When Everything Works Out (A Reader Update)


Yesterday, I received an update from “Should I Stay or Should I Go?,” one of the letter-writers who requested advice from the now-defunct Meghan & her Dad column (her original letter and our responses are below). Here’s what she had to say:

Dear Meghan,

About a year ago, I wrote to you (and your dad) asking for some advice about my career (I was Should I Stay or Should I Go?), and you both wonderfully, sweetly, gave me a kick in the rear about going and doing the things that actually made me happy. I want to thank you for that, and let you know how it turned out. While I had some intervening mental health things that meant it took longer than I expected, I applied for graduate schools and a fellowship, and I wanted to let you know that I got it! I’m now a fellow for a program that gets people into the US Foreign Service; I leave my job in two months to move to DC, get my MA, and I’ll be a diplomat for (at least) five years after that. I just wanted to say thank you, THANK YOU so much to you and your lovely dad, for reminding me that my dreams are worth pursuing. As your dad said, my guy was on another bus; I’ve found him now, and he’s pretty great.

All the best,


Follow your dreams! Everything will work out! Elvis Costello is always right! This is a great lesson in the good that comes from listening to your better self, and doing the work that follows. We’re so happy for you, dear letter writer. You inspire us.

Dear Meghan and her Dad,

I’m 24 and I’ve been at my first job for about a year; it’s typically a two-year position. My supervisor has recently quit, and according to several coworkers in our (very small) office, I would be a good fit for it. I know the region of specialization, I just submitted a report to my big boss on long-term strategy that she really liked, and one of the other people in our office who works at the same level as my supervisor mentioned to the big boss that (as far as she’s concerned) I would be a good fit.

The problem? I don’t want to stay in this work long-term. It’s near-ish to what I want my career to be (I’m in international education, and want to join the Foreign Service), but this isn’t quite it. On the one hand, if I go for it, I get stability, a promotion/raise (and the attendant ability to not have roommates), and a job I’m reasonably good at in a community I like. On the other hand, I’m really scared that my desire to be stable and responsible will lead me to stay not just in a field I’m not in love with, but in an office where, beyond this position, I wouldn’t be able to grow long-term. Plus, taking the position would mean putting off grad school for at least another couple of years, and I have the feeling that if I wait too long, I won’t do it. I know I’m really fortunate to be in a position like this, but I don’t want to make the wrong choice just because I should be grateful to have it. So, come on and let me know: Should I stay or should I go?

All the best,

Aspiring Diplomat

Meghan’s dad says:

Dear Aspiring Diplomat,

Oh yes — that immortal riddle posed by The Clash in 1982 (eight years before you were even born, if my math hasn’t eluded me) — is as intractable in one’s work life as it is in one’s personal life. When do you step off one bus and onto another? Or worse — off one bus and onto … nothing?

You have done an excellent job of assessing your current situation — looks like you have a good head on your shoulders. You also have a job and one that has the potential to be meaningful, so you have already achieved much more than many of your generation or, indeed, the general working population have achieved. For the past half century, many kids have grown up thinking that they would get a job that was interesting and challenging. For the vast majority of people, and for life before the ’60s, that was and is an illusion. Work is work. For most, it is hard and thankless and engaged in only to put the proverbial food on the table. And yet, for about 50 years or so, a large number of kids primarily in the Western world have thought it should be more, and for the lucky few, it was. Work could be important; you could “make a difference;” you could have fun and get paid for it. A very novel and recent concept, but one borne of privilege. It is a luxury and if you are fortunate enough to find yourself in that position, logic suggests you shouldn’t give up your seat on that bus.

But you clearly want to: “I don’t want to stay in this work long-term.”

Once you say that, I begin to wonder what the debate is about. You have made up your mind and you are looking to be reassured. Here goes.

Sure, there is risk. But you are 24, for crying out loud. You want grad school (you might want to check out the GMAT just in case it turns out to be a limiting factor) followed by the foreign service. This nice, sort-of-makes-a difference-but-maybe-not-really job just doesn’t cut it. Roll the dice. Say it blows up. So what. Then you are 26 or 27 and are trying to get back into the job market — not easy, but not impossible. On the other hand, you stay for three or four or five years and then try to jump into grad school (by which point you might feel that the G in GMAT stands for Gibberish) and you will be left wondering about what could have been.

So let’s revert to the land of punk with none other than Elvis Costello.

“I said ‘I’m so happy I could die’ / She said ‘Drop dead’ and left with another guy”

You are “she”; “I” is your possible new job as supervisor; “another guy” is your potential.

Okay — it’s a big stretch, but it is one of my favorite punk lyrics so I had to try to make it work (“Angels Want to Wear My Red Shoes” from My Aim Is True). And you could do worse than look to Elvis for pithy words of wisdom.

Go chase the other guy. He’s on a different bus.

Meghan says:

Man, remember 24? I do. I think. Correct me if I’m wrong, Dad (you always do), but I’m pretty sure I was living at home at 24, having recently finished driving solo around America for three months. (That sounds more purposeful than it was; in actuality, I woke up one morning so terribly depressed in my post-college haze that all I could think to do was try to drive away from it.) I was sleeping in a bedroom next to my parents, working as a barista where the median age of my coworkers was 16, and kept coming home to find innocuous-seeming papers on my bed that read things like, “The Top 50 MFA Programs” that I would sweep off the duvet before climbing under it to weep about my lost youth, my lack of direction, my interminable loneliness.


I thought 24 was old. Now I’m 30 and I realize I will probably never be old, not really. Old compared to what? According to whom? This time last year, I got fired from a job that I had thought would be mine for the long-haul, in a field I had chosen as my end-stop. Cue montage, throw in a breakup, add a dash of SSRIs, and a year of serious grindstoning, and now I have a career I didn’t even know existed, and am more professionally fulfilled than I could have ever imagined.

So I could ramble about best laid plans, etc. etc,, but I think what you’re really looking for is someone to tell you that it will be okay to leave. And it will. You’ve already left, I think. The worst way to do a job is with one foot out the door. It is unfair to those who have invested in you and it is unfair to your 30-year-old self, who is out there whispering — begging — you to go, go, just go already. Of course you should be grateful for your luck (on the back of your tenacity and dedication), and of course there is the chance that it won’t work out the way you’ve planned (it hardly ever does), but at the age you are, even in an economy like this one, it is always, always okay to go.

Trust me. I’m old.