Tradeoffs, Pro-Con Lists… And Lies I was told as a kid

I remember lots and lots of these one-off idioms as a kid.

Maybe you’ve heard them too:

  • Practice makes perfect.
  • Don’t shit where you eat.
  • The grass is always greener on the other side.
  • There’s pros and cons of every decision.

They always seemed so disconnected from truth. And, add to it that there was always someone saying it that I didn’t feel like I looked up to or didn’t know that well: a teacher, a friend’s dad cooking burgers on the grill, that weird old lady that always walked by the house really, really slowly.

It never landed. It never stuck.

Then, along comes life and suddenly, I find myself believing in these concepts as I go to make choices.

I had internalized them, especially, “The grass is always greener on the other side.”

This quote is really about how when we look across at other ‘grass,’ it might look greener, but what we stand on and already have is totally better.

It’s about valuing what we have. Or so I thought.

And then, on the cusp of quitting my job, I realized that what was holding me back most was thinking that it was only an illusion – that running my own company (or companies as it should be) was NOT actually best for me.

That the grass was just fine where I was, and that I was chasing something unreal.

I would arrive to the other ‘side’ and look back at my job – secure, consistent, predictable – and envy it again too, for it was now the “other side.”

Maybe you’ve had this fear. Maybe you’ve felt something just as dagger-like when you go to make choices.

We all have these fears based on expectations of the outcome of our choices.

But, I want to talk about what a tradeoff really is, and how, if we’re clear about our values, tradeoffs don’t mean we lose.

Remember this line: There’s pros and cons of every decision. Let’s debunk where I got stuck, so you don’t do the same.

Conceptual Example:

You’ve got a great job, or at least a job. And you’re comparing and contrasting options as you consider a change. You’re a great employee, healthy eater, and find happiness in helping others.

Job One (that you currently have) has a good salary, offers a great retirement package, and has a cafeteria on site, where you can get a fast lunch provided to you paid for by the company, but you don’t really help people. You just crunch the numbers. But you’re not happy here, so you have another potential match lined up.

At Job Two, you’ll make a 10% more, keep the same benefits, but no cafeteria. You’ll also be working directly with clients to help them navigate challenging financial waters via services you provide.

And as you go to make this decision, you make a little pros cons list.

Ever done this?

Ah, yes, the ol’ post it note pro-con list! My favorite way to make tough decisions!

I did this with cars, apartments…….lots of things.

Now my choice is way complicated. Now my numbers are almost even – what will I do?!?! This choice is going to rip me apart! AHHHH!! That $1000 isn’t worth all this stress!

<Slams head into wall>

Why do we do this to ourselves? And better yet, how can we do it better.

There’s a HUGE issue with the way we go about this, and it’s simple and addressable.

Instead of our pros and cons list being a strengths and weaknesses chart, it becomes a shortlist for ANYTHING we can think of that we’re either giving up or passing off.

Here’s what I mean.

Remember above that you’re a healthy eater. You value eating well, and your cafeteria doesn’t serve healthy options. It’s fast food basically.

It’s all in the details, right? If we just look at the data comparing the jobs, we miss how our values impact these decisions.

A healthy eater is not likely to value fast food, and you probably meal prep and bring your lunch daily. If that’s the case FREE LUNCH, does NOT belong on the pros cons list for something you’re giving up.


Because you don’t value it.

If we then look at the list rewritten, it might be more like this:

Suddenly, choices aren’t nearly as tough to make – especially when I know my values. If all that changes in this case is I have to reset the reputation I’ve built, I can make a much better call.

Because truthfully, if I don’t care about free unhealthy lunches, then I shouldn’t put it on the list! Don’t value something you don’t value! (seems obvious)

I value freedom to plan my day, an unlimited income potential, meaningful work, helping others, and ability to travel and work.

So when I compare that to my corporate world job:

  • fixed salary
  • can’t plan my day
  • no option on what to work on
  • can’t travel except with paid leave
  • not very meaningful
  • Benefits were paid for
  • Retirement savings was done for me
  • My apartment was paid for

Yes, there are some really awesome perks at the bottom. But, who cares about paying for benefits, an apartment, and savings when I can earn an unlimited amount and I’m happy!

In fact, when I pro-con this situation, I don’t even list “paying for benefits” as a con. I’ll happily pay for health insurance, etc given what I’ve got now. Think about that. I’m HAPPY to pay benefits in exchange for what I have now.

And thus, we have debunked the adage. The grass is TOTALLY GREENER!!!! And when I got here, I looked back at grass I didn’t value.

And here I stay. Because it aligns with my values.  

When you know your values, you can easily create better tradeoff decisions, and eliminate things you don’t care about.

Don’t need your car to have baby soft leather? Cool, then don’t pay for the upgrade package.

Don’t travel very much, and really like hosting friends at your house? Great! Get the more open floor plan at your apartment complex.

Values are what help us make better choices, but the ultimate game to be played here is about how we use our values to eliminate elements of choices.

If you don’t value something, it doesn’t belong in the conversation when you’re considering two options.

What are some choices you’ve made where you were doing pros-cons and wrote down every single detail, complicating everything?

Share your answers in the comments or email me. I read every single response!

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