I often question if I'm making any progress. How am I supposed to know that I'm advancing (personally, professionally, emotionally, etc.) in life?

I think that the reason progress has become such an important metric in our society is because we use one's concept of progress to estimate outcomes. Equating progress to an expected outcome can be a dangerous mindset to have.

Above is a simple diagram. 

On the left is what I call “recent memory." It depicts the progress made over a smaller unit of time. Relatively little progress was made with some periods of regression and other periods of "coasting" where no real progress was made.

On the right is what I called “hindsight.” It depicts the progress made over a larger unit of time. Relatively larger progress was made, and it encompassed the period where it felt as though no real progress was being made.

As time moves forward our progress on whatever we are doing should go up. That’s not to say it can’t go down or ebb and flow a bit either. I think it is completely normal to regress in the amount of "progress" made - especially in the short-term.

The period in the present moment ("recent memory") when I felt like I was just coasting often plays a key role is getting me to where I want to be. Sometimes I fail miserably or fall on my ass. When examining one's "progress" we don't always have the correct context or period to analyze. A person can make huge strides in progress and the end outcome can still go awry. That is perfectly normal. 

I want to try and include the “hindsight” way of thinking in the present moment when I am trying to gauge my own progress.