A person wearing a black shirt who’s grinning.

4 Questions That Measure Your Life’s Progress

Net worth may be an indicator, but it’s far from the only one.

Tucked into my left bicep is a series of black lines. Some are curved, others are straight. Some form circles and others form triangles. When you take a step back, you see that my tattoo resembles a mountain range. But unlike your standard mountain range, this one means something special to me. It represents how I see life.

As you look at my arm, your eyes move from left to right. On the left side, the mountain range is small. Grand, but small. As your eyes scroll to the right, the range grows taller, more impressive. At the far right side, the mountain ends at a high point. At a peak. It concludes higher than any other point before it. This is life as I see it. Each year, life gets better. Yes, there are trials and tribulations. There are low points just as there are high. However, over time life improves. Eventually, the low points you encounter today are higher than any high you’ve experienced in the past.

When you evaluate the trajectory of your life, there are four questions that can help you measure your progress. Questions to help determine where you are on your climb up the mountain.


Are you sad about better things?

You are curled up in a ball on the floor. You just failed another exam. The school board has requested an audience. You think they’re going to kick you out. The thing is, you can’t go home. You had a big fight with your parents right before you went off to school and haven’t spoken with them much since.

Now, jump ahead ten years. You’re curled up in a ball once more. However, instead of laying on the floor, worried about where you’re going to live, you’re on your comfortable bed. This time, you’re worried over whether or not you’ll get that big promotion. You really want it, but even if you don’t, you still have plenty of money in the bank, food in the pantry, a place to live, and people you love spending time with. You’ll be sad if you don’t get it, but it won’t be the end of the world.

One way to measure your life’s progress is by looking at what you’re sad about. If your worries of today pale in comparison to your worries of a few years ago, you’re moving in the right direction.


Do your wins show growth?

I have a doc where I record all of my business wins. Wins being those things that make me jump up and down with excitement. The doc is listed in chronological order so as I scroll through, I can see the various victories I’ve experienced. From that doc, one thing is clear: I’m moving in the right direction. From the podcasts I’ve done to the sales I’ve made, from the people visiting my site at a given time, and everything in between. My wins show a pattern of growth. Years ago I was thrilled if 100 people saw my work in a single day. Now I expect to see hundreds or thousands to view in that same period.

One way to measure your life’s progress is by reflecting on your wins. Are the wins you’re experiencing today grander than wins in your past? It doesn’t have to be about business. It could be comparing your dating life. Are the people you’re dating more compatible than the ones you dated five years ago? It could be comparing your physical health. Can you run a marathon today where you could only run a 5k in the past? Look to your wins to spot growth.


Are you still complaining about the same ol’?

“I really struggle to save my money. As soon as it comes in, I spend it. It’s so annoying!” you say. “What do you spend it on?” I ask. “The usual,” you reply, “Clothes, food, drinks. I love going out to eat. But I can’t keep living like this,” you say. “That sounds rough. I’m sorry. But I’m sure you’ll figure it out,” I say. “Thanks,” you reply.

Five years pass. We’ve since lost touch but happen to run into each other at the mall. “How have you been!” I exclaim, half-question half-shout. “Oh good, good,” you say, “I’m just out here shopping. You know how it is,” you say. “Well, you look great! How’s the whole money situation? Were you able to get it worked out?” I ask. “Don’t get me started,” you say, “Money is tight as ever. It’s crazy. As soon as it comes in, it goes out. If it’s not a new phone then it’s a nice place to eat.” I feel like I’ve heard that before… but where… 

One way to measure your life’s progress is by looking at what you complain about. If you complain about things today that you complained about half a decade ago, you’re not learning. You’re not testing, experimenting, or trying. In short, you aren’t progressing. It’s similar to the first question, though it addresses a different emotion.


Do you feel like you’re in a better place?

A friend asked me how my business was doing. I replied, “You know, it’s funny. When I look at the metrics, everything is the same. Year-over-year, my subscribers are about the same. My income is about the same. My traffic is about the same. And yet… I don’t know… something feels different. I can’t put a finger on it, but it just feels like something’s happening. Something good. Again, I have no real data to prove this. It’s just a feeling.”

That conversation took place earlier this year. Since then, that feeling has turned into real data. I can quantitatively see that what I sensed was right. Something good was happening and still is. My business is having one of its best years ever and I’m grateful for it.

One way to measure your life’s progress is by a simple feeling. A feeling that, though you can’t point to something specific, makes you feel that you are moving in the right direction. Like a wave whose surface is calm and glassy, yet underneath has momentum. Momentum that builds and builds until finally you rise out of the sea.


Moving forward with your life’s progress

Life is no smooth ride. However, it does get better with time. When you find yourself forgetting that, think of my tattoo as a reminder. Then consider the progress you’ve been making. It’s hard to notice day-to-day but when you look up you will be amazed. My guess is you’re higher up the mountain than you realize. To find out just how far up you are, ask yourself the following four questions:

  1. Are you sad about better things?
  2. Do your wins show growth?
  3. Are you still complaining about the same ol’?
  4. Do you feel like you’re in a better place?

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