Start as a yes man, then it’s “hell yes or no”

Chris Lovejoy

20. Start new things then only pick the best.

Becoming a yes man can be a game changer. It can drag you out of stagnation and frustration. It can lead to experiences and opportunities which greatly facilitate personal and professional development.

It is particularly useful when starting something out. At the start of Derek Sivers’ music career, he said yes to all kinds of gigs. He said yes to performing at a pig show, which someone else had rejected, and as a chance occurrance was later offered to play at a circus where he played for a long time. If he had said no to the first, he never would have had the opportunity for the second.

However, it has limitations. If you are at a point where you have many great opportunities, saying yes to more things will reduce your ability to get the most out of each of those opportunities.

In this situations, a better approach to take is “Hell Yes or No”. If it’s not an opportunity that gets you excited or that you are sure you will love, don’t do it. This ensures you have the ability to say ‘hell yes’ when that great opportunity comes around.

The ‘yes man’ attitude is a necessary transition to get to this point but it is not a sustainable end goal.

Exposing yourself to lots of opportunities calibrates your ability to predict how something will be which enables better ‘hell yes or no’ decision-making.

Let’s use the example of drawing:

You have always wanted to draw but never got round to it. You see a drawing class advertised, ‘yes man’ and do the course. You enjoy the course and having tried something new.

A few months later a friend, who is an artist, asks if you want to go on a trip and draw some landscapes. Having taken the ‘yes man’ approach earlier and attended the course, you are better place to make the appropriate ‘hell yes or no’ decision. If you found drawing so-so, then ‘no’ is appropriate but if you found a passion you would say ‘hell yes’.

In summary:

  • if you feel bored with life, that you have stagnated or that you don’t have a lot to look forward, become a yes man and say yes to eveything
  • if you have too many good things that you want to do, no more yes – either ‘hell yes or no’

[note: I realised half-way through this post that it almost exactly follows a pre-existing Derek Sivers post (I had previously read the hell yes or no one but not this one). I decided to finish it anyway to fulfill my daily writing commitment and for the practice but would highly recommend his original post for greater clarity.]