Would you rather have a choice or not have a choice?


Would you rather have to choose or not have to choose?

Me: “Would you rather have a yacht or a mansion?”

Mark: Do I have to pick?

Yes, just choose one, it’s not that serious.

Uhhh… Yacht, I guess.

Would you rather go camping in the mountains or to a beach somewhere tropical?


Sports car or SUV?… Christmas or Birthdays?

If you had to choose between having to choose or not having to choose, what would you choose? 

Come again?

Last weekend while road tripping from Huntington Beach to Ventura with my friend Mark this conversation happened. I made him repeat his last statement. Was he asking:

Would you rather have a choice or not have a choice? 


Would you rather have to choose or not have to choose?

Think about your own answer to each of those separately and re-read them if needed.

This idea of wanting a choice, but not wanting to have to make a choice, has been referred for over a decade as The Paradox of Choice, thanks to Barry Schwartz who documented his arguments in his highly influential book in 2004.

Schwartz shows how the abundance of options to choose from actually have a negative impact on our psyche and overall well being – becoming overwhelming, increasing anxiety (FOMO), and wasting time. I can attest to this – I’m always the annoying one at meals still looking at the menu when the server comes over saying “I’ll be ready by the time you get to me!”

In a world where we are often obsessed with wanting freedom to make our own choices, it’s hard to determine how much is actually too much.

Even the emotions that occur when you ask me if I want to have a choice vs. how I feel when having to choose are quite the opposite – the former of excitement and freedom, the latter of pressure and uncertainty.

I’ve seen this increase in waves the past few years.

“Nobody makes plans because something better might turn up, and the result is that nobody ever does anything.” Barry Schwartz

How many times have you sat around trying to figure out what to do and who was going to join you, and as a result miss not even minutes but literally hours of what could have been action – whether perfect or imperfect – but turned into just an abyss of absolutely nothing but time spent weighing options?

You might even be doing it right now while you read this. I don’t want to exhaust the topic as it’s already been thoroughly covered here in Paul Hiebert’s interview last year with Schwartz, and here with Schwartz’s well-stated reply to his critics: Is the famous ‘paradox of choice’ a myth?

I want to offer my very simple thoughts on how to make important choices. And that is, to think about your legacy. I’m constantly thinking about legacy. I think about death so much that I’ve even thought about becoming an Actuary.

But really, if I’m choosing between A and B, I need to have a conversation with myself on:

How are A and B going to result in creating my legacy?

And if you don’t know what your legacy is, how do you decide? If creating a meaningful legacy is important to you, take the time to figure that out.

The first step to determining the legacy you want to create is to know your core values. Once you know your core values, making choices becomes a lot easier. 

When I was about 23 years old someone asked me what my core values were and I really, truly, had no idea how to answer that. So if that’s where you’re at, don’t worry, I figured it out and so can anyone else.

A few years ago I was managing six English Pubs in greater Atlanta, constantly interviewing prospective employees. I almost always asked the interviewee what his/her core values were. If they answered with “partying with my friends” (I was in the bar business), that person did not get hired. If they said “time with my friends” my response was “why?” I wanted them to engage in a conversation with me that would allow me to figure out what he or she would do when faced with an important decision.

I’m smiling thinking back – most of these people were probably very confused and hated my interviews. Hope it got them thinking, though ;).

Here’s a hypothetical example. Let’s say I’m deciding between

Going to a Bachelorette Party for a friend – call her Megan – who is marrying one of my best friends from college – call him Matt.


Attending a business conference with some of the best speakers in my industry and one of the go-to events of the year.

Tons of things could be going through my head.

  • Megan isn’t technically my friend. I mean, she is a friend now because she’s marrying Matt, but we really haven’t spent that much time together at all and actually now that I think about it we haven’t spent barely any time together without Matt there.
  • But now that they are finally tying the knot, she is basically family and I really want to get to spend this time with her to grow our friendship. Plus it’s going to be a lot of fun, and I haven’t seen her in a while, and I’ll be glad to hang out with her separately from Matt. Although maybe she only invited me based on his suggestion. Maybe she doesn’t even care if I go? But maybe she does. Shit.
  • This conference is going to be a great way to network and gosh, I’ve really been trying to get my business growing in the right direction, and the lifetime value of going could be incredible. 
  • That being said, sometimes these conferences are more of a ra-ra cheer fest and inspiring but don’t teach actual real tools to excel. What if it’s more of what I’ve already heard before and seen before and it ends up being a huge waste of money?

If I choose the party, I’m afraid I’ll miss a great opportunity for my business.

If I choose the conference, I’m afraid I’ll disappoint someone I care about.

How do I choose with confidence that I’m making the right decision

Well, my friends, this is where values are extremely important. A couple years ago I spent some time really thinking about my core values. Things like: Integrity. Faithfulness. Generosity. Connecting with people I love. Grace – acting with grace and giving grace – Gratitude.

And at the end of my life, I’m going to hold more dear the relationships I have with the people I love, and I want people to remember me as someone who loved my family and friends, and made decisions that reflected that.

Seems like a no brainer at this point! I hypothetically can’t even believe I was trying to decide between the two.

Now this situation was a hypothetical.

But what about YOU? When is the last time you had to make an important choice and were torn? Do you think you did right by your core values, and your legacy?

Moreover, do your core values reflect the legacy you want to create?

Everything is tied together.

Values determine choices. Choices translate to actions. Actions create legacy.

If you need help figuring out your core values, or determining what legacy you want to create, hit me up or write a comment below!

I’m planning on putting more content together but in the meantime, it’s never too late to start thinking about these things and I’d be more than happy to help you figure some of it out.

Until then, my recommendation is to remember that you’re blessed to have a choice, and not to let having to choose be negative. Embrace it!

We live in an amazing world and most people reading this have freedoms some people literally could not even dream of.

What do you think? I’d love your take, whether you agree or disagree!