I think I made the wrong choices

OH Dear 02: On midlife, regret, and how to reconcile past expectations with present reality

Welcome to the 2nd edition of the Outsourced Help column: Dear Tami (‘OH Dear…’ for short) where I’ll provide real advice for a fictional character you probably know and (maybe) love.

While I’ll admit that my input is unsolicited, my advice is prompted by something the character says in the course of their story and then elaborated on using my imagination (and years of actor training in character development and embodiment).

You may recognize today’s guest from the tv adaptation of Taffy Brodesser-Akner’s best selling book, Fleishman Is In Trouble.

Please note: All advice is meant for fun and entertainment purposes only. I am not a therapist…but I (could) play one on TV.

OH Dear Tami,

I am lost. I don't know what I'm doing with my life. I’ve been thinking about marriage and money and friendship and career and how all these things coalesce in middle age. How they make you miserable right at the exact point that you're supposed to have everything set. 

I know it sounds crazy, but we always fantasize about what it would be like not to struggle and we don’t realize what it would actually feel like to get the things we want. Because the truth is, contentment breeds quiet, which breeds complacency, which breeds unrest. 

…I kind of ran away from my family for a while. I was there, but not really. I came back. I was always going to come back. But there was a time when I wasn’t really sure, because being sure would have made the whole thing feel less…dangerous? And now I think maybe I needed a little bit of danger in order to feel like I know what matters. 

I also know the problem wasn’t my marriage. It was just that my marriage was a witness to all my other failures, like a comorbidity to how I’m just getting old. I mistook the person closest to me for my misery. I thought, "Maybe if I changed this, I'd be me again." But I’m not me anymore. I haven't been me in a long time. And it's not his fault. And it’s not like not being married is ever gonna make me feel young again.

Nothing can unmake the choices that I’ve made.

I just didn’t know when I was making those choices, that they were gonna limit all the other choices that I could make in the future. How can you live when you used to have unlimited choices, and you don't have them anymore? 

Sincerely,

Runaway Regret

Dear Runaway Regret,

Oof.

Your letter asks the question I imagine is at the root of every midlife crisis. Probably every existential one, too. What do we do with the absolute limitedness of our time?

I’ve been reading Oliver Burkeman’s book, ‘Four Thousand Weeks’¹ and this passage stopped me in my tracks:

“As I make hundreds of small choices throughout the day, I’m building a life– but at one and the same time, I’m closing off the possibility of countless others, forever. Any finite life – even the best one you could possibly imagine– is therefore a matter of ceaselessly waving goodbye to possibility.”

That part hit a wordless, airless pit inside me– one that I mostly dance around, sometimes inching towards it to see if it’s as scary as I think it is. (It is). It sounds like you’re peering over the same blind edge.

I don’t mean to pile on to your anxiety. And I’m not here to paste your walls with other people’s wisdom like inspirational posters that will fix everything, but I do want to recognize the very real and very heavy weight of what you’re holding. It’s a lot. It’s kind of the whole thing.

And I don’t think it can be fixed. But I do think it can be tended to.

Time is a wall I’ve been bumping up against for awhile, but this year, like you, I’ve had a full ‘stop-what-you’re-doing-and-question-everything’ confrontation with it. I think it has something to do with age and the milestones that bring you to a crossroads in the wilderness when you thought you were arriving to backyard graduation party. The idea you mentioned that this is the part where we’re supposed to be set. That everything after this is just enjoying the cake.

I have been trying, unsuccessfully, to untangle the stubborn knot of this belief that, after 40, we are just living out the decisions we made in our 30s. That after a certain point, your life is fixed. The direction you chose, your career, your family, your finances, your home, your body…whatever is, is frozen in time.

It’s no wonder we are panicking. Desperately naming our dissatisfaction, chasing our wanting, battling our disappointment like an enemy. It’s no wonder we are gripping so tightly to all those other options and could-have-beens. Like, maybe, if we’re still holding them, they can still belong to us. And then, of course, all of this is positioned against the expectation that we should be happy and fulfilled. The fullness of our lives in contrast to the deep hollowness of that pit.

