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Talented but insecure

Confidence is a really poor metric for success. 

I’ve coached some of the most talented, driven, ambitious, successful, wealthy and intelligent people on the planet. Many of them lacked confidence in at least one area of their life.

Meryl Streep is often described as the best actress of her generation. She has received a record 21 Academy Award nominations and won three. She has received a record 32 Golden Globe Award nominations and won eight.

She once said, “I have varying degrees of confidence and self-loathing… You can have a perfectly horrible day where you doubt your talent… Or that you’re boring and they’re going to find out that you don’t know what you’re doing.” 

Maya Angelou was an American poet, memoirist, and civil rights activist. She published seven autobiographies, three books of essays, several books of poetry, and many plays, movies and television shows, over 50 years. She received dozens of awards and more than 50 honorary degrees.

She once said, “I have written 11 books, but each time I think, Uh oh, they’re going to find out now. I’ve run a game on everybody, and they’re going to find me out.”

Kobe Bryant was widely regarded as one of the greatest basketball players of all time. He played in the NBA for 20 years, winning 5 championships, including 3 in a row. He was an 18-time All-Star, a 15-time member of the All-NBA Team. He was fluent in many languages, including English, Spanish, and Italian. 

He once said, “I have self-doubt. I have insecurity. I have fear of failure. I have nights when I show up at the arena and I’m like, ‘My back hurts, my feet hurt, my knees hurt. I don’t have it. I just want to chill.’”

Taylor Swift has sold over 200 million records worldwide. She is one of the best-selling music artists of all time. 11 Grammy Awards, 29 Billboard Music Awards and 58 Guinness World Records. 

She once said, “I doubt myself 400,000 times per 10-minute interval. I have a terrifying long list of fears… [including] people getting tired of me.” 

Will Smith said, “I still doubt myself every single day. What people believe is my self-confidence is actually my reaction to fear.” 

John Lennon’s biographer Larry Kane, wrote: “People would be surprised at how insecure John Lennon was… Throughout his life, even during the height of Beatle mania, he had poor self esteem, even though he exuded confidence.”

Keira Knightley said, “It’s been my nature not to want to believe in my own success and that I don’t deserve my success.” 

Confidence is a result, not a requirement. It’s also often a pretty fleeting result. 

As Erich Fromm said, 

The task we must set for ourselves is not to feel secure, but to be able to tolerate insecurity.

You and I are both on that journey… 

Insecure overachievers

Laura Empson spent decades researching elite firms, where she witnessed many brilliant, successful and apparently confident people regularly describe themselves as insecure.

She refers to these people as insecure overachievers – exceptionally capable and fiercely ambitious, but driven by a profound belief in their own inadequacy.

The big consulting firms have actively hired insecure achievers for decades. They are sometimes described as the perfect consultant because they’re driven to achieve, in the hope of proving themselves or feeling significant. Of course that moment never comes, so they never stop achieving.

It’s unhealthy for the consultant but great for the consulting firm because their employees accomplish so much, even though they’re often burned out in the process.

Sound familiar?

Yep, they are not exclusive to the field of consulting. Many successful coaches have the same secret drive. 

I should know. I’m one of them. 

The perfect coach is often driven to achieve, in the hope of proving themselves or feeling significant. Of course that moment never comes, so they never stop achieving.

It’s unhealthy for the coach but great for their clients because they give them such incredible support, even though they’re often burned out in the process.

Again, sound familiar?

3 ways to coach insecure achievers

  1. Honor yourself. Don’t wait for others to be proud of you. That’s a fool’s errand. Start every day by saying, “I am proud of me. I approve of me. I trust me. I like me. I am enough.” Start each day by imagining you have all the praise and recognition you secretly crave before you begin, instead of trying to get it during the day. 
  2. Define success in your own terms, not other people’s. Create metrics for success that work for you. Create an “I Know I’m Successful When” list. Mine includes items like: “My life is simple, effortless and fun. I am stronger, fitter and healthier each year than the year before. Our passive revenue exceeds our lifestyle desires.”
  3. Celebrate your successes. After all, it’s not bragging if you’ve done it. Insecure overachievers tend to quickly dismiss their successes before setting the bar even higher. They’re constantly looking at the horizon instead of the rear view mirror. It makes them visionaries but it’s unhealthy in excess. When you have achieved something or overcome a challenge, take a moment to celebrate. Find a trusted advisor or friend to celebrate with – and take a breath (or a holiday) before moving onto your next accomplishment.

Love. Rich


PS. Dramatically increase your confidence as a coach by mastering enrolling clients. Drastically increase your ability to raise your fees and up-level your clients. And learn to have fun making money. Join me on The 90 Day Money Game. There’s still time to join us…


PLUS, whenever you’re ready – here are 4 more ways you can drastically increase your income and impact as a world-class coach:

  1. Assess your current coaching level and learn how to get to your next level. Read – or remind yourself of – The Litvin Levels, from The Prosperous Coach.
  2. Watch me coach some of the top coaches on the planet, in order to drastically uplevel your coaching skills. Join me on How To Coach A Superhero: The 4PC edition
  3. Imagine joining a Deep Coaching experience alongside the members of 4PC, my community of high-level coaches… We only offer The 4PC Accelerator once a year and it always sells out in advance. Save $1,000 with early-bird pricing. 
  4. Learn how to enroll and coach successful, talented and ambitious clients – with power and impact. Join my flagship program, Project Kairos – for 8 months of guidance, challenge and support to master creating clients. 


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If this sounds like you, let’s talk and explore if working together is a good fit.

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