Rich, Free, & Miserable Pt. 2

Part 2 – Breaking the Suck

In Part 1 of this post I shared some of the biggest problems successful people face when they step into their own. These problems cause stress for people who are successful, and if they aren’t dealt with, then they can rob much of the happiness and freedom that success can offer.

In today’s post I’ll share some solutions I’ve seen, which create powerful change in the lives of people who have achieved not just success, but a deep satisfaction that comes from bringing their best selves forward in every area of their lives.

How to Overcome the Problems of Success

As a great Chinese general once said after conquering a whole country, “It is easier to conquer an entire nation than to conquer one’s own mind.

While the solutions aren’t simple, here are the things I have found that make the biggest difference in achieving deep joy on the path to success:

1. Cultivate Challenging People –
You have people in your life who are nice but don’t challenge you. They are fun to hang out with, but they don’t really question you.

If you’re lucky, you also know some people who do challenge you. These are the people who ask hard questions, call you out on your bullshit, and aren’t afraid to tell you you’re wrong.

These are the people you need to have in your life, and you should look for them everywhere. You should look for them in mentors, your friends, your partner, your spiritual teacher, and your business.

Find these people and spend a ton of time with them.

If you don’t have any of these people, you can either start looking for them or you can hire them. You can hire employees that question the norm, find friends that push you, and date people that challenge your ideas.

Hiring a coach is another way to find this kind of person. But again, your coach needs to be someone who pushes you, who asks you hard questions, who cares more about you being a better person than you liking them. If you meet with a coach and they don’t ask you at least one insightful question that really makes you think, DON’T HIRE THEM. Even if it’s me. Well especially if it’s me.

2. Forget about Dollars, Think About Lifestyle –
Money is only useful for one thing: buying a lifestyle. You don’t want money so you can swim around in it, unless of course your name is Scrooge McDuck. You want money because of what it will allow you to buy.

But too often successful people seek the money without ever really thinking about what lifestyle they want and why. People just assume that more is better because you can try more things. But often this just leads to very rich, very spoiled, and very bored people.

Before you begin creating success- and even more so after – you have to ask yourself what kind of lifestyle do I want? And then ask yourself tough questions to really determine why it matters.

Do you want to make a bunch of money so you can retire and travel? Why not travel now?

Do you want to have a nice home for your kids? How nice does it really need to be? What’s more important, a nice house or a mom or dad that’s around?

Don’t just create a dream of your perfect house and car. Create a dream of a life that is deeply fulfilling on every level.

3. Never Believe Your Own Hype –
Confidence is great, but the biggest mistake you can make is to believe your own hype. Yes you are a total badass, an asskicking leader, and a titan of industry. But your awesomeness is not correlated to your success and your success doesn’t secure your legendary status for all time.

A successful dick is still a dick. And a poor wise man is still a wise man. Never forget that you are a real person with real problems. And never forget that everyone around you has something to teach you. It’s not up to them to impress you. It’s up to you to be open to listening to it.

One way to do this is to make sure you have people around you who don’t believe your hype. Another way is to be deeply interested in everyone you meet. Not everyone will be fascinating, but if you can stay curious it will help you in staying humble.

4. Keep Learning –
And not about business. Yes there are always more business books you could read, but you should read other things too. Read great works of literature. Read personal development books. Read books that make you question yourself and ways of thinking.

Don’t just become a success; become a person.

5. Give a Shit –
Successful people don’t have to care as much about the plight of people around them. When so many people treat you with deference you don’t have to pay attention to their feelings. Your money and power can insulate you from the world around you.

Don’t let that happen. Doing things like volunteering and giving to charity are great, but you also need to get your hands dirty. Pay attention to the people who work for you, care about what their lives are like. Pay attention to your family and your friends. Be interested in their success and not just your own.

6. Remember it can all vanish –
Just because you achieved success doesn’t mean it will last forever. In fact it definitely won’t. Successful people still face suffering, illness, and pain. You may have more resources to deal with these problems, but the success isn’t a panacea.

Remember that your success is a blessing and a gift. You may have worked hard to get here, but you didn’t do it alone. Say thank you to those people that have helped you, repay old favors while you can, help other people find success for themselves, and appreciate how lucky you are.


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.