40 Days of Whatever

Do something, anything, for 40 days. Observe how it changes you.

Alex Sharp
3 min readSep 9, 2013

I recently discovered the Internet phenomenon 40 Days of Dating. The website chronicles two friends, Timothy Goodman and Jessica Walsh, who try dating each other for 40 days and chronicle their experience every day with a journal entry. It’s a really fascinating experiment in human interaction and psychology.

One of the rules of the experiment is that the two people dating MUST see each other everyday for 40 days. And they must document it everyday with a questionnaire.

Reading through the series got me thinking, what if I did something for 40 days straight? How would that effect my life? Would it make me happier? More energetic? Would the routine give me a newfound confidence? I’m curious.

So I’m going to give it a shot.

Everyday for 40 days, I’m going to write a private journal entry to myself, and I’m going to exercise in some way.

For the exercise part, when I’m in San Francisco, I’m going to swim everyday, and when I’m home in Los Angeles, I’ll jog at least a mile a day.

My hypothesis, somewhat validated by 40 Days of Dating, is that simply the act of doing something repeatedly for 40 Days can have a profound effect on you.

It can cause you to look at yourself in new ways, grow as an individual, evolve in your own self-understanding.

The concept of following a routine everyday is an exciting change in behavior for me. I’m not really a “routine person.” My only real routine, if you can call it that, is my work. I love my work, it’s both my profession and my hobby, and I do it everyday.

But it’s not a routine. It’s just my default state.

I believe to grow as individuals, we must be exposed to new things. We must step outside of our comfort zones. We must do things that do not seem natural.

And for me that’s doing something, anything, consistently for 40 days straight.

The Questionnaire

A key part to the writing part of this system is that the daily journaling is not free-form writing, it’s a questionnaire. I’ve tried journaling before, and I never keep up with it. I always fail a few days in.

The idea of sitting down and starting new, blank slate, with no guard rails everyday can just be daunting. You never know how much to write, what to write about, how deep to go, whether to truly look inside yourself, or just bitch about work.

The questionnaire format takes a lot of the guesswork and uncertainty out of the daily journaling exercise. It creates an approachable scope to the exercise that doesn’t take too much time or energy.

These are the questions I’ll be answering everyday:

  1. How are you feeling today?
  2. How was your day yesterday?
  3. Would you change anything about yesterday if you could do it again?
  4. How are you feeling about the program?
  5. Did you exercise today?
  6. Did you learn anything about yourself today?
  7. Did you learn anything new about the world or the people around you?

Follow Up

At the conclusion of the 40 days, I’ll write another post describing my findings.



Alex Sharp

🛠 building https://followreset.com. https://sharesecret.co. platform @upfrontvc. prev consultant, founding team @zaarly. long ago: health care tech, economics.