Ask Ash: 'I Want to Travel Italy. Learn How to Cook. People Watch in Courtyards. And Spend My Afternoons Writing a Book.'

"But all of that costs money, and I'm just an average woman who's spent her whole life working an average job, at an average company, for average pay." —Reader

Dear Ash,

I’m a 50-year-old woman who’s spent her whole life working an average job, at an average company, for average pay. I’ve recently realized that life is passing me by, and I’ve lived it too long without any great adventures. My soul is slowly being suffocated from banality, and I’m aching for a second act. What I really want to do? Travel to Italy. Learn how to cook. People watch in courtyards. And write a book. I’ve always wanted to write a book. (Don’t we all!) But, of course, all of that costs money. While I have some savings, what I really need to do is find a new career path that lights me up…that lets me be in Italy (or maybe even Greece!) full-time, living a bigger life than I have ever let myself live. The only trouble is…I don’t have any real passions, and I don’t have any real, transferable skills. For the past twenty years, I’ve been working as an administrative assistant to a corporate executive. I don’t have any real ‘specialties,’ so to speak. Sure, I can organize one hell of a meeting. I can keep other people on task. I can do research and I can support an organization well. But, short of seeking employment at a company in Italy for a similar-type role (which I don’t really want to do because, who would hire me anyway when I don’t even speak Italian?), I don’t know how else I would make enough money to make this happen. But, at the same time, I don’t want to just slowly fade into oblivion here in my small little uneventful town. Something’s gotta give, but what? How can I follow my passions if I don’t yet know what they are??? Or, should I just accept that maybe this ship has sailed???

Sincerely yours,

Wannabe Italian Lady in a Long-Ass Dress Drinking Grappa and Eating Orecchiette

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Dear Wannabe,

CAN I JOIN??? Though I will say, I look like a squatty wash woman from the 1600s whenever I put on a long dress, and my grappa tolerance is embarrassingly low. (I also had to Google which pasta was “orecchiette,” which only means that I need to come on this trip even more.)

In reading this message, you know what made me want to reach out and give you a weird, creepily-long, socially-unacceptable hug? That very last line: “that maybe this ship has sailed.”

Can we talk about this first? Because I think so many of us secretly think this about ourselves, and I suspect that those six words are the silent murderers of all potential that is good and whole and innocent and bright. Because, think about this: who could possibly live up to their potential when they’re in their 20s? Or 30s? Or at any stage in life when you still don’t even know how to properly baste a turkey? You don’t even know what your potential IS yet, because you hardly even know yourself yet. Which means that, you really can’t start living up to your potential until you’ve reached a certain age that allows for meaningful reflection. You need to have enough perspective to see yourself clearly. And THAT means that, even though getting older makes us all worry that “our ship has sailed”—that you’re too old to make a big change—what if we’re finally in the best position TO sail?

Knowing who you are and what you want from life is a luxury most young people do not yet have. Most young people spend all their time throwing countless different options against the wall, just trying to see what might tickle their fancy. You, on the other hand, already know what you want from life next: you want to go to Italy, and you want to learn how to cook, and you want to write a book. WHAT A COMMENDABLE, FULL, RICH, FUN, BEAUTIFUL GOAL. And that means one thing: you are already 50% there. If you had a punch ticket for this ride, you’d already have half of ‘em filled.

Your ship hasn’t sailed; you are sailing it RIGHT NOW. Even if it feels like you are stalling. Half of the work is invisible work: it’s the mental labor and the emotional labor of figuring your shit out. Do not discount all of the time and effort you have put into that. You are already 50% of the way. Do not stop now! So much of success is just deciding what kind of success you want to have. You have done this work. You are doing the work. You are already so far ahead of the game. You just can’t see it because progress moves at a microscopic pace.

The second thing I want to bring up is this quote, which I promise isn’t an annoying quote, even though I DID find it on one of those annoying cards:

I bought the card for myself because like everyone, I, too, am always experiencing a new beginning. Did you ever think of it that way? That every decision we make is a new beginning? My decision to write this column, for example, is a new beginning. My decision to buy a house in the American countryside is a new beginning. But even just my decision to dress myself the way I did today was a decision that gave me a new beginning: a new opportunity to make a new impression. To be a new version of myself. To change my image; tweak reality ever so slightly. We are all here tweaking our own realities little by little, day by day. Hopefully, the tweaks we make get us closer to a life we enjoy.

