Before You Envy Other’s Success, Ask Yourself These 4 Questions

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In my private coaching practice, I have dealt with many successful and even famous folks. I have much first-hand experience to share that being rich and famous, or alternatively successful has its very real costs. While we should all endeavor to grow and reach mastery and excellence, success can be different.

It’s easy to admire—or even envy—someone else’s success. Maybe it’s the entrepreneur with a thriving business, the celebrity with an enviable lifestyle, or the friend who always seems to be winning at life. We see their achievements, their highlight reel, their polished Instagram feed. What we don’t see are the sacrifices they made to get there.

Every major success story comes with a trade-off. The next time you catch yourself comparing your journey to someone else’s, pause and ask:

  1. What relationships fell by the wayside?
  2. What health and stress impacts did they endure?
  3. What freedom did they give up?
  4. What happiness did they delay?

Let’s take a closer look at the hidden costs of success and what it truly means to chase big dreams.


1. What Relationships Fell by the Wayside?

Success often demands relentless focus, and focus comes at a cost: time. Time that could have been spent with family, friends, or nurturing personal relationships.

Consider Steve Jobs. His dedication to Apple revolutionized technology, but it came at the expense of personal relationships. In his early years, Jobs famously denied paternity of his daughter Lisa, a decision that strained their relationship for years. Later in life, he admitted that he wished he had spent more time with his children.

Or look at Elon Musk. The billionaire entrepreneur has been open about how his work at Tesla and SpaceX has impacted his personal life. “I would not recommend running two companies,” he once said, referring to the toll it took on his marriages. His success came with long work hours, and his personal relationships suffered because of it.

🚀 Reality Check: If you admire someone’s achievements, ask yourself—would you be willing to sacrifice personal connections the way they did?


2. What Health and Stress Impacts Did They Endure?

Burnout, stress, sleep deprivation—these often ride shotgun on the road to success.

Look at Howard Schultz, the former CEO of Starbucks. He worked tirelessly to build the coffee empire but admitted that his intense work schedule led to serious stress and health issues. Many CEOs and high achievers suffer from chronic sleep deprivation, anxiety, and even depression.

Even Serena Williams, one of the greatest athletes of all time, has spoken about the pressure of success. “I’ve had to learn to prioritize my mental health,” she revealed, acknowledging the burnout that comes with being at the top.

🔥 Reality Check: Are you prepared for the stress, long hours, and possible toll on your health that high levels of success demand?


3. What Freedom Did They Give Up?

Success often requires structure, discipline, and the loss of personal freedom.

Consider Mark Zuckerberg. The billionaire behind Facebook once said that he wears the same gray t-shirt every day to reduce “decision fatigue” and maximize productivity. His life is meticulously planned, with little room for spontaneity.

Or take Olympic athletes. Their daily routines revolve around rigid training schedules, strict diets, and countless sacrifices. While most people enjoy social outings, indulgent meals, or spontaneous vacations, elite athletes are in the gym or training for the next big competition.

📌 Reality Check: Would you be okay giving up a flexible lifestyle for extreme discipline and structure?


4. What Happiness Did They Delay?

Many successful people put off happiness for “someday.” They chase goals with the idea that joy will come after they hit a milestone.

Jeff Bezos, the founder of Amazon, worked long hours with minimal pay in the early years. He lived in a tiny office, sacrificed vacations, and reinvested every dollar into his business.

Oprah Winfrey, despite reaching global fame, has spoken about her struggles with overworking and the constant pressure to achieve more. It wasn’t until later in life that she fully embraced slowing down and finding balance.

Reality Check: If success requires delaying happiness, how long are you willing to wait? And at what cost?


The Takeaway: Success Isn’t Free

The next time you feel envious of someone’s success, remember—you’re only seeing the result, not the cost. You’re seeing the trophies, the money, the accolades—not the sleepless nights, lost friendships, or health struggles.

That’s not to say success isn’t worth it. But true success should be defined on your own terms. Maybe you want a balanced life, with financial stability but also time for relationships, hobbies, and health. Maybe your definition of success isn’t about making millions, but about waking up happy and stress-free.

So before you chase someone else’s dream, ask yourself:

✔ What am I willing to sacrifice?
✔ What am I not willing to give up?
✔ What does success actually mean to me?

Success isn’t one-size-fits-all. Don’t ever confuse success, fame, and fortune with happiness. Sometimes, the happiest person isn’t the one with the biggest bank account, but the one who has enough—and still has time to enjoy it.

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