5 or 6 years ago I couldn’t do a proper push up. Not a single one. I was overweight and believed I was too heavy to push up my own body weight.

Around that time, I implemented a lot of changes in my life. I began eating healthier and started exercising. I lost weight. I quit smoking. I took a year of leave from university to pursue some of my entrepreneurial dreams. I did a lot of things that gave me a lot more confidence in myself. I also started doing push ups – on the stairs leading down to the basement of my parent’s house where no one would see me.

In the beginning, I didn’t know how to tackle the push ups. I couldn’t even do one, so how would I get started? I remember reading about the “100 push ups challenge” online, but to get started you had to do a test session to see how many push ups you could do. The training program was based on that initial session. Useless in my case.

One of the ways people recommended getting started was doing push ups on your knees. I could do that without any problems, but I still couldn’t figure out how to move on to proper, real push ups.

One day I figured I’d try to do the push ups on stairs instead… I walked down the basement, put my hands on the 4th step up from the floor and I actually did a few “proper” push ups. It was a revelation. Seriously.

I decided my goal was to do 20 push ups on that step. Then move down 1 step. Do 20 push ups. Then continue doing that until I was doing 20 proper push ups on the floor. I don’t remember how long that took, but it worked. Every other day or so, I’d do a few sessions with as many push ups I could do. Slowly I worked my way down the stairs and in the end I had cracked the code and was doing 20 push ups on the floor.

The title of this blog post is a tribute to Rob Walling’s legendary “The Stairstep Approach to Bootstrapping” post, because the exact same principles apply. I think they apply to nearly everything. I honestly believe that no matter what skill you are trying to acquire, there’s always a way to stairstep it. No matter if you are literally doing your push ups on the stairs or you are trying to learn how to build and run a business.


  1. I applaud your effort. When I was younger, I set my goal at doing number of pushups = current age. Now that I am 73, it appears to be an elusive goal.


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