What does it mean to be successful? It’s a complex topic and there is no single definition that fits. What success means is both highly personal but at the same time is wrapped up in societal expectations. I’ve been noting various definitions of success over the past few years. Here are my three favorites.

1. The Power of Napping

I love a good nap (here’s a prior IFOD on The Power of Napping!). A great definition of success is: You are successful when you have enough control over your life that you can schedule your day around a nap.

I think this definition of success is profound and subtle. It suggests that success is being in control of your schedule rather than your schedule being in control of you. It’s simple and it’s intimately related to the following two definitions.

2. Trading Time for Money

Tim Ferriss is an author and podcaster who has had huge success. A theme that runs through his books and thoughts is that time is a non-renewable and scarce resource while money is fungible and renewable. His definition of success relates to whether you need to trade time for money, namely success is when most of what you do is stuff you actually want to do rather than doing stuff you don’t want to do just because it pays you to do it.

Here’s an example: years ago I went to lunch with an acquaintance who is a lawyer. During our lunch the lawyer said he didn’t really like being a lawyer and would love to do something different. He found practicing law a grind: he worked long hours, it was stressful, and the work itself was unfulfilling. He said he couldn’t find a way to leave the practice of law because he made a great living being a lawyer and doing anything else would result in a huge cut in pay and would squander all his legal training and experience. He had a nice house with a big mortgage, his kids went to private school, he drove a leased Audi, and had big student loan payments from all his education. He was trapped doing something he didn’t like. He was trading his time for the money necessary to support his lifestyle. Everyday he looked forward to retirement.

At the other end of the spectrum, I have a friend who lives a very modest lifestyle. He and his family live off what seems to me to be a ridiculously small amount of money each month. He retired from his job in sales in his early thirties and now owns and manages a handful of rental properties. My friend spends a lot of time with his kids, exercises everyday, reads a lot of books, helps friends with projects, manages investment portfolios for a few friends and family members for free, and enjoys repairing and improving his properties. He trades very little of his time for money. His days are productive but revolve around what he wants to do and learn.

Who is more successful? The lawyer with the prestigious job and large paychecks or my friend who makes a lot less money but is in control of his time?

The point of this definition of success isn’t that we shouldn’t work or make money. It doesn’t mean we should all live our lives in a spartan fashion. Rather it suggests that you become more successful as your days revolve more around what you want to do vs. what you are doing just to earn a living. Or as venture capitalist and philosopher Naval Ravikant says, “retirement is when you stop sacrificing today for an imaginary tomorrow.” It’s possible to “retire” and still work at a job — it all depends whether you are doing what you want to do vs. just doing it because you need to in order to earn a living. This definition of success is a pretty high bar.

3. Who You Are vs. What You Do

Years ago I read a book that said the following in its opening paragraph:

There is a huge secret about income that only a small percentage [of people] ever figure out and use to their advantage . . . the secret is that the higher up in income you go, in almost any category, the more you are paid for who you are rather than what you do.

Lead the Field, by Adam D. Witty

This is an interesting concept and I think there is a lot of truth to it. Early on in most careers people get paid for producing “work” whether that is actually physical work or information based. As a person progresses in their career what they bring to the table shifts from the tangible to the intangible.

Here’s an example from my life right now. We’re having one of our bathrooms remodeled and so various people are in our house doing work on a daily basis. I’ll divide these people into three categories:

• The workers. These guys do things like lay tile, put in trim and paint. They are good at what they do but their main value to our project is their physical output each day. Someone else (the contractor) tells them what to do and they do it.

• The specialists. The plumber and electrician have specialized knowledge. What they bring to the project is their physical output (installing the plumbing and wiring) but they also bring their design expertise. For example, the plumber had to figure out the best way to change the design of the plumbing to fit the new layout. So, these specialists’ value is in what they “do” but also who they “are” — meaning that their thinking, design abilities, and problem-solving are ingredients of the value they bring.

• The contractor. Our contractor is an amazing guy. But rarely does any of the actual “work” himself. He’s capable of doing the “work” (I’ve seen him do it!) but his real value is that he has a reputation for quality projects built up over decades, brings in new clients, has great client communication skills, is a creative problem solver, has good design ideas, and provides the overall plan of the project. He provides value and most of this value is intangible. Clients hire him based on who he is: his personality, how he thinks, his skills in managing a project, and his ability to hire and manage workers and specialists.

This hierarchy of “doing” vs. “being” translates pretty well to most businesses. I remember early in my career when my main contribution was “doing” I would look at those higher up in the organization and it seemed that they didn’t do much work because their tangible output wasn’t that much. I now realize that what these higher-ups brought to the table was mostly intangible. They brought the power of their networks, business strategy and insight, and the ability to make hard decisions and have hard conversations, and so on.

The paradox of this definition of success is that you must first “do” before you can shift to having your value defined primarily by “being.” Using my contractor as an example again — I’m sure he started out laying tile, painting, doing carpentry and the like. He couldn’t bring value by “being” until he had done enough “doing.”

Over the years I’ve seen people chomping at the bits to bring value by being before they’ve done enough “doing.” On the flip side, I’ve also observed talented people who have held themselves back and staying in their comfort zone of mainly doing. Making the jump to more intangible work is hard and it’s scary. There is no map of what to do because each of us is unique and the value we bring by “being” inherently varies by each of our own unique talents and personalities. Of course, it’s fine to decide that you’re happy mainly doing, but I think it’s important to consciously make that decision rather than just unintentionally staying in your safe area of what you know and are good at out of fear.

When I was 30 I worked at Arthur Andersen and had a performance review that changed my life. The head of the tax department told me I was great technically in terms of tax and investment knowledge and was a huge resource for the firm. But then he said that if I stayed on this path of being a technician that I’d only have middling career success. The people that were the most successful at Andersen developed the soft skills of client relationship management, building networks, investing in and leading others, developing new business. He suggested that I take the scary step of moving from my tangible technical skills to developing intangible talents. His advice and insight was great. 20+ years later I still thank him periodically.