Five years ago, I was on vacation with my husband.  A beautiful, week-long winter retreat in Colorado.  And I was crying.  I was supposed to be on vacation.  Instead of enjoying the powdery ski slopes, I spent most of my time inside of our hotel room… working.  And my husband was not happy about it.

At that point in my life, I was a corporate cog, fully submerged in the 9-to-9 lifestyle. My style and reputation at work were polished, my career path set, the money was good. But my health was suffering, I was working through vacations, and my perfectionism was pushing me to my breaking point.

On that snowy day in Colorado, I realized that the work that I was doing–and the way in which I was doing it–was slowly killing me. And though the realization wasn’t pleasant, looking back at it now I feel such relief for pushing this issue to the surface.

My husband had been wanting to start our own business.  A digital company that we managed while living on the road.  A “freedom” lifestyle. (You can hear more about this story in the “Why I Decided to Design My Life” article.)

But I wasn’t on board.  I’m a perfectionist!  In a startup, nothing is perfect.  It’s messy, and risky, and chaotic.  I couldn’t wrap my head around “starting from zero.”  There are very few absolutes in life, but I knew this:  you absolutely cannot be a perfectionist and start a business successfully.

Right then, crying over my laptop in my hotel room, I discovered a phrase that changed my relationship to perfectionism: TAKE MASSIVE, IMPERFECT ACTION.

This phrase gave me a way out of my perfectionism.  A path into the scary but beautiful future I wanted to create for myself.  We’ve all heard the saying “A good plan today is better than a perfect plan tomorrow.”  But this was different.  These words seem to say:  “Go ahead.  Throw it hard against the wall, and something is gonna stick.” It gave me permission to get into a messy game and start scoring points.

Massive Imperfect Action

Let’s break this phrase down a little:


This means giving it ALL you’ve got.  Swinging hard at every pitch without judging when you miss the ball, or hit a foul.  If you think it requires 1 unit of action, throw 10 units of action at it.  Go full force.


News flash:  perfection doesn’t exist!  “Imperfect” reminds us that we don’t NEED to be perfect. It frees us of the restraints of perfectionism. You know full well that you don’t need to hit every ball into the stands to be a great baseball player.  Missing two out of three balls is still great batting average!


At the end of the day, we have to take action.  A huge trap that a lot of perfectionists get stuck in is “perfect planning”:  until you know every tiny minute detail, you won’t take action. But there are a million things you aren’t going to know when taking a big risk (like starting a business).  Small actions add up to big success.

When you take massive, imperfect action, the results are instant.  You’re going to be noticeably MORE productive. You will be getting MORE done, because you’re not going to be spending time stressing about projects — you’ll be pushing them off of your plate as soon as they’re ready!

Relaxing after a good day's work on the beach in Thailand

I’m not saying it’s easy:  it took a bit of reprogramming for me. I had to teach myself to accept that not all of the ideas that I think are great are going to work out. And that there comes a point in a project where the work I’ve done is good enough, even if it’s not up to my own (impossible) personal standards.

And while these small changes were pretty painful at first, they cumulated in the massive imperfect action that helped me do a 180 on my fatiguing lifestyle, and allowed my husband and I turn our passion project into our career.

Now, instead of working through vacations, I’ve created a business and lifestyle that allows me to do both at the same time.  Right now, I’m sitting in our villa in Thailand overlooking the beach.  And instead of stressing over what isn’t perfect in my business, I’m content and satisfied with a good day’s work.

  • Sheldon Ramsamooj

    The best advice ever!

    • admin

      Thanks so much Sheldon!