Ask Ash: 'I Am Worried I Am Old, Ridiculous & Irrelevant. The Idea of Putting Myself Out There is So Daunting.'

Dear Ash,

All my life I’ve been responsible. I’ve worked hard, kept my head down, made sure the bills were paid, and did everything I could to make a good life for my son (who was born when I was just a kid myself). At the time, that meant sacrificing my dreams in order to make ends meet. Instead of going to school in Florence to study art, like I’d once imagined myself doing, I stayed in my small town here in Kentucky and started a cleaning business. Not the most glamorous job—one time I found a dead man on the toilet (I can’t make that up)—but it offered a ton of autonomy and the flexibility I needed, and was a way that I could earn a decent living without a degree. Well, who knew that decision would end up changing my life? Fast forward twenty-five years, and my little cleaning business turned into a big cleaning business, with over twenty employees. We’ve won local awards and we’ve had success. I am proud of what I’ve built. I never thought I could do anything like that. A random decision I made out of desperation turned into a successful career. And, I’m grateful for that. But…now that my son is all grown up and has a family of his own, I’ve been finding myself daydreaming about what it would be like to start fresh. Despite my success, I am left feeling jaded and uninspired in my work. I am worn down. The truth is, I secretly fantasize about closing the business and doing something extraordinary before life passes me by.

There’s only one problem: I worry I am old, ridiculous, and irrelevant. My face is aged. I’m carrying extra weight. I’m not cool. I don’t know what kind of jeans to wear. The idea of putting myself out there and having to be liked by people is daunting. I worry I’ll seem like a tragic, out-of-touch Karen. You know, like the person you know who can’t figure out audio messages?

Then there’s the whole “starting over” thing. Do I really want to start from scratch? Part of me keeps fantasizing about just buying a plane ticket and going to Florence, and actually enrolling in art school, and just saying “to hell with it” and doing something exhilarating, but the other part of me is embarrassed: embarrassed to be old, embarrassed to be a beginner, embarrassed that I don’t know how to use TikTok, embarrassed that all the other students would think I was weird. I keep picturing them cringing at me, or secretly whispering about me behind my back, or just thinking I was pathetic.

And THEN there’s the whole question of: to what end? To what end would I go to art school and study art? Would I really be able to make a living doing that? Would I really be good enough to become an artist? I’m not “cool” anymore—so can I still be relevant?

I’m worried I have lost my nuggets.

Yours,

Florence Dreamer

Dear Florence Dreamer,

Book the fucking plane ticket.

How I want to reach through the screen and give you a gentle hug and then whip you around and sit you down at the computer and help you book a ticket direct for Italy—all while downing an ice-cold glass of limoncello and picking out a sensational dress for you to wear to the airport.

YOU NEED TO GO TO ITALY. AND IT NEEDS TO BE THIS YEAR. AND YOU NEED TO LET ME MOTHER YOU, BECAUSE IT’S BEEN TOO LONG SINCE YOU’VE BEEN IN A POSITION TO MOTHER YOURSELF.

You’ve been a mother to your son.

You’ve been a mother to your business.

You’ve been a mother to your employees.

You’ve been a mother to your clients.

And, based on your very honest and vulnerable email, you seem like an empath who’s probably been a mother to everyone else’s emotions, too. The friend who needs support. The neighbor who needs a favor. The acquaintance who, for some reason, just doesn’t seem to like you. (So you overcompensate being EVEN NICER, and the little shit never responds.)

There has been very little time for you to be a mother to yourself all these years. So, allow me to step in & mom your ass.