Like you pointed out, the problem is not these things or these people or these places. It’s not a lack of love or even of wanting them. It’s that, in these confrontations, everything we do have exists in the context of that gap. Pinned to the board with resentment for not being enough to make up for everything we don’t have. The unmet expectations we held for ourselves. The dreams never actualized. The potential never realized. It is a lack within us, not around us, that we have to answer to.

I once made a list of everything that will never be.

I will never be ____

I will never do ___

I will never have ____

Yes, it was (more than) a little depressing, but it was also very therapeutic. And what surprised me more than anything was how many of those ‘nevers’ were tied to a timeline.

I will never be (insert age) and have accomplished ____

I will never do ____ by the time I’m (insert age)

Should I choose to reframe and reprioritize them, some of those early visions are still available to me. There are also plenty that aren’t and I had to let those go. Or, more honestly, I am in the process of letting those go.

I don’t think there is any way around feeling that sense of loss, but maybe if we are willing to release what will never be, that disappointment can break open into grief and not harden into regret.

You said you needed some danger to put everything into perspective. I get that. It also sounds like you didn’t necessarily want to blow up your life or leave it all behind; you just desperately needed something and you weren’t sure how else to get it. The shame of feeling a certain way that (you think) you shouldn’t feel often drives us to extremes.

So, for what it’s worth, I think it’s ok to feel lost. I also think it’s ok to want to run away. That’s real. Acknowledging it doesn’t mean acting on it. But it does give it space to exist, lets it pull up a chair so you sit with it. Hopefully, if you meet it with curiosity you can begin to understand it. Maybe it will tell you what it needs.

Maybe then you can tell your husband. I bet he’ll be relieved to know what’s going on (and that it’s not actually him you’re running away from). Maybe he can help. Maybe he feels the same. Maybe, in the end, you will still need to run away for a little bit. Maybe you can do it together. Maybe the danger you’re looking for doesn’t have to be an independent thrill. Then again, maybe it does. Then again, maybe it’s not about the danger you’re seeking, but the aliveness you feel when you step from the known into the new. We’re better at doing that when we’re young, but we don’t have to be young to do it.

There’s another exercise I’ve been practicing lately. This one equally powerful, but much less depressing. I lay out the cards of my current life, I go through each one and I choose them again. Or I don’t. Either way, I am actively building a life that is made up of Present Tami’s choices, not Past Tami’s consequences.

It’s true that you are no longer the you you used to be. But who we are is not fixed, either. Our identities need updating, probably as often as our devices. There is probably some mourning to be done over parts you’ve outgrown, but I’d bet there is just as much to celebrate for what, and who, has grown in its place.

It’s true that the choices you have made can’t be undone. They have shaped you into who you are and where you are now. They have collectively determined what possibility is now available to you. But don’t forget that, for every choice you trimmed, new opportunities sprouted. I wonder what options you have now that are only available to you, because you said yes when you could have said no.

It’s true that you will never be as young as you are right now. But I don’t believe this is as good as it will ever be. I think that’s up to you. It only is if you say so.

You get to choose.

Heart,

Tami

Let’s keep the conversation going! (borrow any of the prompts below or share whatever is on your mind)

1. What is one thing you’re happy worked out differently than you expected?

   This question is borrowed from

   Jane Ratcliffe
   ’s delightful interview with
   Austin Kleon
   this week. In it, he also references his post Never Waste Your Midlife Crisis, which is a great read if the fear of getting older is on your mind.

2. Fill in these blanks: I will never be ______ but I can still ______ if I want to.

3. Any advice to add? Insert your two cents in the comments below.

4. Was Jesse Eisenberg made to be Toby Fleishman? Was Toby Fleishman written for Jesse Eisenberg? Could anyone else have played this part? I don’t think so, but tell me I’m wrong…

Thinking about getting older, what to do with your time, or making the right choices? You may also enjoy these reads from the Outsourced Archive:

Season Endings & Series Finales

The Unlikely Hope In Giving Up

1. Read: Four Thousand Weeks: Time Management For Mortals by Oliver Burkeman