How to start playing a game you can win

In this report, I will describe “how to start playing a game you can win.”

In life, all of us start out playing a game defined by others. There is no other way. When we are young kids we seek our parent’s approval. It becomes clear fairly quickly. When mom is happy, we seem to be able to get more cookies.

When mom is not happy, we just don’t seem to get any cookies at all. Sure, when we get a little older, we may be tempted to steal cookies out of the jar. But if we keep that up for long, things could go bad for us. That cookie jar could stay empty for weeks or months.

We learn to brush our teeth, shower, and get dressed for school in the morning. We do our homework so mom will let us play with friends in the park.

Eventually, most of us learn how to get cookies out of mom without stealing them. We learn what mom and dad need to stay happy. We slowly get hooked on a steady stream of cookies and other goodies by keeping our parents somewhat happy.

When you are a kid, you figure out your parent’s game of life, and you play it in order to keep a smile on your own face. Most of us need help from our parents at least until our teen years. For most of us, our parents seem to be the only ones willing to feed us and keep clothes on our backs when we are growing up.

We may not always be happy about it, but our parents teach us how to play by someone else’s rules. Our parents set us up for behavioral patterns in our life at an early age. And that pattern seems to repeat itself where ever we go after that in life.

One day mom or dad drives us to school and introduces us to a teacher. Our parents tell us to be kind and respectful to our teachers. We quickly learn that we need to keep our teachers happy so mom and dad will still be smiling when we get home.

Before you know it, you will have a job and a boss to keep happy. From an early age, society trains us how to keep one person happy after another. Parents, teachers, bosses, policemen, you name it.

Whenever we find ourselves in a new game, we look around for who it is we need to make happy. We may test their authority for a time. But when the consequences of defying authority become too expensive, we figure out how to keep a smile on people’s faces.

So making other people happy is how most of us learn to win in this life. If we keep the right people happy, we are seen by others as successful and may even make lots of money. Some of us will end up with prestigious jobs that make lots of money but leave us very little free time to enjoy the money our success has given us.

Keeping other people happy while you do what they want is not the same as playing your own game. So, when are we supposed to start thinking about playing our own game? Once we have been winning games defined by others for a decade or two, we become handcuffed to those jobs. We can’t quit anymore because our expenses have gone up as fast as our success.

Before I can start explaining how I started playing a game I could truly win, I need to define what winning means for me. We are not all the same.

How I define winning

I didn’t Google this question. I don’t care what Google thinks, or anyone else.

And, winning for me does not mean beating others at something. Nor, does it mean measuring myself against others. I don’t even know if anyone else is playing my game. I don’t care what anyone else thinks. What others are doing might be interesting to me but not as a measuring stick against my life.

Winning for me just means playing a game that I am excited about. Winning is living a life that is exciting to me.

With age, I have become less excited about winning games defined by others, and more excited about playing games I enjoy. You have to really start paying attention to what you love to get good at this new game.

If you define winning as the luxury of being able to play games you are excited about, then you don’t spend much time worrying about what anyone else is doing around you.

My only measurement of winning is … do I have the luxury to do what I am most excited about at this moment? For me, the answer is yes. So today I am winning. Winning is being in charge of my life and doing whatever I am most excited about doing … at this very moment.

Winning for me is the luxury I have created in my life that I am getting to do what I want to do right now. I thought about 30 different topics to write about today. You see, I love to write. I picked this topic to write about because I am most excited about this topic today.

Now that you know how I define winning, I want to talk about how I finally started to play a game I could actually win. I quit playing other people’s games and I started playing by my rules. Here is how I did that.

But first, do you know why retirement may be the first time many people are able to start playing a game they can actually win? Yes, of course, because now they have the free time to decide what to do with their day. Retirement is also the last time they can play by their own rules … if they have the courage.

But I started playing to win even before my official retirement age. I am still only 61. Here is how I did it.

How to start playing a game you can win?

The first thing I had to do was admit to myself that my daily actions were not under my control. I was not doing what I was most excited about each day. I was still that boy that had to figure out how to please others in order to get my cookies. So I made a list of things that I wanted in my life and what I didn’t want.

I knew at the time I was not winning by my own definition. But I didn’t see a clear path to get there either. I just didn’t know how to do anything that I loved that would pay me enough to travel the world. I only knew about jobs where people were willing to pay me to do things I didn’t love anymore. I didn’t want golden handcuffs.

