Rich, Free, & Miserable Pt. 1

Part 1 – Making the Suck

Click Here to Read the Executive Summary

For much of my life I’ve dreamed of dramatic and lasting success. At different ages I’ve dreamed of being a successful actor, politician, lawyer, and speaker. But of course I dreamed of more than just achieving success; I dreamed of how success would solve all my problems.

I thought that if I was successful, then I’d never have to worry about money. I’d have tons of friends, be popular with the ladies, and have more fun than ever. But of course this was a very immature view of success.

As I’ve grown up and experienced success in my life and worked with extremely successful people, I’ve discovered that while success can be wonderful, it also comes with a price and a set of problems all it’s own.

Here are some of the problems of success I’ve seen in my life and the lives of my clients.

1. It’s lonely at the top –
One downside to being successful is that there aren’t a lot of people at your level. Some of the people you meet idolize you. Others want to be you, and still others are hard to relate to. Of course there are always people who have achieved what you achieved or even more, but they’re often too busy to help you with your problems. And that means that success can feel isolating at times.

2. Not Enjoying Your Success –

One phrase I hear a lot around success is, “When I (achieve this goal) then I’ll (do this thing I want).” Yet so often when you find success it’s not how you thought it would be. It’s so easy to get caught up in the next project and the next challenge and never really create the life you set out for.

Success has a way of distracting people from their dreams. So whether you’re seeking success or have found it, it’s important to keep track of what really matters.

3. Too many Yes’s-
If you are the big wig in the room, people think you know your stuff. And you probably do. But having too many people who look to you for answers means that you have very few people who will push you to think harder about what’s best for you, your family, and your business.

Successful people get out of whack and off kilter, because they don’t have anyone in their lives keeping them honest.

4. This isn’t what I signed up for –
Maybe you’ve worked towards success in the hope of what it will give you. And yet even though you’ve filled out the bullet points of success, you feel like something is missing. Your relationships have suffered, and success didn’t give you want you hoped it would.

I’ve met so many people who figured that when they found some measure of success they would also find some measure of happiness, but that simply wasn’t the case. Because they’ve been functioning on this wavelength for so long, they don’t know what else to do.

Success can give you freedom, or it can imprison you especially if you don’t keep looking for a life that is deeply satisfying.

5. What about my relationships? –
Success can be hard on your relationships. Sometimes in your drive to the top, some of the people who get stepped on along the way are those closest to you. It’s also possible that even though you’re successful, you still struggle to create deep connection and play nice with others.

What works in the business world won’t work at home. And the contrast between the deference you get paid at work, often doesn’t apply to your more complex relationships at home.

Successful people have to be even more diligent than most to take care of their fundamental relationships because the cost of success doesn’t just fall on their shoulders, but the shoulders of everyone around them.

6. The truth bubble –
Everyone lies to successful people. The story of the emperor’s new clothes is so powerful, because it’s so true. As you get more power and more success people stop telling you the truth. I saw it all the time when I worked with rock stars. The more people admire you, the more they insulate you from what’s really going on.

This insulation can lead to problems in your company (see Enron) but it can also lead to problems in your personal life. If you let success shield you from reality, then it often will, which is why it’s important to stay diligent and curious.

7. Who am I? –
I remember the days after I finished my first marathon I wasn’t sure what to do with myself. After so many months of training and planning my race was over. It felt like there was this big empty hole in my life that I wasn’t’ sure how to fill.

Successful people often struggle for years to create success. They maneuver for promotions, kiss up, and sacrifice personal time to build business and get ahead.

But what happens when all of that is over? It can feel like you’ve lost a part of yourself. And you might begin to wonder who you are and what all of this was for.

If you’re not careful, then that striving part can rule your life, driving you to move higher and higher even though you know that it won’t make you happier. When approached correctly, these questions can deepen your understanding of yourself and give you a clear mandate to deepen the joy in your life.

But if you neglect these questions, then you might end up achieving a kind of success that is hollow and unfulfilling. And it’s this and not failure that is actually the biggest threat to all the hard work you’ve put in to getting to where you are now.

In Part 2 of this post I’m going to share some solutions I’ve seen successful people use to overcome these challenges.


I used to think once I was successful all of my problems would be solved. But of course this simply wasn’t true. Success brings it’s own unique set of problems.

  • Success can be isolating, because you’ve achieved something other people only dream about.
  • Success can be tiring because once you’ve started striving it’s hard to stop.
  • Success can limit your growth, because while many people look to you for answers, not very many people will really challenge you.
  • Success can feel disappointing, but often it doesn’t deliver on the promise of freedom or happiness you hoped for.
  • Success can be deceptive, because as you gain status people tend to offer deference rather than honesty.
  • Success can be confusing because your identity was so tied up in achieving it, you’re not sure who you are once you do.

All of these things make success challenging, but they also offer rich areas of growth. If you can notice them and use them to become a better person.

The key is to not just worry about how successful you are, but to really look deeply and how success can serve your life and only which aspects of it may be holding you back.


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