Success vs. Significance: A Conversation with the Precocious Ryan Holiday

Tony Dungy, former Head Coach of the Indianapolis Colts, has written a new book entitled Uncommon: Finding Your Path to Significance. Since I watch ESPNews almost incessantly I was able to catch a brief interview with him about it. The thrust of his book is that there are two lives one can strive for: a successful one or a significant one. He shuns the first. He points out that one can be very successful in life through making money or accumulating material objects. A significant life, he notes out, is one that positively impacts others, changes the lives of those around you. Coach Dungy said that before the Super Bowl in 2007 he told his players that winning the game, making money and becoming famous is all well and good, but if the team as a whole doesn’t make Indianapolis a better community for the people, their success means very little.

In one form or another I’ve tried to convey the notion of success vs. significance to my clients, while noting that they are not mutually exclusive. It’s particularly difficult, however, with two groups of people I work with: the very poor and the very wealthy. The indigent are struggling to get their basic needs met and it’s very hard if not impossible to ask them to shift their thinking toward helping the community or improving other people’s lives. Certain fundamentals need to be obtained first. That being said, however, I have met patients who will share their limited food with others, give away any extra clothing and even talk to children at their schools about the importance of education to help stave off hardships. These are acts that lead to a life of significance despite the fact that many would not view these people as successful in the traditional sense of the word.

Wealthy people, on the other hand, are clearly in an advantageous position to live a significant life. Their resources are plentiful and can easily be shared. From a psychological perspective, however, it is important to realize that every reward in life can have a tolerance factor. In other words, humans can become less than satiated with almost anything and require more of it in order to feel a level of satisfaction. For the wealthy this often involves money, and a surfeit of it is sometimes needed to get that rush of happiness that we all seek. Therefore they become hyper-focused on making more money rather than doing pro-social things with their success. This is the premise of greed, and when viewed this way it is a psychological phenomenon rather than a character flaw.


However, many wealthy people lead both successful and significant lives. They donate time, their funds and use their resources to change policies that benefit others. They create organizations, they foster a pro-social attitude in their children. They know that success and significance aren’t in opposition of each other
and strive to have both.

This notion of success vs. significance started me thinking about one of my writing colleagues, Ryan Holiday. At 19 years of age, Ryan left college to pursue his own goals (which, admittedly, is probably something I would have strangled my nephew for doing) and his writings inspire many younger people to develop and seize what they want in life. Ryan is unique in that he strives for something other than simply money, power, women and the other gold nuggets that many people in his age bracket are taught to believe are the secrets to happiness. As someone who influences a large number of young readers I wanted to get Ryan’s take on success vs. significance:

1) At this stage of your life do you feel you’ve achieved either success or significance? Perhaps both?

This is one of those questions that I don’t feel I’m far enough along to answer. I’m delusional if I pick either one. A few months ago though, in therapy (which I go to and think has been really helpful for me) I realized for the first time that no matter what happens to me, I’m going to be ok. That my happiness or even credibility wasn’t dependent on my jobs or my stuff. That I could get fired, give up my apartment, my bear and go back to where I started a few years and I would still be good. If I went back to college tomorrow, that would still be a positive step. I think my point is that it’s too soon to pick between successful or significant – frankly, maybe a little presumptuous too – but I can say that I’m getting to a space where I’m less and less affected by external circumstances and that is really important to me.

2) Your website has a large readership, and while this might be a poor assumption, many of those readers are young men and women who are trying to find their place in the world. Do you feel an obligation to assist them through your writing and sharing your experiences?

When I first started writing, I felt like the people reading it were either just like me or were much older and had gotten to where I wanted to go. Now, I sort of feel like it’s in this weird transition phase where a lot of them are much younger than me – high school often times – and are asking me for advice. I’m not sure exactly where to head with it because I don’t relate to them at all. Frankly, some of them are just awkward and almost a different breed. I wish I could say there was this kindred spirit between us but a lot of times I see them heading in the complete opposite direction. They aren’t all like this but it’s definitely something I didn’t expect.

So it might be selfish but I’m mostly writing for me. At least, I’m definitely not writing for those people. It’s a nice way to work out the things I’m experiencing or dealing with the first time. I never really had anyone sit me down and explain anything to me. Most of my posts are about basic stuff too, so I have lots of “a ha!” moments which I think are important philosophically but literally should probably be obscured since most people already knew that you’re supposed to have table manners or that you don’t really get anything out of bad mouthing people.

A couple days ago though, someone emailed me who had just taken an internship at a music marketing company and his question had to do with how all the stuff you read about blogs isn’t really well-received inside actual, successful businesses. It was like FINALLY someone gets what I’ve been talking about. So if anything, when I’m writing I’m trying to nudge people in that direction. I’ve been very lucky to be plunged right into the middle of some high-level stuff and I kind of feel like it’s my duty to get across what it’s actually like.