First thing’s first:

1. I am so proud of you for everything you’ve accomplished. You did it! You are smart, driven, and determined, it’s almost sickening. You are a supernova. Your talent shines through in all that you do. Go, go, go! Be brave, strong, and do exactly what you need to do. Trust yourself, kid. If anybody’s got this, it’s you.
2. I know you’ve been feeling jaded and uninspired in your work lately—but the work just isn’t big enough for you anymore, baby. You’ve outgrown this work. It served its purpose, which was a solid stepping stone for you to gather up time, and confidence, and experience, and a healthy financial safety net so when you were ready, you could do something magical. But, all magic takes time. And even though it might feel like you’ve been stagnating, nothing could be further from the truth: every thought you have moves you forward in some way. Every time you’ve secretly wished for something different, you have been making progress. Everything is progress. You are closer right now to your dreams than you’ve ever been. Remember: dissatisfaction is an indicator. It’s ambition’s low-fuel light. It’s there to signal to you that, hello, you need more. Without dissatisfaction, we’d forever stay in roles that were beneath our potential, because we’d never know better. It’s our dissatisfaction that gives us our guidance. You’ve got to make friends with your dissatisfaction. Call it up. Ask it what it needs from you. See what it says. I hope you realize that nothing is wrong with you, baby. Being dissatisfied is merely a state of being unfinished. It simply means you’re ready for what’s next.
3. With regards to your statement that you are “old, ridiculous, and irrelevant,” I will not let you talk to yourself the way you’ve been talking to yourself any longer. I want you to imagine your son, and I want you to imagine his brightest dream, and then I want you to imagine you stomping on it by telling him that his face is wrinkly, he’s too fat, he’s not cool, and he’s sorta tragic. That would fall firmly under the category of abuse. It would certainly also be considered emotional bullying. You would never speak to your son that way, and I am not going to let you speak to yourself that way. Beyond being cruel and malicious, it’s also inaccurate. You’re 45! Woo! And your life is entirely yours to own: you can do whatever you please. You can take up pottery. Take up singing. Take up dance. Take up a whole new sexual identity, if you want! You get to own your life. You get to decide what happens. And what a privilege, to get to decide one’s own path. Which is all to say: if you don’t enroll in art school in Florence, even if only for a summer, or a season, or a month, or even just ten days, I would consider it very irresponsible. You have a responsibility to yourself to make yourself happy. You have a responsibility to be full of joy. And every decision you make that acts in opposition to that goal? Is negligence. And, it’s causing you harm.
4. I also heard you when you said you were worried that following your dreams might lead to a dead end; to what end would you study art, and would you really be able to build a career doing that? Or, are you too old to start over? (You know, in your condition, as a fucking awesome forty-five-year-old woman.) Let me teach you something about the world, my little dove: Art does not discriminate. Creativity does not discriminate. Ambition does not discriminate. All of these things are available to you, anytime. Morning, noon, and night, you can be an artist. You can be a creative. You can choose to show up. And no one can stop you. So, of COURSE you can really be an artist. Of COURSE you can really change paths. Of COURSE you can just decide to switch everything up, one day, without needing any more reason than because I wanted to. And, yes, you can make a damn good living with your art in today’s economy, too. This is one of the best things about opportunity + the internet: it’s for all of us. It’s for anyone who has ambition dripping down their neck—even if it is a wrinkly neck, like mine.
   
   My favorite example of this is @brunchwithbabs — she’s a 74-year-old grandma & retired teacher who now has 3.9M TikTok followers, and 3.3M Instagram followers, labeling herself as “the internet’s favorite grandma.” She posts recipes and life hacks and they are SO GOOD, that she’s now doing brand deals with all sorts of companies who want her to do a video featuring their product. She’s also got a cookbook, and is working on a kitchen line—all because she started from a place of curiosity, rather than competition. And, maybe that’s the key here: maybe the key is to let yourself off the hook from it being THE MOST AMAZING, PERFECT THING YOU HAVE EVER DONE, EVER, and just focus on exploring your curiosity. Of course, that’s not to say you have to become an influencer—that’s not the point. The point is that simply, great work is great work, no matter how old (or young) you are. Focus on making great work, and then let go of any expectation.
   
