To Settle or Not to Settle?

To settle or not to settle?

To settle or not to settle?

This is our generations’ greatest question.

Heck, I’d say SETTLING is Millennials GREATEST FEAR – the thought of settling giving us nightmares. Like the time we watched Stephen King’s IT and slept with the nightlight until we were fourteen. (I still can’t look a clown in the eye).


We’re the, I Can Do Anything, Get the Freak Out of My Way, Generation. We are the, I’ll-work-how-I-want, when-I-want, where-I-want, Generation.

Yet, what happens when our way becomes no way in hell?

What happens when Plan A is shredded like an old tax statement?

What happens when you’re working, well, just to work? You know, to pay those silly things called bills.

What happens when moving in with your parents, or a cardboard box, becomes your only two options?

What happens when it feels like you have two choices — to settle or not to settle? 

The fear of settling swirling in your stomach like a blender turned on high, the expectations of the big life you envisioned pureed like a jar of baby food.

Yet, is to settle or not to settle actually the right question?

To Settle or Not to Settle?
Is That the Right Question?

Well, what is settling?

Is it taking a job just to pay the bills? Is it moving in with your parents? Is it some external setback?

Well, no, I don’t think so.

Our generation must not confuse setbacks for settling.

Sure many in our Millennial Generation might not be acting out our greatest dreams right now.

But we can settle for a season without settling.

Too many of us view pursuing our dream as this black and white proposition. Either we go for it or we let our dream die.

Yet, in reality those who are successful pursue their big dream, while at the same time, work their all-too-real job.

As I wrote in my book All Groan Up: Searching For Self, Faith, and a Freaking Job!:

You work at your job to feed you while you work at your dream. And you work at your dream to feed you while you work at your job.”

Setbacks Can Have Purpose

Dreams don’t happen void of setbacks, dreams happen as you push through a thousand of them.

Setbacks aren’t dream-killers, they are dream-refiners. (click to tweet that)

As I wrote in 101 Secrets For Your Twenties, “Sometimes frustration can be the best guide to leading you where you need to go.”

They only time you’ll really settle is if you completely give up. If you let your dreams be suffocated by your current reality and believe too many lies that twenty-somethings have bought into.

However, if I know our generation, I don’t see us throwing in the towel anytime soon.

Sure maybe we’ve joined forces with a not-so-glamorous life. Maybe we’re not going to be a feature article in our alumni magazine anytime soon.

But I think our generations most important characteristic is that we have the ability to stay optimistic, even when the world turns quite depressing.

So if it feels like you’re not where you want to be in life — that’s okay.

You can settle for a season without settling. You’re not settling. You’re visiting. This is a season, a stage, the perfect place in time to help us take a step to the next.

Life will never feel like it’s supposed to and that’s exactly how it’s supposed to be. 

To settle or not to settle? It’s not the right question.


  1. Jacqui

    Great reference to IT! I have the same issue with clowns.

    On a serious note, though, you definitely hit the nail with this one.

    • Paul

      Thanks Jacqui. Not sure which freaks me out more — settling or the painted on smile. Ha

  2. Louise

    I would say you are definitely onto something! We have this fear of settling for something mediocre but then we end up not choosing anything at all. It’s a hard juggling act to balance. I think we (me, at least) could look at any life direction we decide to take as not necessarily settling, but more experimentation in figuring out what works.

    • Paul

      “not necessarily settling, but more experimentation in figuring out what works.”

      Yep. Exactly. So much of the growing up and growing into process for me has been figuring out what I don’t want in life, which has then clarified what I do. Thanks Louise

  3. Justice Wordlaw IV

    Some times you’re not going to land that amazing job or make $1000 per month on that new product you just released. But, at least you’re starting something in your life besides sitting on your ass and relaxing. Our generation needs to realize that you don’t have to feel bad just because things aren’t going the way that you want things to be right now. In time with a strong set of skills and experiences you’re going to accomplish those goals that you have in life you just have to be patient and continue to have a focused work ethic and you’re going to bypass the lazy people and the “i wish” people.

  4. Paul

    Right on Justice. For too many years post-college I existed in the “I Wish” and If Only.

    If only I would’ve stopped sooner…

  5. Rashida Thompson

    I don’t believe we’re settling if, while we’re in a rut, we get creative and continue to hone our talent & skills in our area(s) of interest.

    I’m 25, I live with my mom, I have a full-time job that is less than fulfilling, and I’m working on my MBA (also full-time). My time is limited but in the free time that I do have, I commit it to increasing my knowledge of social media, which is the career that I’m passionate about.

    I’m exploring and like you’ve mentioned above, experimenting, with things that I like and that I don’t like so that when the time comes, I’ll be prepared to walk into the job of my dreams…whenever that happens. And it will happen 🙂

    • Paul

      “I don’t believe we’re settling if, while we’re in a rut, we get creative and continue to hone our talent & skills in our area(s) of interest.”

      Couldn’t agree more Rashida. I think that’s the key to doing this twentysomething transtion well. Our 20’s are about preparation more than anything, if we’re willing…

  6. Kelsea

    Great post! This definately speaks to me where I’m at right now, whith the seemingly never-ending question of ‘Am I settling?’. Thanks for the reminder that this is just a season in life, preparing us for something bigger that God has planned 🙂

  7. Financial Samurai

    I think everything is rational. If you settle, it’s because you love to chill and relax! IF you don’t settle, it’s b/c you want more.

    Everything is aligned! I couldn’t be more happier for Gen Y.



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