I think my peers are really letting everyone down by not doing that. They’re so concerned with making themselves feel important or getting traffic (which feels nice but is worthless) that don’t care that they’re not saying anything. All they’re doing in parroting what they’re supposed to say. So what’s better? That you built up some farcical house of cards pretending to be a “social media consultant/Gen-Y enthusiast” or that you spoke honestly and openly about what you’re doing with your life?

3) As I discussed with Philalawyer, at the end of a person’s life he reflects and views it with either integrity or despair. Keeping in mind this notion of success vs. significance, what do you want to be able to say about your own life as you look back on it years from now?

I’m going to try not to pontificate about the whole meaning of life question but I like to judge stuff on whether its gives me a sinking feeling in my stomach. So when I think of all the different directions I could go, I try to use that as a guiding benchmark. So I look at someone, a lot of people actually, and I think, man, I would do anything not to be that person.

You look at someone like Brittany Spears – everything she’s gotten as a celebrity and she’s basically circumvented at every turn from being mentally healthy. It doesn’t take a psychologist to see that she is dealing with major trauma and some hardcore mental problems. But she’ll never be able to deal with them because I think it would mean admitting that everything she has and has done is worthless, comparatively. She’s sort of a crappy example because she’s difficult to relate to but I think people will get my point.

So I guess looking back it would be the ability to be proud of the person that I am. That I didn’t delude myself or walk around pretending it was all above level when it wasn’t. That I was straightforward and well aware of my shortcomings. I think a track record of at junctures where you had to choose what I wanted to do and what other people wanted or thought I should do, that I chose myself. And probably lastly, that I limited how often I embarrassed myself by making it all sound too important.

Ryan presents some excellent insights here, many of which take a lifetime to acquire, if at all. Trust me on this: if you can adopt some of these perspectives you’ll be a much happier person.

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8 Responses to “Success vs. Significance: A Conversation with the Precocious Ryan Holiday”

  1. Cassandra says:

    Ryan is supercool. It’s very heartening to read about someone so young who is incredibly self-possessed instead of amazingly self-absorbed. I wish I could have had that kind of insight at his age. I’m so much older and it’s only in the last few years that I’m starting to really feel, understand, and manifest (on a very preliminary level) the difference between success and significance.
    This is a very nice post. Thanks Dr. Rob!

  2. I believe a person can have “success” while being “significant”, but I think most people miss the point. I’m striving for both, but it is harder than I thought.

  3. […] -They are obsessed with what other people think of them, specifically (and not surprisingly), how smart and “worldly” they are.  Their careers are more about social status and prestige than contribution and prosperity for all (also know as “Success vs. Significance”). […]

  4. […] after awhile. Thanks for donating,” he said, and walked away. Seeing the man reminded me of this post about Success vs. Significance. Here’s a man who, in all likelihood, dedicated his entire day to improving the quality of […]

  5. EGB says:

    I feel like using this as a model is BS personally… Ryan (IMO) is not particularly happy or stable. He shuns the “what makes sammy run?” mentality, but in a way has replaced it with his own obsession. He’s running just as hard to be the antithesis to Sammy…. but in the end, it won’t save you kid.

  6. Lisa says:

    I suspect that if you strive for significance, you will always find it just beyond your grasp. If your motivation is significance, you will have missed the point entirely. A goal of helping others, however, is less selfish and more rewarding in the long run.

    I also wonder about the role of self-discipline and self-denial in the making of a “significant” life. If you’re wealthy, you can give away a lot of your money, be “significant,” but never feel a dent in your wallet. But if instead of giving away huge sums of cash, you decide to devote significant amounts of your free time to, say, serving at a homeless shelter, would that not be more character developing?

    I also admire people who fast for specified amounts of time in order to grow spiritually. I’m not saying that people should starve themselves, but sometimes denying yourself something, delaying gratification, can help you to see more of the needs around you. The danger, of course, is that in doing so, you may find yourself focusing way too much on yourself and your own perceived “needs”. This has been a temptation I have fallen into myself since I became a vegetarian about 3 years ago. I did so for reasons of respect of animal life, and while I remain firmly committed to that stand, I know I can easily become smug about it in the presence of carnivore friends when they see my “sacrifice” for my principles. It’s a tightrope walk, for sure.

    What are your thoughts on this, Rob?

  7. Rob Dobrenski says:

    Whenever I delay gratification, I get the ridiculous thoughts of “I have to have this” out of my head. It clears my mind because I recognize that I have very few true needs, only wants.

  8. Lisa says:

    Which is why I put “needs” in quotation marks. I agree with you completely, as I too have very few true needs, only wants. Initially when I delay gratification, I do tend to focus on those needs (which are actually wants), but that passes quickly and then I am able to see more clearly the difference between my needs and my wants. For example, I’ve noticed that when I fast, at first my hunger dominates my thoughts. But then that passes and I’m able to perceive that I won’t actually drop dead if I skip breakfast. And then I am freer to focus on the reason for my fast, whether it is a spiritual discipline or an exercise in solidarity with those who are enmeshed in poverty.