The Man Behind Serena Williams: Secrets for 2016 New Year’s Resolutions & Beyond

Caitlin Roberson
9 min readJan 11, 2016

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(This post is an excerpt from my first book, 30 Ways to Happy: When trying to be perfect stops being fun.)

Seven years ago, I saw a guy doing a plank on two medicine balls. I was pretty impressed… until he started doing pushups. Then, I was just dumbfounded: The plank had been his version of active rest!

NOT active rest.

I didn’t find out until later that this man (Abdul Sillah) was one of Serena Williams’ private trainers. I also didn’t know he’s been a professional athlete himself. What I did instinctively recognize, however, was why countless athletes work with Abdul — from several of Stanford’s leading stars to a smattering of Silicon Valley executives: With Abdul, we learn lessons that help us contribute to the world, in work and in life.

Here are seven of those work-life lessons. I hope they’ll also help you find happiness in 2016 and beyond.

1) See people for who they really are

I first asked Abdul if we could work together because I wanted to lose 10 pounds. Looking back, I find it funny that I was so stunned by the first program he gave me. He wanted me to do… WHAT?!

Only later did I realize that Abdul had instinctively seen me for who I wanted to be: a winner and a hard worker. He also observed that, to get there, I needed to be pushed.

And push he (we?) did. Over the next few months, I lost the weight and kept it off. But what I gained mattered more: a partner.

Potential is cheap. Everyone has it, but only a few work hard enough to extract success. That’s one reason why the process of helping each other bring possibilities to life is priceless — in our families and friendships, as equally with our bosses and direct reports.

To self-assess, stop for a minute and consider the following questions:

  • How often do you make others laugh? Inspire them to play?
  • Do you have aspirational discussions?
  • How often do you exchange concrete constructive criticism?

As I’ve learned with Abdul (and from Harvard Business Review), such is the paradox of high-potential interactions: They require mutual trust and shared benefit — and a continuous dialogue that stretches, challenges, and coaches. Research shows that what we obsess over, and visualize in detail, produces our future experiences. In other words, seeing is believing: Our brains experience thoughts and actions in the same way.

2) Loyalty never gets a divorce

My drive into the gym one morning. Not so bad?!

When we first met, I told Abdul there was no way I could wake up to work out at 5:00 a.m. He capitulated that he’d do it for me. God, I hated him. Every day at 4:35 a.m., on the mother-freaking dot: RINGGGG.

“Good morning! It’s a beautiful day!” (I am here to tell you, it was not.)

Loyalty comes easy when people are giggly and well-rested. I’ve had plenty such moments with Abdul. We’ve also had many where I’m pissed off, tired, and frustrated… and Abdul’s been just as consistent — even when I can’t say the same for myself.

A giggly moment.

We all have demons to work through, especially when it comes to wanting to be happy and succeed, especially perfectionists. Trying to win requires stepping outside of our comfort zones, and I can personally attest that it can produce immature behavior. When I head that direction, Abdul accepts me, but he doesn’t indulge the child that wants to come out. And every time I re-orient around the person I want to be — someone defined by thoughtfulness, receptivity, other-centeredness, and strength — he re-welcomes me, no matter what.

There’s a reason why studies show loyalty characterizes the most successful friendships, in the same way it drives long-term sales. It may also explain why “customer centricity” (though it’s an overused phrase) now describes the leading modern-day enterprise, according to Ernst & Young. People, like companies, instinctively go and stay where they know their long term success matters.

3) When you want results to yell about, whisper

About a year into our friendship, Abdul suggested we start a weekly running group with a few friends. That core group has changed over the years, as has how often we meet, but one thing remains the same: The challenge, what it means, and the fact that it’s shared.

Our running group from left to right: Me, Alyssa Rapp, Abdul Sillah, Lisa Davis, and Alex Giovannotto

I can still remember the first day I gave a workout everything I had and the almost inaudible words when I finished. Soft, soft, almost missed. To this day, permanently in my memory:

“Good job, CR.” (That’s what he calls me.)

He’d seen the battle I’d just won, and we celebrated the victory with a whisper.

The Stanford track at dawn.

On the track, as another member of our running group so succinctly observed: “Self-doubt is the greatest hurdle.” Getting your head in gear is the first step to creating happiness and success, not just a bang-up workout. We all doubt ourselves. The question is, how will you respond?

With Abdul, I have learned to explore my own whispers — and when it’s needed, whisper reminders to myself. These internal victories have taught me how to transform self-doubt into daring, on and off the track.

Which is another way of saying that…

4) Courage starts in the mind

As I’ve said before, exercise functions as a way for me to look my fear of underperformance dead on, and conquer.

“You can do this, CR.”

