The most successful people are willing to do these 3 ‘extremely uncomfortable’ things, says expert

“Facing the tough questions — and yourself — will allow you to achieve lasting success,” says Dorie Clark, author of “The Long Game.”

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We all know that becoming successful requires tradeoffs, but few people acknowledge just how painful those tradeoffs can feel. 

While researching my book, “The Long Game: How to Be a Long-Term Thinker in a Short-Term World,” I discovered that it’s the willingness to make hard decisions, optimized for the long-term, that truly sets top performers apart. 

Even more challenging than doing the work is being willing to sit with the discomfort that comes from emotionally difficult tasks. But facing the tough questions — and yourself — will allow you to achieve lasting success.

Here are three extremely uncomfortable things the most successful professionals are willing to do. 

1. Say no to good opportunities 

Top professionals recognize they have to leave room in their calendar for great opportunities — and unfortunately, the only way to do it is to say no to some good ones. 

My wife and I were recently invited to stay for a week at a colleague’s house in Tuscany for free. It would have been magical, but the visit was only a few weeks before my wife’s book launch. Reluctantly, we turned it down. While we could have said yes and attempted to do everything, we realized that it inevitably would have meant a vacation that wasn’t restful — and a book launch that potentially fell flat.

Ask yourself, on a scale of 1 to 10:

  • “How excited am I about this opportunity?”
  • “How much do I think it will move the needle for my career?”
  • “What would I have to say no to or pull back on if I say yes to this?”

Most of us get in trouble with sixes or sevens on that scale of 1 to 10, and end up clogging our calendar with so-so obligations that prevent us from scanning the horizon for even better opportunities.

2. Practice your craft even when no one seems to care 

Encouragement from others helps build momentum around a skill, project, or idea. It’s far harder to stay accountable when you’re embarking on a new initiative or learning a new set of skills and no one else seems to care. If you miss a day, a week, or even a month, you begin to tell yourself, “Who would actually notice?” 

But putting in repetitions helps you achieve your goal, whether it’s to become a better writer, a more engaging public speaker, or a prolific vibecoder. Progress may be frustrating for a long time, but eventually you develop deeper expertise and a community that pays attention.

Kara Cutruzzula, a journalist and author I profiled in “The Long Game,” started a daily email newsletter and, at the time I interviewed her, had written more than 800 editions. Initially, she sent it to a small number of friends, but over time her audience grew. She eventually landed a book deal when a book editor who subscribed to her newsletter cold-emailed her and suggested that Kara would be the perfect person to write a motivational journal. 

Being willing to work in seeming obscurity while you master your craft can feel frustrating and lonely — but those compound advantages can ultimately change your life. 

3. Acknowledge when your goals or identity shift

Sometimes the hardest thing to do is to acknowledge that you, and your goals, have changed. It’s much easier to cling to your past self-conception when changing your focus can feel like a betrayal of your past self, who worked so hard to get you to this point. But it’s important to shift course as soon as possible, rather than working hard toward an outcome you no longer want.

Ali, another professional I profiled, had spent 10 years working in corporate finance and knew that something felt off. But it took her four years to leave her job and transition into a new career as a consultant and coach, because she was afraid of letting go of her identity as a successful executive. 

It’s critical to stay attuned to changes and notice small signs like a reluctance to head to work in the morning when you’ve previously enjoyed it, a pull toward a new area of inquiry, or a sense that the way people describe you no longer fits. 

We need to dissect who we are and what’s going on right now, Ali told me. Because, as she put it: “Sometimes the stories we tell ourselves about our professional lives hold us back.”

Dorie Clark taught executive education for more than a decade at Columbia Business School and Duke University’s Fuqua School of Business. She is a keynote speaker, former presidential campaign spokeswoman, and bestselling author of “The Long Game.” You can subscribe to her e-newsletter here. 

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