 and was among the 10 percent who didn’t die.… I went through a very serious three-month crisis and learned that working like crazy is not everything.
CEO of Caruso Affiliated, a real estate company that owns major shopping centers in California
At 25, I was a commissioner at a very big public utility. Some of the engineers were casting shadows over certain facts to have their projects accepted by the communities they served. Seeing that helped me understand the importance of honor and integrity in how you conduct yourself, and making sure it’s part of the culture at the business you’re running.
In the long run, being honest pays off in spades, and it has in my organization for 20 years. The key issue in getting development projects through governments is support from the community, and it helps immensely if you have a reputation for being honest and doing what we say we’re going to do.
Lesley Jane Seymour
Editor in chief of More magazine
When you work for large corporations, often things move more slowly than you would like. [In] quick-moving smaller private companies, sometimes all you need is the approval of the person at the top to move forward. In larger companies, you need to build consensus; if you are a smaller brand, operate like an intrapreneur. No one tells you this; you just have to figure it out over time. The irony is that because of the careful and deliberate nature of larger corporations, you sometimes lose the opportunity to move quickly on some things.
President of global learning-services provider GP Strategies Corp.
When I was 30, I was assigned as lead on-site staff for a new, large account. A few months in, we came across a technically challenging problem, the outcome of which had cost, schedule and political ramifications well beyond our scope of work. I briefed the client, ending with the question, “What do you think we should do?”
His reply taught me a life- and career-benefiting lesson: “I have some thoughts, but I’m not paying you for my thoughts.” With millions of dollars and professional reputations on the line, I quickly learned to do my homework, think before speaking and back my recommendations with solid rationale. As a leader, your input reflects on your team, your company and maybe even your industry and profession.
Founder and board chairman, Lumber Liquidators
I founded a successful construction company when I was around 16, but I was always going out and blowing the money by starting other crazy businesses [such as a travel-based TV show and a home refurbishment company]. When I opened the first Lumber Liquidators store in Massachusetts in 1996, I could tell it was going to do well. I was 35 or 36 and decided… I wasn’t going to do anything else unless it had to do with hardwood flooring; no other company ideas could enter my head. And it turned out to be a much better way to run a business.
Best-selling personal-finance author and host of radio’s The Dave Ramsey Show
If my sales team makes more calls, has a better product and serves customers better, the natural result is increased revenues.
Ever since I was a teenager, I have written out prioritized to-do lists. Now I make sure I recognize the A1, top priority must-dos. This way I manage my activities, recognize the steak-sauce priorities, accomplish goals and get the results that are best for everyone in the organization.
President of the independent record label Signature Sounds
I would say turning 40 in 1998 was the turning point when I realized something that still holds true today: Our [Massachusetts-based] company could be successful carving out a particular niche rather than just looking for artists who might have commercial appeal. So we began to work with a sustainable musical community of Americana artists local to the Northeast. They helped us grow organically and have turned out to be very good talent scouts for us. We didn’t have to go far for our A&R [artists and repertoire] because our family brought people in.
Brian D. Kessler
CEO of Maui Toys
I was 30 in 1988, when I started Maui Inc. My dad invented a hula hoop in 1950, but it hadn’t been updated in a long time. In the 1980s, around the time of the hoop’s 30th anniversary, I saw an opportunity for outdoor summer toys, which at the time were unimaginative…. I never expected to invent toys or consumer products, [but] now I have developed more than 2,600 new toys and hold many patents.
Former crew chief for Jeff Gordon’s NASCAR team and ESPN analyst, host of the Velocity Channel’s Americarna
From my 30s and heading into my 60s—I’m 57 now—I’ve moved along a sliding scale of risk versus reward. At 30, I didn’t know what I didn’t know [and] was willing to take a lot of risks. These days… I take the time to evaluate the risks and decide if they’re actually worth taking. I’m still competitive and have that entrepreneurial drive, but now it’s based on 30 more years of experience.
New York Giants football great
I was 24 when my son was born.
I couldn’t look at things as just being happy in the moment…. I started negotiating my contracts with consideration for the longer term, how the salary and benefits would sustain my family over the years. For a negative role model, I could look at people like the fighter Joe Louis, who had unprecedented fame and wealth but lost it all through various misfortunes and squandering. The Internal Revenue Service took whatever was left. My mantra was that I didn’t want that to happen to my family.
Pro football players don’t prepare themselves for life after the game [only about half earn degrees, and 78 percent face financial difficulties such as bankruptcy within two years of retirement]. I went back to college and got the degree that was interrupted by my playing career, and that was one of the best things I ever did.
There is a stereotype about the absence of male role models in the African-American community, but my dad was always there, and I wanted to emulate him. Even when I was playing, I wanted to minimize being away from home—I was never a party animal. And I couldn’t wait to retire because I wanted a more normal life.