In Atomic Habits, James Clear writes about the importance of 1% changes. The math is startling:

Improving by 1% isn’t particularly notable—sometimes it isn’t even noticeable—but it can be far more meaningful, especially in the long run. The difference a tiny improvement can make over time is astounding. Here’s how the math works out: if you can get 1 percent better each day for one year, you’ll end up thirty-seven times better by the time you’re done. Conversely, if you get 1 percent worse each day for one year, you’ll decline nearly down to zero. What starts as a small win or a minor setback accumulates into something much more.

I LOVE THIS. I THINK ABOUT THIS INCESSANTLY. (ASK ME HOW OFTEN I’VE APPLIED IT TO EXERCISE THOUGH HAHAHAHAHAHA.)

While the 1% rule is most commonly applied to habits, it can also be applied to passions. What if you became 1% more passionate about something every day? What if you spent every day become 1% more interested in your actual interests? By the end of the year, you’d be 37% more passionate, alive, inspired. Whereas, on the other hand, if you dedicate no time to your own interests, eventually you’ll have none.

And that makes me want to put this emoji: 👹 Which is apparently an ogre, according to my keyboard.

So in this whole “trust in the magic of new beginnings” stuff, maybe we should not only trust in that magic, but devote resources to making that magic.

When it comes to finding a career path that lights you up, this is the work we must do. The 1% work. The work of getting to know your talents, your aptitudes, your flair, your own creative spark. This is different from knowing what you want from life (which you have already figured out); this is knowing what you want from your career. And, ugh, it’s a doozy, am I right???

Let’s forget about “marketable skills” for a minute. Let me give you permission to forget about everything that is “rational” and “makes sense.” Let us forget about your past, and your career history, and your own perception of your value—which, by the way, is gravely underestimated. Let us forget about your resume, your chosen career path, your current identity. Let us forget about who you have been for your first act on earth, and let’s talk about who you want to become for your second.

What things interest you when you’re all alone on a Sunday?

What do you find yourself scrolling on Instagram? Or Pinterest? Or online?

Which emails do you find yourself reading in your inbox?

What are you drawn toward, naturally, without the pressure of employment?

For me, this is home interiors. I LOVE INTERIORS. I’ve always loved interiors, ever since I was a young girl in that Pennsylvania trailer park, trying like hell to do whatever I could to make life in the trailer more beautiful. I learned that you can take even the most basic of things and turn them into something beautiful, with enough thoughtful consideration. (Isn’t it funny that the things we care about are sometimes connected to our childhood? This might be another useful clue.)

If the work is to get 1% more passionate every day, then why not start tracking your actual interests every day? Why not take it as seriously as any work you might do? Pull up a spreadsheet. Make some columns. Track what kinds of things pique your interest as you go about your days. When you watch a TV show and become fascinated with the life of a travel host, WRITE IT DOWN. No career or passion is too “big,” or too “hard” or too “unreasonable.” You aren’t trying to be reasonable right now, you’re trying to be passionate. Passion cannot include reason, or it would be rationale. And no passion is rational. Most passions are an emotional response to something you discover, or find, or see, and instantly like. Whenever I see the Brits and their incredible gardens, for example, I go wild. LOOK AT THESE GARDENS!!!!!!!!! It makes no sense because I have no green thumb, but do you know how many British gardeners I follow on Instagram? It’s entirely illogical! It makes no sense! And yet? It gives me profound joy.

Stop policing your joy.

Start paying attention to it, instead.

And, why not take it seriously with, literally, a spreadsheet, or even a Pinterest board??? Take notes on yourself. Act as if you are the most interesting artifact in the world. Study it. Observe it. And see what conclusions you can draw about yourself—just like an anthropologist. If, for example, you notice that the things that are piquing your interest are:

• Millinery

• Historic outfits

• Horses and carriages

• And antiques

…then it might be safe to conclude that you’re passionate about history! And, once you have some notes on yourself, it’ll help you more deeply investigate different types of work you could do.

For as much as I balk at certain aspects of social media, one very useful aspect is research. FOR EXAMPLE, if I just type “millinery” into Instagram, a bunch of fun accounts come up of people who are working in this industry. This is great for inspiration. You cannot know what is possible until you see someone doing it. And, seeing is very, very important. It helps you believe. When we see other people doing something, all the sudden it becomes possible for ourselves.

Do not count yourself out of ANYTHING.

You are capable. You are ready. You are possible.

That said, you probably don’t want to wait three years until you figure it out, get some experience, and launch a side hustle doing your new thing. And guess what? I don’t think you should have to!

I have a unique perspective on this because personally, I’m much better with my feet in the fire than any other way of learning. So, I create scenarios for this to happen as much as I can…on purpose. If I found myself in your position, wanting to go to Italy and enroll in cooking school…but without an anywhere business that can support it, the first thing I would do is create a “bridge business.”