Since I didn’t know exactly what my new life would look like, at least I could identify activities that were causing pain and what activities were causing pleasure.

So here is what I did. I started by thinking about the factors in my life that resulted in pain or annoyance. I listed them. Then I thought about the behaviors in my life that resulted in pleasure. So, I listed them also.

Things I didn’t want:

I didn’t want to have a boss. I didn’t want to have hours. I didn’t want to have a schedule. I didn’t want to have to be anywhere. I didn’t want to be in meetings. I didn’t want any due dates or deliverables imposed by others. I didn’t want any creative control over me. I didn’t want to receive any projects defined by others. I didn’t want any employees. I didn’t want to answer the phone anymore. I didn’t want a large monthly overhead. I didn’t want a permanent office or home. I didn’t want any physical inventory or products. I didn’t want to entertain anyone whose company I didn’t truly enjoy. I didn’t want to depend on others in my creativity supply chain. If I created anything, I didn’t want it to be in physical form (only digital). I didn’t want any financial obligations like scheduled monthly payments. I didn’t want to keep an empty bed anywhere in the world waiting for me since I don’t know when or if I will return.

Things I wanted:

I wanted to travel the world. I wanted to be able to go wherever I wanted, for as long as I wanted, and leave when I wanted. I wanted to learn all about the world with my feet on the ground as I studied. I wanted to study whatever I found fascinating, including food, history, arts, architecture, music, and religion. I wanted to write about what I learned as I traveled the world. I wanted to wander the globe with only my laptop so I could access all the information in the world. I wanted to have complete control over the time and quality of the creative process. I wanted to be involved in something that I believed in and was excited about. I wanted to affect people in positive ways. I wanted to inspire people to live the life they deserved. I wanted my daily creative activities to be focused on what I was most excited about, believed in. I wanted a stream of income that exceed my needs and followed me all over the world so I could travel the world freely without money fears. I wanted to learn how to cook and eat really delicious and healthy food. I wanted to fall in love, wander the world with my lover and have a ton of fun and a really great sex life.

Where I started:

When I wrote these goals, I was working as a consultant for a single client. So I had to keep them happy to get paid. The work wasn’t totally horrible, but I just wasn’t excited about it and I didn’t feel like I was helping any real people in any significant way.

Plus, I had a very creative side that was not being expressed in my daily at all. But the pay was great, I only worked part-time, I was allowed to work from anywhere with an Internet connection, and the income was more than I needed to travel the world.

I went through several phases, trying to reach my dream life. But I will just talk about the last phase I went through before I started playing 100% by my own rules. The last thing I failed at before I was finally successful was called affiliate marketing in the travel industry.

Since I was traveling, I started blogging about things to do in each place I visited as I traveled the world. That didn’t work for me because I didn’t and still don’t have a large enough audience to create income from affiliate links. So I gave that up after a few years.

But at about the same time, I heard about making money by selling information as memberships. But I didn’t want to just do research and write about random things. But if I could write about something I was excited about, then my daily activities would be exciting to me.

So I started a membership webpage and Youtube channel that helped people learn what I knew and loved most. I loved traveling the world and living on very little money. By living on less money, I had more free time.

So I just started teaching people how to retire cheap in paradise, and how to slow travel the world on way less money than they probably thought possible. I have a membership catalog with reports all over the world that help people retire early and live their dreams. I also have a course that teaches people how to make money online with their hobbies.

So now, instead of just playing the game that someone else assigned to me, I invented my own game. And, that is why I have remained excited this whole time. But it took a long time for everything to line up so that I had an income stream that paid me for what I was excited about instead of what other people wanted from me.

Remember, I am not saying that you define success as traveling the world. I am also not saying you will have the same definition of winning as me. All I am saying is that if define your pain points and your joyful passions, at least you will know what direction to go in when redesigning your life to play a game you can really win.

I can promise you this, if you can get yourself to the place, where you have the luxury of getting up every day and doing what you are truly excited about, then you will know what winning feels like. And you won’t give a damn whether anyone else thinks you are winning.

Thanks for listening to my thoughts on how to start playing a game you can win.  Please subscribe to or our Youtube Channel to watch us move around the world, 15 years and 67 countries so far.

This is Dan of Vagabond Awake, the Youtube channel for Thank you for stopping by. The world is your home. What time will you be home for dinner?