How Do You Make a Big Life Decision?

By: Jen Shoop

*Image via Sir the Label.

How did you know it was the right time to move back to D.C.? How did you decide how many children to have? How did you choose the school your children attend? How did you know to switch jobs? How did you decide to start your own business?

I’ve fielded these questions — and other javelins aimed at major life decisions — many times over the course of the past few years. I am flattered to be trusted with these matters of the heart and equally aware that I cannot answer them accurately. Because the truth is — you never know. There is no right time, no correct choice; there is only now or next year or never, and the things you did and did not do. If you are looking for the correct expression on the other side of the equal sign, there is none. I am not writing from a place of nihilism: these choices do matter and will shape your life, and I believe we are always guided by forces greater than us such that there is profound meaning in the way life unfolds. Instead, I mean to reassure you. I mean to help you down from the high-wire, to ease some of the pressure you have placed upon yourself, to let you know that if I am staring at a big life decision, I try to not let myself fixate on whether I am doing the right or wrong thing at the right or wrong time, and instead remind myself:

+Very little in life is permanent. If I choose something and hate it, there are almost always paths out or back.

+Confirmation bias is a beautiful thing when it comes to the aftermath of making a big choice — it’s the tendency to interpret new evidence as confirmation that the decision I’ve made is the right one. Which is to say, I make the choice, and my subconscious immediately goes to work building a nest around it.

+This is your one wild and precious. My father has always encouraged me to take the chance, try the new job, keep moving forward, exercise optimism in the face of change. In his words: “You’re gonna love it.”

+Do you prefer the pain of being stuck or the pain of new growth? This is my way of reminding myself: don’t let fear of the new override dissatisfaction with my present.

+Life is about making educated guesses using invariably imperfect, incomplete information. I will never have a full and accurate report outlining every pro and con. I can only make the best choice based on the limited insight I have right now. This framing always charges me up, leading me to figure myself as the chief executive officer of my own life. After all, heads of business are constantly making complex decisions based on fragmentary information — they’re making their best guess. I can, too.

+Trust your intuition. I used to hate this hippie-dippie advice, but I have found — especially in my 30s — that listening to my gut has rarely steered me wrong, because it means I am evaluating opportunities against my own internal value set. The older I get, the more I realize that a peaceful, fulfilling life has a lot to do with seeking alignment between the everyday stuff of living and my core values. This is true in matters big and small. For example, the past few weekends, I have taken my children on short hikes. Every time I spend an hour in nature with them, I feel a profound sense of intactness radiate through me: I am living and modeling for my children some of the small virtues to which I routinely aspire: quiet, curiosity, naturalism. (As C.S. Lewis put it: “I am a product of long corridors, empty sunlit rooms.“). I promise that listening to yourself will rarely leave you high and dry. It may be helpful to spend some time reflecting on your core value set — you know them, of course, but sometimes enumerating them and holding them up against whatever decision you are facing will help. I think this exercise may prove useful in decisions like where to send your children to school and whether to switch jobs or not.

+Deliberations can vary in length. Some decisions come quickly, usually because a time-bound offer forces your hand, but don’t worry too much about the length of your decision-making process. I’ve had some friends say, “Oh, we talked about it but we just never made up our mind so I guess it didn’t matter and we dropped it.” Life is in constant flux. A single phone call can rearrange your entire world. Sometimes what feels wrong now will feel right in a year, or two years, or ten. My point is that it’s good practice to revisit the conversations that matter to you — they aren’t dead just because you’ve said “no for now.” I think this is especially true when contemplating a big move (especially one “back home”) or a second or third child. Do not feel that a “no” today is a permanent foreclosure. Authentic people change! We learn, we unground ourselves. Mr. Magpie and I talked for years about moving back to D.C. before we actually did it, and it felt like this: “No way – not now – no – not now – of course not – no – no – no – what if we did? – I think we could – yes – yes – yes.”

What do you think, Magpies? Do you have any helpful strategies for approaching big life decisions? Please share.

As always —

Onward —


+What was the first book or movie you recall having a strong emotional reaction to?

+What I learned pursuing a degree in English.

+My love story.

+If you want more Magpie, you can subscribe to my Magpie Email Digest for a weekly roundup of top essays, musings, conversations, and finds.

Shopping Break.

+Thanks to a Magpie for pointing out that these amazing Citizens’ jeans I’ve been eyeing for the season ahead in the coolest brown color are fully stocked here.

+Thoroughly enjoying this audiobook. I tuned in during my routine dental cleaning yesterday and it was a fantastic way to pass the time and distract myself.

+Don’t hate me for thinking about outerwear, but this $148 steal is AMAZING. And still not recovered from this Veronica Beard beauty.

+Speaking of VB, you can get an extra 15% off their sale section with code SUMMER15. I think I’m going to treat myself to this mixed-media sweater for fall! So interesting, and love the collar especially. (End ups being $113 instead of $448?!). Also fabulous: this blazer and this shirting stripe dress.

+These take me back to my college years, but you know what they say: what comes around goes around. Loving these flared yoga pants!

+How precious is this corduroy jumper for your little love?! Sweet with a collared top like this.

