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How To Get A “Win-Win” Result From A Tough “50/50” Decision

A family friend asked for career advice the other day — he was trying to make a decision between finding a new job or staying put at his current job.

He was torn — almost manic — about which way to go…so I busted out the “Win-Win” exercise inspired by Yogi/Life Coach Terry.

I like using the “Win-Win Exercise” for making tough decisions — when the choice seems to be close to 50/50 —  because you can literally get the best of both worlds…a true “win-win.”

Here we go!

The 5 Steps Of The “50-50″/”Win-Win” Exercise

This Decision-Making exercise is easy: list off the pros and cons of your two choices (e.g. my friend is deciding between leaving his job or staying at his job.). And then there's a cool twist below!

Step 1: List The The Two Choices At The Top Of A Page

In this case, my friend was making a decision between these two choices:

A) Leave His Job (To get a new job)

B) Stay At His Job (Which has been crappy)

Write those down at the top of a page (one on the left and one on the right) (like in the image above).

Step 2: List Out The Pros And Cons Of Each

I know what you’re thinking:

“Is this just another lame pros and cons exercise?”

No, this is much cooler!

Now you list the pros and cons below each choice.

Ok, so my friend’s pros (for Choice A (leaving his job) were:

  • Career growth
  • Finding a better manager
  • Making more money

Cons for Choice A were:

  • It’s scary (to leave his job)
  • He won’t get to see his friends from his old job as often

Then we did the same with Choice B (in this case “stay at your job”).


  • Convenient location (San Francisco (where he lives!))
  • He’s made friends there (at his current job)


  • He has a crappy manager (she sounds like she truly sucks)
  • He’s not learning much (again, crappy manager)

Step 3: Immediately Do A Gut Check On Which Choice Feels Right

Now that you’ve listed out the pros and cons of each choice, right then and there listen to your gut (and heart) on what feels like the right decision.

Don’t worry about being wrong!

Just pick one…if you’re wrong, it’ll still work out!

If you’re really scared about this, then read what Bruce Lee and others advise in 14 Quotes To Help You Overcome Your Fear.

In the case of my friend, it was clear that his gut was telling him to go for Choice A: to leave his job!

Right on!

Step 4: Focus On The Pros Of Both Choices (To Make A True “Win-Win”)

Ok, now that you have decided that you’re leaning towards once choice  — e.g. my friend wants to leave his job —  I want you to cross out the cons from both choices.

That’s right, cons suck…you don’t want them…they are for losers who don’t take action (check out my 13 Quotes To Help Kick Your Ass Into Gear).

Now take out another piece of paper and write the name of the choice you chose along with just the pros from both choices.

The key of the win-win exercise is to capture the best of both worlds: the pros of the choice your gut tells you to go with AND the pros of the choice you're not making.

Step 5: Look At The Pros From The Choice You Didn’t Make (And Make Them Happen!)

So now my friend has his pros from both choices as:

  1. Career growth
  2. Better manager
  3. More money
  4. Convenient location
  5. Friends he made from his old job (which I now just call “Friends”)

Since you already know you’re going to get the first three pros in your new job, then you simply have to focus on the two other pros from the choice you didn’t make.

In my friend’s case, this is relatively easy:

Convenient location — He wants to keep working in San Francisco so he just needs to focus his new job search on San Francisco

Friends — This is trickier but easily doable: He made good friends at his old job so he’s got to commit himself to keeping in touch with his favorite friends from that old job now that he won’t be seeing them day to day.

And, of course, he should embrace the fact that he will make new friends at his new job.

He left our meeting confident that he should go for the new job and that he would nail all 5 pros.

He had a true win-win.

My favorite part of this exercise is that my friend could have chosen Choice B: Staying put at his job…and we could have done the same exercise to get him a win-win — although it would be a bit more work since we’d have to move him away from his crappy manager!

I just added this win-win exercise to an article I wrote on the 4 Simple Tips To Help You Make Tough Decisions.