“Great workout, today. You gave it all you had. You pushed yourself beyond your limit.”

Stairs. On repeat until you’re nauseous.

These simple phrases soundtrack the moments when I push through booty lock, ignore the howling knots in my quads, and tell my esophagus-meets-stomach that no matter how much bile they churn, breakfast will stay down. They also lend words to something I’ve learned deeply on that track — a priceless affirmation for us all to recite daily:

No matter what happens, I will keep going.

What others say to us, and what we say to ourselves, impacts everything — from love relationships to those in business, from corporate strategy to intra-office politics, so consider these questions:

  • What mantras do you repeat for yourself every day? These are the messages you’ll also send your peer group, your team, your siblings, and your spouse.
  • To what affirmations do your friends and coworkers expose you? Every relationship creates mutual influence.
  • As a leader, what mantras do you socialize with your team? Lead by example, sure, but you’ll fuse a different kind of fusion when you observe and share what they model.

Who we surround ourselves with influences the messages we hear over and over. Both matter.

5) Art operationalizes success

Our little running group loves to tease Abdul about his shoe collection. I swear to God: I’ve never seen him wear a pair more than twice. Man knows how to shop a Nike outlet. (Funny enough, now, so do we.)

The joke illustrates an aspect I love about working out with Abdul: He is walking art, and I don’t just mean his muscles. There’s not a day where his shirt doesn’t match his jacket, match his shorts, match his shoes. And if you think his socks might belie the carefully selected color combination, you’ve got another thought coming.

Abdul embodies a sentiment he recently texted me: “You are the creative force of your life.” There’s a reason first impressions hinge on seven seconds. It’s the same reason that LinkedIn profiles with pictures are seven times more likely to get viewed: Humans are visual. What we see transfers energy.

Many organizations recognize the relationship between inspiration and appearance. For tech firms, NPR reports that serendipitous interaction drives workplace design. What these brands recognize is key: The layout of where we work influences how we work, and shapes the architecture of our results.

How intentionally do you dress yourself? Do you arrange and organize your physical environments — in leisure and at work — for joy and play, in the same way you strategize for productivity and success?

Your happiness takes root in how you answer those questions.

6) Storytelling unlocks, then binds

One summer, Abdul and I swapped stories about our childhoods, divulging details we’ve told only a few. It’s stabilized me to feel so connected and known and impacted much more than my workouts.

The same thing happened on a coincident business trip: A high-performing peer said he’d had similar sensations of self-doubt while onboarding. By sharing, he encouraged me that I also can influence our team, customers, and industry in a big way.

Transparency unifies people and melds groups. It’s why studies [15] show collaborative entrepreneurs create more jobs and profit. As humans, we instinctively like to connect and share with others, particularly with stories. Think about how you learned about the world as a kid. (Or how well you feel like you know me right now, even if we’ve never met.) More people and companies would succeed if they shared their “value propositions” in the manner parents tell fairy tales at bedtime.

Stories activate imagination, and melds minds to spark solutions that are completely re-imagined.

7) Japanese sweet potatoes are the world’s best food

Seriously, something this good should not be this good for you. (Abdul agrees.) Fiber. Vitamin A. Manganese (an important metal for your metabolism and skin). I put mine in the oven before going to the gym and look forward to devouring it — with walnut or hazelnut oil and Himalayan salt — the entiiire time.

Doesn’t this healthy food make you want to EAT healthy?

Personal indulgences aside, what we eat impacts everything: What we feel, how we think, how we sleep. Our diets equally influence our creativity, happiness, and attentiveness, and shape everything from marriages to quarterly reports. Is it any wonder, then, that so many companies ensure their workforce has a virtuous mind-body relationship? Cookies and chips are out. Today, grassfed beef hallmarks the coolest company cafeterias.

And my depiction of it, in progress!

Ask yourself:

  • Do I really know what I’m putting in my body? Seriously, processed food makes you anxious and sleep less.
  • How effective am I at staying hydrated? Often, you’re not hungry; you just need water. Think of all the calories you’ll save.
  • What would I unlock if I got more sleep? According to Arianna Huffington’s TED talk on sleep [16], we stymie our creativity when we are under-slept. Wouldn’t you prefer to sleep your way to the top?

We put stuff in our mouths so many times each day that we forget how much it matters.

I think this picture speaks for itself.

Time to Get Happy

With what experts have you partnered to invest in your own happiness? You can’t learn what you don’t know, so find someone who does. As Marcus Aurelius once said, “The secret to all victory lies in organization of the non-obvious.” Who we trust to help us organize our lives matters.

I highly recommend my good friend and role model’s Forbes article on this topic: “My Secret to Work-Life Balance As an Entrepreneur: Athletics.” Her name is Alyssa Rapp.

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