+Speaking of collared tops, I haven’t mentioned this in a long while since my babies are not babies anymore, but Kissy Kissy’s peter pan collar onesies ARE THE BEST. The best quality, the sweetest whipstitch detail; look great under everything. They last forever. I handed all of mine down! Worth the extra $$ because they last and last.

+A fab wedding guest dress for under $350.

+Everyone needs this slip. The neckline works with SO much. I find I need a slip for 90% of my Doen pieces! (How dreamy are this and this? Ah! I’m having such a shopping weakness for Doen right now.)

+Thanks to the Magpie who discovered this denim dress. Very…Ulla/Isabel Marant? Imagine with sandals like these now and flats like these later (LOVE in the chocolate brown — these are the most comfortable flats ever, right out the box).

+Cute baby swing.

+These olive green utility pants remind me a LOT of my Joe’s Jeans pants I wore all last fall/winter, but less expensive. Can’t recommend enough!

+Neely & Chloe just launched the prettiest patterned garment bags. These feel perfectly-suited to a bridal weekend…

+A fun (bold!) sandal.

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17 thoughts on “How Do You Make a Big Life Decision?

  1. Love this and as usual, you’ve perfectly articulated sentiments that have been swirling around in my head lately. An approaching birthday has me reflecting on how I really like who I am in my early 40s, largely because I’ve proven to myself that I’m someone who is not afraid to take risks or embrace change. And I do love what it’s modeling for my children! I started a new job last spring after ten years at my previous company. A few weeks later, I was a special guest for lunch at my daughter’s school, and I was shocked when she suddenly stood up and in front of her whole Kindergarten class excitedly shouted: “I have an announcement, my mom has a new job!” The pride in her voice– I will carry that in my heart for a long time. (Nevermind that she has no idea what I actually do, ha!) Alternatively, I look back on times I reached for something that didn’t work out and I can clearly see why; I was meant for something else, or something else was meant for me that never would have found me if the original goal had been met. Trust in life’s timing and the universe’s guiding hand is definitely part of the key to a peaceful, fulfilling life as you mention above!

    1. I LOVE this moment and memory — the pride in your daughter’s voice is, of course, a direct derivation of your own attitude toward it, and the way you framed the achievement at home. I love this so much! Bravo, Gina!!


  2. That BR Ella dress is in my cart — I hope they have a promo soon! (Is it just me, or is BR not doing as many promos as they used to in years past?!)

    1. I know – they’re doing fewer promos on the current season stuff! Their sale section is great but I want the dress! xx

  3. Whenever I am waffling on a decision, I like to remind myself that not deciding is, in itself, a form of decision. You think that by doing nothing you are avoiding making a choice, but in doing so you basically force your own hand in one direction.

    1. This is such a good point, Anna. Sometimes when I can’t muster up the energy/conviction/desire to do something I think I “should,” it’s really my intuition telling me it knows best — and it’s holding me back. Thanks for the reminder!


  4. We can all use to hear that very little in life is permanent. My older brother often reminds me of this, and it’s so useful to put things in perspective. Even something as serious and life-altering as marriage isn’t permanent. What a comfort!

  5. The most helpful advice I’ve ever been given regarding making a big decision comes from Ignatian discernment and is a bit of a expansion of the idea of trusting your intuition. When choosing between two paths, mentally commit to one option for a period of time (a week is usually a good benchmark in my experience) and just imagine it and see how it feels, what concerns it brings up, what joys it brings up, etc. Then, after a week, switch to the other option, and do the same thing. I did this in my early 20’s when I was trying to decide if I could go to grad school and immediately realized I couldn’t picture myself doing it at all (!!!), and the choice was immediately clear (I did not go to that program!). Then, a few years later, I did the same thing, and realized oh it was time now. I was ready for the change of graduate studies in a way I hadn’t been a few years before.

    1. This is absolutely genius. I love it! I love the practicality and specificity of it. Going to try this on for size.

      Thank you so much for sharing!


    2. Megan — YES!!! This is exactly the same advice given to me when I was considering grad school, as well. The director of the program to which I was applying didn’t frame it as “Ignatian”, but I went to a Jesuit university for undergrad and this type of discernment resonated with me.

      How amazing that you used this process and it gave you 2 different outcomes. A great reminder that we can change and grow so much, and be ready for something we previously weren’t ready for.

      1. Mia — how fascinating that we were given the same advice for the same situation, but I was also educated by the Jesuits (and given this advice by a Jesuit spiritual director) so I shouldn’t be surprised! 🙂 It’s truly such a helpful tactic.

  6. The cover of that Williams audiobook looks like exactly what I want to read in the summer! Never thought of audiobooks during dental cleanings but why not?

    For those pondering a decision, may I recommend Emily P. Freeman? She has several books and a podcast focused on doing “the next right thing.”

    Also, I loved being reminded that very little in life is permanent! I tend to feel like I’ll be stuck regretting a decision – but I am not powerless to make another decision in a different direction.

    1. Thank you for the rec — I like the idea of “doing the next right thing.” (Also a song from Frozen II? Not a bad message for a children’s flick!)

      Yes, can’t recommend listening to the podcast while in the dental chair. Really distracted me!


  7. Love this reflection, Jen. In my work, I often tell clients there are no right or wrong decisions. There’s just decisions you make for reasons you like. I find that framing takes so much pressure off the situation.

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