The Cook Islands and Where We “Should” Be By Now


A few weeks ago, I found myself in the international departures of LAX eating an overpriced turkey burger and waiting for my best friend who had currently been in line for chicken fingers for almost 45 minutes.

It was close to 10 PM, and yet the tables and shops surrounding us were bustling with people dragging their suitcases and children, looking tired and worn as they made their way to a gate or tried to clean the ketchup spills from plastic chairs.

After a brunch that morning where we had each consumed four mimosas, our bodies were feeling both the weight of the alcohol and the anxious anticipation of the 10-hour flight we were about to board, the one that would fly us across the Pacific Ocean to a tiny cluster of islands called the Cook Islands.

My best friend, Molly, and I have been friends for six years and unofficial sisters for four of those years. This was our first major trip together, and the first time I had been overseas in over three years. Separated geographically by life and grad school, we were looking forward to five whole days of catching up on the white beaches of the biggest island, Raratonga.

Catching up with someone in person after a long period of time can be both exciting and, to us introverts, sometimes overwhelming. There is so much to hash out: how is work going, how to you feel about that, how is dating or the relationship going, what’s the status of your living situation, how is church, who have you been hanging out with, are you exercising, etc.

As we finally disembarked the plane at 6:30 AM and made our way to the small customs line (Raratonga has an open-air airport, by the way), I knew Molly and I were going to have many about all of these things until we reached the inevitable question of if where we were at in life was where we felt we “should” be.


Molly and I are both 26 years old.

Age has always fascinated me. Whenever I read someone’s story, I want to know how old they were when this or that happened. What life experiences had they already lived? Were they equipped to handle whatever was happening to them because of age, or because of mental maturity? I always want to know at what age people attended grad school, when they got married, if they got divorced, when they had their first baby or got their big break or published their first book.

Age becomes a natural measuring tool of where we “should” be in life:

At 20, we “should” be in college.

At 25, we “should” have had at least one serious relationship, and by 30 we “should” be married or be well-immersed in a career.

At 35 we “should” have at least one child.

The list goes on.

This sting, this pressure of “should” feels especially potent in one’s twenties, when many major life decisions or milestones are scattered this way and that, there for the taking if only we would choose the right one, and each appears to be tied directly to both our personal value and identity.

These ideas of where we “should” be seem to plague us even in the midst of living out our chosen, happiest, and most self-affirming circumstances.

Molly and I are living different “shoulds.”

Molly has just started her third year of law school, which she will complete next year before taking on a position at a firm, one she has already been offered and has accepted. Her career is happening, moving forward, opportunities and goals and achievements are falling into place. She is in the midst of it; her dreams are coming true.


And yet, Molly feels like she should be in a relationship.

She’s 26-years-old, dammit, and hasn’t had a boyfriend in years. She’s met and dated numerous men of different ages, backgrounds, religions, and hair color. She moved to a city teeming with singles in similar life stages. She’s gone out. She’s been online. She’s got the career – now she’s ready to have the guy to support her in that career. She should have found someone by now…shouldn’t she?

And then there’s my “should.”

I have the “should” Molly wants. I have the amazing relationship, the lovely, supportive marriage. I’m in love with him and he’s in love with me. My driveway is literally lined with a white picket fence. And Molly is living my own “should.”

I think that I should have more of my career, hell, my day figured out. That after all this time of trying, thinking, planning, failing, wanting, I should have a grip by now. I should be waking up, every day, with my nose to the grindstone. I should be making money. I should have monthly goals, yearly goals. I should have something concrete I’m working towards. I should have written the book by now. Lord, I should have at least had a solid idea for the book by now. I should be more successful, more recognized, better motivated. I should know what the f*ck I’m doing.

I should have done this or that by now.

Some shoulds are good for us. Some can push us out of our ruts or propel us into the more-alive versions of ourselves. But others, especially when it comes to our expectations about age, about where we should have been by now, can eat at us until they convince us we are not enough.

And they’re mostly not true.


“Should” is a formula, and formulas feel safe.

If I’m this age and I’ve done X, Y, and Z, I should get this result. “Shoulds” are found in the idea that there is one way to do life, to do our own life, that we are all walking the same path and some of us will cross whatever finish line at the correct time.

This is probably one of the most un-glorious ways to live, and yet a way of thinking that is drastically difficult to extricate ourselves from.

On our final morning in the Cook Islands, I walked along the empty beach as the sun was gently rising behind dusty purple clouds. In the distance, over the horizon, I could see a patch of rainbow. Not a full arc, but rather a streak of unassuming color. Even in the stillness, all my “shoulds” raced in my head as I thought about returning to normal life, to the day-to-day of trying to make it.

And I said out loud, “It’s time to put those thoughts to rest.”

How do we do this? I don’t know. They are not all at rest, though many of them have become less loud.

I think of Ann Voskamp’s words, that woman genius who wrote One Thousand Gifts and who says this: “Anxiety can wear anger’s mask. Fear of failing, fear of falling, of falling behind, it can make us fierce…The answer to anxiety is the adoration of Christ.”

The answer to anxiety – anxiety over where we “should” be – is the adoration of Christ.

In her book, Voskamp defines adoration as the act of giving thanks. We learn how to give thanks for what we have, where we are, and the opportunity every single moment of every day, no matter our career or relationship status, to love the Lord and be with Him.

Thankfulness casts out fear, anxiety, grief, uncertainty.

It is easier said than done to be sure, but I believe it is the first antidote in a series of antidotes to combat the suffering caused by all our “shoulds.”



What are your “shoulds”? Where do you believe you “should” be by now? What “shoulds” have you struggled with in the past?

4 replies »

  1. I feel like I “should” be in grad school by now. I feel like I “should” be passionate about my job because I get to teach kids how to read. When I settle myself back into the present moment and think about it’s holistic life benefits rather than where it’s projecting my career, I find a sense of peace again.

  2. I can only speak for myself, Julia, but in many ways, our ‘shoulds’ never leave us. One of my longest lasting shoulds is “I should have a great job.” This will run through my head simultaneously with the certain knowledge that what I do (and don’t do) is so precisely what God wants for me that it was nearly impossible to resist.
    Sometimes, a should will nudge us in the right direction. The opposite is true, as well! Sometimes a should is a symptom of our drive to move forward. Conversely, a should can make us reluctant to grow or change.
    Right now, I struggle with a hurtful, and, I believe, ultimately damaging, should that says my relationships with my daughters should look vastly different than they now look.
    When I am weary enough of the struggle, too weary even to actively adore, I know I can first rest in Him until I am able to adore as I – again – lean heavily. Thanks be to God!!!

  3. No matter what you write about, I find myself pondering it for days and weeks after reading. I believe this to be a sign of your greatness.
    “Shoulds” are such a part of our culture, and they are hard to ignore – whether you believe yourself to be successful and happy or not. I guess “should” ought to come from our heart…and let the chips fall where they may. But that gets easier to live out as one ages.
    My “shoulds” are basically all about fitness anymore…less and less about my vocation. Although financial “shoulds” are a nagging stress – I should have investments, I should have a 401K, I should be saving more for later…and yet, a couple days ago I bought 2 tickets to see Bob Seger! So yeah – don’t let the “shoulds” hold you down 🙂

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