   By the way? Julia Child wrote her first cookbook when she was 50. Vera Wang didn’t get into the fashion industry until she was 40. Ray Croc reinvented McDonald’s at age 52. And, perhaps most aptly, Grandma Moses didn’t pick up a paint brush until age 78. She exhibited her work internationally into her 90s, and in 2006, one of her paintings sold for $1.2 million. Of course, there’s always the fear that if you make a career change like this, you’re going to have to start again from scratch. But, I think Sheryl Sandberg said it best:
   
   

Sweet child, you told me you were ‘embarrassed to be old, embarrassed to be a beginner, embarrassed that I don’t know how to use TikTok, embarrassed that all the other students would think I was weird.’ Please know something VERY, VERY REAL: everyone is embarrassed to be themselves. Literally everyone! Being human is embarrassing, at all stages of life. We’re all just embarrassed about different things, that’s all. When you’re young, you’re embarrassed you’re not old (and look green and have no experience). When you’re old, you’re embarrassed you’re not young (and aren’t ‘cool’ anymore.) But I can promise you this: every single person who’s ever done anything interesting with their lives, has done so while feeling mortified. Mortification is another indicator we have as humans that lets us know we’re growing. Think of it as putting fuel back into your tank. You can’t get anywhere wonderful without being embarrassed to be doing it. That’s because anything new is always embarrassing. When we’re doing something new, we’re clumsy, we’re disoriented, we’re anxious, we’re weird—AND IT IS ALL SO BEAUTIFUL AND EMBARRASSING AND GREAT. This is what it feels like to be alive! Imagine if you always just felt 100% fine. Do you know how boring that would be??? Embarrassing ourselves is the only way forward. So, would you rather embarrass yourself by going to work for some slob in a suit? Or would you rather embarrass yourself by going to Florence and trying art school? Either way you’re gonna be mortified: might as well pick the most thrilling option you have.

“There are so many times I’ve seen people not make that jump because they’re afraid they’ll ‘move backward.’ So let’s say you’re a lawyer and you’ve decided you don’t want to be a lawyer, you’d really rather be in marketing, and you’re 35… but you’re at a certain level and you’ve never done marketing so no one’s going to hire you at that level, so you’re gonna need to take a step back, meaning go down a couple levels. If you can financially afford it, and you’re gonna work the next, I don’t know, 30 years, who cares about ‘going down?’…I came in [to Google] as what we call the business unit general manager. The first team I ran at Google had four people. The Treasury had tens of thousands.”

Remember: everything is progress—even when you feel like you’re going backwards. There really IS no “going down.” Try thinking about your career on a horizontal timeline, rather than a vertical one. You went through one phase, and now you’re entering another. Naturally, you’d start at the beginning of the next phase. Being at the beginning is okay. In fact, it’s more than okay: it’s FUN. It’s exciting. And, it’s a privilege.

So if this is me, being a mother to you, let me wrap this up by telling you what I know to be true:

Human beings are not irrelevant.
Authenticity is not irrelevant.
Great work is not irrelevant.
Creativity is not irrelevant.
Enthusiasm is not irrelevant.
Good ideas are not irrelevant.
Sharp observations are not irrelevant.
Fantastic writing is not irrelevant.
Beautiful artwork is not irrelevant.
Jaw-dropping photography is not irrelevant.
Wonderful intentions are not irrelevant.
Honesty is not irrelevant.
Community is not irrelevant.
Showing up is not irrelevant.
Being yourself is not irrelevant.
Being brave is not irrelevant.
Being happy is not irrelevant.

…And that means that you, little sweetpea, couldn’t be irrelevant if you tried.

There is no dishonor in being true to yourself.

No matter what you look like, or who you are, or what color nail polish you have on, or the sound of your voice, or the way you draw a stick figure, or eat your apples, or sit on the subway, or the way a tee-shirt emphasizes your muffin top.

Book the fucking plane ticket, Florence Dreamer.

The world is waiting for you to shine.