Here’s How to Know When to Let Go

5 min readJul 16, 2022


How do you know when it’s time to let go — of a specific outcome, a dream, a job, a relationship? This past Fourth of July weekend, I sat with a group of friends, both old and new, and we got to talking about letting go. Well, sort of. While that wasn’t the exact topic of the conversation, it surfaced as a theme of each story being told.

One older man shared about physically letting go of his rental properties just a few years ago. At the time, they’d felt like more of a headache than a help, and he’d needed to free up some funds (and time) to care for his aging mom. Still, these assets would be worth over $100k more if he’d waited to sell now. So, he’s still doing some inner work to mentally let go of the lost additional income.

Another friend — a guy much younger than me — shared about his pending eviction. His landlord is selling his property, and with rental prices so unbelievably high in Missoula, this friend is leaning toward living in his camping trailer until he knows what comes next. Facing the reality of much less physical space, he’s using the opportunity to purge the things he amassed over the last couple of years, physically letting go of “things” while also mentally letting go of what “home” looks like.

And then, there’s me, considering the idea of sending my kids to public school next year rather than homeschooling. I never thought I’d be in this position to begin with. We’d always planned on public schooling, but then COVID showed up and shut down our facilities just as Joey was about to finish up Kindergarten. We dove into homeschool reluctantly, feeling like it was the best choice but not our ideal. Even though I wasn’t able to work as full-time with the kids at home, we soon discovered it gave us something more valuable than money — precious time together. Plus, some time to help me figure out and impart a cohesive value system for my kids to follow — put a bit of solid foundation in place before they re-enter an environment with a wide range of ideas about what’s what in the world.

Now, I’m watching my son begin to stretch his independence muscles, desperately wanting to figure himself out apart from mom and dad. I’m also seeing my daughter flourish at a local acting camp, throwing herself in with 50 other kids and excitedly finding her voice. To me, these seem like road signs pointing toward my direction. Maybe it’s time to let them go, along with a lifestyle I’ve very much come to appreciate (no early wakeups to meet the bus!!!)

But how do you know for sure when to let go? Sometimes, like in the case of my younger friend, letting go is forced on you, and your only real choice is how to move forward. Other times, as with my older friend, it’s a matter of perspective — shifting or reframing your viewpoint so you can see the letting go for what it was: not a failure, but the best choice at the time.

What about when the choice to let go is, more or less, entirely up to you?

I believe it comes down to two central questions:

Who do you want to be? If I can get really clear on who I want to become and the sort of community I’m looking to build, it really helps me determine when it’s worth it to let go or press on. In this case, letting go would line up with the goals we set for ourselves and our kids. We always said we’d return the kids to school when they appeared ready/eager to shoulder the challenges. Plus, I don’t want to cage ’em so long, we end up with a weird Lannister situation. Which leads me to the second question:

What are you letting go for? It stands to reason that, if you’re giving something up, you’re clearing out space for something else. Maybe that “something else” is a healthy, worthwhile gain. Maybe it’s something more complicated, like you’re trying to please someone else or be someone you’re not. In our case — Nick’s and mine — we seem to be at a crossroads where NOT letting go may actually hurt the kids’ development. So my reason for letting go would be to support them in becoming stronger, more independent and capable humans. (Please don’t hear me saying this is true for all homeschooling parents. We aren’t exactly a Grade-A example of keeping our kids engaged and entertained, and might be better off outsourcing those aspects of their learning).

But wait! Even with all the logic and every “pro/con” pointing to Answer A, there’s still a third question I ask myself:

What does God say? This one is totally optional for you, but I think you’ll find it helpful if you can stomach it. I believe in That (Admittedly Overly-Americanized, Grossly Whitewashed) Controversial Higher Power who knows better than I do who I’m becoming, who each of my kids is here to become, and how to best get there. This introduces a third step in my process, and the answer I hear supersedes whatever my human logic has reasoned out. Admittedly, sometimes I can’t hear a damned thing. Other times, it doesn’t make a lick of sense — for example, all I’ve heard lately is “seek first the Kingdom, seek first the Kingdom.” Meaning, I suppose: keep asking, keep knocking, keep giving myself over to this daily, moment by moment process of the invisible Spirit transformation evolving the way I think about my situation, see the paths set before me, and love other people around me.

I don’t know if you noticed, but this is not a precise, step by step formula I just laid out for you. That’s somewhat intentional, as every situation is nuanced, with so many variables and angles perhaps known best to you. And despite the countless complaints I’ve lodged with Management, we’re each here to walk our own path, which means that even if you receive a burning bush-level sign from G*d, you are still the only one who can ultimately choose when it’s time to let go. This fact flat out sucks, there’s just no way around it.

But it’s also sort of beautiful. Much like those choose-your-own-adventure books I loved as a kid (and am now forcing onto my homeschooled second grader), YOU get to choose. I honestly don’t think we’d want it any other way, as humans. We like to feel like the advancer of our own destinies, the captain of our own ships- even if we end up running that ship straight into an iceberg (I’ll never let go, Jack! Wow, I did not even MEAN to land on that wonderfully juxtaposed film anecdote about letting go. #Winning).

In the end, it all comes down to this: we make the best choices we can with the information we have at the time. When we mess it up (because we will sometimes), I take comfort in the fact that G*d saw it coming before I did. And I don’t believe in The G*d Who Just Leaves Us to Fester in Our Mistakes Without Providing a Way Up and Out. But again, it’s up to us to choose.