Actor, producer and director
I became an actor by accident. When I was just 16… someone dared me to try out for the theater department’s production of West Side Story. I loved the movie and had seen it 10 times…. When I auditioned, singing “Maria,” I couldn’t see the audience, but I heard the applause. In that instant, an electric jolt went through me, and I knew I wanted to be an actor more than I wanted anything else in my life.
I didn’t get the part, but a week later I heard one of the actors had sprained his ankle, so I sought out the drama teacher to find out if I could have his part. The teacher, whose name was Jack Leckel, said the actor was fine, but he liked my spunk and was going to break some rules and put me in his advanced acting class. I had never taken an acting class before, but from that moment, I have never looked back. I was going to become an actor. I was obsessed, and there was no Plan B.
I often point to that day because it put me on my path. I never left, and it taught me the importance of sticking to something you really want. It’s unfortunate that a lot of people don’t end up doing what they really care about.
Personal-finance author and host of television’s The Suze Orman Show
In my 30s, I learned two major things:
And when one door closes, another one opens as long as you are willing to keep knocking on doors.
In my 40s, I learned that you never know what is in store for you. That if you just keep your options open and give 100 percent to everything, you may end up on a path that takes you to places you never dreamed possible.
In my 50s, I learned that when you totally get rid of everything you settled for and clear space for what you really, really want, your life can become richer than you’d have ever imagined.
In my 60s, I learned that true success is being able to let go of all that you created and to define yourself simply by who you are and not what you do or what you have. I also learned that as every day becomes more and more precious, to go for goals that have to do with health even more than wealth.
Singer-songwriter, actor and owner of Dolly Parton Enterprises
Over the years, I think I’ve learned who I am and how to get what I want. People who know me say I’m as nice as I can be unless you cross me. I can tell you where to put it if I don’t like where you got it. I’m open and I’m honest. I don’t dillydally. If there’s something going on, I just say it. Sometimes if I get mad, I’ll throw out a few cuss words just to prove my point. I’ve often said I don’t lose my temper as much as I use it, but only if really necessary, because I love peace and harmony. And I like it when people do their jobs.
But when things are not like that, or when people step in my territory and start messing with things, I will call them on it. No doubt about it.
People say, “Oh, you just always seem so happy.” I make my joke, “Well, that’s the Botox.”
President and CEO of comic book pioneer Stan Lee’s POW! Entertainment
By the time I turned 50, I learned an invaluable lesson:
You have to know when to stop selling. It’s been key to POW! coming up with myriad new stories over the years that transcend generations of superhero fans.
My biggest influence was my father, an amazing businessman who, by being creative and innovative, inspired me to become an artist. But when I was in my early 20s, I met a yogi in Paris, Swami Satchidananda, and was immediately captivated. I asked him if I could bring him to America, he said yes, and soon after that he was talking to 70 people in my living room. Right there, people volunteered $8,000 to $9,000, a lot of money in 1966, to get him established. I helped him open 52 yoga centers, most of which are still open today.
Swami Satchidananda’s message was:
His message has served me well in business and in life.
Founder/chief creative officer of Martha Stewart Living Omnimedia and author (Clean Slate: A Cookbook and Guide, December 2014)
Stewart’s lessons include:
• Learn something new every day. This has always been my motto.
• When I was 12, my father told me that with my personal characteristics, I could, if I set my mind to it, do anything I chose. This… instilled in me a great sense of confidence. It is so necessary for parents to help build confidence in their children.
• The actual work of any job may be much different than what you imagine. I learned this after modeling, working as a stockbroker and my brief time in real estate.
• Healthy living never stops. You have to keep at it on a regular basis and make it part of your lifestyle.
• Don’t let age limit you; age really comes down to spirit.
• Wisdom is knowing what to do with knowledge, and good judgment comes with age.
Executive chairman of the Jack Welch Management Institute at Strayer University; chairman/CEO of GE 1981–2001
It’s only been in the past decade, after turning 70, that it’s dawned on me that every great manager I’ve known has shared one distinct, immutable trait that really galvanizes people and organizations. I call it the “generosity gene.”
Generosity-gene managers give frequent, thoughtful feedback and coaching. They eagerly and openly give credit where credit is due. They love to see people grow and get promoted. They get a massive kick out of rewarding people in the soul with praise and in the pocketbook with cash. And when the news is not good, they do not sugarcoat hard messages; they understand people prefer candor, and they deserve it….
We’ve all had good bosses and bad along the way. The bad ones were stingy, right? They played their emotions close to their chest. They counted pennies. Usually such Scrooge-like behavior was not about fiscal responsibility. It was just about being tight.
Managers with the generosity gene are exactly the opposite of that; their instinct is always to go big with candor, support, involvement, praise and, when appropriate, rewards.
The generosity gene has always been around…. But in the last decade, identifying it and giving it a name has been a heck of an aha moment for me.